Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole and 5- (3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives

Cai-Jun Chen; Bao-An Song; Song Yang; Guang-Fang Xu; Pinaki S. Bhadury; Lin-Hong Jin; De-Yu Hu; Qian-Zhu Li; Fang Liu; Wei Xue; Ping Lu; Zhuo Chen

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Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole and 5- (3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives

机译：5-（3,4,5-三甲氧基苯基）-2-磺酰基-1,3,4-噻二唑和5-（3,4,5-三甲氧基苯基）-2-磺酰基-1,3,4的合成及抗真菌活性-恶二唑衍生物

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Starting from the key intermediate 5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazole-2-thiol (4) or the oxadiazole analogue (5), the title compounds 9 and 10 are synthesized by a two-step process. Thioetherification reaction of 4 or 5 with an organic halide catalyzed by indium or indium tribromide first affords appropriate sulfide 7 or 8, which is then converted into title compounds 9 or 10 by hydrogen peroxide oxidation catalyzed by ammonium molybdate in ionic liquid [bmim]PF_6. The structures are unequivocally confirmed by spectroscopic (IR, ~1H and ~(13)C NMR) data and elemental analyses. The structures of 8d and 10q are further established by X-ray crystallographic diffraction analysis. The compounds have been shown to be fungicidally active. Title compounds 10i and 10j can inhibit mycelia growth by approximately 50% (EC_(50)) at 2.9-93.3 μg/mL in vitro against 10 kinds of fungi.

机译：从关键中间体5-（3,4,5-三甲氧基苯基）-1,3,4-噻二唑-2-硫醇（4）或恶二唑类似物（5）开始，标题化合物9和10由两个步骤过程。 4或5与由铟或三溴化铟催化的有机卤化物的硫醚化反应首先得到合适的硫化物7或8，然后通过在离子液体[bmim] PF_6中由钼酸铵催化的过氧化氢氧化将其硫化为标题化合物9或10。通过光谱（IR，〜1H和〜（13）C NMR）数据和元素分析明确证实了该结构。通过X射线晶体衍射分析进一步建立了8d和10q的结构。该化合物已显示具有杀真菌活性。标题化合物10i和10j在体外对10种真菌的抑制作用为2.9-93.3μg/ mL，可抑制菌丝体生长约50％（EC_（50））。

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来源
《Bioorganic and Medicinal Chemistry》 |2007年第12期|3981-3989|共9页
作者
Cai-Jun Chen; Bao-An Song; Song Yang; Guang-Fang Xu; Pinaki S. Bhadury; Lin-Hong Jin; De-Yu Hu; Qian-Zhu Li; Fang Liu; Wei Xue; Ping Lu; Zhuo Chen;
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作者单位

Center for Research and Development of Fine Chemicals, Key Laboratory of Green Pesticide and Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, PR China;

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正文语种 eng
中图分类药学;生物化学;
关键词
sulfone; antifungal activity; synthesis; catalyst; ionic liquid; thiadiazole moiety; oxadiazole moiety;

机译：砜抗真菌活性合成;催化剂;离子液体噻二唑部分;恶二唑部分;

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1. Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole and 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives [J] . Cai-Jun Chen, Bao-An Song, Song Yang, Bioorganic and medicinal chemistry . 2007,第12期

机译：5-（3,4,5-三甲氧基苯基）-2-磺酰基-1,3,4-噻二唑和5-（3,4,5-三甲氧基苯基）-2-磺酰基-1,3,4的合成及抗真菌活性-恶二唑衍生物
2. Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole and 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives [J] . Cai-Jun Chen, Bao-An Song, Song Yang, Bioorganic and Medicinal Chemistry . 2007,第12期

机译：5-（3,4,5-三甲氧基苯基）-2-磺酰基-1,3,4-噻二唑和5-（3,4,5-三甲氧基苯基）-2-磺酰基-1,3,4的合成及抗真菌活性-恶二唑衍生物
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4. Synthesis, characterization of some new l,3-oxazine-4-one derivatives containing 1,3,4-oxadiazole and 1,3,4-thiadiazole moiety with screening some of their biological activity. [C] . Raneen Hashim Rida, Maysoon Tariq Tawfiq International Scientific Conference on Pure Sciences, Brilliant Creativity and Renewed Building . 2019

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7. Synthesis and Crystal Structure of 5-(3,4-Dimethoxyphenyl)-4-(hydroxymethyl)tetrahydro-3-furanyl(3,4,5-trimethoxyphenyl)methanone [O] . G. Y. S. K. SWAMY, K. RAVIKUMAR, S. V. S. RADHAKRISHNAN, 2007

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Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole and 5- (3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives

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