Recent Advancement of Synthesis of Isatins as a Versatile Pharmacophore: A review

Abstract

Isatin (1 H-indole-2, 3-Dione) and its derivatives are versatile compounds which acts as a precursor for a large number of pharmacologically active compounds. Therefore isatins have a significant importance in the synthesis of different heterocyclic compounds. Isatins show variety of biological activities. In this review we focus on synthetic methods of isatins and their biological activities such as antimicrobial, anticonvulsant, anti-inflammatory and analgesic activity, antitubercular activity.

Key words

anti-inflammatory drugs - adverse drug reactions - pharmacology

Publication History

Received: 19 July 2020

Accepted: 03 August 2020

Article published online:
09 December 2020

• References

• 1 Da silva JFM, Garden SJ, Pinto AC. The Chemistry of Isatins: A review from 1975–1999. J Braz Chem Soc 2001; 12: 273-324
• 2 Bergman J, Lindstrom JO, Tilstam U. The structure and properties of some indolic constituents in Couroupita guianensis aubl. Tetrahedron 1985; 44: 2879-2881
• 3 Nath R, Pathania S, Grover G. et al. Isatin containing heterocycles for different biological activities: Analysis of structure activity relationship. J of Molecular Str 2020; 1222: 128900
• 4 Almeida MR, Leitao GG, Silva BV. et al. Counter-Current Chromatography Separation of Isatin Derivatives using the Sandmeyer Methodology. J Braz Chem Soc 2010; 21: 764
• 5 Kapadia GJ, Shukla BK, Chowdhary SP. et al. Phenylpentylisatins: a novel class of alkaloids from Melochia tomentosa. J Chem Soc Chem Commun 1977; 535-536
• 6 Monier M, Abdulaziz A, Bukhari H. et al. Designing and characterization of copper (II) ion-imprinted adsorbent based on isatin functionalized chitosan. Inter J of Bio Macromol 2020; 155: 795-804
• 7 Kapadia GJ, Shukla YN. Melosatin D: A New Isatin Alkaloid from Melochia tomentosa Roots. Planta Med 1993; 59: 568-569
• 8 Grafe U, Radics L. Isolation and structure elucidation of 6-(3'-methylbuten-2'-yl)isatin, an unusual metabolite from Streptomyces albus Antibiot J. (Tokyo) 1986; 39: 162-163
• 9 Breinholt J, Demuth H, Heide M. et al. Prenisatin (5-(3-Methyl-2-butenyl)-iodole-2,3-dione): an Antifungal isatin derivative from chaetomium globosum. Acta Chem Scandinavica 1996; 50: 443-445
• 10 Kekule A. Ueber die Constitution des Isatins, der Isatinsäure und des Indols, Ber. Deutsch. Chem. Ges. 1869; 2: 748-749
• 11 Sumpter WC. The Chemistry of Isatin. Chem Rev 1944; 34: 393-434
• 12 Propp FD. The Chemistry of Isatin. Adv Heterocycl Chem 1975; 18: 1-58
• 13 Alam M, younas M, Zafar MA. et al. An improved synthesis of isatin, Pak J Sci Ind Res 1989; 32: 246
• 14 Loloui G, Maior O. Cheminform Abstract 1997; 28: 67
• 15 Hong Min MA, Zhan Zhu LIU. Shiz Chineese. Chem lett 2003; 14: 468-470
• 16 Gassman PG, BerKeley WC, Luh Tien-yau. A general method for the synthesis of isatins. J Org Chem 1977; 42: 1344-1348
• 17 Haewawasam P, Meanwell N. A general method for the synthesis of isatins: Preparation of regiospecifically functionalized isatins from anilines. Tetrahedron Lett 1994; 35: 7303-7306
• 18 Palenik GK, Koziol AE, Katritzky AR. et al Nonbonded interactions. The influence of lone pair repulsions on bond lengths. J Chem Soc Chem Commun 1990; 715
• 19 Frolova NA, Kravtsov VK, Biyushkin VN. et al. Zh. Strukt Khim 1988; 29: 155 (CA 109:161025w)
• 20 Rathana A, Chandrasekhar J. The influence of lone-pair repulsions on C–C bond lengths: A critical evaluation of the experimental and theoretical evidence. J Chem Soc Perkin Trans-2 1991; 1661-1666
• 21 Zukermann-Schpector J, Castellano EE, Pinto AC. et al. Structure of 1-acetylindole-2,3-dione. Acta Cryst 1992; C48: 760-762
• 22 Zukermann-Schpector J, Pinto AC, Silva JFM. et al. 1-α-Chloroacetylisatin Acta Cryst 1995; C51: 675-676
• 23 Zukermann-Schpector J, Pinto AC, Silva JFM. et al. Diethl(2,3-dihydro-2-0x0-3-indolylidene) propanedioate, Acta Cryst 1994; C50: 945-946
• 24 Black DSC, Chaichit N, Gatehouse BM. et al. Metal Template Reactions. XXV. N-Acyl Isatin Precursors for the Synthesis of Malonamido Macrocyclic Metal Complexes. Aust J Chem 1987; 40: 1745-1754
• 25 Miehe G, Sussei P, Kupick V. et al. Light Absorption as well as Crystal and Molecular Structure of N,N′-Dimethylindigo : An Example of the Use of Synchrotron Radiation. Angew Chem Int Ed Engl 1991; 30: 964
• 26 Zukermann-Schpector J, Pinto AC, Silva JFM. et al. Structure of 3,3-di-chloro-1H-indol-2(3H)-one. Acta Cryst 1993; C49: 173-175
• 27 De A. Structure of a potential anticonvulsant: 5'-bromospiro[1,3-dioxolane-2,3'-indolin]-2'-one. Acta Cryst 1992; C48: 660-662
• 28 Baba K, Kozawa M, Hata K. et al. The Structures of Yellow Pigments from the Rhizomes of Cimicifuga dahurica MAXIM. Chem Pharm Bull 1981; 2182-2187
• 29 Tomchin AB, Fradkina SP, Krylova IM. et al. Zh Org Khim 1986; 22: 2409
• 30 Laatsch H, Thomson RH, Cox PJ. Spectroscopic properties of violacein and related compounds: crystal structure of tetramethylviolacein. J Chem Soc Perkin Trans-2 1984; 1331
• 31 Albright TA, Freeman W. Nuclear magnetic resonance studies: VII-13C and 15N N.M.R. of diazo compounds. J Org Magn Res 1977; 9: 75-79
• 32 Winkler T, Ferrini PG, Hass G. The 13C NMR spectrum of coumarandione. Org Magn Res 1979; 12: 101-102
• 33 Ballontine JA. The purple pigments produced by acetylation of 2-(2-oxoindolin-3-yl)glyoxylates in the presence of pyridine. Some new evidence. J Chem Soc Perkin Transac-1 1979; 1182-1184
• 34 Angell EC, Black DSC, Kumar N. 13C NMR study of N-acyl- and N-sulphonyl-isatins and their ring-opened derivatives. Magn Res Chem 1992; 30: 1-5
• 35 Katrizky AR, Fan WQ, Liang DS. et al. Novel dyestuffs containing dicyanomethylidene groups. J Heterocyclic Chem 1989; 26: 1541-1545
• 36 Jarapula R, Gangarapu K, Mand S. et al. Synthesis, In Vivo Anti-Inflammatory Activity, and Molecular Docking Studies of New Isatin Derivatives. International Journal of Medicinal Chemistry 2016; 2181027: 9
• 37 Raja M, Veerasamy N, Singh VK. Highly enantioselective synthesis of 3-cycloalkanone-3-hydroxy-2-oxindoles, potential anticonvulsants. Tetrahedral Lett 2010; 51: 2157-2159
• 38 Kulkarni AA, Wankhede SB, Dhawale ND. et al. Synthesis, characterization and biological behavior of some Schiff's and Mannich base derivatives of Lamotrigine. Arabian Journal of Chemistry 2017; 10: s184-s189
• 39 Abdu-Allah HHM, Youssif BGM, Abdelrahmann MH. et al. Synthesis and anti-mycobacterial activity of 4-(4-phenyl-1H-1,2,3-triazol-1-yl)salicylhydrazones: Revitalizing an old drug. Arch Pharm Res 2017; 40: 168-179
• 40 Shaikh MH, Subhedar DD, Khan FAK. et al. Synthesis of novel triazole-incorporated isatin derivatives as antifungal, antitubercular, and antioxidant agents and molecular docking study. J Heterocyclic Chem 2017; 54: 413-421
• 41 Hu YQ, Xf Song, Fan J. Design, synthesis, and in vitro antimycobacterial activity of propylene-tethered isatin dimmers. J Heterocyclic Chem 2018; 55: 265-268