(E)-3-(methylsulfonyl)-2-propenoic acid

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: (E)-3-(methylsulfonyl)-2-propenoic acid
• 英文别名: (E)-3-(methylsulfonyl)acrylic acid；(E)-3-methylsulfonylprop-2-enoic Acid
• 化学式: C₄H₆O₄S
• 分子量: 150.155
• InChiKey: KUKIFRWOPQFZKI-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  肼基甲酸叔丁酯 、 (E)-3-(methylsulfonyl)-2-propenoic acid 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以62%的产率得到tert-butyl (E)-2-(3-(methylsulfonyl)acryloyl)hydrazine-1-carboxylate
  参考文献：
  名称：

  Aza vinyl sulfones: Synthesis and evaluation as antiplasmodial agents

  摘要：

  A series of novel aza vinyl sulfones were designed, synthesized in good yields and evaluated as antiplasmodial agents. Tested compounds did not show activity against papain or the Plasmodium falciparum cysteine protease falcipain-2. However, a number of the new compounds effectively inhibited the in vitro development of P. falciparum. Compounds containing a squaramide group were the most active, with IC(50) values between 0.95 and 4.5 mu M, suggesting that these are potential lead compounds for the development of new antimalarial agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.018
• 作为产物：
  描述：

  (E)-3-(甲硫基)丙烯酸 在 间氯过氧苯甲酸 作用下， 生成 (E)-3-(methylsulfonyl)-2-propenoic acid
  参考文献：
  名称：

  Aza vinyl sulfones: Synthesis and evaluation as antiplasmodial agents

  摘要：

  A series of novel aza vinyl sulfones were designed, synthesized in good yields and evaluated as antiplasmodial agents. Tested compounds did not show activity against papain or the Plasmodium falciparum cysteine protease falcipain-2. However, a number of the new compounds effectively inhibited the in vitro development of P. falciparum. Compounds containing a squaramide group were the most active, with IC(50) values between 0.95 and 4.5 mu M, suggesting that these are potential lead compounds for the development of new antimalarial agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.018

文献信息

• An Economical and Convenient Synthesis of Vinyl Sulfones
  作者：Yong-Min Liang、Zheng-Hui Guan、Wei Zuo、Lian-Biao Zhao、Zhi-Hui Ren

  DOI：10.1055/s-2007-966039

  日期：——

  A general process for the efficient synthesis of vinyl sulfones has been developed using commercially available sulfinic acid sodium salts and dibromides. A variety of phenyl and methyl vinyl sulfones have been formed in good yields, in the absence of any catalyst.

  已经使用市售的亚磺酸钠盐和二溴化物开发了一种有效合成乙烯基砜的通用方法。在没有任何催化剂的情况下，各种苯基和甲基乙烯基砜都以良好的收率形成。
• Nrf2 Activating Compounds and Uses Thereof
  申请人：Rigel Pharmaceuticals, Inc.

  公开号：US20170217922A1

  公开（公告）日：2017-08-03

  Aspects of the present disclosure include compounds that activate Nrf2. Such compounds find use in the treatment of autoimmune and inflammatory diseases and disorders, such as for example psoriasis and multiple sclerosis. Embodiments of the present disclosure also relate to pharmaceutical compositions that include these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes.

  本公开涉及激活Nrf2的化合物，这些化合物可用于治疗自身免疫和炎症性疾病和疾患，例如牛皮癣和多发性硬化症。本公开实施例还涉及包括这些化合物的制药组合物，使用这些化合物治疗各种疾病和疾患的方法，制备这些化合物的过程以及这些过程中有用的中间体。
• Synthesis of amides from Glycosmis species: Methylthiopropenoic acid, methylsulfonylpropenoic acid, thiocarbamic acid S-methyl ester, and senecioic acid amides
  作者：Sabine Hinterberger、Otmar Hofer、Harald Greger

  DOI：10.1016/s0040-4020(97)10297-6

  日期：1998.1

  Representative samples of several types of naturally occurring amides from south and southeast Asian Glycosmis species were synthesized for proof of structures and for bioactivity testing. With one exception (senecioic acid) all these amides were characterized by sulfur containing acid components (methylthiopropenoic acid methylsulfonylpropenoic acid and thiocarbamic acid) in combination with phenethylamine derived amino moieties. (C) 1997 Elsevier Science Ltd. All rights reserved.
• Total synthesis and biological evaluation of methylgerambullone
  作者：Jong Taik Moon、Sung Hoon Ha、So Hyung Lee、Tae Hui Kwon、Chun Rim Oh、Young Deuk Kim、Jungahn Kim、Dong Joon Choo、Jae Yeol Lee

  DOI：10.1016/j.bmcl.2009.11.040

  日期：2010.1

  First total synthesis of methylgerambullone (MGB, 1) isolated from Glycosmis angustifolia was completed via a convergent route. The effect of MGB on the contractile responses of the isolated guinea-pig ileum induced by acetylcholine was investigated. As a result, it showed a potent relaxation rate (78.66 +/- 4.30% at 100 mg/L) in a concentration-dependent manner on longitudinal smooth muscle contraction of isolated guinea-pig ileum induced by 1 mu M acetylcholine. (C) 2009 Elsevier Ltd. All rights reserved.
• Aza vinyl sulfones: Synthesis and evaluation as antiplasmodial agents
  作者：Paulo M.C. Glória、Jiri Gut、Lídia M. Gonçalves、Philip J. Rosenthal、Rui Moreira、Maria M.M. Santos

  DOI：10.1016/j.bmc.2011.10.018

  日期：2011.12

  A series of novel aza vinyl sulfones were designed, synthesized in good yields and evaluated as antiplasmodial agents. Tested compounds did not show activity against papain or the Plasmodium falciparum cysteine protease falcipain-2. However, a number of the new compounds effectively inhibited the in vitro development of P. falciparum. Compounds containing a squaramide group were the most active, with IC(50) values between 0.95 and 4.5 mu M, suggesting that these are potential lead compounds for the development of new antimalarial agents. (C) 2011 Elsevier Ltd. All rights reserved.

表征谱图