Synthesis and biological activities of methylenebis-4H -1,2,4-triazole derivatives

Yıldız UYGUN; Hacer BAYRAK; Havva ÖZKAN

doi:https://doi.org/10.3906/kim-1212-66

Makale detayları

Synthesis and biological activities of methylenebis-4H -1,2,4-triazole derivatives

Yazarlar:

Yıldız UYGUN | Hacer BAYRAK | Havva ÖZKAN

Yayıncı:

TUBITAK

Ana Başlıklar:

Uygulamalı fizik

Dergi:

Turkish Journal of Chemistry 2013 Vol.37 Issue 5, pp.812-823

Belge Tipi:

Makale

Yayın Tarihi:

4/2013

Belge Dili:

İngilizce

Document ID (Org No.):

2000727343

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

DOI:

https://doi.org/10.3906/kim-1212-66

Özet:

 

5,5'-Methylenebis(4--phenyl-4H-1,2,4-triazole-3-thiol) (2) was   synthesized starting from hydrazinecarbothioamide compound (1).   Treatment of compound 2 with ethyl bromoacetate produced diethyl   5,5'-{methylenebis[(4-phenyl-4H-1,2,4-triazole-5,3-diyl)thio]}diacetate   (3), which was converted to the corresponding diacetohydrazide   derivative (4) by treatment with hydrazine hydrate. The reaction of   compound 4 with several aldehydes produced the corresponding   arylidene hydrazides, 5a--d. Syntheses of Mannich bases   6a--c were carried out by the treatment of compound 2 with   several amines in the presence of formaldehyde.   (4{[5-({5-[(4-Amino-2-chlorophenyl)thio]-4-phenyl-4H-1,2,4-triazol-3-ylmethyl)-4-phenyl-4H-1,2,4-triazol-3-yl]thio}-3-chlorophenyl)amine   (8) was prepared by reduction of 2 nitro groups of 3,3'  -methylenebis{5-[(2-chloro-4-nitrophenyl)thio]-4-phenyl-4H-1,2,4-triazole}   (7) that were obtained from the condensation of 2} with   3,4-dichloronitrobenzene.     The newly synthesized compounds were screened for their antimicrobial   activities; some of them were found to be active towards the test   microorganisms as the results demonstrated that the synthesized compounds   exhibited a broad spectrum of activity with minimum inhibitory concentration   (MIC) values of 31.3--500 m g/mL against gram-positive and gram-negative   bacteria, Candia albicans and Saccharomyces cerevisiae. All compounds displayed lower activity in this series   against the microorganisms with MIC values of 31.3--500 m g/mL than did   the compared control drugs of ampicillin, streptomycin, and fluconazole.

 

5,5'-Methylenebis(4--phenyl-4H-1,2,4-triazole-3-thiol) (2) was   synthesized starting from hydrazinecarbothioamide compound (1).   Treatment of compound 2 with ethyl bromoacetate produced diethyl   5,5'-{methylenebis[(4-phenyl-4H-1,2,4-triazole-5,3-diyl)thio]}diacetate   (3), which was converted to the corresponding diacetohydrazide   derivative (4) by treatment with hydrazine hydrate. The reaction of   compound 4 with several aldehydes produced the corresponding   arylidene hydrazides, 5a--d. Syntheses of Mannich bases   6a--c were carried out by the treatment of compound 2 with   several amines in the presence of formaldehyde.   (4{[5-({5-[(4-Amino-2-chlorophenyl)thio]-4-phenyl-4H-1,2,4-triazol-3-ylmethyl)-4-phenyl-4H-1,2,4-triazol-3-yl]thio}-3-chlorophenyl)amine   (8) was prepared by reduction of 2 nitro groups of 3,3'  -methylenebis{5-[(2-chloro-4-nitrophenyl)thio]-4-phenyl-4H-1,2,4-triazole}   (7) that were obtained from the condensation of 2} with   3,4-dichloronitrobenzene.     The newly synthesized compounds were screened for their antimicrobial   activities; some of them were found to be active towards the test   microorganisms as the results demonstrated that the synthesized compounds   exhibited a broad spectrum of activity with minimum inhibitory concentration   (MIC) values of 31.3--500 m g/mL against gram-positive and gram-negative   bacteria, Candia albicans and Saccharomyces cerevisiae. All compounds displayed lower activity in this series   against the microorganisms with MIC values of 31.3--500 m g/mL than did   the compared control drugs of ampicillin, streptomycin, and fluconazole.

Makale detayları

Synthesis and biological activities of methylenebis-4H -1,2,4-triazole derivatives

Yazarlar: Yıldız UYGUN | Hacer BAYRAK | Havva ÖZKAN

Yayıncı: TUBITAK

Ana Başlıklar: Uygulamalı fizik

Dergi: Turkish Journal of Chemistry 2013 Vol.37 Issue 5, pp.812-823

Belge Tipi: Makale

Yayın Tarihi: 4/2013

Belge Dili: İngilizce

Document ID (Org No.): 2000727343

Sıklık: İki Aylık

eISSN: 1303-6130

pISSN: 1300-0527

DOI: https://doi.org/10.3906/kim-1212-66

Sayı

Yazarlar:

Yıldız UYGUN | Hacer BAYRAK | Havva ÖZKAN

Yayıncı:

TUBITAK

Ana Başlıklar:

Uygulamalı fizik

Dergi:

Turkish Journal of Chemistry 2013 Vol.37 Issue 5, pp.812-823

Belge Tipi:

Makale

Yayın Tarihi:

4/2013

Belge Dili:

İngilizce

Document ID (Org No.):

2000727343

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

DOI:

https://doi.org/10.3906/kim-1212-66