(E)-2-methyl-3-(4-phenylthiophen-2-yl)acrylic acid | 941281-24-9

• 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: (E)-2-methyl-3-(4-phenylthiophen-2-yl)acrylic acid
• 英文别名: (E)-2-methyl-3-(4-phenyl-thiophen-2-yl)-acrylic acid；(E)-2-methyl-3-(4-phenylthiophen-2-yl)prop-2-enoic acid
• CAS: 941281-24-9
• 化学式: C₁₄H₁₂O₂S
• 分子量: 244.314
• InChiKey: WTNVILKJFASWTL-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-methyl-3-(4-phenylthiophen-2-yl)acrylic acid 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 2-Methyl-3-(4-phenyl-thiophen-2-yl)-acryloyl azide
  参考文献：
  名称：

  Compounds

  摘要：

  描述了一种钾通道抑制剂的噻吡啶类化合物。还披露了包括这些化合物的药物组合物以及它们在治疗或预防癌症、心律失常、自身免疫疾病和炎症性疾病中的用途，包括胃癌、心房颤动、2型糖尿病、类风湿性关节炎、1型糖尿病、炎症性肠道疾病和多发性硬化等脱髓鞘疾病。

  公开号：

  US20070161672A1
• 作为产物：
  描述：

  4-溴-2-噻吩甲醛 在 哌啶 、 吡啶 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.08h， 生成 (E)-2-methyl-3-(4-phenylthiophen-2-yl)acrylic acid
  参考文献：
  名称：

  Design and synthesis of natural product derivatives with selective and improved cytotoxicity based on a sesquiterpene scaffold

  摘要：

  Brasilamide E (1) is a bisabolane sesquiterpenoid isolated from the solid-substrate fermentation cultures of a plant endophytic fungus Paraconiothyrium brasiliense. The compound specifically inhibited proliferation of the MCF-7 cells, but did not show cytotoxicity towards the negative controls HaCaT and NIH3T3 cells (IC50 > 50 mu M). To improve its potency while maintain selectivity, a total of 27 derivatives of 1 were designed, synthesized, and evaluated for in vitro cytotoxicity against six tumor cell lines and the negative control NIH3T3 cells. Among these compounds, compound 12b showed significantly improved potency against the MCF-7, HeLa, and HO8910 cells with IC50 values of 0.13-0.25 mu M compared to 1 (IC50 8.47-18.00 mu M), and remained nontoxic to the NIH3T3 cells. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.03.022

文献信息

• Thieno[3,2-c]pyridine potassium channel inhibitors
  申请人：Ford John

  公开号：US09216992B2

  公开（公告）日：2015-12-22

  The present invention provides thienopyridine compounds which are potassium channel inhibitors. In another embodiment, the invention provides pharmaceutical compositions comprising thienopyridines. In another embodiment, the invention provides methods of using thienopyridines in the treatment or prevention of cancer, arrhythmias, autoimmune diseases and inflammatory diseases, including gastric cancer, atrial fibrillation, type-2 diabetes mellitus, rheumatoid arthritis, type-1 diabetes, inflammatory bowel disorder and demyelinating disorders such as multiple sclerosis.

  本发明提供了一种钾通道抑制剂-噻吩嘧啶化合物。在另一实施方案中，本发明提供了包含噻吩嘧啶的药物组合物。在另一实施方案中，本发明提供了使用噻吩嘧啶治疗或预防癌症、心律失常、自身免疫性疾病和炎症性疾病的方法，包括胃癌、心房颤动、2型糖尿病、类风湿性关节炎、1型糖尿病、炎症性肠病和多发性硬化等脱髓鞘疾病。
• THIENO (3,2-C) PYRIDINE COMPOUNDS
  申请人：Xention Discovery Ltd.

  公开号：EP1968982A2

  公开（公告）日：2008-09-17
• US9216992B2
  申请人：——

  公开号：US9216992B2

  公开（公告）日：2015-12-22
• [EN] COMPOUNDS<br/>[FR] COMPOSES
  申请人：XENTION DISCOVERY LTD

  公开号：WO2007066127A2

  公开（公告）日：2007-06-14

  [EN] Thienopyridine compounds which are potassium channel inhibitors are described. Pharmaceutical compositions comprising the compounds and their use in the treatment or prevention of cancer, arrhythmias, autoimmune diseases and inflammatory diseases, including gastric cancer, atrial fibrillation, type-2 diabetes mellitus, rheumatoid arthritis, type-1 diabetes, inflammatory bowel disorder and demyelinating disorders such as multiple sclerosis are also disclosed.
  [FR] La présente invention concerne des composés de thiénopyridine qui sont des inhibiteurs des canaux potassiques. L'invention concerne également des compositions pharmaceutiques comprenant les composés et leur utilisation dans le traitement ou la prévention du cancer, des arythmies, des maladies auto-immunes et des maladies inflammatoires, y compris le cancer de l'estomac, la fibrillation atriale, le diabète sucré de type 2, la polyarthrite rhumatoïde, le diabète de type 1, les affections abdominales inflammatoires et les troubles de démyélinisation tels que la sclérose en plaques.
• Design and synthesis of natural product derivatives with selective and improved cytotoxicity based on a sesquiterpene scaffold
  作者：Yang Zhang、Zhuowei Zhang、Bo Wang、Ling Liu、Yongsheng Che

  DOI：10.1016/j.bmcl.2016.03.022

  日期：2016.4

  Brasilamide E (1) is a bisabolane sesquiterpenoid isolated from the solid-substrate fermentation cultures of a plant endophytic fungus Paraconiothyrium brasiliense. The compound specifically inhibited proliferation of the MCF-7 cells, but did not show cytotoxicity towards the negative controls HaCaT and NIH3T3 cells (IC50 > 50 mu M). To improve its potency while maintain selectivity, a total of 27 derivatives of 1 were designed, synthesized, and evaluated for in vitro cytotoxicity against six tumor cell lines and the negative control NIH3T3 cells. Among these compounds, compound 12b showed significantly improved potency against the MCF-7, HeLa, and HO8910 cells with IC50 values of 0.13-0.25 mu M compared to 1 (IC50 8.47-18.00 mu M), and remained nontoxic to the NIH3T3 cells. (C) 2016 Elsevier Ltd. All rights reserved.