Abstract
In the current investigation, we prepared a series of novel spiro[indole-thiazolidines] derivatives (5a–5h) from 5-substituted isatin derivatives and thioglycolic acid (TGA) with ZrSiO2 as an efficient catalyst under microwave irradiation. The significant merits of this protocol have some significant merits such as simplicity in operation, simple, efficient workup, good practical yields of product and the employment of recyclable catalyst. All the new synthesized scaffold has been well characterized by various spectroscopic methods and elemental analysis. All the spiro scaffolds were subjected to in vitro anti-mycobacterial activity against the Mycobacterium tuberculosis (H37Rv) strain. We have carried out molecular docking study of our synthesized compounds. We also calculated theoretically ADME–Tox parameters for synthesized compounds.
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Zumla A, George A, Sharma V, Herbert N (2013) WHO’s 2013 global report on tuberculosis: successes, threats, and opportunities. Lancet 382(9907):1765–1767
Yew WW, Leung CC (2008) Update in tuberculosis 2007. Am J Respir Crit Care Med 177(5):479–485
Ballell L, Field RA, Duncan K, Young RJ (2005) New small-molecule synthetic antimycobacterials. Antimicrob Agents Chemother 49(6):2153–2163
García A, Bocanegra-García V, Palma-Nicolás JP, Rivera G (2012) Recent advances in antitubercular natural products. Eur J Med Chem 49:1–23
Kappe CO, Stadler A, Dallinger D (2012) Microwaves in organic and medicinal chemistry. Wiley, London
Borad MA, Bhoi MN, Parmar JA, Patel HD (2015) Microwave assisted synthesis of novel N-(benzo [d] thiazol-2-yl)-2-((2,4′-dioxospiro [indoline-3,2′-thiazolidin]-3′-yl) amino) acetamide derivatives as potent antibacterial agents. Int Lett Chem Phys Astron 53:122
Mohan SB, Kumar BR, Dinda SC, Naik D, Seenivasan SP, Kumar V, Rana DN, Brahmkshatriya PS (2012) Microwave-assisted synthesis, molecular docking and antitubercular activity of 1, 2, 3, 4-tetrahydropyrimidine-5-carbonitrile derivatives. Bioorg Med Chem Lett 22(24):7539–7542
Marti C, Carreira EM (2003) Construction of spiro [pyrrolidine-3, 3′-oxindoles]—recent applications to the synthesis of oxindole alkaloids. Eur J Org Chem 2003(12):2209–2219
Venkatesan H, Davis MC, Altas Y, Snyder JP, Liotta DC (2001) Total synthesis of SR 121463 A, a highly potent and selective vasopressin V2 receptor antagonist. J Org Chem 66(11):3653–3661
Reifscheider W, Ershadi B, Dripps J, Barron J (1992) In US Patent 5075293, 1991, Chem. Abstr, p 129249f
Bhoot D, Khunt R, Shankhavara V, Parekh H (2006) Synthesis of some new heterocyclic compounds with potential biological activity. J Sci I R Iran 17(4):323–325
Kutschy P, Suchý M, Monde K, Harada N, Marušková R, Čurillová Z, Dzurilla M, Miklošová M, Mezencev R, Mojžiš J (2002) Spirocyclization strategy toward indole phytoalexins. The first synthesis of (±)-1-methoxyspirobrassinin, (±)-1-methoxyspirobrassinol, and (±)-1-methoxyspirobrassinol methyl ether. Tetrahedron Lett 43(52):9489–9492
Banting L (1996) Inhibition of aromatase. Prog Med Chem 33:147–184
Srivastava S, Srivastava S, Srivastava S (2001) Synthesis of 5‐arylidene‐2‐aryl‐3‐(2‐chlorophenothiazinoacetamidyl)‐1,3‐thiazolidin‐4‐ones as antifungal and anticonvulsant agents. ChemInform 32(17)
Sharma R, Kumar D (2000) Synthesis of some new thiazolidin-4-ones as possible antimicrobial agents. J Indian Chem Soc 77(10):492–493
Holmes CP, Chinn JP, Look GC, Gordon EM, Gallop MA (1995) Strategies for combinatorial organic synthesis: solution and polymer-supported synthesis of 4-thiazolidinones and 4-metathiazanones derived from amino acids. J Org Chem 60(22):7328–7333
Srivastava T, Haq W, Katti S (2002) Carbodiimide mediated synthesis of 4-thiazolidinones by one-pot three-component condensation. Tetrahedron 58(38):7619–7624
Gududuru V, Nguyen V, Dalton JT, Miller DD (2004) Efficient microwave enhanced synthesis of 4-thiazolidinones. Synlett 13:2357–2358
Bremner DH (1994) Recent advances in organic synthesis utilizing ultrasound. Ultrason Sonochem 1(2):S119–S124
Eynde JJV, Mutonkole K, Van Haverbeke Y (2001) Surfactant-assisted organic reactions in water. Effect of ultrasound on condensation reactions between active methylene compounds and arylaldehydes. Ultrason Sonochem 8(1):35–39
Bhoi MN, Borad MA, Pithawala EA, Modi S, Patel HD (2015) Synthesis of N’-(7-chloroquinolin-4-yl)-6-methyl-2-oxo-4-phenyl-1, 2, 3, 4-tetrahydropyrimidine-5-carbohydrazide derivatives as potent antibacterial agents. Int Lett Chem Phys Astron 56:82
Patel NB, Patel JC (2010) Synthesis and antimicrobial activity of 3-(1, 3, 4-oxadiazol-2-yl) quinazolin-4 (3H)-ones. Sci Pharm 78(2):171
Akhaja TN, Raval JP (2012) Design, synthesis and in vitro evaluation of tetrahydropyrimidine–isatin hybrids as potential antitubercular and antimalarial agents. Chin Chem Lett 23(7):785–788
Desai N, Shukla H, Thaker K (1984) Some new 2-aryl-3-isonicotamido-4-thiazolidinones and their 5-carboxymethyl homologs as potential antitubercular and antibacterial agent. J Indian Chem Soc 61(3):239–240
Lipinski CA (2000) Drug-like properties and the causes of poor solubility and poor permeability. J Pharmacol Toxicol Methods 44(1):235–249
Lu S-H, Wu JW, Liu H-L, Zhao J-H, Liu K-T, Chuang C-K, Lin H-Y, Tsai W-B, Ho Y (2011) The discovery of potential acetylcholinesterase inhibitors: a combination of pharmacophore modeling, virtual screening, and molecular docking studies. J Biomed Sci 18(8):22
Rozwarski DA, Grant GA, Barton DH, Jacobs WR, Sacchettini JC (1998) Modification of the NADH of the isoniazid target (InhA) from Mycobacterium tuberculosis. Science 279(5347):98–102
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The authors (MNB and MAB) are very thankful to UGC-BSR for financial support and other institutes for given that amenities for our research work.
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Borad, M.A., Bhoi, M.N., Rathwa, S.K. et al. Microwave-Assisted ZrSiO2 Catalysed Synthesis, Characterization and Computational Study of Novel Spiro[Indole-Thiazolidines] Derivatives as Anti-tubercular Agents. Interdiscip Sci Comput Life Sci 10, 411–418 (2018). https://doi.org/10.1007/s12539-016-0195-2
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DOI: https://doi.org/10.1007/s12539-016-0195-2