Ethyl 2-[(4-phenyl-1,2,3-thiadiazol-5-yl)sulfanyl]acetate | 338408-09-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: Ethyl 2-[(4-phenyl-1,2,3-thiadiazol-5-yl)sulfanyl]acetate
• 英文别名: ethyl 2-(4-phenylthiadiazol-5-yl)sulfanylacetate
• CAS: 338408-09-6
• 化学式: C₁₂H₁₂N₂O₂S₂
• 分子量: 280.371
• InChiKey: MGTQBMIGNHMCIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 2-[(4-phenyl-1,2,3-thiadiazol-5-yl)sulfanyl]acetate 在 氢氧化钾 、 水 作用下， 以 乙醇 为溶剂， 生成 2-((4-phenyl-1,2,3-thiadiazol-5-yl)thio)acetic acid
  参考文献：
  名称：

  1,2,3-Thiadiazole thioacetanilides as a novel class of potent HIV-1 non-nucleoside reverse transcriptase inhibitors

  摘要：

  A novel series of 1,2,3-thiadiazole thioacetanilide (TTA) derivatives have been designed, synthesized and evaluated for its anti-HIV activities in MT-4 cells. Some derivatives proved to be highly effective in inhibiting HIV-1 replication at nanomolar concentrations. Among them, 2-[4-(2,4-dichlorophenyl)-1,2,3-thiadiazol-5- ylthio]-N-(2-nitrophenyl)acetamide 7d2 was identified as the most promising compound (EC(50) = 0.059 +/- 0.02 mu M, CC(50) > 283.25 mu M, SI > 4883). The structure-activity relationship (SAR) of these novel structural congeners is discussed. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.055
• 作为产物：
  描述：

  ethyl 2-(1-phenylethanone-2-thio)acetate hydrazone 在 氯化亚砜 作用下， 生成 Ethyl 2-[(4-phenyl-1,2,3-thiadiazol-5-yl)sulfanyl]acetate
  参考文献：
  名称：

  1,2,3-Thiadiazole thioacetanilides as a novel class of potent HIV-1 non-nucleoside reverse transcriptase inhibitors

  摘要：

  A novel series of 1,2,3-thiadiazole thioacetanilide (TTA) derivatives have been designed, synthesized and evaluated for its anti-HIV activities in MT-4 cells. Some derivatives proved to be highly effective in inhibiting HIV-1 replication at nanomolar concentrations. Among them, 2-[4-(2,4-dichlorophenyl)-1,2,3-thiadiazol-5- ylthio]-N-(2-nitrophenyl)acetamide 7d2 was identified as the most promising compound (EC(50) = 0.059 +/- 0.02 mu M, CC(50) > 283.25 mu M, SI > 4883). The structure-activity relationship (SAR) of these novel structural congeners is discussed. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.055

文献信息

• 1,2,3-Thiadiazole thioacetanilides as a novel class of potent HIV-1 non-nucleoside reverse transcriptase inhibitors
  作者：Peng Zhan、Xinyong Liu、Yuan Cao、Yan Wang、Christophe Pannecouque、Erik De Clercq

  DOI：10.1016/j.bmcl.2008.09.055

  日期：2008.10

  A novel series of 1,2,3-thiadiazole thioacetanilide (TTA) derivatives have been designed, synthesized and evaluated for its anti-HIV activities in MT-4 cells. Some derivatives proved to be highly effective in inhibiting HIV-1 replication at nanomolar concentrations. Among them, 2-[4-(2,4-dichlorophenyl)-1,2,3-thiadiazol-5- ylthio]-N-(2-nitrophenyl)acetamide 7d2 was identified as the most promising compound (EC(50) = 0.059 +/- 0.02 mu M, CC(50) > 283.25 mu M, SI > 4883). The structure-activity relationship (SAR) of these novel structural congeners is discussed. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.