2-Bromothiazole-4-carbothioamide | 1333153-67-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-Bromothiazole-4-carbothioamide
• 英文别名: 2-bromo-1,3-thiazole-4-carbothioamide
• CAS: 1333153-67-5
• 化学式: C₄H₃BrN₂S₂
• 分子量: 223.117
• InChiKey: MWOLMGQYDWUUKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Bromothiazole-4-carbothioamide 、 碘甲烷 以 丙酮 为溶剂， 生成 Methyl 2-bromo-1,3-thiazole-4-carboximidothioate
  参考文献：
  名称：

  [EN] NUCLEAR TRANSPORT MODULATIORS AND USES THEREOF
  [FR] MODULATEURS DE TRANSPORT NUCLÉAIRE ET LEURS UTILISATIONS

  摘要：

  公开号：

  WO2011109799A8
• 作为产物：
  描述：

  2-溴-4-氰基噻唑 在 sodium hydrogen sulfide 、 magnesium(II) chloride hexahydrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以82.95%的产率得到2-Bromothiazole-4-carbothioamide
  参考文献：
  名称：

  [EN] NUCLEAR TRANSPORT MODULATIORS AND USES THEREOF
  [FR] MODULATEURS DE TRANSPORT NUCLÉAIRE ET LEURS UTILISATIONS

  摘要：

  公开号：

  WO2011109799A8

文献信息

• Tapcin, an In Vivo Active Dual Topoisomerase I/II Inhibitor Discovered by Synthetic Bioinformatic Natural Product (Syn‐BNP)‐Coupled Metagenomics
  作者：Zongqiang Wang、Amanda Kasper、Mai Takahashi、Adrian Morales Amador、Abir Bhattacharjee、Jingbo Kan、Yozen Hernandez、Melinda Ternei、Sean F. Brady

  DOI：10.1002/anie.202317187

  日期：2024.4.22

  DNA topoisomerases are attractive targets for anticancer agents. Dual topoisomerase I/II inhibitors are particularly appealing due to their reduced rates of resistance. A number of therapeutically relevant topoisomerase inhibitors are bacterial natural products. Mining the untapped chemical diversity encoded by soil microbiomes presents an opportunity to identify additional natural topoisomerase inhibitors. Here we couple metagenome mining, bioinformatic structure prediction algorithms, and chemical synthesis to produce the dual topoisomerase inhibitor tapcin. Tapcin is a mixed p‐aminobenzoic acid (PABA)‐thiazole with a rare tri‐thiazole substructure and picomolar antiproliferative activity. Tapcin reduced colorectal adenocarcinoma HT‐29 cell proliferation and tumor volume in mouse hollow fiber and xenograft models, respectively. In both studies it showed similar activity to the clinically used topoisomerase I inhibitor irinotecan. The study suggests that the interrogation of soil microbiomes using synthetic bioinformatic natural product methods has the potential to be a rewarding strategy for identifying potent, biomedically relevant, antiproliferative agents.
• [EN] NUCLEAR TRANSPORT MODULATIORS AND USES THEREOF<br/>[FR] MODULATEURS DE TRANSPORT NUCLÉAIRE ET LEURS UTILISATIONS
  申请人：KARYOPHARM THERAPEUTICS INC

  公开号：WO2011109799A8

  公开（公告）日：2011-12-22