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

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.

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

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.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

Reaction kinetics of carbon dioxide with 2-amino-2-hydroxymethyl-1,3-propanediol in aqueous solution obtained from the stopped flow method

Cyril Sunday UME, Erdoğan ALPER

Synthesis and antimicrobial evaluation of some annelated phthalazine derivatives and acyclo C-nucleosides from 1-chloro-4-(2,4,6-trimethylphenyl) phthalazine precursor

Maher Abdel Aziz EL-HASHASH, Ahmed Youssef SOLIMAN, İbrahim Essam EL-SHAMY

Optimization of a new cloud point extraction procedure for the selective determination of trace amounts of total iron in some environmental samples

Celal DURAN, Duygu ÖZDEŞ, Elif Çelenk KAYA, Halit KANTEKİN

Transmission FT-IR spectroscopic analysis of human kidney stones in the Hyderabad region of Pakistan

Muhammad Hassan KHASKHELI, Syed Tufail Hussain SHERAZI, Huma Mazhar UJAN

Evaluation of thermodynamic parameters of cadmium adsorption on sand from Temkin adsorption isotherm

Abdul Sattar Ali KHAN

Synthesis, characterization, and antioxidant activities of new trisubstituted triazoles

Kemal SANCAK, Yasemin ÜNVER, Dilek ÜNLÜER, Esra DÜĞDÜ, Gülcan KÖR

Silica nanoparticles as a high efficient catalyst for the one-pot synthesis of 3-oxo-3-phenylpropanamid derivatives from isocyanides, phenylacetaldehyde and secondary amines

Ali RAMAZANI, Kourosh DASTANRA, Fatemeh Zeinali NASRABADI

Copolymerization of N-Vinyl pyrrolidone with methyl methacrylate by Ti(III)-DMG redox initiator

Ajithkumar Manayan PARAMBIL, Yashoda Malagar PUTTAIAHGOWDA

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

Deniz ŞAHİN, Hacer BAYRAK, Ahmet DEMİRBAŞ, Neslihan DEMİRBAŞ

Synthesis, anti-inflammatory, antiplatelet and in silico evaluations of (E)-3-(3-(2,3-dihydro-3-methyl-2-oxo- 3H-benzoxazole-6-yl)-1-phenyl-1H-pyrazole- 4-yl)acrylamides

Sultan BAYTAŞ, Nilüfer Nermin Turan DURAL, Yeşim ÖZKAN