Synthesis, structural activity relationship and anti-tubercular activity of novel pyrazoline derivatives

• Published in: European journal of medicinal chemistry 2007-02, Vol.42 (2), p.268-275
• Main Authors: Ali, Mohamed Ashraf, Shaharyar, Mohammad, Siddiqui, Anees Ahamed
• Format: Article
• Language: English
• Subjects: Aniline Compounds - chemical synthesis; Aniline Compounds - chemistry; Aniline Compounds - pharmacology; Anti-tubercular; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antitubercular Agents - chemical synthesis; Antitubercular Agents - chemistry; Antitubercular Agents - pharmacology; Biological and medical sciences; Isothiocyanate; Medical sciences; Microbial Sensitivity Tests; Mycobacterium tuberculosis; Mycobacterium tuberculosis - drug effects; Pharmacology. Drug treatments; Pyrazoles - chemical synthesis; Pyrazoles - chemistry; Pyrazoles - pharmacology; Pyrazoline
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2006.08.004

In the present investigation, a series of 5-(-4-(substituted) phenyl)-3-(4-hydroxy-3-methylphenyl)-4,5-dihydro-1 H-1-pyrazolyl-2-toluidino methane thione and 5-(substituted) phenyl-3-(4-hydroxy-3-methylphenyl)-4,5-dihydro-1 H-1-pyrazolyl-2-methoxyanilino methane thione were synthesized by the reaction between hydrazine hydrate and chalcones ( 3a– k) followed by condensation with appropriate aryl isothiocyanate which yielded N-substituted pyrazoline derivatives. Newly synthesized compounds were tested for their in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system. Among the synthesized compounds, compound anilino-3-(4-hydroxy-3-methylphenyl)-5-(2,6-dichlorophenyl)-4,5-dihydro-1 H-1-pyrazolylmethanethione ( 6i) was found to be more active agent against M. tuberculosis H37Rv with minimum inhibitory concentration of 0.0034 μM. In the present investigation, a series of 5-(-4-(substituted) phenyl)-3-(4-hydroxy-3-methylphenyl)-4,5-dihydro-1 H-1-pyrazolyl-2-toluidino methane thione and 5-(substituted) phenyl-3-(4-hydroxy-3-methylphenyl)-4,5-dihydro-1 H-1-pyrazolyl-2-methoxyanilino methane thione were synthesized by the reaction between hydrazine hydrate and chalcones ( 3a– k) followed by condensation with appropriate aryl isothiocyanate which yielded N-substituted pyrazoline derivatives. Newly synthesized compounds were tested for their in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system. Among the synthesized compounds, compound anilino-3-(4-hydroxy-3-methylphenyl)-5-(2,6-dichlorophenyl)-4,5-dihydro-1 H-1-pyrazolylmethanethione ( 6i) was found to be more active agent against M. tuberculosis H37Rv with minimum inhibitory concentration of 0.0034 μM. ▪