Synthesis and antimicrobial screening of N-[coumarin-6-yl-amino] thiazolidinone and its derivatives

Abstract

6-(2-Chloroacetyl)-aminocoumarins 2a-c were prepared by reacting the 6-aminocoumarins 1a-c and chloroacetylchloride in dry benzene. Compound 2a-c on treatment with thiourea yields 6-(2'-amino-1',3'-thiazol-4'-yl)aminocoumarins 3a-c. Compounds 3a-c were treated with aromatic aldehydes, resulted in the formation of 6-(arylidenimino-1'-3'-thiazole-4'-yl)aminocoumarin 4a-f. The arylidenoiminos 4a-f on cyclisation with chloroacetylchloride/triethylamine and thioglycollic acid gave 6-[2'-(3''-chloro-2''-oxo-4''-phenyl-1''-azetidinyl)-1',3'thiazole-4'-yl]aminocoumarins 5a-f and 6-[2'-(2''-phenyl-4''-thiazolidinone-3''-yl)-1', 3''-thiazole-4'-yl]aminocoumarin 6a-f respectively. Compounds 4a-f were also treated with aniline and sodium nitrite in the presence of conc. HCl to yield 6-[2'-(1''-phenyl-3''-phenylformazane-4''-yl)-1',3'-thiazole-4'-yl]aminocoumarins 7a-f. The structure of these compounds have been established on the basis of their analytical and spectroscopic data. All the above compounds were screened for their antimicrobial activity. Some were found to show significant antimicrobial activity.

Synthesis and antimicrobial activity of some methyl‐2‐[N‐coumarin‐6′‐yl]‐3‐oxo‐2,3‐dihydro‐1H‐isoindolone‐5‐carboxylates

“…Likewise, coumarins have also gained considerable synthetic and pharmacological interest for a long time because of their various biological activities [5–9]. In continuation of our work [10–15], keeping the biological profile of the two class of compounds in view, it appeared of interest to synthesize a molecular entity displaying the structural features of both the class of compounds.…”

Synthesis and <i>In Vitro</i> Antibacterial and Antifungal Evaluation of Quinoline Analogue Azetidin and Thiazolidin Derivatives

“…The β-lactam ring is the main feature of the most of the penicillins and other antibiotics. The β-lactam ring shows various biological activities such as antifungal [7,8], antibacterial [9,10], antitubercular [11,12], anticonvulsant [13], analgesic, anti-inflammatory [14], synthetic precursor for amino acids [15], antiviral [16] and many more. Variety of heterocyclic products including drugs [17,18], dyes and intermediates such as thiazol yellow, thioflavin T., thidiazuron [19], herbicides [20], insecticides [21,22] and many more attributed to possess thiazolidin-4-one.…”

An eco-compatible synthesis of novel spiro[acenaphthylene-1,2′[1,3]-thiazolidine]-2,4′(1H)-diones using thiamine hydrochloride as efficient catalyst in aqueous medium

“…A literature survey reveals various reports on synthesis of spiro-indole thiazolidinones [47][48][49][50][51][52][53], but to the best of our knowledge there is no report on the synthesis of spiro compounds by incorporating acenapthaquinone and 4-thiazolidinone rings together. Hence, inspired by these findings and in continuation of our ongoing work to develop environmentally benign methodologies [54][55][56][57][58][59][60][61] for the synthesis of biologically useful heterocycles, we have investigated a threecomponent protocol for the synthesis of drug-like spiro[acenaphthylene-1,2 0 [1,3]-thiazolidine]-2,4 0 (1H)-diones from the multi-component reaction of acenapthaquinone, substituted anilines, and a-mercaptoacetic acid in good yield using thiamine hydrochloride as a green, inexpensive, and reusable catalyst in aqueous medium.…”