Pyrazole derivatives from azines of substituted phenacyl aryl/cyclohexyl sulfides and their antimycobacterial activity

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 23, 2010, Pages 6920-6924

  Manikannan, Ramaiyan ^a   Venkatesan, Ramaiyan ^a   Muthusubramanian, Shanmugam ^a   Yogeeswari, Perumal ^b   Sriram, Dharmarajan ^b  

^a MADURAI KAMARAJ UNIVERSITY   (India)

^b BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE   (India)

Author keywords

Substituted acetophenone azines; Antimycobacterial activity; Microwave irradiation; Pyrazole derivatives; Vilsmeier's reagent

Indexed keywords

N,N DIMETHYLFORMAMIDE; PHOSPHORUS DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRAZOLE DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMER; MICROWAVE IRRADIATION; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; REACTION ANALYSIS; STRUCTURE ANALYSIS;

ANTI-BACTERIAL AGENTS; ANTITUBERCULAR AGENTS; FORMAMIDES; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM TUBERCULOSIS; PYRAZOLES; SULFIDES;

MYCOBACTERIUM TUBERCULOSIS;

EID: 78149286076     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.09.137     Document Type: Article

References (24)

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18. General procedure for the synthesis of pyrazole derivatives 3 and 4 and pyrrole derivative 5: To a mixture of 1-aryl-2-(aryl/cyclohexylsulfanyl)-1- ethanone N-[(Z)-1-aryl-2-(aryl/cyclohexylsulfanyl)ethylidene]hydrazones 2 (0.003 mol) and 3 mL of dimethyl formamide kept in ice bath at 0 °C, phosphorous oxychloride (0.024 mol) was added dropwise for 5-10 min. The reaction mixture was then irradiated under microwaves for 30-60 s. The process of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into crushed ice and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate. The different compounds present in the mixture, 3, 4 and 5 were separated by column chromatography using petroleum ether and ethyl acetate mixture as eluent.
19. 2: C, 58.01; H, 3.02; N, 4.67. Found: C, 58.09; H, 3.08; N, 4.73.
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22. 3): δ 21.2, 21.3, 105.5, 114.0, 127.1, 127.2, 127.4, 128.9, 129.0, 129.1, 129.4, 129.6, 131.0, 131.8, 132.6, 133.7, 134.9, 135.4, 137.0, 137.5, 138.4, 139.3, 153.2.
23. 2: C, 58.65; H, 2.99; N, 2.44. Found: C, 58.75; H, 3.12; N, 2.52.
24. Manikannan, R.; Muthusubramanian, S. J. Heterocycl. Chem. Accepted for publication.