[2-tert-butyl-4-((E)-2-cyanoethenesulfonyl)phenoxy]acetic acid | 1394819-48-7

• 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-tert-butyl-4-((E)-2-cyanoethenesulfonyl)phenoxy]acetic acid
• 英文别名: [2-tert-Butyl-4-((E)-2-cyano-ethenesulfonyl)-phenoxy]-acetic acid；2-[2-tert-butyl-4-[(E)-2-cyanoethenyl]sulfonylphenoxy]acetic acid
• CAS: 1394819-48-7
• 化学式: C₁₅H₁₇NO₅S
• 分子量: 323.37
• InChiKey: ZNYCOILWEZPTAP-XBXARRHUSA-N

物化性质

• 沸点：
  550.4±50.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [2-tert-butyl-4-((E)-2-cyanoethenesulfonyl)phenoxy]acetic acid 在 甲烷磺酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 3.0h， 生成 (E)-3-[3-tert-butyl-4-(5-methylbenzoxazol-2-ylmethoxy)benzenesulfonyl]acrylonitrile
  参考文献：
  名称：

  [EN] VINYL -ARYL - SULFONES FOR USE IN PERITONEAL CARCINOMATOSIS
  [FR] COMPOSÉS SOUFRÉS AROMATIQUES SUBSTITUÉS ET PROCÉDÉS DE LEUR UTILISATION

  摘要：

  公开号：

  WO2012116151A3
• 作为产物：
  描述：

  2-(4-bromo-2-tert-butylphenoxy)acetic acid 在 溶剂黄146 、 苯基锂 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 1.66h， 生成 [2-tert-butyl-4-((E)-2-cyanoethenesulfonyl)phenoxy]acetic acid
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Sulfonyl Acrylonitriles as Novel Inhibitors of Cancer Metastasis and Spread

  摘要：

  The spread of intra-abdominal cancers is a vexing clinical problem for which there is no widely effective treatment. We discovered previously that (2E)-3-[(4-tert-butylphenyl)sulfonyl]acrylonitrile (1) induced cancer cell apoptosis during adhesion to normal mesothelial cells which line the peritoneum. We recently demonstrated that the sulfonylacrylonitrile portion of 1 and hydrophobic aryl substitution were essential for pro-apoptotic activity in cancer cells. Here we synthesized a diverse series of analogues of 1 in order to improve the efficacy and pharmaceutical properties. Analogues and 1 were compared in their ability to cause cancer cell death during adhesion to normal mesothelial cell monolayers. Potent analogues identified in the in vitro assay were validated and found to exhibit improved inhibition of intra-abdominal cancer in two clinically relevant murine models of ovarian and pancreatic cancer spread and metastasis, highlighting their potential clinical use as an adjunct to surgical resection of cancers.

  DOI：

  10.1021/jm501437v

文献信息

• Substituted Aromatic Sulfur Compounds and Methods of Their Use
  申请人：Cephalon, Inc.

  公开号：US20140005175A1

  公开（公告）日：2014-01-02

  Compounds of formula II are described: wherein D, n, R a , R b , and R c are as herein defined, along with pharmaceutical compositions and methods of using compounds of formula II for treating or reducing the risk of peritoneal carcinomatosis in a patient.

  描述了化学式II的化合物：其中D、n、Ra、Rb和Rc的定义如本文所述，以及使用化学式II的化合物治疗或减少患者腹膜癌转移风险的药物组合物和方法。
• US9475766B2
  申请人：——

  公开号：US9475766B2

  公开（公告）日：2016-10-25
• [EN] SUBSTITUTED AROMATIC SULFUR COMPOUNDS AND METHODS OF THEIR USE<br/>[FR] COMPOSÉS SOUFRÉS AROMATIQUES SUBSTITUÉS ET PROCÉDÉS DE LEUR UTILISATION
  申请人：CEPHALON INC

  公开号：WO2012116151A2

  公开（公告）日：2012-08-30

  Compounds of formula II are described, wherein D, n, Ra, Rb, and Rc are as herein defined, along with pharmaceutical compositions and methods of using compounds of formula II for treating or reducing the risk of peritoneal carcinomatosis in a patient.
• Design, Synthesis, and Biological Evaluation of Sulfonyl Acrylonitriles as Novel Inhibitors of Cancer Metastasis and Spread
  作者：Yi Shen、Craig A. Zificsak、Jill E. Shea、Xuegang Lao、Oana Bollt、Xiufen Li、Joseph G. Lisko、Jay P. Theroff、Courtney L. Scaife、Mark A. Ator、Bruce A. Ruggeri、Bruce D. Dorsey、Scott K. Kuwada

  DOI：10.1021/jm501437v

  日期：2015.2.12

  The spread of intra-abdominal cancers is a vexing clinical problem for which there is no widely effective treatment. We discovered previously that (2E)-3-[(4-tert-butylphenyl)sulfonyl]acrylonitrile (1) induced cancer cell apoptosis during adhesion to normal mesothelial cells which line the peritoneum. We recently demonstrated that the sulfonylacrylonitrile portion of 1 and hydrophobic aryl substitution were essential for pro-apoptotic activity in cancer cells. Here we synthesized a diverse series of analogues of 1 in order to improve the efficacy and pharmaceutical properties. Analogues and 1 were compared in their ability to cause cancer cell death during adhesion to normal mesothelial cell monolayers. Potent analogues identified in the in vitro assay were validated and found to exhibit improved inhibition of intra-abdominal cancer in two clinically relevant murine models of ovarian and pancreatic cancer spread and metastasis, highlighting their potential clinical use as an adjunct to surgical resection of cancers.
• [EN] VINYL -ARYL - SULFONES FOR USE IN PERITONEAL CARCINOMATOSIS<br/>[FR] COMPOSÉS SOUFRÉS AROMATIQUES SUBSTITUÉS ET PROCÉDÉS DE LEUR UTILISATION
  申请人：CEPHALON INC

  公开号：WO2012116151A3

  公开（公告）日：2013-01-03