2-(3-Cyanophenyl)ethyl methanesulfonate | 655250-92-3

• 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: 2-(3-Cyanophenyl)ethyl methanesulfonate
• 英文别名: 2-(3-cyanophenyl)ethyl methanesulfonate
• CAS: 655250-92-3
• 化学式: C₁₀H₁₁NO₃S
• 分子量: 225.268
• InChiKey: CVADGFMFLLMIII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  75.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-Cyanophenyl)ethyl methanesulfonate 在 四氯化钛 、 sodium hydride 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 19.08h， 生成 (S)-3-hydroxy-1-((R)-4-isopropyl-2-thioxothiazolidin-3-yl)-3-(3-(2-(tritylthio)ethyl)phenyl)propan-1-one
  参考文献：
  名称：

  Evaluation of class I HDAC isoform selectivity of largazole analogues

  摘要：

  Largazole is a potent class I selective histone deacetylase (HDAC) inhibitor. The majority of largazole analogues to date have modified the thiazole-thiazoline and the warhead moiety. In order to elucidate class I-specific structure-activity relationships, a series of analogues with modifications in the valine or the linker region were prepared and evaluated for their class I isoform selectivity. The inhibition profile showed that the C2 position of largazole has an optimal steric requirement for efficient HDAC inhibition and that substitution of the trans-alkene in the linker with an aromatic group results in complete loss of activity. This data will aid the design of class I isoform selective HDAC inhibitors.

  DOI：

  10.1016/j.bmcl.2014.07.006
• 作为产物：
  描述：

  甲基磺酰氯 、 2-(3-氰基苯基)乙醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-(3-Cyanophenyl)ethyl methanesulfonate
  参考文献：
  名称：

  Evaluation of class I HDAC isoform selectivity of largazole analogues

  摘要：

  Largazole is a potent class I selective histone deacetylase (HDAC) inhibitor. The majority of largazole analogues to date have modified the thiazole-thiazoline and the warhead moiety. In order to elucidate class I-specific structure-activity relationships, a series of analogues with modifications in the valine or the linker region were prepared and evaluated for their class I isoform selectivity. The inhibition profile showed that the C2 position of largazole has an optimal steric requirement for efficient HDAC inhibition and that substitution of the trans-alkene in the linker with an aromatic group results in complete loss of activity. This data will aid the design of class I isoform selective HDAC inhibitors.

  DOI：

  10.1016/j.bmcl.2014.07.006

文献信息

• [EN] BIS(SULFONAMIDE) DERIVATIVES AND THEIR USE AS MPGES INHIBITORS<br/>[FR] DÉRIVÉS DE BIS (SULFONAMIDE) ETLEUR UTILISATION COMME INHIBITEURS DE MPGES
  申请人：ACTURUM LIFE SCIENCE AB

  公开号：WO2016085391A1

  公开（公告）日：2016-06-02

  The present invention relates to bis(sulfonamide) compounds and pharmaceutically acceptable salts thereof. The present invention also relates to pharmaceutical compositions comprising these compounds and to their use as a medicament for the treatment and/or prevention of a disease, disorder or condition in which modulation of microsomal prostaglandin E synthase-1 activity is beneficial, such as pain, inflammation and cancer.

  本发明涉及双(磺酰胺)化合物及其药用盐。本发明还涉及包含这些化合物的药物组合物，以及它们作为药物用于治疗和/或预防微粒体前列腺素E合成酶-1活性调节有益的疾病、紊乱或状况，如疼痛、炎症和癌症。
• Bis(sulfonamide) derivatives and their use as mPGES inhibitors
  申请人：Acturum Real Estate AB

  公开号：US10227296B2

  公开（公告）日：2019-03-12

  The present invention relates to bis(sulfonamide) compounds and pharmaceutically acceptable salts thereof. The present invention also relates to pharmaceutical compositions comprising these compounds and to their use as a medicament for the treatment and/or prevention of a disease, disorder or condition in which modulation of microsomal prostaglandin E synthase-1 activity is beneficial, such as pain, inflammation and cancer.

  本发明涉及双磺酰胺化合物及其药学上可接受的盐类。本发明还涉及包含这些化合物的药物组合物，以及它们作为药物用于治疗和/或预防微粒体前列腺素 E 合酶-1 活性调节有益的疾病、紊乱或病症，如疼痛、炎症和癌症。
• [EN] MACROCYCLIC COMPOUNDS AND METHODS OF TREATMENT<br/>[FR] COMPOSÉS MACROCYCLIQUES ET MÉTHODES DE TRAITEMENT ASSOCIÉES
  申请人：UNIV FLORIDA

  公开号：WO2015200699A3

  公开（公告）日：2016-05-26
• BIS(SULFONAMIDE) DERIVATIVES AND THEIR USE AS MPGES INHIBITORS
  申请人：Acturum Real Estate AB

  公开号：EP3224241A1

  公开（公告）日：2017-10-04
• Evaluation of class I HDAC isoform selectivity of largazole analogues
  作者：Bumki Kim、Heekwang Park、Lilibeth A. Salvador、Patrick E. Serrano、Jason C. Kwan、Sabrina L. Zeller、Qi-Yin Chen、Soyoung Ryu、Yanxia Liu、Seongrim Byeon、Hendrik Luesch、Jiyong Hong

  DOI：10.1016/j.bmcl.2014.07.006

  日期：2014.8

  Largazole is a potent class I selective histone deacetylase (HDAC) inhibitor. The majority of largazole analogues to date have modified the thiazole-thiazoline and the warhead moiety. In order to elucidate class I-specific structure-activity relationships, a series of analogues with modifications in the valine or the linker region were prepared and evaluated for their class I isoform selectivity. The inhibition profile showed that the C2 position of largazole has an optimal steric requirement for efficient HDAC inhibition and that substitution of the trans-alkene in the linker with an aromatic group results in complete loss of activity. This data will aid the design of class I isoform selective HDAC inhibitors.