2-mercapto-5-(4-chlorobenzyl)-1,3,4-thiadiazole | 66464-85-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-mercapto-5-(4-chlorobenzyl)-1,3,4-thiadiazole
• 英文别名: 5-[(4-Chlorophenyl)methyl]-1,3,4-thiadiazole-2(3H)-thione；5-[(4-chlorophenyl)methyl]-3H-1,3,4-thiadiazole-2-thione
• CAS: 66464-85-5
• 化学式: C₉H₇ClN₂S₂
• 分子量: 242.753
• InChiKey: URGDKNGYJZEFJG-UHFFFAOYSA-N

物化性质

• 沸点：
  358.6±44.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  81.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-mercapto-5-(4-chlorobenzyl)-1,3,4-thiadiazole 在 potassium permanganate 、 溶剂黄146 、 sodium hydroxide 作用下， 生成 2-ethylsulfonyl-5-(4-chlorobenzyl)-1,3,4-thiadiazole
  参考文献：
  名称：

  Design, synthesis, and antibacterial activity against rice bacterial leaf blight and leaf streak of 2,5-substituted-1,3,4-oxadiazole/thiadiazole sulfone derivative

  摘要：

  A series of 2,5-substituted-1,3,4-oxadiazole/thiadiazole sulfone derivatives were synthesized and evaluated for their antibacterial activities against rice bacterial leaf blight and leaf streak caused by Xanthomonas oryzae pv. oryzae and Xanthomonas oryzae pv. oryzicolaby via the turbidimeter test in vitro. Antibacterial bioassay results indicated that most compounds demonstrated good inhibitory effect antibacterial bioactivities against rice bacterial leaf blight and leaf streak. Among the title compounds, compound 6c demonstrated the best inhibitory effect against rice bacterial leaf blight and leaf streak with half-maximal effective concentration (EC50)values of 1.07 and 7.14 mu g/mL, respectively, which were even better than those of commercial agents such as Bismerthiazol and Thiediazole Copper. In vivo antibacterial activities tests at greenhouse conditions demonstrated that the controlling effect of compounds 6c (43.5%) and 6g (42.4%) against rice bacterial leaf blight were better than those of Bismerthiazol (25.5%) and Thiediazole Copper (37.5%). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.060
• 作为产物：
  描述：

  对氯苯乙酸甲酯 在 一水合肼 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 5.0h， 生成 2-mercapto-5-(4-chlorobenzyl)-1,3,4-thiadiazole
  参考文献：
  名称：

  Antibacterial activities against rice bacterial leaf blight and tomato bacterial wilt of 2-mercapto-5-substituted-1,3,4-oxadiazole/thiadiazole derivatives

  摘要：

  In this study, a series of 2-mercapto-5-substituted-1,3,4-oxadiazole/thiadiazole derivatives were synthesized and evaluated for their antibacterial activities against rice bacterial leaf blight and tomato bacterial wilt caused by Xanthomonas oryzae pv. oryzae (Xoo) and Ralstonia solanacearum (R. solanacearum) via the turbidimeter test in vitro. Antibacterial bioassays indicated that most compounds demonstrated appreciable antibacterial bioactivities against Xoo and R. solanacearum. Among the title compounds, compound 4i demonstrated the best inhibitory effect against Xoo and R. solanacearum with half-maximal effective concentration (EC50) values of 14.69 and 15.14 mu g/mL, respectively, which were even better than those of commercial agents Bismerthiazol and Thiodiazole Copper. In vivo antibacterial activities tests under greenhouse conditions revealed that the control efficiency of compound 4i against rice bacterial leaf blight and tobacco bacterial wilt were better than those of Bismerthiazol and Thiodiazole Copper. Meanwhile, field trials also indicated that compound 4i demonstrated appreciable control efficiency against rice bacterial leaf blight and tomato bacterial wilt. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.12.038

文献信息

• Synthesis and biological assessment of indole derivatives containing penta-heterocycles scaffold as novel anticancer agents towards A549 and K562 cells
  作者：Guanglong Zhang、Zhenhua Tang、Sili Fan、Chengpeng Li、Yan Li、Weiqin Liu、Xuesha Long、Wenjing Zhang、Yi Zhang、Zhurui Li、Zhenchao Wang、Danping Chen、Guiping Ouyang

  DOI：10.1080/14756366.2022.2163393

  日期：2023.12.31

  2-chloro-N-(5-(2-oxoindolin-3-yl)-4H-pyrazol-3-yl) acetamide derivatives containing 1,3,4-thiadiazole (10a–i) and 4H-1,2,4-triazol-4-amine (11a–r) moiety was designed, synthesised as novel anticancer agents. The antiproliferative activity values indicated that compound 10 b stood as the most potent derivative with IC50 values of 12.0 nM and 10 nM against A549 and K562 cells, respectively. Mechanism investigation and

  摘要 在此，一系列新的 2- chloro- N- (5-(2-oxoindolin-3-yl)-4 H -pyrazol-3-yl) 乙酰胺衍生物包含 1,3,4 - thiadiazole ( 10a – i ) 和4 H -1,2,4-triazol-4-amine ( 11a – r ) 部分被设计、合成为新型抗癌药物。抗增殖活性值表明化合物10b是最有效的衍生物，对 A549 和 K562 细胞的 IC 50值分别为 12.0 nM 和 10 nM。10 b的机理调查和对接研究表明它具有良好的凋亡特性和剂量依赖性的 A549 和 K562 细胞生长停滞，阻断细胞周期进入 G2/M 期。有趣的是，10 b通过调节 EGFR 和 p53-MDM2 介导的途径抑制了 A549 和 K562 细胞的生长。
• Thiadiazole-based Thioglycosides as Sodium-glucose Co-transporter 2 (SGLT2) Inhibitors
  作者：Yunlong Gao、Guilong Zhao、Wei Liu、Yuli Wang、Weiren Xu、Jianwu Wang

  DOI：10.1002/cjoc.201090120

  日期：——

  AbstractA series of thiadiazole‐based thioglycosides were synthesized as SGLT2 inhibitors from D‐glucose, D‐galactose and a variety of phenylacetic acids via a convenient protocol in 8 steps and evaluated in vivo with an oral glucose tolerance test (OGTT), and 5‐benzyl‐1,3,4‐thiadiazol‐2‐yl 1‐thio‐β‐D‐glucopyranoside (1a) was the most efficacious to suppress the blood glucose excursion during OGTT.
• Design, synthesis, and antibacterial activity against rice bacterial leaf blight and leaf streak of 2,5-substituted-1,3,4-oxadiazole/thiadiazole sulfone derivative
  作者：Pei Li、Li Shi、Xia Yang、Lei Yang、Xue-Wen Chen、Fang Wu、Qing-Cai Shi、Wei-Ming Xu、Ming He、De-Yu Hu、Bao-An Song

  DOI：10.1016/j.bmcl.2014.02.060

  日期：2014.4

  A series of 2,5-substituted-1,3,4-oxadiazole/thiadiazole sulfone derivatives were synthesized and evaluated for their antibacterial activities against rice bacterial leaf blight and leaf streak caused by Xanthomonas oryzae pv. oryzae and Xanthomonas oryzae pv. oryzicolaby via the turbidimeter test in vitro. Antibacterial bioassay results indicated that most compounds demonstrated good inhibitory effect antibacterial bioactivities against rice bacterial leaf blight and leaf streak. Among the title compounds, compound 6c demonstrated the best inhibitory effect against rice bacterial leaf blight and leaf streak with half-maximal effective concentration (EC50)values of 1.07 and 7.14 mu g/mL, respectively, which were even better than those of commercial agents such as Bismerthiazol and Thiediazole Copper. In vivo antibacterial activities tests at greenhouse conditions demonstrated that the controlling effect of compounds 6c (43.5%) and 6g (42.4%) against rice bacterial leaf blight were better than those of Bismerthiazol (25.5%) and Thiediazole Copper (37.5%). (C) 2014 Elsevier Ltd. All rights reserved.
• Antibacterial activities against rice bacterial leaf blight and tomato bacterial wilt of 2-mercapto-5-substituted-1,3,4-oxadiazole/thiadiazole derivatives
  作者：Pei Li、Li Shi、Man-Ni Gao、Xia Yang、Wei Xue、Lin-Hong Jin、De-Yu Hu、Bao-An Song

  DOI：10.1016/j.bmcl.2014.12.038

  日期：2015.2

  In this study, a series of 2-mercapto-5-substituted-1,3,4-oxadiazole/thiadiazole derivatives were synthesized and evaluated for their antibacterial activities against rice bacterial leaf blight and tomato bacterial wilt caused by Xanthomonas oryzae pv. oryzae (Xoo) and Ralstonia solanacearum (R. solanacearum) via the turbidimeter test in vitro. Antibacterial bioassays indicated that most compounds demonstrated appreciable antibacterial bioactivities against Xoo and R. solanacearum. Among the title compounds, compound 4i demonstrated the best inhibitory effect against Xoo and R. solanacearum with half-maximal effective concentration (EC50) values of 14.69 and 15.14 mu g/mL, respectively, which were even better than those of commercial agents Bismerthiazol and Thiodiazole Copper. In vivo antibacterial activities tests under greenhouse conditions revealed that the control efficiency of compound 4i against rice bacterial leaf blight and tobacco bacterial wilt were better than those of Bismerthiazol and Thiodiazole Copper. Meanwhile, field trials also indicated that compound 4i demonstrated appreciable control efficiency against rice bacterial leaf blight and tomato bacterial wilt. (C) 2014 Elsevier Ltd. All rights reserved.