Design and synthesis of new 1,2,4-triazole derivatives containing morpholine moiety as antimicrobial agents

Deniz ŞAHİN; Hacer BAYRAK; Ahmet DEMİRBAŞ; Neslihan DEMİRBAŞ

doi:https://doi.org/10.3906/tar-1210-28

Makale detayları

Design and synthesis of new 1,2,4-triazole derivatives containing morpholine moiety as antimicrobial agents

Yazarlar:

Deniz ŞAHİN | Hacer BAYRAK | Ahmet DEMİRBAŞ | Neslihan DEMİRBAŞ

Yayıncı:

TUBITAK

Ana Başlıklar:

Uygulamalı fizik

Dergi:

Turkish Journal of Chemistry 2012 Vol.36 Issue 3, pp.411-426

Belge Tipi:

Makale

Yayın Tarihi:

2/2012

Belge Dili:

İngilizce

Document ID (Org No.):

2000727617

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

DOI:

https://doi.org/10.3906/tar-1210-28

Özet:

 

2-Morpholine-4ylethyl-3H-1,2,4-triazole-3-ones (2a, 2b) were  obtained from the condensation between the corresponding  ethoxycarbonylhydrazones and 2-morpholinoethanamine.  2a was converted  to acetohydrazide (4) via the formation of an ester derivative (3).  Treatment of 2a and 2b with several aryl sulfonyl chlorides afforded  the corresponding 2-arylsulfonyl-1,2,4-triazole-3-ones (5a-c and 6).  The reaction of hydrazide (4) with benzyl iso- and benzyl  isothiocyanate produced the corresponding carboxamide (8a) and  carbothioamide (8b).  The basic treatment of 8b yielded  5-mercapto-4H-1,2,4-triazol-3-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one  (10).  The synthesis of 1,3-thiazol-2(3H)-ylidene-1,2,4-triazol-1-  ylacetohydrazide (11) and 1,3-oxazole-2(3H)-ylidene-1,2,4-triazole-  1-yl)acetohydrazide (9) derivatives was performed from the reaction of  8a and 8b with substituted phenacyl bromides.  All the newly synthesized compounds were screened for their antimicrobial   activities and some of them were found to possess good or moderate   antimicrobial activity.

 

2-Morpholine-4ylethyl-3H-1,2,4-triazole-3-ones (2a, 2b) were  obtained from the condensation between the corresponding  ethoxycarbonylhydrazones and 2-morpholinoethanamine.  2a was converted  to acetohydrazide (4) via the formation of an ester derivative (3).  Treatment of 2a and 2b with several aryl sulfonyl chlorides afforded  the corresponding 2-arylsulfonyl-1,2,4-triazole-3-ones (5a-c and 6).  The reaction of hydrazide (4) with benzyl iso- and benzyl  isothiocyanate produced the corresponding carboxamide (8a) and  carbothioamide (8b).  The basic treatment of 8b yielded  5-mercapto-4H-1,2,4-triazol-3-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one  (10).  The synthesis of 1,3-thiazol-2(3H)-ylidene-1,2,4-triazol-1-  ylacetohydrazide (11) and 1,3-oxazole-2(3H)-ylidene-1,2,4-triazole-  1-yl)acetohydrazide (9) derivatives was performed from the reaction of  8a and 8b with substituted phenacyl bromides.  All the newly synthesized compounds were screened for their antimicrobial   activities and some of them were found to possess good or moderate   antimicrobial activity.

Makale detayları

Design and synthesis of new 1,2,4-triazole derivatives containing morpholine moiety as antimicrobial agents

Yazarlar: Deniz ŞAHİN | Hacer BAYRAK | Ahmet DEMİRBAŞ | Neslihan DEMİRBAŞ

Yayıncı: TUBITAK

Ana Başlıklar: Uygulamalı fizik

Dergi: Turkish Journal of Chemistry 2012 Vol.36 Issue 3, pp.411-426

Belge Tipi: Makale

Yayın Tarihi: 2/2012

Belge Dili: İngilizce

Document ID (Org No.): 2000727617

Sıklık: İki Aylık

eISSN: 1303-6130

pISSN: 1300-0527

DOI: https://doi.org/10.3906/tar-1210-28

Sayı

Yazarlar:

Deniz ŞAHİN | Hacer BAYRAK | Ahmet DEMİRBAŞ | Neslihan DEMİRBAŞ

Yayıncı:

TUBITAK

Ana Başlıklar:

Uygulamalı fizik

Dergi:

Turkish Journal of Chemistry 2012 Vol.36 Issue 3, pp.411-426

Belge Tipi:

Makale

Yayın Tarihi:

2/2012

Belge Dili:

İngilizce

Document ID (Org No.):

2000727617

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

DOI:

https://doi.org/10.3906/tar-1210-28