Synthesis, Crystal Structure and Biological Activity of Two 1,2,3-Thiadiazole Derivatives / Wang Shou-Xin,Huang Jie,Fan Zhi-Jin,Wang Huan,Fu Yi-Feng,Mi Na,Zhang Zheng-Cai,Song Hai-Bin,Belskaya Nataliya P.,Bakulev Vasiliy A. // JOURNAL OF CHEMICAL CRYSTALLOGRAPHY. - 2011. - V. 41, l. 9. - P. 1348-1354.

ISSN/EISSN:

1074-1542 / нет данных

Type:

Article

Abstract:

The title compounds, quinolin-8-yl 4-methyl-1,2,3-thiadiazole-5-carboxylate 2a and 2-nitrophenyl 4-methyl-1,2,3-thiadiazole-5-carboxylate 2b, synthesized by the reaction of 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride with 8-hydroxyquinoline and 2-nitrophenol, were confirmed by single-crystal X-ray diffraction {[}CCDC 783328 and 784970]. The 2a crystallizes in triclinic space group P-1 with cell parameters a = 7.957(7) , b = 8.378(7) , c = 10.097(10) , alpha = 100.63(2)A degrees, beta = 112.742(17)A degrees, gamma = 93.287(4)A degrees and Z = 2. The 2b crystallizes in triclinic space group P-1 with cell parameters a = 7.134(4) , b = 8.154(4) , c = 10.254(5) , alpha = 99.501(9)A degrees, beta = 91.311(7)A degrees, gamma = 109.518(8)A degrees and Z = 2. Packing in the compound 2a is dominated by weak C-H center dot center dot center dot N and C-H center dot center dot center dot O hydrogen bonds. In the compound 2b, molecules are linked through intermolecular C-H center dot center dot center dot O hydrogen bonds interactions. The preliminary bioassay showed that the title compound 2a had excellent antifungal activity with the EC(50) detected as from 2.99 to 28.35 mu g/mL and the EC(90) detected as from 21.041 to 175.17 mu g/mL. Both of the title compounds 2a and 2b had good inhibition activity of tobacco mosaic virus (TMV) and good induction activity of tobacco against TMV with potential systemic acquired resistance.

Author keywords:

X-ray diffraction; Single crystal structure; Synthesis; 1,2,3-Thiadiazole; Biological activity UGI REACTION

DOI:

10.1007/s10870-011-0101-z

Web of Science ID:

ISI:000293756700018

Соавторы в МНС:

Другие поля

Поле	Значение
Month	SEP
Publisher	SPRINGER/PLENUM PUBLISHERS
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
Keywords-Plus	UGI REACTION
Research-Areas	Crystallography; Spectroscopy
Web-of-Science-Categories	Crystallography; Spectroscopy
Author-Email	fanzj@nankai.edu.cn
ResearcherID-Numbers	Belskaya, Nataliya/S-3953-2017 G, Neela/H-3016-2014
ORCID-Numbers	Belskaya, Nataliya/0000-0002-2509-7916
Funding-Acknowledgement	National Natural Science Foundation of China {[}20872071, 20911120069]; Natural Science Foundation of Tianjin {[}10JCZDJC17500]; National Key Project for Basic Research {[}2010CB126105]; National Key Technology Research and Development Program {[}2011BAE06B02, 2011BAE06B05]; Foundation of Achievements Transformation and Spreading of Tianjin Agricultural Science and Technology {[}201002250]; Key Laboratory of Pesticide Chemistry and Application, Ministry of Agriculture (MOA) {[}MOAPCA200903]; Russian Foundation for Basic Research {[}RFBR 08-03-00376a, RFBR/NNSF 08-03-92208 a]
Funding-Text	We are grateful to the National Natural Science Foundation of China (Nos. 20872071 and 20911120069), the Natural Science Foundation of Tianjin (10JCZDJC17500), the National Key Project for Basic Research (2010CB126105), National Key Technology Research and Development Program(2011BAE06B02 and 2011BAE06B05) and the Foundation of Achievements Transformation and Spreading of Tianjin Agricultural Science and Technology (No. 201002250), the Key Laboratory of Pesticide Chemistry and Application, Ministry of Agriculture (MOA) (No. MOAPCA200903), and the Russian Foundation for Basic Research (grant numbers RFBR 08-03-00376a and RFBR/NNSF 08-03-92208 a) for support of this crystallographic investigation and biological activity determination.
Number-of-Cited-References	29
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	6
Journal-ISO	J. Chem. Crystallogr.
Doc-Delivery-Number	805VI