6-(3,4-二甲氧基苯基)-3-吡啶羧醛 | 898796-17-3

• 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: 6-(3,4-二甲氧基苯基)-3-吡啶羧醛
• 英文名称: 2-(3,4-dimethoxyphenyl)-5-formylpyridine
• 英文别名: 6-(3,4-Dimethoxyphenyl)nicotinaldehyde；6-(3,4-dimethoxyphenyl)pyridine-3-carbaldehyde
• CAS: 898796-17-3
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: JRWHCFWWJIMXRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-(4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid 、 6-(3,4-二甲氧基苯基)-3-吡啶羧醛 在 sodium acetate 、 溶剂黄146 、 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 以86%的产率得到(S)-2-(5-((6-(3,4-dimethoxyphenyl)pyridin-3-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid hydrochloride
  参考文献：
  名称：

  Structural Insights into the Design of Small Molecule Inhibitors That Selectively Antagonize Mcl-1

  摘要：

  The screening of a small focused library of rhodanine derivatives as inhibitors of Bcl-2 proteins led to the discovery of two structurally related compounds with different binding profiles against the Bcl-XL and the Mcl-1 proteins. Subsequent NMR studies with Mutant proteins and in silico docking studies provide it possible rationale for the observed specificity.

  DOI：

  10.1021/jm901469p
• 作为产物：
  描述：

  3,4-二甲氧基苯硼酸 、 2-溴-5-醛基吡啶 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium phosphate tribasic 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 16.0h， 以77%的产率得到6-(3,4-二甲氧基苯基)-3-吡啶羧醛
  参考文献：
  名称：

  Structural Insights into the Design of Small Molecule Inhibitors That Selectively Antagonize Mcl-1

  摘要：

  The screening of a small focused library of rhodanine derivatives as inhibitors of Bcl-2 proteins led to the discovery of two structurally related compounds with different binding profiles against the Bcl-XL and the Mcl-1 proteins. Subsequent NMR studies with Mutant proteins and in silico docking studies provide it possible rationale for the observed specificity.

  DOI：

  10.1021/jm901469p

文献信息

• [EN] BIARYLRHODANINE AND PYRIDYLRHODANINE COMPOUNDS AND THEIR USE<br/>[FR] COMPOSÉS DE BIARYLRHODANINE ET DE PYRIDYLRHODANINE ET LEUR UTILISATION
  申请人：AGENCY SCIENCE TECH & RES

  公开号：WO2010024783A1

  公开（公告）日：2010-03-04

  The present invention pertains generally to the field of therapeutic compounds, and more specifically to compounds related to rhodanine, which compounds are inter alia inhibitors and/or binders of antiapoptotic/pro-survival Bcl-2 proteins such as Bcl-XL and/or Mcl-1. More specifically, the present invention is concerned with Rhodanine- based Pan-Bcl-2 inhibitors and Mcl-1 -specific inhibitors as anti-cancer compounds. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit and/or bind Bcl-2 proteins such as Bcl-XL and/or Mcl-1, and in the treatment of diseases and conditions that are mediated by Bcl-2 proteins, that are ameliorated by the inhibition of Bcl-2 protein function (such as Bcl-XL and/or Mcl-1 ) including proliferative conditions such as cancer, optionally in combination with another agent.

  本发明一般涉及治疗化合物领域，更具体地涉及与罗丹宁相关的化合物，这些化合物是抑制剂和/或结合剂，用于抑制和/或结合抗凋亡/促存活的Bcl-2蛋白，如Bcl-XL和/或Mcl-1。更具体地，本发明涉及基于罗丹宁的Pan-Bcl-2抑制剂和Mcl-1特异性抑制剂作为抗癌化合物。本发明还涉及包括这些化合物的药物组合物，以及在体外和体内使用这些化合物和组合物来抑制和/或结合Bcl-2蛋白，如Bcl-XL和/或Mcl-1，并用于治疗由Bcl-2蛋白介导的疾病和症状，通过抑制Bcl-2蛋白功能（如Bcl-XL和/或Mcl-1）改善的疾病和症状，包括增殖性疾病如癌症，可选择地与另一药剂联合使用。
• Synthesis, Spectroscopic Characterization, Structural Studies, and <i>In Vitro</i> Antitumor Activities of Pyridine-3-carbaldehyde Thiosemicarbazone Derivatives
  作者：Wilfredo Hernández、Fernando Carrasco、Abraham Vaisberg、Evgenia Spodine、Jorge Manzur、Maik Icker、Harald Krautscheid、Lothar Beyer

  DOI：10.1155/2020/2960165

  日期：2020.9.14

  structure of 7 has been also confirmed by single crystal X-ray diffraction. In the solid state 7 exists in the E conformation about the N2-N3 bond; 7 also presents the E conformation in solution, as evidenced by 1H NMR spectroscopy. The in vitro antitumor activity of the synthesized compounds was studied on six human tumor cell lines: H460 (lung large cell carcinoma), HuTu80 (duodenum adenocarcinoma), DU145

  八种新型缩氨基硫腙衍生物，6-(1-trifluoroethoxy)pyridine-3-carbaldehyde thiosemicarbazone (1), 6-(4'-fluorophenyl)pyridine-3-carbaldehyde thiosemicarbazone (2), 5-chloro-pyridine-3-carbaldehyde thiosemicarbazone (3), 2-chloro-5-bromo-pyridine-3-carbaldehyde thiosemicarbazone (4), 6-(3',4'-dimethoxyphenyl)pyridine-3-carbaldehyde thiosemicarbazone (5), 2-chloro-5-fluor -pyridine-3-carbaldehyde thiosemicarbazone, (6)
• INHIBITORS OF HISTONE DEACETYLASE
  申请人：Methylgene, Inc.

  公开号：EP1280764A2

  公开（公告）日：2003-02-05
• [EN] INHIBITORS OF HISTONE DEACETYLASE<br/>[FR] INHIBITEURS D'HISTONE DESACETYLASE
  申请人：METHYLGENE INC

  公开号：WO2001070675A2

  公开（公告）日：2001-09-27

  The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.
• Structural Insights into the Design of Small Molecule Inhibitors That Selectively Antagonize Mcl-1
  作者：Paul H. Bernardo、Thirunavukkarasu Sivaraman、Kah-Fei Wan、Jin Xu、Janarthanan Krishnamoorthy、Chun Meng Song、Liming Tian、Jasmine S. F. Chin、Diane S. W. Lim、Henry Y. K. Mok、Victor C. Yu、Joo Chuan Tong、Christina L. L. Chai

  DOI：10.1021/jm901469p

  日期：2010.3.11

  The screening of a small focused library of rhodanine derivatives as inhibitors of Bcl-2 proteins led to the discovery of two structurally related compounds with different binding profiles against the Bcl-XL and the Mcl-1 proteins. Subsequent NMR studies with Mutant proteins and in silico docking studies provide it possible rationale for the observed specificity.