(Z)-N-(4,5-dihydro-1,3-thiazol-2-yl)-3-(4-propan-2-ylphenyl)prop-2-enamide | 1426576-94-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-N-(4,5-dihydro-1,3-thiazol-2-yl)-3-(4-propan-2-ylphenyl)prop-2-enamide
• CAS: 1426576-94-4
• 化学式: C₁₅H₁₈N₂OS
• 分子量: 274.387
• InChiKey: OHHJNGLKVUGETM-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基-2-噻唑啉 、 (Z)-3-(4-isopropylphenyl)acrylic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (Z)-N-(4,5-dihydro-1,3-thiazol-2-yl)-3-(4-propan-2-ylphenyl)prop-2-enamide
  参考文献：
  名称：

  Cinnamides as selective small-molecule inhibitors of a cellular model of breast cancer stem cells

  摘要：

  A high-throughput screen (HTS) was conducted against stably propagated cancer stem cell (CSC)-enriched populations using a library of 300,718 compounds from the National Institutes of Health (NIH) Molecular Libraries Small Molecule Repository (MLSMR). A cinnamide analog displayed greater than 20-fold selective inhibition of the breast CSC-like cell line (HMLE_sh_Ecad) over the isogenic control cell line (HMLE_sh_eGFP). Herein, we report structure-activity relationships of this class of cinnamides for selective lethality towards CSC-enriched populations. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.01.025

文献信息

• [EN] COMPOUNDS AND METHODS FOR THE TREATMENT OF CANCER STEM CELLS<br/>[FR] COMPOSÉS ET PROCÉDÉS POUR LE TRAITEMENT DE CELLULES SOUCHES CANCÉREUSES
  申请人：BROAD INST INC

  公开号：WO2013032907A1

  公开（公告）日：2013-03-07

  The invention relates to compounds of Formula I or a pharmaceutically acceptable salt, ester or prodrug thereof: Formula (I).

  该发明涉及式I的化合物或其药学上可接受的盐，酯或前药：式(I)。
• Cinnamides as selective small-molecule inhibitors of a cellular model of breast cancer stem cells
  作者：Andrew R. Germain、Leigh C. Carmody、Partha P. Nag、Barbara Morgan、Lynn VerPlank、Cristina Fernandez、Etienne Donckele、Yuxiong Feng、Jose R. Perez、Sivaraman Dandapani、Michelle Palmer、Eric S. Lander、Piyush B. Gupta、Stuart L. Schreiber、Benito Munoz

  DOI：10.1016/j.bmcl.2013.01.025

  日期：2013.3

  A high-throughput screen (HTS) was conducted against stably propagated cancer stem cell (CSC)-enriched populations using a library of 300,718 compounds from the National Institutes of Health (NIH) Molecular Libraries Small Molecule Repository (MLSMR). A cinnamide analog displayed greater than 20-fold selective inhibition of the breast CSC-like cell line (HMLE_sh_Ecad) over the isogenic control cell line (HMLE_sh_eGFP). Herein, we report structure-activity relationships of this class of cinnamides for selective lethality towards CSC-enriched populations. (C) 2013 Published by Elsevier Ltd.