Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties

Hakan BEKTAŞ; Ahmet DEMİRBAŞ; Neslihan DEMİRBAŞ

doi:https://doi.org/10.3906/sag-1208-65

Article Details

Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties

Authors:

Hakan BEKTAŞ | Ahmet DEMİRBAŞ | Neslihan DEMİRBAŞ

Publisher:

TUBITAK

Main Topics:

Applied physics

Journal:

Turkish Journal of Chemistry 2010 Vol.34 Issue 4, pp.517-528

Document Type:

Article

Publication Date:

3/2010

Document Language:

English

Document ID (Org No.):

2000728007

Frequency:

Bimonthly

eISSN:

1303-6130

pISSN:

1300-0527

DOI:

https://doi.org/10.3906/sag-1208-65

Abstract:

 

2-(4-Amino-3-(4-chlorophenyl)-5-oxo-4,5--dihydro-1H-1,2,4-triazol-  1-yl)-N'-[(2,6-dihalogenophenyl)-methylene]acetohydrazides (3a,b) was   obtained via the formation of 2-(4-amino-3-(4-chlorophenyl)-5-oxo-4,5-  dihydro-1H-1,2,4-triazol-1-yl)acetohydrazide (2), which was obtained starting  from 4-amino-5-(4-chlo\-rophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one  (1) in 2 steps. 2-{[4-amino-3-(4-chlorophenyl)-5-oxo-4,5--dihydro-1H-  1,2,4-triazol-1-yl]acetyl}-N-phenylhydra-zine carbothioamide (4),  which was prepared starting from 2, was converted to the corresponding  1,3,4-thiadiazole derivative (5) in acidic media.  Moreover, the basic  treatment of 4 resulted in the formation of 4-amino-5-(4-chlorophenyl)-  2-[(4-phenyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]-2,4-  dihydro-3H-1,2,4-triazol-3-one (7).  The reactions of compounds 5 and  7 with methyl iodide in the presence of sodium ethoxide afforded the  corresponding N-methyl (6) and S-methyl (8) derivatives, respectively.  The synthesis of Mannich bases (10a and 10b) was performed from the  reaction of 7 with morpholine or piperazine in the presence of  formaldehyde.    All the newly synthesized compounds were screened for their  antimicrobial activity.  The antimicrobial activity study revealed  that compounds 3a, 3b, and 5 showed good antimicrobial activities  against the test microorganisms as compared with ampicillin.

 

2-(4-Amino-3-(4-chlorophenyl)-5-oxo-4,5--dihydro-1H-1,2,4-triazol-  1-yl)-N'-[(2,6-dihalogenophenyl)-methylene]acetohydrazides (3a,b) was   obtained via the formation of 2-(4-amino-3-(4-chlorophenyl)-5-oxo-4,5-  dihydro-1H-1,2,4-triazol-1-yl)acetohydrazide (2), which was obtained starting  from 4-amino-5-(4-chlo\-rophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one  (1) in 2 steps. 2-{[4-amino-3-(4-chlorophenyl)-5-oxo-4,5--dihydro-1H-  1,2,4-triazol-1-yl]acetyl}-N-phenylhydra-zine carbothioamide (4),  which was prepared starting from 2, was converted to the corresponding  1,3,4-thiadiazole derivative (5) in acidic media.  Moreover, the basic  treatment of 4 resulted in the formation of 4-amino-5-(4-chlorophenyl)-  2-[(4-phenyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]-2,4-  dihydro-3H-1,2,4-triazol-3-one (7).  The reactions of compounds 5 and  7 with methyl iodide in the presence of sodium ethoxide afforded the  corresponding N-methyl (6) and S-methyl (8) derivatives, respectively.  The synthesis of Mannich bases (10a and 10b) was performed from the  reaction of 7 with morpholine or piperazine in the presence of  formaldehyde.    All the newly synthesized compounds were screened for their  antimicrobial activity.  The antimicrobial activity study revealed  that compounds 3a, 3b, and 5 showed good antimicrobial activities  against the test microorganisms as compared with ampicillin.

Article Details

Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties

Authors: Hakan BEKTAŞ | Ahmet DEMİRBAŞ | Neslihan DEMİRBAŞ

Publisher: TUBITAK

Main Topics: Applied physics

Journal: Turkish Journal of Chemistry 2010 Vol.34 Issue 4, pp.517-528

Document Type: Article

Publication Date: 3/2010

Document Language: English

Document ID (Org No.): 2000728007

Frequency: Bimonthly

eISSN: 1303-6130

pISSN: 1300-0527

DOI: https://doi.org/10.3906/sag-1208-65

Issues

Authors:

Hakan BEKTAŞ | Ahmet DEMİRBAŞ | Neslihan DEMİRBAŞ

Publisher:

TUBITAK

Main Topics:

Applied physics

Journal:

Turkish Journal of Chemistry 2010 Vol.34 Issue 4, pp.517-528

Document Type:

Article

Publication Date:

3/2010

Document Language:

English

Document ID (Org No.):

2000728007

Frequency:

Bimonthly

eISSN:

1303-6130

pISSN:

1300-0527

DOI:

https://doi.org/10.3906/sag-1208-65