REACTION OF SCHIFF BASES WITH THIOGLYCOLIC ACID: SYNTHESIS OF THIAZEPIN-1(2H)-ONE AND THIAZOLIDIN-4-ONE COMPOUNDS

Dương Quốc Hoàn

DOI: http://dx.doi.org/10.26459/hueuni-jns.v127i1A.4516

Abstract


Reaction of Schiff bases with thioglycolic acid was set up with Dean stark apparatus in toluene. The Schiff bases containing aniline derivatives 1a and 2a gave thiazolidin-4-one containing compounds 1b and 2b only; 1-naphthyl amine gave a mixture of thiazolidin-4-one (3b) and thiazepin-1(2H)-one (3b’) containing compounds; 2-naphthyl amine (4a) gave and thiazepin-1(2H)-one containing compound 4b. The yields of reaction were moderate to high. The structures of these compounds were elucidated by 1H and 13C NMR and mass spectral analysis. Biological test results showed that Schiff base 4a was not active on any bacteria. Thiazolidine-4-one compound 1b was not active on bacteria and fungi, but was active against KB with IC50 21.33 (mg/mL). Thiazepine compound 4b exhibited activity on Staphyloccccus aureus bacterium at IC50 64.00 (mg/mL) and cancer cell line KB at IC50 11.52 (mg/mL).

 


Keywords


thiazolidin-4-one, thiazepin-1(2H)-one, 2-naphthyl amine, 1-naphthyl amine, Schiff base, thioglycolic acid

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References


. Gaikwad, N. J., Bonde, C. G., Synthesis and preliminary evaluation of some pyrazine containing thiazolines and thiazolidinones as antimicrobial agents. Bioorg. Med. Chem., 12 (9), 2151-2161, (2004).

. Kavitha C.V., Basappa, S. Nanjunda Swamy, Mantelingu K., Doreswamy S., Sridhar M. A., Prasad, J. S., Rangappa, K. S., Synthesis of new bioactive venlafaxine analogs: Novel thiazolidin-4-ones as antimicrobials. Bioorg. Med. Chem., 14 (7), 2290-2299, (2006).

. Soković M., Omar, K., Geronikaki, A., Zoumpoulakis, P., Camoutsis, C., Ćirić, A., Glamočlija, J., Novel 4-thiazolidinone derivatives as potential antifungal and antibacterial drugs. Bioorg. Med. Chem., 18 (1), 426-432, (2010).

. Isloor, A. M., Sunil, D., Shetty, P., Malladi, S., Pai, K. S. R.., Maliyakkl, N., Synthesis, characterization, anticancer, and antioxidant activity of some new thiazolidin-4-ones in MCF-7 cells, Med Chem Res, 22(2), 758-767 (2013).

. Kato, T., Ozaki, T., Tamura, K., Suzuki, Y., Akima, M., Ohi, N., Novel Calcium Antagonists with Both Calcium Overload Inhibition and Antioxidant Activity”, 1,2-(3,5-Di-tert-butyl-4-hydroxyphenyl)-3-(aminopropyl)thiazolidinones. J. Med. Chem., 41, 4309-4316, (1998).

. Ottanà, R., Maccari, R., Ciurleo, R., Paoli, P., Jacomelli, M., Manao, G., Camici, G., Laggner, C., Langer, T., 5-Arylidene-2-phenylimino-4-thiazolidinones as PTP1B and LMW-PTP inhibitors, Bioorg. Med. Chem., 17 (5), 1928-1937 (2009).

. Cheeseman, G. W. H., Hawi, A. A., Synthesis of some Pyrrolobenzothiazepines via N-Aryl-2-thiocyanatopyrroles (1), J. Heterocyclic Chem., 20, 585-589 (1983).

. Ericsson, J. M.; Sherris, J. C., Antibiotic sensitivity testing: report of an international collaborative study, Acta Pathol Microbiol Scand, 217, 1–90, (1971).

. Duong Quoc Hoan, Nguyen Hien, A Short, Effective Protocol For Shciff Base Synthesis, in manuscript and published soon (2017).

. Carey, F.A., Sundbrg, R. J., Advanced organic chemistry: Part A Structure and mechanism, 4th, Springer, 2000.