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Asif, Mohammad
- Biological Potential and Chemical Properties of Pyridine and Piperidine Fused Pyridazine Compounds: Pyridopyridazine a Versatile Nucleus
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Source
Asian Journal of Chemistry and Pharmaceutical Sciences, Vol 1, No 1 (2016), Pagination: 29-35Abstract
Pyridopyridazine compounds are important nitrogen atom containing heterocyclic compounds due to their pharmacological versatility. This heterocycle system characterized a structural feature for different types of bioactive compounds that exhibiting various types of biological activities which make it an attractive scaffold for the design and development of new drug molecules. This article provided information about the pharmacological properties of pyridopyridazines derivatives.Keywords
Pharmacological Properties, Pyridopyridazine, PyridopyridazinoneReferences
- Sainsbury M. Heterocyclic chemistry, basic concepts in chemistry. Bristol: Wiley Interscience and Royal Society of Chemistry; 2002.
- Taniguchi T, Ogasawara K. A diastereo controlled synthesis of (+)-febrifugine: A potent antimalarial piperidine alkaloid. Organic Letters. 2000; 2(20):3193β5.
- Takeuchi Y, Azuma K, Takakura K, Abe H, Harayama T. Asymmetric synthesis of febrifugine and isofebrifugine using yeast reduction. Chemical Commun. 2000; 17:1643β4.
- El-Subbagh HI, Abu-Zaid SM, Mahran MA, Badria FA, Al-Obaid AM. Synthesis and biological evaluation of certain πΌ,-unsaturated ketones and their corresponding fused pyridines as antiviral and cytotoxic agents. J Med Chem. 2000; 43(15):2915β21.
- Perumal RV, Adiraj M, Pandiyan PS. Synthesis, analgesic and anti inflammatory evaluation of substituted 4-piperidones. Indian Drugs. 2001; 38(3):156β9.
- Katritzky AR, Fan W-Q. A novel and versatile synthesis of 1-alkyl-, 1-aryl-, 1-(alkylamino)-, or 1-amido-substituted and of 1,2,6-trisubstituted piperidines from glutaraldehyde and primary amines or monosubstituted hydrazines. The J Org Chem. 1990; 55(10):3205β9.
- Aridoss G, Amirthaganesan S, Ashok Kumar N, et al. A facile synthesis, antibacterial, and antitubercular studies of some piperidin-4-one and tetrahydropyridine derivatives. Bioorg and Med Chem Lett. 2008; 18(24):6542β8.
- Margaretha VM, Armin H, Ivonne JL, et al. Novel selective PDE4 inhibitors. 1. Synthesis, structure-activity relationships, and molecular modeling of 4-(3,4-dimethoxyphenyl)- 2H-phthalazin-1-ones and analogues. J Med Chem. 2001; 44(16):2511β22.
- Eicher T, Hauptmann S. The Chemistry of Heterocycles: Structure, reactions, syntheses, and applications. 2nd ed. Wiley-VCH; 2003.
- Asif M, Singh A, Lakshmayya. The development of structurally different new antitubercular molecules containing pyridazine ring system. Chronicle of Young Scientist. 2013; 4(1):1β8.
- Asif M, Anita Singh A, Siddiqui AA. The effect of pyridazine compounds on the cardio-vascular system. Med Chem Res. 2012; 21:3336β46.
- Asif M, Singh A, Ratnakar L. Antimicrobial Agents: Brief study of pyridazine Derivatives against some phathogenic microrganisms. J Pharm Res. 2011; 4(3):664β7.
- Asif M, Singh A. Exploring potential, synthetic methods and general chemistry of pyridazine and pyridazinone: A brief introduction. Inter J Chem Tech and Res. 2010; 2(2):1112β28.
- Asif M. Antifeedant, herbicidal and molluscicidal activities of pyridazinone compounds. Mini Rev in Org Chem. 2013; 10(2):113β22.
- Asif M. The study of pyridazine compounds on prostanoids: Inhibitors of COX, cAMP phosphodiesterase, and TXA2 Synthase. J Chem. 2014. Available from: http://dx. doi.org/10.1155/2014/703238
- Abubshait SA. An efficient synthesis and reactions of novel indolylpyridazinone derivatives with expected biological activity. Molecules. 2007; 12(1):25β42.
- Youssef ASA, Marzouk MI, Madkour HMF, El-Soll AMA, El-Hashash MA. Synthesis of some heterocyclic systems of anticipated biological activities via 6-aryl-4-pyrazol-1-ylpyridazin- 3-one. Canadian J Chem. 2005; 83(3): 251β9.
- Cherng S-C, Huang W-H, Shiau C-Y, Lee A-R, Chou T-C. Mechanisms of antiplatelet activity of PC-09, a newly synthesized pyridazinone derivative. Eur J Pharmacol. 2006; 532(1-2):32β7.
- Dogruer DS, Onkol T, Ozkan S, Ozgen S, Sahin MF. Synthesis and antimicrobial activity of some 3(2H)-pyridazinone and 1(2H)-phthalazinone derivatives. Turkish J Chem. 2008; 32(4):469β79.
- Taleb HA. Design and synthesis of novel tetrahydro- 2HPyrano[3,2-c]Pyridazin-3(6H)-one derivatives as potential anticancer agents. Eur J Med Chem. 2010; 45(12):5724β31.
- Ibrahim MA, Elmenoufy AH, Elagawany M, Ghoneim, MM, Moawad A. βPyridopyridazineβ: A Versatile Nucleus in Pharmaceutical Field. J Biosci and Med, 2015; 3:59β66.
- Brown DJ. 10. Halogenophthalazines (H 178; E 514). Cinnolines and Phthalazines. The Chemistry of Heterocyclic Compounds Series. Hoboken, NJ: John Wiley and Sons, Inc; 2005. p. 203.
- Hoffmann J, Thien, T, vanβLaar A. Effects of intravenous endralazine in essential hypertension. British J Clin Pharmacol. 1983; 16:39β44.
- Meredith PA, Elliott H, McSharry DR, Kelman AW, Reid JL. The pharmacokinetics of endralazine in essential hypertensives and in normotensive subjects. British J Clin Pharmacol. 1983; 16:27β32.
- Carling WR, Castro PJL, Mitchinson A, Street LJ. Pyrido- pyridazine derivatives as ligands for gaba receptors. Pyrido-pyridazine derivatives as ligands for gaba receptors. Google Patents; 2001.
- Gore PM, Looker BE, Procopiou PA, Vile S. Phthalazine and pyrido[3, 4-D]pyridazine compounds as H1 receptor antagonists. Google Patents; 2008.
- Pettus LH, Tasker A, Wu B. Pyrido[3,2-d]pyridazine- 2(1H)-one compounds as p38 modulators and methods of use thereof. Google Patents; 2013.
- Tynebor RM, Chen M-H, Natarajan SR, OβNeill EA, Thompson JE, Fitzgerald CE, et al. Synthesis and biological activity of pyridopyridazin-6-one p38 MAP kinase inhibitors. Part 1. Bioorg and Med Chem Lett. 2011; 21:411β6.
- Pakulska W, Malinowski, Z Szczesniak, AK, Czarnecka E, Epsztajn J. Synthesis and pharmacological evaluation of N-(Dimethylamino)ethyl derivatives of benzo- and pyridopyridazinones. Archiv der Pharmazie. 2009; 342:41β7.
- Kaizerman J, Lucas B, Mcminn DL, Zamboni R. Annelated pyridazines for the treatment of tumors driven by inappropriate hedgehog signalling. Google Patents; 2010.
- Whilhelm R, Loe B, Alvarez R, Devens B, Fong A. pyrido-[ 2,3-d]pyridazinones as potent and selective type IV phosphodiesterase inhibitors. 8th RSC-SCI Medicinal Chemistry Symposium; Cambridge, UK. 1995. p. 32.
- Mylari BL, Zembrowski WJ, Beyer TA, Aldinger CE, Siegel TW. Orally active aldose reductase inhibitors: Indazoleacetic, oxopyridazineacetic, and oxopyridopyridazineacetic acid derivatives. J Med Chem, 1992; 35:2155β62.
- Stanasiuk J. Investigation on the synthesis and properties of 2-(alkyl, aryl)-1,4,5-trioxo-1,2,3,4,5,6-hexahydropyrido[ 3,4-d]pyridazine, derivatives with potential biological activity. Acta Pol Pharm. 2005; 63:420β1.
- Elassar A-ZA. Synthesis and antimicrobial activity of new polyfunctionally substituted pyridines and their fused derivatives. Indian J Chem. 2004; 43:1314β9.
- Matyus P. 3(2H)-pyridazinones: Some recent aspects of synthetic and medicinal chemistry. J Heterocycl Chem. 1998; 35:1075β89.
- Tynebor RM, Chen M-H, Natarajan SR, OβNeill EA, Thompson JE, Fitzgerald CE, et al. Synthesis and biological activity of pyridopyridazin-6-One p38Ξ± MAP kinase inhibitors. Part 2. Bioorg and Med Chem Lett. 2012; 22:5979β83.
- Bishnoi M, Premkumar LS. Changes in TRP channels expression in painful conditions. The Open Pain J. 2013; 6:10β22.
- Εladowska H, Stanasiuk J, Sieklucka-Dziuba M, Saran T, Kleinrok Z. Investigations on the synthesis and properties of 4-aminosubstituted 2,6,7-trimethyl-1,5-dioxo-1,2,5,6- tetrahydropyrido[3,4-d]pyridazines. Il Farmaco. 1998; 53:475β9.
- Epsztajn J, Czarnecka E, Szczesniak A, Pakulska W, Malinowski Z. Benzo- and pyrido-pyridazinones with analgesic and anti inflammatory activity. Google Patents; 2009.
- Nishikawa K, Shimkawa H, Inada Y, Shibouta Y, Kikuchi S, Yurugi S, Oka Y. Structure-activity relationships of the diuretic activity of triaza- and tetraaza-naphthalene compounds. Chem and Pharm Bull. 1976; 24:2057β77.
- Goodacre SC, Hallett DJ. Substituted pyrido-pyridazine derivatives which enhance cognition via the GABA-A Receptors. Google Patents; 2006.
- Mitchinson A, Blackaby WP, Bourrain S, Carling RW, Lewis RT. Synthesis of pyrido [2,3-d]pyridazines and pyrazino[ 2,3-d]-pyridazines- novel classes of GABA receptor benzodiazepine binding site ligands. Tetrahedron Lett. 2006; 47:2257β60.
- Kurosawa M. Role of thromboxane a2 synthase inhibitors in the treatment of patients with bronchial asthma. Clin Ther. 1995; 17:2β10.
- Dal PV, Giovannoni MP, Castellana C, Palacios JM, Beleta J, Domenech T, et al. Novel heterocyclic-fused pyridazinones as potent and selective phosphodiesterase IV inhibitors. J Med Chem. 1997; 40:1417β21.
- Zimmet P, Alberti K, Shaw J. Global and societal implications of the diabetes epidemic. Nature. 2001; 13:782β7.
- Kakimoto S, Tonooka S. Antituberculous compounds. XXV. Some Derivatives of Pyrido [2,3-d] Pyridazine. Bull Chem Soc Japan. 1967; 40:153β9.
- Cancer. Available: http://www.who.int/cancer/en/
- Selvakumar P, Thennarasu S, Mandal AB. Synthesis of novel pyridopyridazin-3(2h)-one derivatives and evaluation of their cytotoxic activity against MCF-7 cells. Inter Scholarly Res Notices; 2014. Article ID: 410716.
- Rennie RP. Current and future challenges in the development of antimicrobial agents. In: Coates, ARM, Ed. Antibiotics Resistance, Handbook of Experimental Pharmacology. Springer-Verlag, Berlin; 2012. p. 45β65.
- Biancanali C, Giovannoni MP, Pieretti S, Cesari N, Graciano A, Vergelli C, Cilibrizzi A, di Gianuario A, Colucci M, Mangano G, Garrone B, Polenzani, L, dal Piaz V. Further studies on arylpiperazinyl alkyl pyridazinones: discovery of an exceptionally potent, orally active, antinociceptive agent in thermally induced pain. J Med Chem. 2009; 52:7397β 409.
- Rodrguez-Ciria M, Sanz AM, Yunta MJR, Gomez-Contreras F, Navarro P, Fernandez I, Pardo M, Cano C. Synthesis and cytotoxic activity of N,N-bis-{3-[N-(4- Chlorobenzo[ g]-phthalazin-1-yl)]aminopropyl}-N-methylamine: A new potential DNA bisintercalator. Bioorg Med Chem. 2003; 11:2143β8.
- Lee SG, Kim JJ, Kim KH, Kweon DH, Kang YJ, Cho SD, Kim SK, Yoon Y. Recent progress in pyridazin-3(2h)-ones chemistry. J Curr Org Chem. 2004; 8:1463β80.
- Orru RVA, de Greaf M. Recent advances in solution-phase multicomponent methodology for the synthesis of heterocyclic compounds. Synthesis. 2003; 10:1471β99.
- Butnariu R, Caprosu M, Bejan V, Ungureanu M, Poiata A, Tuchilus C, Florescu M, Mangalagiu I I. Pyridazine and Phthalazine Derivatives with 1149 Potential Antimicrobial Activity. J Het Chem. 2007; 44:1149β55.
- Coelho A, Sotelo E, Ravina E. Pyridazine derivatives. Part 33: Sonogashira approaches in the synthesis of 5-substituted- 6-phenyl-3(2H)-pyridazinones. Tetrahedron, 2003; 59:2477β88.
- Rathish IG, Kalim J, Shamim A, et al. Synthesis and evaluation of anticancer activity of some novel 6-aryl-2-(psulfamylphenyl)- pyridazin-3(2H)-ones. Eur J Med Chem. 2012; 49:304β9.
- Livermone DGH, Bethell RC, Cammack N, Hancock AP, Hann MM, Green DVS, Lamont RB, Noble SA, Orr DC, Payne JJ, Ramsay MVJ, Shingler AH, Smith AH, Storer R, Williamson C, Willson T. Synthesis and anti-HIV-1 Activity of a series of imidazo[1,5-b]pyridazines. J Med Chem. 1993; 36:3784β94.
- Altomare C, Cellamare S, Summo L, Catto M, Carotti A. Inhibition of monoamine oxidase-b by condensed pyridazines and pyrimidines: effects of lipophilicity and structure- activity relationships. J Med Chem. 1998; 41:3812β20.
- Patil PO, Bari SB, Firke SD, Deshmukh PK, Donda ST, Patil DA. A comprehensive review on synthesis and designing aspects of coumarin derivatives as monoamine oxidase inhibitors for depression and Alzheimerβs disease. Bioorg Med Chem. 2013; 21:2434β50.
- Some Conventional and Convenient Process for Functionalization of 6-Phenyl-4,5-Dihydropyridazinone Compounds
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Source
Asian Journal of Chemistry and Pharmaceutical Sciences, Vol 1, No 1 (2016), Pagination: 41-52Abstract
The pyridazinone derivatives, particularly those bearing substituted different group or atom at a different position, have attracted considerable attention due to their characteristic pharmacological and other anticipated activities. These activities promoted the synthesis of a large number of substituted pyridazinone derivatives in order to explore the usefulness of this heterocyclic system. In the present review, various synthetic methods have been studied for the synthesis of substituted pyridazinone derivatives. The behaviour of the pyridazinone toward formaldehyde/piperidine, ethyl chloroacetate, chloroacetic acid, benzene sulfonyl chloride, bromine/acetic acid and aromatic aldehydes has also been studied. However, the reactions of the chloro derivative resulting from the reaction of pyridazinone with phosphorus oxychloride (POCl3). The behavior of chloropyridazine toward hydrazines, thiourea, sodium azide, anthranilic acid, aromatic amines and sulfa compounds have also been taken into consideration. Thethiopyridazinone derivativeswere prepared from the reaction of pyridazinone with phosphorus pentasulphide (P2S5). All the structures of were established on the based of spectroscopic data.Β
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Keywords
Biologically Active, Pyridazinone, Substitution Reaction, Synthetic MethodsReferences
- Dinesh K, Rosalia C,de la Carmen C, Dharam PJ, Ranju B. Synthesis and evaluation of 2-substituted-6-phenyl-4,5-dihydropyridazin- 3(2H)-ones as potent inodilators. Acta Pharm. 2008; 58:393β405.
- Smolyar NN, Yutilov YM, Gresko SV. Synthesis of 4-amino- 6-(hetaryl)pyridazin-3-ones as analogs of pyridazine-based cardiotonic agents. Pharm Chem J. 2009: 43:87β8.
- Youssef AS, Marzouk MI, Madkour HMF, El-Soll AMA, El-Hashash MA. Synthesis of some heterocyclic systems of anticipated biological activities via 6-aryl-4-pyrazol-1-ylpyridazin- 3-one. Can J Chem. 2005;83:251β9.
- Monge A, Parrado P, Font M, FernΓ‘ndez-Alvarez E. Selective thromboxane synthetase inhibitors and antihypertensive agents. New derivatives of 4-hydrazinopyridazino[ 4,5-a]indole and related compounds. J Med Chem. 1987;30:1029β35.
- Bristol JA, Sircar I, Moss WH, Evans DB, Weishmaar E. Cardiotonic agents. 1. 4,5- Dihydro-6-[4-(1H-imidazol-1- yl)phenyl]-3(2H)-pyridazinones: novel positive inotropic agents for the treatment of congestive heart failure.J Med Chem. 1984;27:1099β101.
- Demirayak S, Karaburun AC, Beis R. Some pyrrole substituted aryl pyridazinone and phthalazinone derivatives and their antihypertensive activities. Eur J Med Chem. 2004;39:1089β95.
- Bansal R, Kumar D, Carron R, de la Calle C. Synthesis and vasodilatory activity of some amide derivatives of 6-(4-carboxymethyloxyphenyl)- 4,5-dihydro-3(2H)-pyridazinone. Eur J Med Chem. 2009; 44(11):4441β7.
- Sircar I, Duell BL, Cain MH, Bruke SE, Bristol JA. Cardiotonic agents. 4. Synthesis and biological evaluation of N-substituted 2,4,4a,5-tetrahydro-3H-indeno[1,2-c]pyridazin- 3-ones: rigid structures derived from CI-930 and analogs.J Med Chem. 1986;29:2142β8.
- Gokce M, Utku S, Kupeli E. Synthesis and analgesic and anti-inflammatory activities 6-substituted-3(2H)-pyridazinone- 2-acetyl-2-(p-substituted/nonsubstituted benzal) hydraz- one derivatives. Eur J Med Chem. 2009; 44(9):3760β4.
- Mirzoeva S, Sawkar A, Zasadzki M, Guo L, Velentza AV, Ramstrom H, Haiech J,van Eldik LJ, Watterson DM, Dunlap V, Bourguignon JJ. Discovery of a 3-Amino-6-phenyl- pyridazine derivative as a new synthetic antineuroinflammatory compound. J Med Chem. 2002;45:563β6.
- Sondhi SM, Sharma VK, Singhal N, Verma RP, Shukla R, Raghubir R, Dubey MP. Synthesis and anti-inflammatory activity evaluation of some acridinyl amino antypyrine, acridinyl amino anthraquinone, acridino thiourea and thiazolino thiourea derivatives. Phosphorus, Sulfur, Silicon Relat Elem. 2000; 156:21β34.
- Turan-Zitouni G, Sivaci M, Kilic FS, Erol K. Synthesis of some triazolyl-antypyrine derivatives and investigation of analgesic activity. Eur J Med Chem. 2001; 36:685β9.
- Asif M, Singh A, Lakshmayya. Anticonvulsant activity of 4-(Substituted Benzylidene)-6-(3-nitrophenyl)-4,5-dihydro pyridazin-3(2H)-ones against maximal electro shock induced seizure. Middle-East J Sci Res. 2011; 9(4):481β5.
- Cao S, Qian X, Song G, Chai B, Jiang Z. Synthesis and antifeedant activity of new oxadiazolyl 3(2H)-pyridazinones. J Agric Food Chem. 2003;51:152β5.
- Chung KT, Chen SC, Wong TY, Wei CI. Effects of benzidine and benzidine analogues on growth of bacteria including Azotobacter vinelandii. Environ Toxicol Chem. 1998;17:271β5.
- El-Hashash MA, Amine MS, Soliman FM, Morsi MA. Behavior of aroylacyclic acids toward hydrazine hydrate and some on the cyclized products. J Serb Chem Soc. 1992;57:563β9.
- Sayed GH, Hamed AA, Meligi GA, Boraie WE, Shafik M. The use of 4-(3,4- dichlorophenyl)-4-oxo-2-(4-antipyrinyl)- butonoic acid in the preparation of some new heterocyclic compounds with expected biological activity. Molecules2003;8:322β32.
- Sotelo E, Pita B, Ravina E. Pyridazines. Part 22:1 Highly efficient synthesis of pharmacologically useful 4-cyano-6-phenyl- 5-substituted-3(2H)-pyridazinones. TetrahedronLett. 2000;41:2863β6.
- Livermore DGH, Bethell RC, Cammack N, Hancock AP, Hann MM, Green DVS, Lamont RB, Noble SA, Orr DC, Payne JJ, Ramsay MVJ, Shingler AH, Smith C, Storer R, Williamson C, Willson T. Synthesis and anti-HIV-1 activity of a series of imidazo[1,5-b]pyridazines. J Med Chem. 1993;36:3784β94.
- References and further reading may be available for this article. To view references and further reading you must purchase this article.Wang T, Dong Y, Wang LC, Chen Z. Synthesis and bioactivity of 6-phenyl-4,5-dihydro- 3(2H)-pyridazinone derivatives. Arzneimittelforschung. 2007; 57(10):641β6.
- Asif M, Singh A. Exploring potential, synthetic methods and general chemistry of pyridazine and pyridazinone: abrief introduction. Inter J Chem Tech Res. 2010:2(2):1112β28.
- El-GhaffarANF, Mohamed MK, Kadah MS, Radwan AM, Said GH, Abdel-al SN. Synthesis and anti-tumor activities of some new pyridazinones containing the 2-phenyl-1H-indolyl moiety. J Chem Pharm Res. 2011; 3(3):248β59.
- Abubshait SA. An efficient synthesis and reactions of novel indolylpyridazinone derivatives with expected biological activity. Molecules.2007;12:25β42.
- Wasfy AAF, Arief MMH, Amine MS, Donia SG, Aly AA. Ξ³-oxo carboxylic acids in heterocyclic synthesis, III. Synthesis of biologically active 4-Benzylamino-6-(5,5-dioxodibenzothiophen- 2-yl)-2,3,4,5-tetrahydropyridazin-3-ones. Verlag der Zeitschrift fur Naturforschung. 2002;668β76.
- Soliman MHA, El-Sakka SS. 4,5-Dihydro-6-(4-methoxy- 3-methylphenyl)-3(2H)-pyridazinone. J Korean Chem Soc. 2011; 55(2):230β34.
- Islam M, Siddiqui AA, Rajesh R. Synthesis, antitubercular, antifungal and antibacterial activities of 6-substituted phenyl- 2-(3-substituted phenyl pyridazin-6-yl)-2,3,4,5-tetrahydropyridazin- 3-one. Acta Pol Pharm. 2008; 65(4):441β7.
- Banerjee PS, Sharma KP, Nema KR. Synthesis and anticonvulsant activity of pyridazinone derivatives. Intr J Chem Tech. 2009; 1(3):522β5.
- Siddiqui AA, Mishra R, Shaharyar M, HusainA, Rashid M, Pal M, Yathirajan HS. Synthesis of 7-Phenyl-3,4,8,9-tetrahydro- 2H-pyridazino[1,6-a][1,3,5]triazin-2-imine. Molbank. 2011; M717.Doi: 10.3390/M717.
- Benchat N, Benalla A, El Kalai F, Ramdani M, Daoui S. Synthesis of 5-benzyl-2,6-dimethylpyridazin-3(2H)-one. Molbank. 2008; M580.
- Asif M, Singh D, Singh A. Analgesic activity of some 6-phenyl-4-substituted benzylidene tetrahydro pyridazin- 3(2H)-ones. Global J Pharmacol. 2011; 5(1):18β22.
- Siddiqui AA, Mishra R, Shaharyar M. Synthesis, characterization and antihypertensive activity of pyridazinone derivatives. Eur J Med Chem.2010; 45(6):2283β90.
- Sayed GH, Sayed MA, Shaaban SS, Mahmoud MR. Synthesis and reactions of 4-(p- bromophenyl)-4-oxo-2-(4- antipyrinyl)butanoic acid and some unexpected products. Egypt J Chem. 2000;43:17β29.
- Islam M, Siddiqui AA, Rajesh R.Synthesis, antitubercular, antifungal and antibacterial activities of 6-substituted phenyl- 2-(3i-substituted phenyl pyridazin-6i-yl)-2,3,4,5-tetrahydropyridazin- 3-one. Acta Pol Pharm.2008;65(3):353β62.
- Burdulene D, Palaima A, Stumbryavichyute Z, Talaikite Z. Synthesis and anti-inflammatory activity of 4-aminoantipyrine derivatives of succinamides. Pharm Chem J. 1999; 33:191β3.
- Coates WJ, McKillop A. One pot preparation of 6-substituted 3(2H)-pyridazinones from ketones. Synthesis. 1993;334β42.
- Dogruer SD, Onkol T, Ozkan S, Ozgen S, Sahin MS. Synthesis and antimicrobial activity of some 3(2H)-pyridazinone and 1(2H)-phthalazinone derivatives. Turk J Chem. 2008; 32:469β79.
- Foks H, Wisterowicz K, Miszke A, Brozewicz K, Wisnlewska K, Dabrowska-Szponar M. Synthesis, fungicidal and antibacterial activity of new pyridazine derivatives. Heterocycles 2009;78:961β75.
- Halasz BD, Monsieurs K, Elias O, Karolyhazy L, Tapolcsanyi P, Maes BU, Riedl Z, Hajos G, Dommisse RA, Lemiere GL, Kosmrlj J, Matyus P. Synthesis of 5-H-pyridazino[4,5-b] indoles and their benzofurane analogues utilizing an intramolecular Heck-type reaction. Tetrahedron. 2004;60:2283β 91.
- Jaihne H, Sayed A, Zaher HA, Sherif O. Reaction of 3-chloro- and 3-hydrazino-6-(p-tolyl) pyridazines. Indian J Chem. 1977;250β1.
- Tao J,Cao L-H, Wang C-F,Wang D-Z. Synthesis of 1,3,4-oxadiazoles and 1,3-thiazolidinones containing 1,4,5,6-tetrahydro- 6-pyridazinone. J Chinese Chem Soc. 2006;53:1193β7.
- KΓ‘rolyhΓ‘zy L, HorvΓ‘th G, MΓ‘tyus P. A novel pyridazino- fused ring system: synthesis of pyridazino[3,4-b]diazepam. Acta Pharm Hung. 2001; 71(2):168β70.
- Kassab RR. Simple synthesis and reactions of some new pyridazinono derivatives and their antimicrobial activity. Egypt J Chem. 2002;45:1055β73.
- Kassab RR, Sayed GH, Radwan AM,El-Azzez NA. Some reactions with (biphenyl)-4-(5-oxo-1,3-diphenyl-2-pyrazolin- 4-yl)-4,5-dihydropyridazin-3-(2H)ones. Rev Roum Chim. 2001;46:649β55.
- Okcelik B, Unlu S, Banoglu E, Kupeli E, Yesilada E, Sahin MF. Investigation of new pyridazinone derivatives for the synthesis of potent analgesic and anti-inflammatory compounds with cyclooxygenase inhibitory activity. Arch Pharm Pharm Med Chem. 2003;336:406β12.
- Piaz VD, Ciciani G, Giovannoni MP. 5-Acetyl-2-Methyl-4- Nitro-6-Phenyl-3(2H)-Pyriazinone: versatile precursor to hetero-condensed pyridazinones. Synthesis.1994;669β71.
- Sayed GH, El-Kady MY,Elhalim MSA. Synthesis and reactions of some Ξ±-aryl-Ξ²-(4-bromobenzoyl)-propionic acids. Indian J Chem. 1981; 20:845β8.
- Sayed GH, Radwan A, Mohamed SM, Shiba SA, Khalil M. Synthesis and reactions of some 6-aryl and 2,6-diaryl- 4(4`-antipyrinyl)-2,3,4,5-tetrahydropyridazin-3-ones and screening for their antibacterial activities. Chin J Chem. 1992; 10:475β80.
- Sotelo E, Coelho A, Ravina E. Pyridazines. Part 34: Retro-ene-assisted palladium-catalyzed synthesis of 4,5-disubstituted-3(2H)-pyridazinones. Tetrahedron Lett. 2003;44:4459β62.
- Toth G, Molnar S, Tamas T, Borbely I. An efficient synthesis of 4,5-dihydro-3(2H)-pyridazinone derivative. Synth Commun. 1997;27:3513β24.
- Vassilev GN, Yonova PA, Bohland H, Vassilev NG, Yordanov B. Synthesis and grouth-regulating activity of some metal coordination compounds with thioureas and antipyrines. Dokl Bulg Akad Nauk 1997; 50:59β62.
- A Mini Review on Biological Activities of 6-(4-Chlorophenyoxy)-Tetrazolo [5,1-A] Phthalazine (Quan-0808) Compound
Authors
1 Department of Pharmacy, GRD(PG) IMT, Dehradun - 248009, (Uttarakhand), IN
Source
Journal of Pharmaceutical Research, Vol 16, No 1 (2017), Pagination: 43-48Abstract
Purpose: QUAN-0808 (6-(4-chlorophenoxy)-tetrazolo[5,1-a]phthalazine) was tested for the anticonvulsant, anti-inflammatory, analgesic, anticoagulant, antithrombotic and antidepressant effects.
Approaches: Anticonvulsant activity was testedby electroshock seizure model and neurotoxicity was tested by the rotarod neurotoxicity test in mice. In chemically induced models of seizure like pentylenetetrazole, isoniazid, thiosemicarbazide and 3-mercaptopropionic acid were further tested for the anticonvulsant activity.
Findings: QUAN-0808 caused significant anticonvulsant activity against all types of seizures. It appreciably reduced xylene-induced ear edema, reduced the prostaglandin E2 and nitric oxide levels on the edema and reduced acetic acid-induced capillary permeability hyperactivity and reduced acetic acid-induced writhing response. It exhibited anti-inflammatory and antinociceptiveeffect in a dose-dependent manner.
Conclusions: The peripheral effect mechanisms of QUAN-0808 may be related to a reduced in the formation of PGE2, NO, bradykinin and additional inflammatory mediators. The anticoagulant and antithrombotic effects of Q808 delayed bleeding and clotting time in mice. QUAN-0808 exerts anticoagulant, antithrombotic and antidepressant effect, exhibited a significant reduction in immobility as antidepressant.
Keywords
Tetrazolo-Phthalazine, Anticonvulsant, Antidepressive, QUAN-0808, Anti-Inflammatory, Antinociceptive, Antithrombotic.References
- Zhang L, Guan LP, Sun XY, Wei CX, Chai KY, Quan ZS. Synthesis and anticonvulsant activity of 6-alkoxy[1,2,4]triazolo[3,4-a]phthalazines. ChemBiol Drug Des, 2009, 73, 313β319.
- Chen J, Sun XY, Chai KY, Lee JS, Song MS, Quan ZS. Synthesis and anticonvulsant evaluation of 4-(4alkoxylphenyl)-3-ethyl-4H-1,2,4-triazoles as open-chain analogues of 7-alkoxyl-4,5-dihydro[1,2,4]triazolo[4,3a]quinolines. Bioorg Med Chem, 2007, 15, 6775β6781.
- El-Gazzar AR, El-Enany MM, Mahmoud MN. Synthesis, analgesic, anti-inflammatory, and antimicrobial activity of some novel pyrimido[4,5-b]quinolin-4-ones. Bioorg Med Chem, 2008 16, 3261β3273.
- Israili ZH. Clinical pharmacokinetics of angiotensin II (AT1) receptor blockers in hypertension. J Hum Hypertens, 2000, 14, Suppl 1, S73β86.
- Sun X-Y, Wei C-X, Deng X-Q, Sun Z-G, Quan Z-S. Evaluation of the anticonvulsant activity of 6-(4chlorophenyoxy)-tetrazolo[5,-a] phthalazine in various experimental seizure models in mice. Pharmacological Reports, 2010, 62, 273-277.
- Al-Soud YA, Al-Masoudi NA, FerwanahAel-R. Synthesis and properties of new substituted 1,2,4-triazoles: potential antitumor agents. Bioorg Med Chem, 2003, 8, 1701-1708.
- Sun XY, Zhang L, Wei CX, Piao HR, Quan ZS. Characterization of the anticonvulsant activity of doxepin in various experimental seizure models in mice. Pharmacol Rep, 2009, 61, 245β251.
- Castel-Branco MM, Alves GL, Figueiredo IV, Falcao AC, Caramona MM. The maximal electroshock seizure (MES) model in the preclinical assessment of potential n ew antiepileptic drugs. Methods Find ExpClinPharmacol, 2009, 31, 101-106.
- Talarek S, Listos J, Fidecka S. Role of nitric oxide in the development of tolerance to diazepam-induced motor impairment in mice. Pharmacol Rep, 2008, 60, 475-482.
- Karnik AV, Malviya NJ, Kulkarni AM, Jadhav BL. Synthesis and in vitro antibacterial activity of novel heterocyclic derivatives of 18-nor-equilenin. Eur J Med Chem, 2006, 41, 891β895.
- Li CM, Wang MH. Anti-inflammatory effect of the water fraction from hawthorn fruit on LPS-stimulated RAW 264.7 cells. Nutr Res Pract, 2011, 2, 101β106.
- Santos EN, Lima JCS, Noldin VF, Cechinel-Filho V, Rao VSN, Lima EF, Schmeda-Hirschmann G, Paulo T. Sousa Jr.IV; Domingos T.O. Martins. Anti-inflammatory, antinociceptive, and antipyretic effects of methanol extract of Cariniana-rubrastem bark in animal models. An Acad Bras CiΓͺnc, 2011, 2, 557β566.
- Sarkar D, Fisher PB. Molecular mechanisms of aging associated inflammation. Cancer Lett, 2006, 236, 13-23.
- Silva LMCM, Lima V, Holanda ML, Pinheiro PG, Rodrigues JAG, Lima MEP, Benevides NMB. Antinociceptive and anti-inflammatory activities of lectin from marine red alga Pterocladiella-capillacea. Biol Pharm Bull, 2010, 5, 830β835.
- Huang GJ, Huang SS, Lin SS, Shao YY, Chen CC, Hou WC, Kuo YH. Analgesic effects and the mechanisms of anti-inflammation of ergostatrien-3b-ol from Antrodiacam-phoratasubmerged whole broth in mice. J Agric Food Chem, 2010, 58, 7445β7452.
- Karin M, Lawrence T, Nizet V. Innate immunity gone awry: linking microbial infections to chronic inflammation and cancer. Cell, 2006, 124, 823β835.
- Yu H-L, Zhang F, Lan, T, Quan Z-S. Effects of 6-(4chlorophenoxy)-tetrazolo[5,1-a]phthalazine on Anticoagulation in Mice and the Inhibition of Experimental Thrombosis in Rats. J Cardiovasc Pharmacol, 2014, 64(6), 560β566.
- Abdullah GZ, Abdulkarim MF, Salman IM, Ameer OZ, Yam MF, Mutee AF, Chitneni M, Elrashid S Mahdi, Mahiran Basri, Munavvar A Sattar, and Azmin M Noor. In vitro permeation and in vivo anti-inflammatory and analgesic properties of nanoscaled emulsions containing ibuprofen for topical delivery. Int J Nanomed, 2011, 6, 387β396.
- Barros WM, Rao VSN, Silva RM, Lima JCS, Martins DTO. Anti-inflammatory effect of the ethanolic extract from Bowdichiavirgili-oidesH.B.K stem bark. An Acad Bras CiΓͺnc, 2010, 3, 609β616.
- Bars D, Gozariu M, Cadden SW. Animal models of nociception. Pharmacol Rev, 2001, 53, 597β652.
- Okusada K, Nakamoto K, Nishida M, Fujita-Hamabe W, Kamiya K, Mizushina Y, Satake T, Tokuyama S. The antinociceptive and anti-inflammatory action of the CHCl3-soluble phase and its main active component, damnacanthal, isolated from the ischolar_main of Morindacitrifolia. Biol Pharm Bull, 2011, 1, 103β107.
- Jedinak A, Dudhgaonkar S, Wu QL, Simon J, Sliva D. Anti-inflammatory activity of edible oyster mushroom is mediated through the inhibition of NF-kB and AP-1 signaling. Nutr J, 2011, 10, 52.
- Salvemini D, Ischiropoulos H, Cuzzocrea S. Roles of nitric oxide and superoxide in inflammation. Methods MolBiol, 2003, 225, 291β303.
- Botting RM. Vane's discovery of the mechanism of action of aspirin changed our understanding of its clinical pharmacology. Pharmacol Rep, 2010, 62, 518β525.
- Yun KJ, Kim JY, Kim JB. Inhibition of LPS-induced NO and PGE2 production by asiatic acid via NF-kB inactivation in RAW264.7 macrophages: possible involvement of the IKK and MAPK pathways. IntImmunopharmacol, 2008, 3, 431β441.
- Capone ML, Tacconelli S, Rodriguez LG, Patrignani P. NSAIDs and cardiovascular disease: transducing human pharmacology results into clinical read-outs in the general population. Pharmacol Rep, 2010, 62, 518-525.
- Harris SG, Padilla J, Koumas L, Ray D, Phipps RP. Prostaglandins as modulators of immunity. Trends Immunol, 2002, 3, 144β150.
- MullaWA, Kuchekar SB, Thorat VS, Chopade AR, Kuchekar BS. Antioxidant, antinociceptive and antiinflammatory activities of ethanolic-axtract of leaves of Alo-casiaindica (Schott.). J Young Pharm, 2010, 2, 137-143.
- Yoon WJ, Ham YM, Kim KN, Park SY, Lee NH, Hyun CG, Lee WJ. Anti-inflammatory activity of brown alga Dictyotadichotomain murine macrophage RAW264.7 cells. J Med Plant Res, 2009, 3, 1β8.
- Crain SM, Shen KF. Acute thermal hyperalgesia elicited by low-dose morphine in normal mice is blocked by ultralow dose naltrexone, unmasking potent opioid analgesia. Brain Res, 2001, 88, 75β82.
- Chu C, Huang Y, Chen YF, Wu JH, Rahman K, Zheng HC, Qin LP. Anti-nociceptive activity of aqueous fraction from the MeOH extracts of Paederiascandensin mice. J Ethnopharmacol, 2008, 118, 177β180.
- da Silveira e SΓ‘ Rde C, de Oliveira LE, NΓ³brega FF, Bhattacharyya J, de Almeida RN. Antinociceptive and toxicological effects of Dioclea grandiflora seed pod in mice. J Biomed Biotechnol, 2010, 10, 1β6.
- Mbiantcha M, Kamanyi A, Teponno RB, Tapondjou AL, Watcho P, Nguelefack TB: Analgesic and antiinflammatory properties of extracts from the bulbils of Dioscoreabul-biferaL. varsativa (Dioscoreaceae) in mice and rats. Evid Based Complement Alternat Med, 2011, 10, 1β9.
- Yu H-L, Feng-Zhang, Li Y-J, Gong G-H, Quan Z-S. Antiinflammatory and antinociceptive effects of 6-(4- chlorophenoxy)-tetrazolo[5,1-a] phthalazine in mice. Pharmacological Reports, 2012, 64 (5), 1155-1165.
- Feng Z, Jiang H-C, Chen X-R, Ma Z, Yu H-L, Quan Z-S. Antidepressant-like effect of 6-(4-chlorophenoxy)tetrazolo[5,1-a] phthalazine in mice. Chinese J Pharmcol & Toxicol, 2013, 27(5), 10.3867/j.issn.10003002.2013.05.003.
- Effect of Naringin Co-administration on Oral Bioavailability Of Efavirenz in Rabbit
Authors
1 Department of Pharmacognosy, Lachoo Memorial College of Science and Technology, Jodhpur,, IN
2 Department of Pharmacognosy, S.K Patel College of Pharmaceutical Education and Research, Gujarat, IN
3 Department of Basic Health Sciences, Preparatory Year, Princess Nourah Bint Adbulrahman University, Riyadh,, SA
Source
Research Journal of Pharmacy and Technology, Vol 15, No 4 (2022), Pagination: 1641-1647Abstract
Efavirenz is a first line anti-retroviral drug belonging to category of non-nucleoside reverse transcriptase inhibitor (NNRTIs), However, it has variable bioavailability due to its limited aqueous solubility. Naringin is a bioavailability enhancer which has been used to increase bioavailability of several drugs. Therefore, the purpose of this study was to investigate the possibility of improving the bioavailability of Efavirenz using Naringin in experimental rabbits. The experimental rabbits were divided into four groups. Group I received Efavirenz 9.33 mg/kg, p.o (which corresponded to 200mg of human dose), Group II received Efavirenz 9.33mg/kg, + Naringin 20.8mg/kg, p.o; Group III received Efavirenz 28mg/kg, p.o (which corresponded to 600mg of human dose); Group IV received Efavirenz 28mg/kg + Naringin 20.8mg/kg, p.o. Afterwards, plasma from each group of rabbits was extracted and at fixed time interval drug plasma concentration was estimated using HPLC. Pharmacokinetic parameters of were determined for each group. Efavirenz (9.33mg/kg and 28mg/kg) - Naringin (20.8mg/kg) co-administration significantly increased absorption rate constant (Ka) and elimination rate constant (Kel), Cmax, T1/2, Tmaxsignificantly. Efavirenz 9.33mg/kg - Naringin (20.8mg/kg) co-administration increased area under the curve significantly. The relative bioavailability of Efavirenz 9.33 mg/kg - Naringin (20.8mg/kg) co-administration and Efavirenz 28mg/kg - Naringin (20.8mg/kg) co-administration was found to be 113.77% and 106.75% respectively. Based on the results it can be concluded that Naringin co-administration increased the oral exposure of Efavirenz to some extent. Bioavailability of Efavirenz with Naringin was found to be higher than Efavirenz control.Keywords
Efavirenz, Naringin, HPLC, Area under the curve, Pharmacokinetic parameters.References
- Kesarwani K, Gupta R, Mukerjee A. Bioavailability enhancers of herbal origin: an overview. Asian Pacific Journal of Tropical Biomedicine. 2013 Apr; 3(4):253-66. doi:10.1016/S2221-1691(13)60060-X
- Rachana Bhimanwar, Lata Kothapalli, Akshay Khawshi. Quercetin as Natural Bioavailability Modulator: An Overview. Research Journal of Pharmacy and Technology. 2020 Apr; 13(4):2043-50. doi: 10.5958/0974-360X.2020.00368.6
- Randhawa GK, Kullar JS, Rajkumar. Bioenhancers from mother nature and their applicability in modern medicine. International Journal of Applied Basic Medical Research. 2011 Jan;1(1):5-10. doi:10.4103/2229-516X.81972
- Ajazuddin, Alexander A, Qureshi A, Kumari L, Vaishnav P, Sharma M, Saraf S, Saraf S. Role of herbal bioactives as a potential bioavailability enhancer for Active Pharmaceutical Ingredients. Fitoterapia. 2014 Sep; 97:1-14. doi: 10.1016/j.fitote.2014.05.005.
- Gaur PK, Mishra S, Bajpai M, Mishra A. Enhanced oral bioavailability of Efavirenz by solid lipid nanoparticles: in vitro drug release and pharmacokinetic studies. Biomed Research International 2014; 2014:363404. doi:10.1155/2014/363404
- Usach I, Melis V, Peris JE. Non-nucleoside reverse transcriptase inhibitors: a review on pharmacokinetic, pharmacodynamics, safety and tolerability. Journal of International AIDS Society. 2013 Sep 4; 16(1):1-14. doi:10.7448/IAS.16.1.18567
- Mohd. Yaqub Khan, Maryada Roy, Imtiyaz Ahmad, Irfan Aziz, Manju Panday. Formulation and Evaluation of Efavirenz 600 mg Tablet. Asian Journal Research in Pharmaceutical Sciences. 2015 July-Sept; 5(3): Page 153-67. doi: 10.5958/2231-5659.2015.00024.7
- Samir Shah, Kintu Patel, Mohsin Pathan. Evaluation of the Effect of Piperine on Bioavailability and Pharmacokinetics of Macrolides in Rats. Asian Journal Research in Pharmaceutical Sciences. 2018 Apr-Jun; 8(2):61-67. doi: 10.5958/2231-5659.2018.00013.9
- Rohini S. Koli, Aslam S. Patel, Kamlesh N. Chaudhari, Khushbu R. Patil. A Review on HPLC and Its New Trends. Asian Journal of Pharmaceutical Analysis . 2018 Oct-Dec; 8(4): 233-36. doi: 10.5958/2231-5675.2018.00042.X
- Hamid Khan, Javed Ali. UHPLC: Applications in Pharmaceutical Analysis. Asian Journal of Pharmaceutical Analysis. 2017; 7(2): 124-31. doi: 10.5958/2231-5675.2017.00020.5
- Paget GE. And. Barnes JM. Toxicity tests. Evaluation of Drug Activities. In Pharmacometrics, Edited by Lawrence DR and Bacharach A L. Academic Press, London. 1964; pp. 140β161.
- Hiwale AR, Dhuley JN, Naik SR. Effect of co-administration of piperine on pharmacokinetic of beta-lactam antibiotics in rats. Indian Journal of Experimental Biology. 2002 Mar; 40(3):277-281.
- Ramachandran G, Kumar AK, Swaminathan S, Venkatesan P, Kumaraswami V, Greenblatt DJ. Simple and rapid liquid chromatography method for determination of Efavirenz in plasma. Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 2006 May 1; 835(1-2):131-135. doi:10.1016/j.jchromb.2006.03.014
- Choi JS, Shin SC. Enhanced paclitaxel bioavailability after oral coadministration of paclitaxel prodrug with Naringin to rats. International Journal of Pharmaceutics. 2005 Mar 23; 292(1-2):149-156. doi:10.1016/j.ijpharm.2004.11.031
- Choi JS, Han HK. Enhanced oral exposure of diltiazem by the concomitant use of Naringin in rats. International Journal of Pharmaceutics. 2005 Nov 23;305(1-2):122-128. doi:10.1016/j.ijpharm.2005.09.004
- Soldin OP, Elin RJ, Soldin SJ. Therapeutic drug monitoring in human immunodeficiency virus/acquired immunodeficiency syndrome. Quo vadis?. Archives of Pathology & Laboratory Medicine. 2003 Jan; 127(1):102-105. doi:10.5858/2003-127-102-TDMIHI
- Kang JS, Lee MH. Overview of therapeutic drug monitoring. Korean J Intern Med. 2009; 24(1):1-10. doi:10.3904/kjim.2009.24.1.1
- Tamargo J, Le Heuzey JY, Mabo P. Narrow therapeutic index drugs: a clinical pharmacological consideration to flecainide. European Journal of Clinical Pharmacology,. 2015 May; 71(5):549-567. doi:10.1007/s00228-015-1832-0
- Tsibris AMN. And. Hirsch MS. Antiretroviral Therapy for Human Immunodeficiency Virus Infection. In Mandell, Douglas, and Bennett's Principles and Practice of Infectious Diseases, Edited by Bennett JE, Dolim R, Blaser MJ. W.B. Saunders. 2015; pp. 1622-1641.
- Bumpus NN, Kent UM, Hollenberg PF. Metabolism of Efavirenz and 8-hydroxyEfavirenz by P450 2B6 leads to inactivation by two distinct mechanisms. The Journal of Pharmacology and Experimental Therapeutics. 2006 July; 318(1):345-351. doi:10.1124/jpet.106.102525
- Venkatesh S, Pagilla B, Chiluka R, Alvala R, Pola RK, Mullangi R. Bioenhancing effects of Naringin on atrovastatin. ADMET and DMPK. 2019 Jun 6; 7(3):174β182. doi:10.5599/admet.647
- P. Hinderliter P, S.A. Saghir SA. Pharmacokinetic. In Encyclopedia of Toxicology, Edited by Wexler P. Academic Press; 2014; 3rd ed: pp.849-855.