NDLI: Synthesis, Crystal Structure and Biological Activity of Two 1,2,3-Thiadiazole Derivatives

Content Provider	Springer Nature Link
Author	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.
Copyright Year	2011
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) Å, b = 8.378(7) Å, c = 10.097(10) Å, α = 100.63(2)°, β = 112.742(17)°, γ = 93.287(4)° and Z = 2. The 2b crystallizes in triclinic space group P-1 with cell parameters a = 7.134(4) Å, b = 8.154(4) Å, c = 10.254(5) Å, α = 99.501(9)°, β = 91.311(7)°, γ = 109.518(8)° and Z = 2. Packing in the compound 2a is dominated by weak C–H···N and C–H···O hydrogen bonds. In the compound 2b, molecules are linked through intermolecular C–H···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 μg/mL and the EC$_{90}$ detected as from 21.041 to 175.17 μg/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.Two 1,2,3-thiadiazole derivatives C$_{13}$H$_{9}$N$_{3}$O$_{2}$S (2a) and C$_{10}$H$_{7}$N$_{3}$O$_{4}$S (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. The preliminary bioassay shows that the title compound 2a has excellent antifungal activity. 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.
Starting Page	1348
Ending Page	1354
Page Count	7
File Format	PDF
ISSN	10741542
Journal	Journal of Chemical Crystallography
Volume Number	41
Issue Number	9
e-ISSN	15728854
Language	English
Publisher	Springer US
Publisher Date	2011-04-30
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	X-ray diffraction Single crystal structure Synthesis 1,2,3-Thiadiazole Biological activity Physical Chemistry Organometallic Chemistry Inorganic Chemistry Crystallography
Content Type	Text
Resource Type	Article
Subject	Chemistry Condensed Matter Physics

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