trans-3-(5-ethylfuran-2-yl)propenoic acid | 1310567-98-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: trans-3-(5-ethylfuran-2-yl)propenoic acid
• 英文别名: 3-(5-Ethylfuran-2-yl)prop-2-enoic acid；(E)-3-(5-ethylfuran-2-yl)prop-2-enoic acid
• CAS: 1310567-98-6
• 化学式: C₉H₁₀O₃
• mdl: MFCD03002770
• 分子量: 166.177
• InChiKey: COIVWIYBIUGQGM-AATRIKPKSA-N

物化性质

• 沸点：
  277.5±25.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丙二酸 、 5-乙基-2-糠醛 在 哌啶 作用下， 以 吡啶 为溶剂， 反应 3.0h， 以74%的产率得到trans-3-(5-ethylfuran-2-yl)propenoic acid
  参考文献：
  名称：

  Structure–activity relationships of trans-substituted-propenoic acid derivatives on the nicotinic acid receptor HCA2 (GPR109A)

  摘要：

  Nicotinic acid (niacin) has been used for decades as an antidyslipidemic drug in man. Its main target is the hydroxy-carboxylic acid receptor HCA2 (GPR109A), a G protein-coupled receptor. Other acids and esters such as methyl fumarate also interact with the receptor, which constituted the basis for the current study. We synthesized a novel series of substituted propenoic acids, such as fumaric acid esters, fumaric acid amides and cinnamic acid derivatives, and determined their affinities for the HCA2 receptor. We observed a rather restricted binding pocket on the receptor with trans-cinnamic acid being the largest planar ligand in our series with appreciable affinity for the receptor. Molecular modeling and analysis of the structure-activity relationships in the series suggest a planar trans-propenoic acid pharmacophore with a maximum length of 8 angstrom and out-of-plane orientation of the larger substituents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.091

文献信息

• [EN] (E)-4-(4-ACRYLAMIDOPHENOXY)-N-METHYLPICOLINAMIDE CONJUGATES AS POTENTIAL ANTICANCER AGENTS<br/>[FR] CONJUGUÉS DE (E)-4-(4-ACRYLAMIDOPHÉNOXY)-N-MÉTHYLPICOLINAMIDE EN TANT QU'AGENTS POTENTIELS CONTRE LE CANCER
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2017125946A1

  公开（公告）日：2017-07-27

  The present invention relates to a compound of formula A useful as potential anticancer agents against human cancer cell lines and process for the preparation thereof.

  本发明涉及一种化合物A，其可用作潜在的抗人癌细胞系的抗癌剂，以及其制备方法。
• (E)-4-(4-acrylamidophenoxy)-N-methylpicolinamide conjugates as potential anticancer agents
  申请人：Council of Scientific & Industrial Research

  公开号：US11174230B2

  公开（公告）日：2021-11-16

  The present invention relates to a compound of formula A useful as potential anticancer agents against human cancer cell lines and process for the preparation thereof.

  本发明涉及一种可用作人类癌细胞株潜在抗癌剂的式 A 化合物及其制备工艺。
• (E)-4-(4-ACRYLAMIDOPHENOXY)-N-METHYLPICOLINAMIDE CONJUGATES AS POTENTIAL ANTICANCER AGENTS
  申请人：Council of Scientific & Industrial Research

  公开号：US20210163413A1

  公开（公告）日：2021-06-03

  The present invention relates to a compound of formula A useful as potential anticancer agents against human cancer cell lines and process for the preparation thereof.
• US5514679A
  申请人：——

  公开号：US5514679A

  公开（公告）日：1996-05-07
• US5567717A
  申请人：——

  公开号：US5567717A

  公开（公告）日：1996-10-22