2,2,2-trichloroethyl (Z)-6-((12Z,22Z,24R,5S,8R)-5-isopropyl-24-methyl-3,6,10-trioxo-24,25-dihydro-7-oxa-4,11-diaza-1(4,2),2(2,4)-dithiazolacyclododecaphane-8-yl)hex-4-enoate | 1132667-15-2

• 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: 2,2,2-trichloroethyl (Z)-6-((12Z,22Z,24R,5S,8R)-5-isopropyl-24-methyl-3,6,10-trioxo-24,25-dihydro-7-oxa-4,11-diaza-1(4,2),2(2,4)-dithiazolacyclododecaphane-8-yl)hex-4-enoate
• CAS: 1132667-15-2
• 化学式: C₂₅H₃₁Cl₃N₄O₆S₂
• 分子量: 654.035
• InChiKey: YQPJVJIMFOVBRI-RCORYJIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  40.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  136.05
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloroethyl (Z)-6-((12Z,22Z,24R,5S,8R)-5-isopropyl-24-methyl-3,6,10-trioxo-24,25-dihydro-7-oxa-4,11-diaza-1(4,2),2(2,4)-dithiazolacyclododecaphane-8-yl)hex-4-enoate 在 ammonium acetate 、 水 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以93%的产率得到(Z)-6-[(5R,8S,11R)-5-methyl-6,9,13-trioxo-8-propan-2-yl-10-oxa-3,17-dithia-7,14,19,20-tetrazatricyclo[14.2.1.12,5]icosa-1(18),2(20),16(19)-trien-11-yl]hex-4-enoic acid
  参考文献：
  名称：

  Synthesis and Histone Deacetylase Inhibitory Activity of Largazole Analogs: Alteration of the Zinc-Binding Domain and Macrocyclic Scaffold

  摘要：

  Fourteen analogs of the marine natural product largazole have been prepared and assayed against histone deacetylases (HDACs) 1, 2, 3, and 6. Olefin cross-metathesis was used to efficiently access six variants of the side-chain zinc-binding domain, while adaptation of our previously reported modular synthesis allowed probing of the macrocyclic cap group.

  DOI：

  10.1021/ol900078k
• 作为产物：
  描述：

  在 N,N-二异丙基乙胺 、 1-羟基苯并三唑 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 16.5h， 生成 2,2,2-trichloroethyl (Z)-6-((12Z,22Z,24R,5S,8R)-5-isopropyl-24-methyl-3,6,10-trioxo-24,25-dihydro-7-oxa-4,11-diaza-1(4,2),2(2,4)-dithiazolacyclododecaphane-8-yl)hex-4-enoate
  参考文献：
  名称：

  Synthesis and Histone Deacetylase Inhibitory Activity of Largazole Analogs: Alteration of the Zinc-Binding Domain and Macrocyclic Scaffold

  摘要：

  Fourteen analogs of the marine natural product largazole have been prepared and assayed against histone deacetylases (HDACs) 1, 2, 3, and 6. Olefin cross-metathesis was used to efficiently access six variants of the side-chain zinc-binding domain, while adaptation of our previously reported modular synthesis allowed probing of the macrocyclic cap group.

  DOI：

  10.1021/ol900078k

文献信息

• [EN] METHOD FOR PREPARING LARGAZOLE ANALOGS AND USES THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION DE PARTICULES CREUSES ET LEURS UTILISATIONS
  申请人：UNIV COLORADO STATE RES FOUND

  公开号：WO2016144665A1

  公开（公告）日：2016-09-15

  Analogs of largazole are described herein. Methods of treating cancer and blood disorders using largazole and largazole analogs and pharmaceutical compositions comprising the same are additionally described herein. Methods for preparing largazole analogs are likewise described.

  本文描述了类似largazole的类似物。此外，还描述了使用largazole和largazole类似物治疗癌症和血液疾病的方法，以及包含它们的药物组合物。同样描述了制备largazole类似物的方法。