Page Banner

United States Department of Agriculture

Agricultural Research Service

Research Project: Chemistry of Natural Products for Nutraceutical Use, Pest Management and Crop Development

Location: Natural Products Utilization Research

Title: Synthesis and biological activity of substituted urea and thiourea derivatives containing 1,2,4-triazole moiety

Authors
item Kaymakcioglu, Bedia -
item Celen, Ahmet -
item Nurhayat, Tabanca -
item Abbas, Ali -
item Khan, Shabana -
item Khan, Ikklas -
item Wedge, David

Submitted to: Molecules
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: March 11, 2013
Publication Date: March 19, 2013
Citation: Kaymakcioglu, B., Celen, A.O., Nurhayat, T., Abbas, A., Khan, S.I., Khan, I.A., Wedge, D.E. 2013. Synthesis and biological activity of substituted urea and thiourea derivatives containing 1,2,4-triazole moiety. Molecules. 18(3):3562-3576.

Interpretive Summary: A series of novel thiourea and urea derivatives carrying 1,2,4-triazole moiety were synthesized and evaluated for their antifungal and larvicidal activity. All of synthesized compounds were characterized to determine the proposed structures using elemental analysis. Compounds were then evaluated for antifungal activity against plant pathogens, larvicidal activity againt Aedes aegypti L. mosquito and in vitro cytotoxicity and anti-inflammatory activity against human cell lines. Phomopis species were the most sensitive fungi to these compounds. Several compounds demonstrated good selective activity against Phomopis obscurans and two compounds showed same level of activity against P. viticola.

Technical Abstract: A series of novel thiourea and urea derivatives carrying 1,2,4-triazole moiety were synthesized and evaluated for their antifungal and larvicidal activity. Thiourea (1a-e) and urea derivatives (2a-e) were prepared by reacting 4-(aminophenyl)acetic acid with corresponding isothiocyanates and isocyanates. Triazole derivatives (3a-e and 4a-e) were synthesized by reacting thiourea and urea compounds with thiocarbohydrazide at 130-140oC oil bath. All of synthesized compounds were characterized to determine the proposed structures using elementary analysis, UV, IR, 1H-NMR and mass spectroscopy. All compounds were evaluated for antifungal activity against plant pathogens, larvicidal activity againt Aedes aegypti L. and in vitro cytotoxicity and anti-inflammatory activity against human cell lines. Phomopis species were the most sensitive fungi to these compounds. Compounds 1b, 1c, 3a and 4e demonstrated selectively good activity against Phomopis obscurans and only 1b and 4e showed same level of activity against P. viticola. Compound 3d showed the highest mortality followed by 1c and 3e) against Aedes aegypti larvae. No cytotoxicity was observed against human cancer cell lines. No anti-inflammatory activity was observed against NF-Kappa B dependent transcription induced by PMA (phorbol myristate acetate) in human chondrosarcoma cells.

Last Modified: 9/2/2014
Footer Content Back to Top of Page