Synthesis, characterization and primary antituberculosis activity evaluation of 4-(3-coumarinyl)-3-benzyl-4-thiazolin-2-one benzylidenehydrazones

In this study a new series of 4-(3-coumarinyl)-3-benzyl-4-thiazolin-2-one benzylidenehydrazones 3a-t was synthesized. Structures of the title compounds Were elucidated by elemental analyses and spectrometric data (IR, H-1-NMR, C-13-NMR and EIMS). 3a-t were evaluated for antituberculosis activity against Mycobacterium tuberculosis H37Rv in BACTEC 12B medium using the BACTEC 460 radiometric system

Synthesis and anticonvulsant activity of new acylthiosemicarbazides and thiazolidones

A number of 1-(3-phenyl-4(3H)-quinazolinone-2-ylmercaptoacetyl)-4-substituted thiosemicarbazide and 2-(3-phenyl-4(3H)-quinazolinone-2-ylmercaptoacetylhydrazone)-3-substituted 4-thiazolidone derivatives were synthesized and evaluated for anticonvulsant activity. Some of the tested compounds showed significant activity against MES and ScMet induced seizures

Synthesis and structure-activity relationships of 3-hydrazono-1H-2-indolinones with antituberculosis activity

A series of 3-[S-(4-substituted phenacyl)-4-substituted-isothiosemicarbazono]-1H-2-indolinones 2a-h and 3-[(3,4-disubstituted-4-thiazolin-2-ylidene)hydrazono]-1H-2-indolinones 3a-f were synthesized. These new hydrazonoindolinone derivatives and 3-(4-substituted-thiosemicarbazono)-1H/1-acetyl-2-indolinones 1a-g 3-[(2-substituted-4-thiazolidinon-2-ylid drazono]-1H-2-indolinones 4a-o, 3-[(2-substituted-4-carboxy/carbetoxy-5-methyl-4-thiazolin-2-ylidene) hydrazono]-1H-2-indolinones 5a-e and 3-substituted-hydrazono-1H-2-indolinones 6a-o which had been previously reported were evaluated for antituberculosis activity against Mycobacterium tuberculosis H37Rv. These compounds exhibited varying degrees of inhibition in the in vitro primary screening that was conducted at 12 mu g/ml against M. tuberculosis H37Rv in BACTEC 12B medium using the BACTEC 460 radiometric system. 2a, 2c, 2f-h, 3c and 3f demonstrating activity in the primary screen were re-tested at lower concentrations against M. tuberculosis H37Rv to determine the actual minimum inhibitory concentration (MIC) in CABTEC 460. The structure-activity relationships of the derivatives were investigated

Synthesis and primary cytotoxicity evaluation of new 5-bromo-3-substituted-hydrazono-1H-2-indolinones.

In this study a new series of 5-bromo-3-[(3-subtituted-5-methyl-4-thiazolidinone-2-lidene)-hydrazono]-1H-2-indolinones (3a-i) and 5-bromo-3-[(2-thioxo-3-substituted-4,5-imidazolidinedione-1-yl)imino]-1H-2-indolinones (4a-f) was synthesized by the cyclization of 5-bromo-3-(N-substituted-thiosemicarbazono)-1 H-2-indolinones (2 a-i) with ethyl 2-bromopropionate in anhydrous ethanolic medium and oxalyl cloride in anhydrous diethyl ether, respectively Six compounds chosen as prototypes were evaluated in the 3-cell line, one dose in vitro primary cytotoxicity assay. Four of them were evaluated against the full panel of 60 human tumor cell lines at a minimum of five concentrations at 10-fold dilutions. Among the compounds tested, the 4-fluorophenylthiosemicarbazone derivative 2f showed the most favorable cytotoxicity This compound demonstrated the most marked effects on a breast cancer cell line (BT-549, log(10)GI(50) value -6.40), a non small cell lung cancer cell line (NCl-H23, log(10)GI(50) value -6.10), and an ovarian cancer cell line (IGROV1, log(10)GI(50) value -6.02)

Synthesis, characterization and primary antimicrobial activity evaluation of 3-phenyl-6-methyl-4(3H)-quinazolinone-2-yl-mercaptoacetic acid arylidenehydrazides

3-Phenyl-6-methyl-4(3H)-quinazolinone-2-yl-mercaptoacetic acid hydrazide (3) was reacted with substituted aldehydes in absolute ethanol to obtain a new series, 3-phenyl-6-methyl-4(3H)-quinazolinone-2-yl-mercaptoacetic acid arylidenehydrazides (4a-q). The structures of 4a-q were elucidated by elemental analyses and from spectrometric (UV, IR, H-1-NMR, C-13-NMR and EIMS) data. Then 4a-q were evaluated for antibacterial, antifungal and antitubercular activities. No significant activity was observed against the selected microorganisms

New cyclohexylidenehydrazide and 4-aza-1-thiaspiro[4.5]decan-3-one derivatives of 3-phenyl-4(3H)-quinazolinones

In this study, the synthesis of (3-phenyl-4(3H) -quinazolinon-2-yl) mercaptoacetic acid cyclohexylidenehydrazides and 4-[(3-phenyl-4(3H) -quinazolinon-2-yl) mercaptoacetylamino] -4-aza-1-thiaspiro [4.5] decan-3-ones and the results of the study on their antifungal activity are reported. Most of the tested compounds were found to be active against Microsporum gypseum NCPF-580, Microsporum canis, Tricophyton mentagrophytes NCPF-375 var. erinacei and Tricophyton rubrum at 25 mu g/ml. (C) 1998 Elsevier Science S.A. All rights reserved

Synthesis and preliminary CNS depressant activity evaluation of new 3-[(3-substituted-5-methyl-4-thiazolidinon-2-ylidene)hydrazono]-1H-2-indolinones and 3-[(2-thioxo-3-substituted-4,5-imidazolidine-dion-1-yl)imino]-1H-2-indolinones

A series of (+/-) 3-[(3-substituted-5-methyl-4-thiazolidinon-2- ylidene)hydrazono]-1H-2-indolinones (2a-h) and 3-[(2-thioxo-3-substituted-4,5- imidazolidinedion-1-yl)imino]-1H-2-indolinones (3a-g) were synthesized by the cyclization of 3-(4-substituted-thiosemicarbazono)-1H-2-indolinones (la-h) with ethyl 2-bromopropionate in anhydrous ethanolic medium and oxalyl chloride in anhydrous diethyl ether, respectively. The structures of 2 and 3 were confirmed by analytical and spectral data (IR, H-1 NMR, C-13 NMR, and EIMS) The configuration of 3 was assigned on the basis of H-1 NMR and C-13 NMR data. 2c, 2d, 2g, 2h, and 3a-g were evaluated for anticonvulsant activity against maximal electroshock (MES) and subcutaneous pentylenetetrazol (ScMet) induced seizures. Among the compounds tested, only 2d exhibited some activity in anticonvulsant identification (Phase I) trials in mice. 2a, 2b, 2d, 2g, 2h, and 3a-g were additionally tested for potentiating effects on pentobarbital induced hypnosis in mice. All of the test compounds increased the sleeping time of pentobarbital significantly (p < 0.05) and the most potent compound was found to be 3a

Synthesis and antimicrobial activity of some benzazole derivatives

212-216A series of 2-(1H-benzimidazol/ 1 ,3-benzoxazol/ 1,3-benzothiazol-2-ylmercapto )-N -(1,5-dimethy1-2-phenyl-3-oxo-2,3-dihydro-1H-pyrazol-4-y l)acylamines 5a-h and 2-(1H-benzimidazol-2-yl mercapto)-N-(5-substituted-2-oxo-1,2-dihydro-3H- indol-3-ylidene) acetohydrazides 8a-e have been synthesized. Their structures are determined by the elemental analyses and spectral data (IR, 1H-NMR, EIMS). These new derivatives arc evaluated for in vitro antimicrobial activity against Staphylococcus aureus ATCC 6538, Staphylococcus epidermidis ATCC 12228, Escherichia coli ATCC 8739, Klebsiella pneumoniae ATCC 4352, Pseudomonas aeruginosa A TCC 1539. Salmonella typhi, Shigella flexneri, Proteus mirabilis ATCC 14153 and Candida albicans ATCC 10231.8a, 8c and 8e demonstrating activity against Staphylococcus epidermidis ATCC 12228 in the primary screen are re-tested at lower concentrations to determine the actual minimum inhibitory concentrat ion (M IC)