(2Z)-3-(3-吡啶基)丙烯酸 | 155170-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: (2Z)-3-(3-吡啶基)丙烯酸
• 英文名称: (Z)-3-(pyridin-3-yl)acrylic acid
• 英文别名: (Z)-3-pyridin-3-ylprop-2-enoic acid
• CAS: 155170-47-1
• 化学式: C₈H₇NO₂
• 分子量: 149.149
• InChiKey: VUVORVXMOLQFMO-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-噻吩硫醇 、 (2Z)-3-(3-吡啶基)丙烯酸 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 以96%的产率得到3-Pyridin-3-yl-3-(thiophen-2-ylsulfanyl)-propionic acid
  参考文献：
  名称：

  Utilization of .alpha.,.beta.-unsaturated acids as Michael acceptors for the synthesis of thieno[2,3-b]thiopyrans

  摘要：

  DOI：

  10.1021/jo00236a003
• 作为产物：
  描述：

  3-(3'-pyridinyl)-(Z)-propenoic acid ethyl ester 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以53%的产率得到(2Z)-3-(3-吡啶基)丙烯酸
  参考文献：
  名称：

  Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors

  摘要：

  1-O-cis-Cinnamoyl-beta-D-glucopyranose is one of the most potent allelochemicals that has been isolated from Spiraea thunbergii Sieb by Hiradate et al. It derives its strong inhibitory activity from cis-cinnamic acid (cis-CA), which is crucial for phytotoxicity. By preparing and assaying a series of cis-CA analogues, it was previously found that the key features of cis-CA for lettuce root growth inhibition are a phenyl ring, cis-configuration of the alkene moiety, and carboxylic acid. On the basis of a structure-activity relationship study, the substituent effects on the aromatic ring of cis-CA were examined by systematic synthesis and the lettuce root growth inhibition assay of a series of cis-CA analogues having substituents on the aromatic ring. While ortho- and para-substituted analogues exhibited low potency in most cases, meta-substitution was not critical for potency, and analogues having a hydrophobic and sterically small substituent were more likely to be potent. Finally, several cis-CA analogues were found to be more potent root growth inhibitors than cis-CA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.08.013

文献信息

• [EN] MULTICYCLIC COMPOUNDS AND METHODS OF USING SAME<br/>[FR] COMPOSÉS MULTICYCLIQUES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：KARYOPHARM THERAPEUTICS INC

  公开号：WO2015042414A8

  公开（公告）日：2015-08-06
• MODULATORS OF THE INTEGRATED STRESS PATHWAY
  申请人：Calico Life Sciences LLC

  公开号：EP3704094A1

  公开（公告）日：2020-09-09
• Multicyclic Compounds And Methods Of Using Same
  申请人：KARYOPHARM THERAPEUTICS INC.

  公开号：US20170096417A1

  公开（公告）日：2017-04-06

  The invention generally relates to compounds represented by Structural Formula I: or a pharmaceutically acceptable salt thereof, wherein the variables are as defined and described herein. The invention also includes the synthesis and use of a compound of structural formula I, or a pharmaceutically acceptable salt or composition thereof, e.g., in treatment of cancer (e.g., mantle cell lymphoma), and other diseases and disorders (e.g., PAK-mediated, for example, PAK4-mediated, diseases and disorders).
• US9994558B2
  申请人：——

  公开号：US9994558B2

  公开（公告）日：2018-06-12
• Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors
  作者：Keisuke Nishikawa、Hiroshi Fukuda、Masato Abe、Kazunari Nakanishi、Tomoya Taniguchi、Takashi Nomura、Chihiro Yamaguchi、Syuntaro Hiradate、Yoshiharu Fujii、Katsuhiro Okuda、Mitsuru Shindo

  DOI：10.1016/j.phytochem.2013.08.013

  日期：2013.12

  1-O-cis-Cinnamoyl-beta-D-glucopyranose is one of the most potent allelochemicals that has been isolated from Spiraea thunbergii Sieb by Hiradate et al. It derives its strong inhibitory activity from cis-cinnamic acid (cis-CA), which is crucial for phytotoxicity. By preparing and assaying a series of cis-CA analogues, it was previously found that the key features of cis-CA for lettuce root growth inhibition are a phenyl ring, cis-configuration of the alkene moiety, and carboxylic acid. On the basis of a structure-activity relationship study, the substituent effects on the aromatic ring of cis-CA were examined by systematic synthesis and the lettuce root growth inhibition assay of a series of cis-CA analogues having substituents on the aromatic ring. While ortho- and para-substituted analogues exhibited low potency in most cases, meta-substitution was not critical for potency, and analogues having a hydrophobic and sterically small substituent were more likely to be potent. Finally, several cis-CA analogues were found to be more potent root growth inhibitors than cis-CA. (C) 2013 Elsevier Ltd. All rights reserved.