(E)-2-cyano-3-(4-(piperidin-1-yl)phenyl)acrylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (E)-2-cyano-3-(4-(piperidin-1-yl)phenyl)acrylic acid
• 英文别名: (E)-2-cyano-3-(4-piperidin-1-ylphenyl)prop-2-enoic acid
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: JADPBIFXTKFCDU-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-苯基哌啶 在 哌啶 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 生成 (E)-2-cyano-3-(4-(piperidin-1-yl)phenyl)acrylic acid
  参考文献：
  名称：

  Monocarboxylate Transporter 1 Inhibitors as Potential Anticancer Agents

  摘要：

  Potent monocarboxylate transporter I inhibitors (MCTI) have been developed based on alpha-cyano-4-hydroxycinnamic acid template. Structure-activity relationship studies demonstrate that the introduction of p-N, N-dialkyl/diaryl, and o-methoxy groups into cyanocinnamic acid has maximal MCT1 inhibitory activity. Systemic toxicity studies in healthy ICR mice with few potent MCTI inhibitors indicate normal body weight gains in treated animals. In vivo tumor growth inhibition studies in colorectal adenocarcinoma (WiDr cell line) in nude mice xenograft models establish that compound 27 exhibits single agent activity in inhibiting the tumor growth.

  DOI：

  10.1021/acsmedchemlett.5b00049

文献信息

• THERAPEUTIC COMPOUNDS
  申请人：Regents of the University of Minnesota

  公开号：US20140371272A1

  公开（公告）日：2014-12-18

  The invention provides compounds of formula (I) or a salt thereof as described herein. The invention also provides pharmaceutical compositions comprising a compound of formula (I), processes for preparing compounds of formula (I), intermediates useful for preparing compounds of formula (I) and therapeutic methods for treating cancer or treating autoimmune diseases or preventing transplant rejection using compounds of formula (I).
• US9296728B2
  申请人：——

  公开号：US9296728B2

  公开（公告）日：2016-03-29
• US9573888B2
  申请人：——

  公开号：US9573888B2

  公开（公告）日：2017-02-21
• [EN] THERAPEUTIC COMPOUNDS<br/>[FR] COMPOSÉS THÉRAPEUTIQUES
  申请人：UNIV MINNESOTA

  公开号：WO2013109972A2

  公开（公告）日：2013-07-25

  The invention provides compounds of formula (I) or a salt thereof as described herein. The invention also provides pharmaceutical compositions comprising a compound of formula (I), processes for preparing compounds of formula (I), intermediates useful for preparing compounds of formula (I) and therapeutic methods for treating cancer or treating autoimmune diseases or preventing transplant rejection using compounds of formula (I).
• Monocarboxylate Transporter 1 Inhibitors as Potential Anticancer Agents
  作者：Shirisha Gurrapu、Sravan K. Jonnalagadda、Mohammad A. Alam、Grady L. Nelson、Mary G. Sneve、Lester R. Drewes、Venkatram R. Mereddy

  DOI：10.1021/acsmedchemlett.5b00049

  日期：2015.5.14

  Potent monocarboxylate transporter I inhibitors (MCTI) have been developed based on alpha-cyano-4-hydroxycinnamic acid template. Structure-activity relationship studies demonstrate that the introduction of p-N, N-dialkyl/diaryl, and o-methoxy groups into cyanocinnamic acid has maximal MCT1 inhibitory activity. Systemic toxicity studies in healthy ICR mice with few potent MCTI inhibitors indicate normal body weight gains in treated animals. In vivo tumor growth inhibition studies in colorectal adenocarcinoma (WiDr cell line) in nude mice xenograft models establish that compound 27 exhibits single agent activity in inhibiting the tumor growth.