2-(3,4-dimethoxyphenyl)-3-hydroxyacrylonitrile | 679426-01-8

• 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: 2-(3,4-dimethoxyphenyl)-3-hydroxyacrylonitrile
• 英文别名: 2-(3,4-Dimethoxyphenyl)-3-hydroxyprop-2-enenitrile
• CAS: 679426-01-8
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: XNYVXXJLDCGDPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  62.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,4-dimethoxyphenyl)-3-hydroxyacrylonitrile 在 tris-(dibenzylideneacetone)dipalladium(0) 、 硫酸 、 三溴化磷 、 sodium t-butanolate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 二苯醚 、 甲苯 为溶剂， 反应 7.0h， 生成 tert-butyl (R)-(2-(5-(1-((4-cyano-6,7-dimethoxyisoquinolin-1-yl)amino)ethyl)thiophen-3-yl)benzyl)(methyl)carbamate
  参考文献：
  名称：

  [EN] SOS1 INHIBITORS
  [FR] INHIBITEURS DE SOS1

  摘要：

  本发明涉及抑制七次七相似物1（SOS1）活性的化合物。具体地，本发明涉及化合物、药物组合物和使用方法，例如使用本发明的化合物和药物组合物治疗癌症的方法。

  公开号：

  WO2021173524A1
• 作为产物：
  描述：

  3-hydroxy-2-(3,4-dimethoxyphenyl)acrylonitrile sodium salt 在 溶剂黄146 作用下， 以 水 为溶剂， 以96%的产率得到2-(3,4-dimethoxyphenyl)-3-hydroxyacrylonitrile
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Novel Thienopyrrolizinones as Antitubulin Agents

  摘要：

  Herein, we describe the structure-activity relationship study of a new 3-aryl-8H-thieno[2,3-b]pyrrolizin-8-one series of antitubulin agents. The pharmacological results from the National Cancer Institute in vitro human disease oriented tumor cell line screening allowed us to identify compound 1d (NSC 676693) as a very efficient antitumoral drug in all cancer cell lines tested. This prompted us to define the structural requirements essential for this antiproliferative activity. Among all analogues synthesized in this study, compound 1o was the most promising, being 10-fold more potent than compound 1d. Its activity over a panel of nine tumoral cell lines was in the nanomolar range for all of the histological types tested, and surprisingly, the resistant KB-A1 cell line was also sensitive to this compound. Moreover, a flow cytometric study showed that L1210 cells treated by the most potent compounds were arrested in the G(2)/M phases of the cell cycle with a significant percentage of cells having reinitiated a cycle of DNA synthesis without cell division. This interesting pharmacological profile, resulting from inhibition of tubulin polymerization, encouraged us to perform preliminary in vivo studies that led to a new prodrug chemical approach.

  DOI：

  10.1021/jm030961z

文献信息

• フェニルイソキサゾール化合物およびその用途
  申请人：——

  公开号：JP2005082550A

  公开（公告）日：2005-03-31

  PROBLEM TO BE SOLVED: To provide a compound having excellent controlling effect on plant blight.

  SOLUTION: A plant blight controlling agent containing a phenylisoxazole compound expressed by formula (1) has excellent controlling effect on plant blight. In the formula, R1is hydrogen atom, a halogen atom or a 1-3C alkyl; R2is hydrogen atom, a halogen atom or a 1-3C alkyl or R1and R2together form trimethylene group, tetramethylene group or CH=CH-CH=CH group; and R3is a 1-3C alkyl or a 3-4C alkynyl.

  COPYRIGHT: (C)2005,JPO&NCIPI

  要解决的问题：提供一种对植物枯萎具有优异控制效果的化合物。

  解决方案：一种含有由式（1）表示的苯并噁唑化合物的植物枯萎控制剂具有优异的控制效果。在该式中，R1为氢原子、卤素原子或1-3C烷基；R2为氢原子、卤素原子或1-3C烷基，或R1和R2共同形成三亚甲基基团、四亚甲基基团或CH=CH-CH=CH基团；R3为1-3C烷基或3-4C炔基。

  版权所有：（C）2005，JPO＆NCIPI

• First synthesis of methyl 3-amino-4-(het)aryl-1H-pyrrole-2-carboxylates as useful scaffolds in medicinal chemistry
  作者：Christophe Rochais、Vincent Lisowski、Patrick Dallemagne、Sylvain Rault

  DOI：10.1016/j.tet.2004.01.019

  日期：2004.3

  The preparation of new methyl 4-(het)aryl-3-amino-1H-pyrrole-2-carboxylates was achieved starting from commercial arylacetonitriles. This four steps synthesis afforded with good yields interesting building-blocks useful in the access to many nitrogen heterocycles with potential therapeutic interest. (C) 2004 Elsevier Ltd. All rights reserved.