Synthesis and Antimicrobial Activity of 4-Carbethoxymethyl-2-[(a-haloacyl)amino] thiazoles and 5-Nonsubstituted/substituted 2-[(4-Carbethoxymethylthiazol-2-yl)imino]-4-thiazolidinones

Abstract

Summary 4-Carbethoxymethyl-2-[(chloroacetyl / ?-chloropropionyl / ?-bromobutyryl / ?-chloro-(?-phenylacetyl)amino]thiazoles (I?IV) were synthesized by reacting 4-carbethoxymethyl-2-ami-nothiazole with chloroacetyl chloride, ?-chloropropionyl chloride, ?-bromobutyryl bromide and ?-chloro-a-phenylacetyl chloride, respectively. Furthermore, I-IV were refluxed with ammonium thiocyanate to give 2-[(4-carbethoxymethylthiazol-2-yl)imino]-4-thiazolidinones (V- VIII). V was refluxed with various aromatic aldehydes to give 5-arylidene-2-[(4-carbethoxyme-thylthiazol-2-yl)imino]-4-thiazolidinones (IX-XIV). The structures of synthesized compounds were confirmed by elemental analyses, hydrolysis, UV, IR, 1H-NMR and EI mass spectral data. The antimicrobial activities of the compounds were assessed by microbroth dilution technique using Mueller-Hinton broth and Mueller-Hinton Agar. In this study, Staphylococcus aureus ATCC 6538, Staphylococcus epidermidis ATCC 12228, Escherichia coli ATCC 8739, Klebsiella pneumoniae ATCC 4352, Pseudomonas aeruginosa ATCC 1539, Salmonella typhi, Shigella flexneri, Proteus mirabilis and Candida albicans ATCC 10231 were used as test microorganisms. Among the tested compounds, XI and XIV showed activity against S. aureus (MIC: 78 ?g/ml, 1.6 ?g/ml), whereas compound V had an activity against S. flexneri (MIC: 39 ?g/ml) and compound I against C. albicans (MIC: 125 (|?g/ml). Compounds I, IV- XIV were also evaluated for antituberculosis activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system and BACTEC 12B medium. Only compounds I and XIV showed 86% and 67% inhibition in the primary screen.

Tiyoüreler, açiltiyoüreler ve 4-tiyazolidinonların sentezi, karakterizasyonu ve antikanser ve antiviral etkilerinin değerlendirilmesi

“…4-Thiazolidinone derivatives among heterocyclic ring systems have been reported to possess various biological properties such as anticancer (18), anti-inflammatory (19,20), antibacterial (21,22), antioxidant (23), anticonvulsant (24), antiviral (25), antimicrobial (26) and antifungal activities (27). The following 1,3-thiazolidin-4-on derivatives are used in medicine: ralitoline (anticonvulsant), piprozolin (choleretic), etozolin, ozolinone (diuretic), dexetozolin (antihypertensive), mezolidon (antiulcer) (28)(29)(30).…”

Synthesis and Evaluation of Antimicrobial and Anticonvulsant Activities of Some New 3-[2-(5-Aryl-1,3,4-oxadiazol-2-yl/4-Carbethoxymethylthiazol-2-yl)imino-4-thiazolidinon-5-ylidene]-5-substituted/nonsubstituted 1H-indole-2-ones and Investigation of Their Structure-Activity Relationships

“…Over the years, 4-thiazolidinones have been synthesized for a wide range of pharmaceutical and biological purposes. Especially, 2-arylimino-4-thiazolidinones are important compounds due to their broad range of biological activities such as antibacterial [1], antifungal [2], anticonvulsant [3], antituberculous [4], besides various other activities. It is also well known that the 2-aminothiazole and 2-amino-1,3,4-oxadiazole structures can be important for significant biological activities [5−9].…”

Synthesis and antibacterial activity of some novel bis-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and bis-4-thiazolidinone derivatives from terephthalic dihydrazide

“…It has also been reported in literature that certain compounds bearing 1,3,4-oxadiazole/thiadiazole and 1,2,4-triazole nucleus possess significant anti-inflammatory activity [4][5][6][7]. 4-Thiazolidinone derivatives are also known to possess antibacterial [8][9][10][11][12], antifungal [13][14][15], antiviral [16][17][18][19][20] and antituberculosis [11,[21][22][23] properties. 4-Thiazolidinones have been reported as novel inhibitors of the bacterial enzyme [24].…”