(5R,11S)-11-((E)-4-mercaptobut-1-en-1-yl)-5-methyl-10-oxa-3,17-dithia-7,14,19,20-tetraazatricyclo[14.2.1.1(2,5)]icosa-1(18),2(20),16(19)-triene-6,9,13-trione | 1315334-21-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (5R,11S)-11-((E)-4-mercaptobut-1-en-1-yl)-5-methyl-10-oxa-3,17-dithia-7,14,19,20-tetraazatricyclo[14.2.1.1(2,5)]icosa-1(18),2(20),16(19)-triene-6,9,13-trione
• 英文别名: (5R,11S)-5-methyl-11-[(E)-4-sulfanylbut-1-enyl]-10-oxa-3,17-dithia-7,14,19,20-tetrazatricyclo[14.2.1.12,5]icosa-1(18),2(20),16(19)-triene-6,9,13-trione
• CAS: 1315334-21-4
• 化学式: C₁₈H₂₂N₄O₄S₃
• 分子量: 454.595
• InChiKey: AFSJJSQBGQDPSE-XHBAHQFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  164
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  methyl 2-(tert-butoxycarbonylaminomethyl)thiazole-4-carboxylate 在 三乙基硅烷 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 、 三氟乙酸酐 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 4.34h， 生成 (5R,11S)-11-((E)-4-mercaptobut-1-en-1-yl)-5-methyl-10-oxa-3,17-dithia-7,14,19,20-tetraazatricyclo[14.2.1.1(2,5)]icosa-1(18),2(20),16(19)-triene-6,9,13-trione
  参考文献：
  名称：

  Total synthesis of largazole and analogues: HDAC inhibition, antiproliferative activity and metabolic stability

  摘要：

  The total synthesis of largazole and four analogues is reported. All analogues were nanomolar HDAC inhibitors. The antiproliferative activity is driven by lipophilicity and cell permeability. In murine liver homogenates, largazole is rapidly metabolized (half-life <= 5 min) to the thiol which has a half-life of 51 min. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.024

文献信息

• Total synthesis of largazole and analogues: HDAC inhibition, antiproliferative activity and metabolic stability
  作者：Hanae Benelkebir、Sabrina Marie、Annette L. Hayden、Jason Lyle、Paul M. Loadman、Simon J. Crabb、Graham Packham、A. Ganesan

  DOI：10.1016/j.bmc.2011.02.024

  日期：2011.6

  The total synthesis of largazole and four analogues is reported. All analogues were nanomolar HDAC inhibitors. The antiproliferative activity is driven by lipophilicity and cell permeability. In murine liver homogenates, largazole is rapidly metabolized (half-life <= 5 min) to the thiol which has a half-life of 51 min. (C) 2011 Elsevier Ltd. All rights reserved.