dimethyl 3-(4-methoxybenzoyl)-6,8-dimethylindolizine-1,2-dicarboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl 3-(4-methoxybenzoyl)-6,8-dimethylindolizine-1,2-dicarboxylate
• 英文别名: US11974991, Code KNV2
• 化学式: C₂₂H₂₁NO₆
• 分子量: 395.412
• InChiKey: WRUCVLBDDYCPEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  83.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 3-(4-methoxybenzoyl)-6,8-dimethylindolizine-1,2-dicarboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以45%的产率得到methyl 1-hydroxy-4-(4-methoxyphenyl)-7,9-dimethylpyridazino[4,5-b]indolizine-10-carboxylate
  参考文献：
  名称：

  Studies on indolizines. Evaluation of their biological properties as microtubule-interacting agents and as melanoma targeting compounds

  摘要：

  With the aim of investigating new analogues of phenstatin with an indolizin-3-yl unit, in particular as the B-ring, three new series of compounds (6-8, 9-34 and 54) were synthesized and tested for interactions with tubulin polymerization and evaluated for cytotoxicity on an NCI-60 human cancer cell lines panel. The replacement of the 3'-hydroxy-4'-methoxyphenyl B-ring of phenstatin with substituted indolizine unit results in the conservation of both antitubulin and cytotoxic effect. Indolizines 9 and 17 were the most effective in the present study and showed the highest antiproliferative effect on melanoma cell lines MDA-MB-435 (GI(50) = 30 nM) and could serve as new lead compounds for the development of anti-cancer therapeutics. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.10.041
• 作为产物：
  描述：

  3,5-二甲基吡啶 在 三乙胺 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 24.0h， 生成 dimethyl 3-(4-methoxybenzoyl)-6,8-dimethylindolizine-1,2-dicarboxylate
  参考文献：
  名称：

  Studies on indolizines. Evaluation of their biological properties as microtubule-interacting agents and as melanoma targeting compounds

  摘要：

  With the aim of investigating new analogues of phenstatin with an indolizin-3-yl unit, in particular as the B-ring, three new series of compounds (6-8, 9-34 and 54) were synthesized and tested for interactions with tubulin polymerization and evaluated for cytotoxicity on an NCI-60 human cancer cell lines panel. The replacement of the 3'-hydroxy-4'-methoxyphenyl B-ring of phenstatin with substituted indolizine unit results in the conservation of both antitubulin and cytotoxic effect. Indolizines 9 and 17 were the most effective in the present study and showed the highest antiproliferative effect on melanoma cell lines MDA-MB-435 (GI(50) = 30 nM) and could serve as new lead compounds for the development of anti-cancer therapeutics. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.10.041

文献信息

• Antitubercular compounds
  申请人：KING FAISAL UNIVERSITY

  公开号：US11530217B1

  公开（公告）日：2022-12-20

  Anti-tubercular compounds include trisubstituted indolizines having the following structural formula: wherein R 1 is selected from the group consisting of 4-OCH 3 , 4-Cl, 4-Br, 4-F, 2-NO 2 , 3,5-CF 3 , CN, CH 3 , R 2 is COOCH 3 , COOC 2 H 5 , and R 3 is H and COOCH 3 .

  抗结核化合物包括具有以下结构式的三取代吲嗪类化合物： 其中 R 1 选自由 4-OCH 3 、4-Cl、4-Br、4-F、2-NO 2 、3,5-CF 3 、CN、CH 3 , R 2 是 COOCH 3 , COOC 2 H 5 和 R 3 是 H 和 COOCH 3 .
• Studies on indolizines. Evaluation of their biological properties as microtubule-interacting agents and as melanoma targeting compounds
  作者：Alina Ghinet、Cristina-Maria Abuhaie、Philippe Gautret、Benoît Rigo、Joëlle Dubois、Amaury Farce、Dalila Belei、Elena Bîcu

  DOI：10.1016/j.ejmech.2014.10.041

  日期：2015.1

  With the aim of investigating new analogues of phenstatin with an indolizin-3-yl unit, in particular as the B-ring, three new series of compounds (6-8, 9-34 and 54) were synthesized and tested for interactions with tubulin polymerization and evaluated for cytotoxicity on an NCI-60 human cancer cell lines panel. The replacement of the 3'-hydroxy-4'-methoxyphenyl B-ring of phenstatin with substituted indolizine unit results in the conservation of both antitubulin and cytotoxic effect. Indolizines 9 and 17 were the most effective in the present study and showed the highest antiproliferative effect on melanoma cell lines MDA-MB-435 (GI(50) = 30 nM) and could serve as new lead compounds for the development of anti-cancer therapeutics. (C) 2014 Elsevier Masson SAS. All rights reserved.