Citation: Qi-Chun DING, Yi-Hui ZOU, Qiu-Ling LI, Jian-Jun HUANG, Li-Xue ZHANG, Hui-Yong YIN. Synthesis, Crystal Structure and Biological Activities of Phenyl(6-phenyl-3-p-tolyl-6, 7-dihydro-5H-[1, 2, 4]triazolo-[3, 4-b][1, 3, 4]thiadiazin-7-yl)methanone[J]. Chinese Journal of Structural Chemistry, ;2020, 39(8): 1531-1538. doi: 10.14102/j.cnki.0254–5861.2011–2671 shu

Synthesis, Crystal Structure and Biological Activities of Phenyl(6-phenyl-3-p-tolyl-6, 7-dihydro-5H-[1, 2, 4]triazolo-[3, 4-b][1, 3, 4]thiadiazin-7-yl)methanone

a.
Department of Pharmacy, Zhangzhou Health Vocational College, Zhangzhou 363000, China
b.
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325027, China
c.
CAS Key Laboratory of Nutrition, Metabolism and Food Safety, Shanghai Institute of Nutrition and Health, Chinese Academy of Sciences (CAS), Shanghai 200031, China
d.
Key Laboratory of Food Safety Risk Assessment, Ministry of Health, Beijing 100021, China

Corresponding author: Qi-Chun DING, 177426824@qq.com
Received Date: 20 November 2019
Accepted Date: 13 February 2020

Fund Project: the grants from Zhangzhou Natural Science Foundation of China ZZ2018J39The work reported in this manuscript has been granted a Chinese Patent ZL201710632570.6

Figures(5)

The title compound phenyl(6-phenyl-3-p-tolyl-6, 7-dihydro-5H-[1,2,4]triazolo[3, 4-b][1,3,4]thia-diazin-7-yl)methanone (PTM), designed using 4-amino-3-p-tolyl-1H-1, 2, 4-triazole-5(4H)-thione as the starting material, was successfully synthesized via a two-step synthesis route and finally characterized by NMR, FT-IR, single-crystal X-ray diffraction and mass spectrometry techniques. The crystal structure of trans-PTM was obtained from X-ray diffraction: C₂₄H₂₀N₄OS, M_r = 412.52, monoclinic system, space group P2₁/c, a = 16.650(3), b = 13.876(3), c = 8.812(2) Å, β = 100.340(3)°, V = 2002.8(7) Å³, F(000) = 865, Z = 4, D_c = 1.3680 g/cm³, λ = 0.71073 Å, μ = 0.186 mm^‑1 and the final R = 0.0786 for 3514 unique reflections with 2044 observed ones (I > 2σ(I)). The biological activities of antimicrobial and regulation of plant growth of PTM were investigated. The results indicated that PTM showed weak antimicrobial activity on Bacillus pumilus, while promoted the growth of radish and inhibited that of wheat in a dose-dependent manner. Therefore, PTM may be developed as a potential drug to promote the growth of dicotyledonous plants or as an herbicide to inhibit that of monocotyledonous plants in the future.
- synthesis,
- 1,2,4-triazole,
- triazolothiadiazine,
- crystal structure,
- FT-IR,
- NMR,
- biological activity
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