5-[(3-chlorophenyl)methyl]-3H-1,3,4-thiadiazole-2-thione | 1231980-35-0

• 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: 5-[(3-chlorophenyl)methyl]-3H-1,3,4-thiadiazole-2-thione
• CAS: 1231980-35-0
• 化学式: C₉H₇ClN₂S₂
• 分子量: 242.753
• InChiKey: LAVOCLKABUECHW-UHFFFAOYSA-N

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：

  5-[(3-chlorophenyl)methyl]-3H-1,3,4-thiadiazole-2-thione 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 sodium hydroxide 、 苄基三乙基溴化铵 作用下， 以 水 、 二氯甲烷 为溶剂， 反应 10.0h， 以87%的产率得到5-(3-chlorobenzyl)-1,3,4-thiadiazol-2-yl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Thiadiazole-based Thioglycosides as Sodium-glucose Co-transporter 2 (SGLT2) Inhibitors

  摘要：

  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.

  DOI：

  10.1002/cjoc.201090120
• 作为产物：
  描述：

  在 硫酸 作用下， 生成 5-[(3-chlorophenyl)methyl]-3H-1,3,4-thiadiazole-2-thione
  参考文献：
  名称：

  Thiadiazole-based Thioglycosides as Sodium-glucose Co-transporter 2 (SGLT2) Inhibitors

  摘要：

  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.

  DOI：

  10.1002/cjoc.201090120

文献信息

• 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.