tert-butyl N-[2-(pent-4-enoylamino)phenyl] carbamate | 1132667-46-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl N-[2-(pent-4-enoylamino)phenyl] carbamate
• 英文别名: tert-butyl N-[2-(pent-4-enoylamino)phenyl]carbamate
• CAS: 1132667-46-9
• 化学式: C₁₆H₂₂N₂O₃
• mdl: MFCD24392661
• 分子量: 290.362
• InChiKey: IIOUZJWQMZJDGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[2-(pent-4-enoylamino)phenyl] carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (E)-N-(2-aminophenyl)-5-[(5R,8S,11S)-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]pent-4-enamide
  参考文献：
  名称：

  [EN] METHOD FOR PREPARING LARGAZOLE ANALOGS AND USES THEREOF
  [FR] PROCÉDÉ DE PRÉPARATION DE PARTICULES CREUSES ET LEURS UTILISATIONS

  摘要：

  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。

  公开号：

  WO2016144665A1
• 作为产物：
  描述：

  4-戊烯酰氯 、 N-Boc-1,2-亚苯基二胺 在 吡啶 作用下， 反应 1.0h， 以67%的产率得到tert-butyl N-[2-(pent-4-enoylamino)phenyl] carbamate
  参考文献：
  名称：

  Cross metathesis with hydroxamate and benzamide BOC-protected alkenes to access HDAC inhibitors and their biological evaluation highlighted intrinsic activity of BOC-protected dihydroxamates

  摘要：

  Conditions for the metathesis of alkenes in the convergent synthesis of HDAC inhibitors have been improved by continuous catalyst flow injection in the reaction media. Intermediate and target compounds obtained were tested for their ability to induce HDAC inhibition and tubulin acetylation, revealing the key role of the tert-butyloxycarbonyl (BOC) group for more HDAC6 selectivity. Molecular modelling added rationale for this BOC effect. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.011

文献信息

• Method for preparing largazole analogs and uses thereof
  申请人：Williams Robert M.

  公开号：US20100029731A1

  公开（公告）日：2010-02-04

  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。
• Extending Cross Metathesis To Identify Selective HDAC Inhibitors: Synthesis, Biological Activities, and Modeling
  作者：Samuel Bouchet、Camille Linot、Dusan Ruzic、Danica Agbaba、Benoit Fouchaq、Joëlle Roche、Katarina Nikolic、Christophe Blanquart、Philippe Bertrand

  DOI：10.1021/acsmedchemlett.8b00440

  日期：2019.6.13

  of a new small series of human histone deacetylases (HDAC) inhibitors. Alkenes bearing Boc-protected hydroxamic acid and benzamide and trityl-protected thiols were used to provide the zinc binding groups and were reacted with alkenes bearing aromatic cap groups. One compound was identified as a selective HDAC6 inhibitor lead. Additional biological evaluation in cancer cell lines demonstrated its ability

  烯烃的不对称交叉复分解作为一种收敛的通用合成策略，允许制备新的小系列人组蛋白脱乙酰基酶（HDAC）抑制剂。带有Boc保护的异羟肟酸和苯甲酰胺和三苯甲基保护的硫醇的烯烃被用来提供锌结合基团，并与带有芳族封端基团的烯烃反应。一种化合物被鉴定为选择性HDAC6抑制剂。癌细胞系中的其他生物学评估表明，它具有刺激上皮标记物E-钙粘着蛋白和肿瘤抑制基因（如SEMA3F和p21）表达的能力，表明该化合物在肺癌治疗中的潜在用途。所有11种HDAC同工型上的分子对接用于使观察到的生物学结果合理化。
• Synthesis and Histone Deacetylase Inhibitory Activity of Largazole Analogs: Alteration of the Zinc-Binding Domain and Macrocyclic Scaffold
  作者：Albert A. Bowers、Nathan West、Tenaya L. Newkirk、Annie E. Troutman-Youngman、Stuart L. Schreiber、Olaf Wiest、James E. Bradner、Robert M. Williams

  DOI：10.1021/ol900078k

  日期：2009.3.19

  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.
• [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。
• Cross metathesis with hydroxamate and benzamide BOC-protected alkenes to access HDAC inhibitors and their biological evaluation highlighted intrinsic activity of BOC-protected dihydroxamates
  作者：Vincent Zwick、Alessandra Nurisso、Claudia Simões-Pires、Samuel Bouchet、Nadine Martinet、Attila Lehotzky、Judit Ovadi、Muriel Cuendet、Christophe Blanquart、Philippe Bertrand

  DOI：10.1016/j.bmcl.2015.11.011

  日期：2016.1

  Conditions for the metathesis of alkenes in the convergent synthesis of HDAC inhibitors have been improved by continuous catalyst flow injection in the reaction media. Intermediate and target compounds obtained were tested for their ability to induce HDAC inhibition and tubulin acetylation, revealing the key role of the tert-butyloxycarbonyl (BOC) group for more HDAC6 selectivity. Molecular modelling added rationale for this BOC effect. (C) 2015 Elsevier Ltd. All rights reserved.