Open Access Open Access  Restricted Access Subscription Access
Open Access Open Access Open Access  Restricted Access Restricted Access Subscription Access

Amino-indane: Fused Heterocycle with Diverse Pharmacological Activity


Affiliations
1 Department of Pharma. Chemistry, Parul Institute of Pharmacy, Limda-391 760, Vadodara, Gujarat, India
2 Darshan Pharma Chem, Plot No. A-1/3621, GIDC Estate, Ankeleshwar Gujarat, India
     

   Subscribe/Renew Journal


Amino-indane is an important structural moiety found in numerous pharmaceutically active compounds. Aminoindane has non-heterocyclic fused ring having six member benzene ring and five member cyclopentane ring with amino group. Amino-indane derivatives play a vital role in the field of medicinal chemistry. This has the important place to synthesis of class of different pharmacological activities. Amino-indane moiety is an important pharmacophore and exhibits outstanding biological activities. A number indane derivatives have acquired a special place in heterocyclic field because of their diversified activities such as antimicrobial, antipyretic, analgesic, anticonvulsant, CNS Depressant anti-inflammatory, anticancer activity. This review emphasized the recent researches in amino-indanes in various diseases and disorders.

Keywords

Indane, Amino-indane, Anti-inflammatory, Pharmacological Activity
Subscription Login to verify subscription
User
Notifications
Font Size


  • Hawley, Gessner G. The Condensed Chemical Dictionary; Van Nostrand Reinhold Company, 1977, pp. 464.
  • Roberts LJ and Morrow JD, Analgesic-Antipyretic and Antiinflammatory Agents and Drugs Employed in the Treatment of Gout. In: Goodman & Gilman’s The Pharmacological Basis of Therapeutics; 10th edition; Limbird AE, Eds., Mc Graw Hill, New York, 2001, pp. 687-733.
  • Frankish N, Byrne, William. Substituted (N-cyclopentyl amino)- indan-1ones act as anti-inflammatory agent, mast cell stabilizer and smooth muscle relaxant. Ind J Chem. 1979: 578-580.
  • Barlow JW, Walsh JJ. Synthesis and evaluation of dimeric 1, 2, 3, 4-Tetrahydro-napthalenylamine and indan-1-yalmine derivative with mast cell stabilizing and anti-allergic activity. Eur. J. Med. Chem., 45; 2010: 25-37.
  • Walsh JJ, Barlow JW. Synthesis and evaluation of 4-amino-3, 4- dihydro-2H-naphthalen-1-one derivatives as mast cell stabilizing and anti-inflammatory compounds. Eur. J. Med. Chem., 43; 2008: 2891-2900.
  • Masereel B, Chazalette C, Rolin S, Supuran CT. Carbonic anhydrase inhibitors. Design of anticonvulsant sulfonamides incorporating indane moieties. Bioorg. Medi. Chem. Letters, 14; 2004: 5781–5786.
  • Ugliarolo EA, Lantano B, Moltrasio GY, Moglioni AG. An efficient approach to homochiral indane nucleosides. Tetrahedron: Asymmetry. 20; 2009: 1848–1853.
  • Bertolinil G, Vecchietti V, Mabilia M, Santangel F. Dopamine receptor agonists. Synthesis and pharmacological evaluation of 4- aryl substituted analogues of 6, 7-dihydroxy-2-amino tetralin (6, 7-ADTN) and related indane compounds. Eur. J. Med. Chem., 27; 1992: 663-672.
  • Ugliarolo EA, Cavallaro LV, Moglioni AG. Synthesis and biological evaluation of novel homochiral carbocyclic nucleosides from 1-amino-2-indanols. Bioorg. Medi. Chem. Letters, 20; 2012: 5986-5991.
  • Patel HR, Patel PK, Sen DJ. Growth inhibition of microorganism by bioisosterism. Int. J. Drug Devel. Res., 2; 2010: 190-196.
  • Masereel B, Thiry A, Ledecq M. Indanesulfonamides as Carbonic Anhydrase Inhibitors of the Tumor-Associated Isozyme CA IX. J. Medi. Chem., 49; 2006: 2743-2749.
  • Beaudoin S, Gross MF, Amato GS, Neil A. Aryl sulfonamide indane inhibitors of the Kv1.5 ion channel. Bioorg. Medi. Chem. Letters, 17; 2007: 2849–2853.
  • Hong Hu, Hollinshead SP, Steven EH. Synthesis and protein kinase c inhibitory activities of indane analogs of balanol. Bioorg. Medi. Chem. Letters, 6; 1996: 973-978
  • Kotha S, Ghosh AK. A Diels–Alder approach for the synthesis of highly functionalized benzo-annulated indane-based -amino acid derivatives via a sultine intermediate. Tetrahedron Letters. 45; 2004: 2931-2934.
  • Miziak P, Zon J, Amrhein N, Gancarz R. Inhibitors of phenylalanine ammonia-lyase: Substituted derivatives of 2-amino indane -2 -phosphoric acid and 1-amino benzyl phosphoric acid. Phyto. Chem., 68; 2007: 407–415.
  • Tarnus C, Defoin A. Amino-benzosuberone a novel warhead for selective inhibition of human aminopeptidase-N/CD13. Bioorg. Medi. Chem., 19; 2011: 1434-1449.
  • Martin P, Said A, William LM. Thrombin inhibitors based on 5, 5 trans-fused indane lactams. Bioorganic and Medi Chem Letters. 9; 1999: 1657-1662.
  • Davies IW, Senanayake CH, Robert D. Application of a Rittertype Reaction to the Synthesis of Chiral Indane-derived C2- Symmetric Bis(oxazolines). Tetrahedron Letters. 37; 1996: 813-814.
  • David CH, William H, Willems MG. The Design of Dipeptide Helical Mimetic: The Synthesis, Tachykinin Receptor Affinity and Conformational Analysis of 1, 1, 6-Trisubstituted Indanes. Bioorg. Medi. Chem. Letters, 4; 1996: 33-42.
  • Coppola M and Mondola R. 5-Iodo-2-aminoindan (5-IAI): Chemistry, pharmacology, and toxicology of a research chemical producing MDMA-like effects. Toxicology Letters. 218; 2013: 24–29.
  • Byrne AJ, Barlow JW, Walsh JJ. Synthesis and pharmacological evaluation of the individual stereoisomer of 3-methyl (1, 2, 3, 4- tetrahydro-2-naphthalenyl) amino-1-indanone, a potent mast cell stabilising agent. Bioorg. Medi. Chem. Letters, 21; 2011: 1191–1194.
  • Ghidini E, Delcanale M, De Fanti R, Rizzi A. Synthesis and anticonvulsant activity of a class of 2-amino 3- hydroxypropanamide and 2-aminoacetamide derivatives. Bioorg. Medi. Chem. Letters, 14; 2006: 3263–3274.
  • Pratt J, Jimonet P. Synthesis and Potent anticonvulsant activities of 4-Oxo-imidazo 1, 2-a indeno 1, 2-e pyrazin-8- and -9- carboxylic (Acetic) Acid AMPA Antagonists. Bioorg. Medi. Chem. Letters, 10; 2000: 2749-2754.
  • Iacazio G, Reglier M. Chemo-enzymatic synthesis of all four diastereoisomers of 1-fluoro-2-amino-indane. Tetrahedron: Asymmetry. 16; 2005: 3633-3639.
  • Stefano DA, Sozio P, Montali M, Pietrantonio DF, Matteo DE. Preparation and Pharmacological Characterization of trans-2- Amino-5(6)-fluoro-6(5)-hydroxy-1-phenyl-2, 3-dihydro-1Hindenes as D2-like Dopamine Receptor Agonists. J. Medi. Chem., 48; 2005: 2646-2654.
  • Ayhan S, Demir, Haluk H. Chemoenzymatic synthesis of 1S, 2R -1-amino-2-indanol, intermediate of HIV protease inhibitor, indinavir” J. Mole. Catalyst. B: Enzyme, 9; 2000: 157–161.
  • Askin D, Rossen K, Robert M. Highly Diastereoselective Reaction of a Chiral, Non-Racemic Amide Enolate with (S)-Glycidyl Tosylate synthesis of the Orally Active HIV-l Protease Inhibitor L-735,524. Tetrahedron Letters. 35; 1994: 673-676.
  • Seralini G, Auvray P, Moslemi S. Evidence for new non-steroidal human aromatase inhibitors and comparison with equine aromatase inhibition for an understanding of the mammalian active site. Eur. J. Medi. Chem., 33; 1998: 451-462.
  • Katsumura S, Kobayashi T, and Tanaka K. Synthesis of new chiral auxiliaries for 6 -azaelectrocyclization: 4- and 7-alkyl substituted cis-1-amino-2-indanols. Tetrahedron: Asymmetry. 15; 2004: 185-188.
  • Reglier M, Mitrochkine A, Gil G. Synthesis of Enantiomerically pure (1S, 2R)-epoxy indane and cis-(1R, 2S)-2-amino-1-indanol. Tetrahedron: Asymmetry. 6; 1995: 59-62.

Abstract Views: 258

PDF Views: 2




  • Amino-indane: Fused Heterocycle with Diverse Pharmacological Activity

Abstract Views: 258  |  PDF Views: 2

Authors

Prafulla M Sabale
Department of Pharma. Chemistry, Parul Institute of Pharmacy, Limda-391 760, Vadodara, Gujarat, India
Meeraben P. Kakadiya
Department of Pharma. Chemistry, Parul Institute of Pharmacy, Limda-391 760, Vadodara, Gujarat, India
Jitendra G. Dobariya
Darshan Pharma Chem, Plot No. A-1/3621, GIDC Estate, Ankeleshwar Gujarat, India

Abstract


Amino-indane is an important structural moiety found in numerous pharmaceutically active compounds. Aminoindane has non-heterocyclic fused ring having six member benzene ring and five member cyclopentane ring with amino group. Amino-indane derivatives play a vital role in the field of medicinal chemistry. This has the important place to synthesis of class of different pharmacological activities. Amino-indane moiety is an important pharmacophore and exhibits outstanding biological activities. A number indane derivatives have acquired a special place in heterocyclic field because of their diversified activities such as antimicrobial, antipyretic, analgesic, anticonvulsant, CNS Depressant anti-inflammatory, anticancer activity. This review emphasized the recent researches in amino-indanes in various diseases and disorders.

Keywords


Indane, Amino-indane, Anti-inflammatory, Pharmacological Activity

References