N-(3-(benzo[d]thiazol-2-yl)phenyl)acrylamide | 1446353-04-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: N-(3-(benzo[d]thiazol-2-yl)phenyl)acrylamide
• 英文别名: 2-Propenamide, N-[3-(2-benzothiazolyl)phenyl]-；N-[3-(1,3-benzothiazol-2-yl)phenyl]prop-2-enamide
• CAS: 1446353-04-3
• 化学式: C₁₆H₁₂N₂OS
• 分子量: 280.35
• InChiKey: FOCYZIXAZWHKST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-(benzo[d]thiazol-2-yl)phenyl)acrylamide 、 二甲胺 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 N-(3-(benzo[d]thiazol-2-yl)phenyl)-3-(dimethylamino)propanamide
  参考文献：
  名称：

  Optimization of the electrophile of chloronitrobenzamide leads active against Trypanosoma brucei

  摘要：

  We previously reported the phenylchloronitrobenzamides (PCNBs), a novel class of compounds active against the species of trypanosomes that cause Human African Trypanosomiasis (HAT). Herein, we explored the potential to adjust the reactivity of the electrophilic chloronitrobenzamide core. These studies identified compound 7d that potently inhibited the growth of trypanosomes (EC50 = 120 nM for Trypanosoma b. brucei, 18 nM for Trypanosoma b. rhodesiense, and 38 nM for Trypanosoma b. gambiense) without significant cytotoxicity against mammalian cell lines (EC50 > 25 mu M for HepG2, HEK293, Raji, and BJ cell lines) and also had good stability in microsomal models (t(1/2) > 4 h in both human and mouse). Overall these properties indicate the compound 7d and its analogs are worth further exploration as potential leads for HAT. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.049
• 作为产物：
  描述：

  3-苯并噻唑-2-苯胺 、 丙烯酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以66%的产率得到N-(3-(benzo[d]thiazol-2-yl)phenyl)acrylamide
  参考文献：
  名称：

  Optimization of the electrophile of chloronitrobenzamide leads active against Trypanosoma brucei

  摘要：

  We previously reported the phenylchloronitrobenzamides (PCNBs), a novel class of compounds active against the species of trypanosomes that cause Human African Trypanosomiasis (HAT). Herein, we explored the potential to adjust the reactivity of the electrophilic chloronitrobenzamide core. These studies identified compound 7d that potently inhibited the growth of trypanosomes (EC50 = 120 nM for Trypanosoma b. brucei, 18 nM for Trypanosoma b. rhodesiense, and 38 nM for Trypanosoma b. gambiense) without significant cytotoxicity against mammalian cell lines (EC50 > 25 mu M for HepG2, HEK293, Raji, and BJ cell lines) and also had good stability in microsomal models (t(1/2) > 4 h in both human and mouse). Overall these properties indicate the compound 7d and its analogs are worth further exploration as potential leads for HAT. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.049

文献信息

• Optimization of the electrophile of chloronitrobenzamide leads active against Trypanosoma brucei
  作者：Jong Yeon Hwang、David C. Smithson、Gloria Holbrook、Fangyi Zhu、Michele C. Connelly、Marcel Kaiser、Reto Brun、R. Kiplin Guy

  DOI：10.1016/j.bmcl.2013.05.049

  日期：2013.7

  We previously reported the phenylchloronitrobenzamides (PCNBs), a novel class of compounds active against the species of trypanosomes that cause Human African Trypanosomiasis (HAT). Herein, we explored the potential to adjust the reactivity of the electrophilic chloronitrobenzamide core. These studies identified compound 7d that potently inhibited the growth of trypanosomes (EC50 = 120 nM for Trypanosoma b. brucei, 18 nM for Trypanosoma b. rhodesiense, and 38 nM for Trypanosoma b. gambiense) without significant cytotoxicity against mammalian cell lines (EC50 > 25 mu M for HepG2, HEK293, Raji, and BJ cell lines) and also had good stability in microsomal models (t(1/2) > 4 h in both human and mouse). Overall these properties indicate the compound 7d and its analogs are worth further exploration as potential leads for HAT. (C) 2013 Elsevier Ltd. All rights reserved.