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Articles

Acid-Catalyzed Synthesis of Thiazolidin-4-ones

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Pages 311-321 | Received 17 Mar 2016, Accepted 25 Jun 2016, Published online: 14 Dec 2016

References

  • Ashvini, P., T. K. Patil, A. R. Patel, C. S. Patil, S. T. Patil, S. Patil, and P. Pawar. “Chemistry & biological activities of 4- thiazolidinones.” World. J. Pharm. Pharmaceut. Sci. 4 (2015): 1780–91.
  • Tripathi, A., S. Gupta, G. Fatima, P. Sonar, A. Verma, and S. Saraf. “4-thiazolidinones: the advances continue.” Eur. J. Med. Chem. 72 (2014): 52–77.
  • Ottana, R., S. Carotti, R. Maccari, I. Landini, G. Chiricosta, B. Caciagli,   Vigorita, and M. Mini. “In vitro antiproliferative activity against human colon cancer cell lines of representative 4-thiazolidinones. Part I.” Eur. Bioorg. Med. Chem. Lett. 15 (2005): 3930–3.
  • Chen, Y., C. Chen, T. Li, P. Wang, L. Liu, F. Chang, Y. Wang, Y. Yu, S. Lin, H. Mersmann, and S. T. Ding. “Docosahexaenoic acid suppresses the expression of FoxO and its target genes.” J. Nutr. Biochem. 23 (2012): 1609–16.
  • Wu, J., L. Yu, F. Yang, J. Li, P. Wang, W. Zhou, L. Qin, Y. Li, J. Luo, Z. Yi, M. Liu, and Y. Chen. “Optimization of 2-(3-(arylalkyl amino carbonyl) phenyl)-3-(2-methoxyphenyl)-4-thiazolidinone derivatives as potent antitumor growth and metastasis agents.” Eur. J. Med. Chem. 80 (2014): 340–51.
  • Gududuru, V., E. Hurh, J. Dalton, and D. Miller. “Synthesis and antiproliferative activity of 2-aryl-4-oxo-thiazolidin-3-yl-amides for prostate cancer.” Eur. Bioorg. Med. Chem. Lett. 14 (2004): 5289–93.
  • Kamel, M., H. Ali, M. Anwar, N. Mohamed, and A. Soliman. “Synthesis, antitumor activity and molecular docking study of novel Sulfonamide-Schiff's bases, thiazolidinones, benzothiazinones and their C-nucleoside derivatives.” Eur. J. Med. Chem. 45 (2010): 572–80.
  • Goel, B., T. Ram, R. Tyagi, E. Bansal, A. Kumar, D. Mukherjee, and J. Sinha. “2-Substituted-3-(4-bromo-2-carboxyphenyl)-5-methyl-4-thiazolidinones as potential anti-inflammatory agents.” Eur. J. Med. Chem. 34 (1999): 265–9.
  • Elbarbary, A., A. Khodair, E. Pedersen, and C. Niesen. “Synthesis and evaluation of antiviral activity of 2′-deoxyuridines with 5-methylene-2-thiohydantoin substituents in the 5-position.” Monatshefte Chem. 125 (1994): 593–8.
  • Zhang, T., J. Li, Y. Dong, D. Zhai, L. Lai, F. Dai, H. Deng, Y. Chen, M. Liu, and Z. Yi. “Cucurbita in E inhibits breast tumor metastasis by suppressing cell migration and invasion.” Breast Cancer Res. Treat. 135 (2012): 445–58.
  • Murphy, G. and J. Holder. “PPAR-gamma agonists: therapeutic role in diabetes, inflammation and cancer.” Trends Pharmacol. Sci. 21 (2000): 469–74.
  • Parmar, S., C. Dwivedi, A. Chaudhari, and T. Gupta. “Substituted thiazolidones and their selective inhibition of nicotinamide-adenine dinucleotide dependent oxidations.” J. Med. Chem. 15 (1972): 99–101.
  • Singh, N., R. C. Aggarnal, and C. P. Singh. “Cardiovascular activity of in doe derivatives by incorporating oxadiazole, azetidinone and thiazolidinone moieties.” Int. J. Drug Dev. & Res. 6 (2014): 30–9.
  • Filippelli, A., M. Angrisani, C. Matera, R. Marrazzo, S. Maione, M. Cazzola, and E. Marmo. “Experimental study with d-ozolinone and l-ozolinone metabolites of etozoline.” Curr. Ther. Res. 41 (1987): 837–44.
  • Joy, M., N. Jacob, and N. Kutty. “Evaluation of hypoglycemic effects of 4-thiazolidinones.” Indian Drugs. 42 (2005): 47–51.
  • Patel, R., P. Desai, K. Desai, and K. Chikhalia. “Synthesis of pyrimidine based thiazolidinones and azetidinones: antimicrobial and antitubercular agents.” Indian J. Chem. 45B (2006): 773–8.
  • Carlson, E., J. May, and L. Kiessling. “Chemical probes of UDP-galactopyranose mutase.” Chem. Biol. 13 (2006): 825–37.
  • Kucukguzel, S., E. Oruc, S. Rollas, F. Sahin, and A. Ozbek. “Synthesis, characterisation and biological activity of novel 4-thiazolidinones, 1, 3, 4-oxadiazoles and some related compounds.” Eur. J. Med. Chem. 37 (2002): 197–206.
  • Homes, C., J. Chinn, C. Look, E. Gordon, and M. Gallop. “Strategies for combinatorial organic synthesis: Solution and polymer-supported synthesis of 4-thiazolidinones and 4-metathiazanones derived from amino acids.” J. Org. Chem. 60 (1995): 7328–33.
  • Srivastava, S. K., S. L. Srivastava, and S. D. Srivastava. “Synthesis of 5-arylidene-2-aryl-3-(2-chlorophenothiazinoacetamidyl)-1,3-thiazolidin-4-ones as antifungal and anticonvulsant agents.” J. Indian Chem. Soc. 77 (2000): 104–5.
  • Sharma, R. and D. Kumar. “Synthesis of some new thiazolidin-4-ones as possible antimicrobial agents.” Indian Chem. Soc. 77 (2000): 492–3.
  • Srivastava, T., W. Haq, and S. Katti. “Carbodiimide mediated synthesis of 4-thiazolidinones by one-pot three-component condensation.” Tetrahedron. 58 (2002): 7619–24.
  • Zhang, X., X. Li, D. Li, G. Qu, J. Wang, P. Loiseau, and X. Fan. “Ionic liquid mediated and promoted eco-friendly preparation of thiazolidinone and pyrimidine nucleoside-thiazolidinone hybrids and their antiparasitic activities.” Bioorg. Med. Chem. Lett. 19 no. 22 (2009): 6280–3.
  • Hongyu, Z., L. Aifeng, L. Xiaofeng, M. Xifeng, F. Wei, Z. Wei, and Y. Bing. “Microwave-assisted fluorous synthesis of 2-aryl-substituted 4-thiazolidinone and 4-thiazinanone libraries.” J. Comb. Chem. 10 (2008): 303–12.
  • Martins Alho, M., A. Moglioni, B. Brousse, G. Moltrasio, and N. D'Accorso. “Synthesis and characterization of 2, 2-disubstituted thiadiazolines.” Arkivoc. 1 (2000): 627–40.
  • Jackson, C., B. Blass, K. Coburn, L. Djandjighian, G. Fadayel, A. Fluxe, S. Hodson, J. Janusz, M. Murawsky, J. Ridgeway, R. White, and S. Wu. “Evolution of thiazolidine-based blockers of human Kv1.5 for the treatment of atrial arrhythmias.” Bioorg. Med. Chem. Lett. 17 (2007): 282–4.
  • Thomas, A., P. Sharma, P. Tupe, R. Badhe, R. Nanda, L. Kothapalli, O. Paradkar, A. Banerjee, and A. Deshpande. “Green route synthesis of 4-thiazolidinone analogs of isonicotinic acid hydrazide.” Green Chem. Lett. Rev. 4 (2011): 211–7.
  • Dandia, A., R. Singh, S. Bhaskaran, and S. Samant. “ Versatile three component procedure for combinatorial synthesis of biologically relevant scaffold spiro[indole-thiazolidinones] under aqueous conditions.” Green Chem. 13 (2011): 1852–9.
  • Heravi, M., F. Derikvand, A. Haeri, H. Oskoie, and F. Bamoharram. “Heteropolyacids as green and reusable catalysts for the synthesis of isoxazole derivatives.” Synth. Commun. 38 (2008): 135–40.
  • Pratap, U., D. Jawale, M. Bhosle, and R. Mane. “Baker's yeast catalyzed one-pot three-component synthesis of polyfunctionalized 4H-pyrans.” Tetrahedron Lett. 52 no. 44 (2011): 5817–19.
  • Wang, S., Y. Zhao, G. Zhang, N. Zhang, Y. Lv, and P. Gong. “Design, synthesis and biological evaluation of novel 4-thiazolidinones containing indolin-2-one moiety as potential antitumor agent.” Eur. J. Med. Chem. 46 (2011): 3509–18.
  • (a)Odyakov, V., E. Zhizhina, Y. Rodikova, and L. Gogin. “Mo-V-Phosphoric heteropoly acids and their salts: Aqueous solution preparation – challenges and perspectives.” Eur. J. Inorg. Chem. (22) (2015): 3618–31; (b)Yarmo, M., R. Shariff, S. Omar, J. Chin, and R. Haron. “New perspective in recent solid acid catalyst.” Mater. Sci. Forum. 517 (2006): 117–22.
  • Nechak, R., S. Bouzroura-Aichouche, Y. Benmalek, L. Salhi, S. Poulain-Martini, V. Morizur, E. Dunach, and B. Nedjar- Kolli. “Synthesis and antimicrobial evaluation of novel 4-thiazolodinones containing a pyrone moiety.” Synth. Commun. 45 (2015): 262–72.
  • Malla, A. M., M. Parveen, F. Ahmad, A. Shaista, and A. Mahboob. “[Et3NH][HSO4]-catalyzed eco-friendly and expeditious synthesis of thiazolidine and oxazolidine derivatives.” RSC Adv. 5 (2015): 19552.
  • Ghanbari Pirbasti, F., N. O. Mahmoodi, and J. Abbasi Shiran. “Synthesis and evaluation of biological activities of 4-cyclopropyl-5-(2-fluorophenyl) arylhydrazono-2,3-dihydrothiazoles as potent antioxidant agents.” J. Sulfur. Chem. 37 no. 2 (2016): 196–210.
  • Kwak, H. S., M. J. Lim, S. E. Lee, T. S. Jang, M. R. Kim, Y. G. Cho, W. Y. Kim, and M. S. Park. “Cellulose acylate film containing retardation agent, with improved permeability utilized for polarizer and liquid crystal display device.” Repub. Korean KongkaeTaeho Kongbo (2014): KR 2014110379 A 20140917.
  • Kassehin, U. C., F. A. Gbaguidi, C. R. McCurdy, and J. H. Poupaert. “Synthesis of antitrypanosomal thiosemicarbazones using anthranilic acid as an innovative Green nucleophilic catalyst.” J. Chem. Pharm. Res. 6 no. 10 (2014): 607–12.
  • Siles, R., M. Zhou, J. F. Ackley, K. G. Pinney, S. E. Chen, W. M. Arispe-Angulo, and M. L. Trawick. “Preparation of aryl (thio) semicarbazones as inhibitors of cysteine proteases for treatment of protozoan infections such as trypanosomiasis, malaria and leishmaniasis.” U.S. Pat. Appl. Publ. (2009): US 20090076076 A1 20090319.
  • Li, L., X. Wang, G. Li, Z. Zhao, and S. Huaxue. “Microwave-assisted synthesis and antibacterial activity of 2, 3-dihydrothiochromen-4-one thiosemicarbazones.” Chemical Reagents 35 (2013): 300–4.
  • Zhong, H. and L. Liu. Faming ZhuanliShenqing. “Method for synthesizing polyhydroxy flavanone thiosemicarbazone schiff base.” CN 103524475 A 20140122 (2014).
  • Gautam, D., P. Gautam, and R. P. Chaudhary. “Efficient synthesis, X-ray diffraction study and antimicrobial activity of some novel thiazolidin-4-ones and perhydro-1,3-thiazin-4-ones.” Heterocycl. Commun. 19 (2013): 43–7.
  • Gupta, A., D. R. Roy, V. Subramanian, and P. K. Chattaraj. “Are strong Brønsted acidsnecessarily strong Lewis acids.” J. Mol. Struct. Theochem. 812 (2007): 13–24.
  • Woodward, S. “HSAB matching and mismatching in selective catalysis and synthesis” Tetrahedron. 58 (2002): 1017–50.

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