2-[4-((E)-2-cyanoethenesulfonyl)phenyl]-2-methylpropionic acid | 1356089-38-7

• 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-[4-((E)-2-cyanoethenesulfonyl)phenyl]-2-methylpropionic acid
• 英文别名: (E)-2-(4-((2-Cyanovinyl)sulfonyl)phenyl)-2-methylpropanoic acid；2-[4-[(E)-2-cyanoethenyl]sulfonylphenyl]-2-methylpropanoic acid
• CAS: 1356089-38-7
• 化学式: C₁₃H₁₃NO₄S
• 分子量: 279.317
• InChiKey: KXIUDNVQBXMHAA-YCRREMRBSA-N

物化性质

• 沸点：
  506.8±50.0 °C(Predicted)
• 密度：
  1.314±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2926909090
• 危险性防范说明：
  P501,P270,P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313,P301+P312+P330
• 危险性描述：
  H302,H315,H319

反应信息

• 作为反应物：
  描述：

  2-[4-((E)-2-cyanoethenesulfonyl)phenyl]-2-methylpropionic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 6.0h， 生成 (E)-3-{4-[1-(5-cyclohexyl[1,3,4]oxadiazol-2-yl)-1-methylethyl]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-溴苯基)-2-甲基丙酸 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-[4-((E)-2-cyanoethenesulfonyl)phenyl]-2-methylpropionic acid
  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

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。
• 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.
• Synthesis and biological evaluation of sulfonyl acrylonitriles as novel inhibitors to peritoneal carcinomatosis
  作者：Craig A. Zificsak、Yi Shen、Joseph G. Lisko、Jay P. Theroff、Xuegang Lao、Oana Bollt、Xiufen Li、Bruce D. Dorsey、Scott K. Kuwada

  DOI：10.1016/j.bmcl.2012.01.085

  日期：2012.3

  The vast majority of cancer patients die from metastasis, the process by which cancer cells spread to secondary tissues through body fluids. Peritoneal carcinomatosis is a type of metastasis in which cancer cells gain access to the intra-abdominal cavity and then implant in the peritoneum, the thin tissue that lines the abdominal wall and internal organs. Unfortunately, peritoneal carcinomatosis can occur following surgical resection of intra-abdominal malignancies. We previously reported proapoptotic activity of (2E)-3-[[4-(1,1-dimethylethyl) phenyl] sulfonyl]-2-propenenitrile (BAY 11-7085, 1) on colon and pancreatic cancer cells during adhesion and demonstrated that this compound could significantly inhibit peritoneal carcinomatosis in mice.(1,2) In order to determine the chemical basis of the anti-metastatic properties of BAY 11-7085, a series of analogs were synthesized and evaluated for their ability to induce apoptosis in pancreatic and ovarian cancer cells during adhesion to mesothelial cells, which line the surface of the peritoneum. The co-culture assay results were validated using a murine peritoneal carcinomatosis model. These analogs may greatly benefit patients undergoing surgical resections of colorectal, pancreatic, and ovarian cancers depending on their tolerability. (c) 2012 Elsevier Ltd. All rights reserved.
• 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.