dimethyl 5-formyl-3-methylpyrrole-2,4-dicarboxylate | 65100-86-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: dimethyl 5-formyl-3-methylpyrrole-2,4-dicarboxylate
• 英文别名: 1H-Pyrrole-2,4-dicarboxylic acid, 5-formyl-3-methyl-, dimethyl ester；dimethyl 5-formyl-3-methyl-1H-pyrrole-2,4-dicarboxylate
• CAS: 65100-86-9
• 化学式: C₁₀H₁₁NO₅
• 分子量: 225.201
• InChiKey: QBIVKKLJRCHHAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  85.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 5-formyl-3-methylpyrrole-2,4-dicarboxylate 在 盐酸 、 氢氧化钾 、 potassium acetate 、 sodium acetate 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 2.33h， 生成 t-butyl 5'-(1,3-dithiolan-2-yl)-3-ethyl-4'-methoxycarbonyl-4,3'-dimethyl-2,2'-dipyrrylmethane-5-carboxylate
  参考文献：
  名称：

  Clezy, Peter S.; Crowley, Richard J.; Hai, Ton That, Australian Journal of Chemistry, 1982, vol. 35, # 2, p. 411 - 422

  摘要：

  DOI：
• 作为产物：
  描述：

  dimethyl 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylate 在 磺酰氯 作用下， 以 溶剂黄146 为溶剂， 反应 1.5h， 生成 dimethyl 5-dichloromethyl-3-methylpyrrole-2,4-dicarboxylate 、 dimethyl 5-formyl-3-methylpyrrole-2,4-dicarboxylate
  参考文献：
  名称：

  Clezy, Peter S.; Crowley, Richard J.; Hai, Ton That, Australian Journal of Chemistry, 1982, vol. 35, # 2, p. 411 - 422

  摘要：

  DOI：

文献信息

• Solvothermal Synthesis of Multiple Dihydropyrimidinones at a Time as Inhibitors of Eg5
  作者：Xiao-Qiang Jiang、Shi-Quan Chen、Yan-Fei Liu、Xin-Guang Pan、Dan Chen、Shi-Fan Wang

  DOI：10.3390/molecules26071925

  日期：——

  Solvothermal synthesis of multiple dihydropyrimidinones at a time has been developed in inexpensive and green bio-based solvent lactic acid without any additional catalysts or additives. By this method, thirty new dihydropyrimidinone derivatives were synthesized in two batches and characterized. All of the compounds were screened by Eg5 motor protein ATPase assay, and the positive compounds were tested against the Caco-2 cell line, HeLa cell line, L929 cell line and T24 cell line in vitro. Among them, compound C9 exhibited the best inhibitory activity against motor protein ATPase with an IC50 value of 30.25 μM and significant cytotoxic activity in the micromolar range against the cells above. The Lineweaver–Burk plot revealed that compound C9 was a mixed-type Eg5 inhibitor. A molecular modeling study using the Discovery Studio program was performed, where compound C9 exhibited good binding interaction with Eg5 motor protein ATPase, and this was consistent with the attained experimental results.

  在廉价且绿色的生物基溶剂乳酸中，已经开发出一种同时合成多个二氢嘧啶酮的溶剂热合成方法，无需任何额外的催化剂或添加剂。通过这种方法，已经合成并表征了30种新的二氢嘧啶酮衍生物。所有化合物均通过Eg5马达蛋白ATP酶活性分析进行筛选，并对阳性化合物进行了体外针对Caco-2细胞系、HeLa细胞系、L929细胞系和T24细胞系的测试。其中，化合物C9对马达蛋白ATP酶表现出最佳的抑制活性，IC50值为30.25 μM，并在微摩尔范围内对上述细胞表现出显著的细胞毒性活性。Lineweaver–Burk图表明，化合物C9是一种混合型Eg5抑制剂。使用Discovery Studio程序进行的分子建模研究显示，化合物C9与Eg5马达蛋白ATP酶有良好的结合相互作用，与实验结果一致。
• [EN] TYROSINE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE LA TYROSINE KINASE
  申请人：MERCK & CO INC

  公开号：WO2003035614A2

  公开（公告）日：2003-05-01

  The present invention relates to compounds that are capable of inhibiting, modulating and/or regulating signal transduction of both receptor-type and non-receptor type tyrosine kinases. The compounds of the instant invention possess a core structure that comprises a 2-carboxy-5-formyl pyrrole. The present invention is also related to the pharmaceutically acceptable salts, hydrates and stereoisomers of these compounds.
• Clezy, Peter S.; Crowley, Richard J.; Hai, Ton That, Australian Journal of Chemistry, 1982, vol. 35, # 2, p. 411 - 422
  作者：Clezy, Peter S.、Crowley, Richard J.、Hai, Ton That

  DOI：——

  日期：——