dimethyl 4-(2-chloroquinolin-3-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate | 121497-60-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: dimethyl 4-(2-chloroquinolin-3-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• 英文别名: 4-(2-Chloro-quinolin-3-yl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester
• CAS: 121497-60-7
• 化学式: C₂₀H₁₉ClN₂O₄
• 分子量: 386.835
• InChiKey: OMMMKSBBPFKASX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氯-3-喹啉甲醛 、 3-氨基巴豆酸甲酯 以 甲醇 为溶剂， 反应 24.0h， 以35%的产率得到dimethyl 4-(2-chloroquinolin-3-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Syntheses and bioevaluation of substituted dihydropyridines for pregnancy-interceptive activity in hamsters

  摘要：

  A number of 2,6-dimethyl-3,5-bis(methoxycarbonyl)-4-substituted-1,4- dihydropyridines were synthesized and evaluated for pregnancy-interceptive activity in mated hamsters. Out of 24 compounds, 12, 15, 21, 22, 28, and 34 caused a marked reduction in the number of implantations when administered on days 3-8 postcoitum. In an in vitro competition assay, none of the compounds exhibited noticeable binding affinity for uterine progesterone receptors. The results reported here have helped to identify new leads for developing pregnancy-interceptive agents and the active compounds do not seem to elicit their interceptive effect through receptor-mediated inhibition of progesterone action in hamster uterus.

  DOI：

  10.1021/jm00130a012

文献信息

• Synthesis of Novel Quinoline-substituted 1,4-dihydropyridine Derivatives via Hantzsch Reaction in Aqueous Medium: Potential Bioactive Compounds
  作者：Morteza Shiri、Atefeh Nejatinezhad-Arani、Zeinab Faghihi

  DOI：10.1002/jhet.2553

  日期：2017.1

  The synthesis of a novel series of substituted 1,4‐dihydropyridines was achieved in aqueous media by base‐catalyzed three‐component Hantzsch reaction of 2‐chloroquinoline‐3‐carbaldehydes, ammonium acetate, and alkyl acteoacetate in good to high yields. Important advantages of this method are easy access to a library of novel quinoline and quinolone derivatives, green reaction conditions with water

  在水性介质中，通过碱催化2-氯喹啉-3-甲醛，乙酸铵和乙酰乙酸烷基酯的三组分Hantzsch反应，可以合成高产率的新型取代的1,4-二氢吡啶。该方法的重要优点是可以轻松访问新型喹啉和喹诺酮衍生物的文库，以水为溶剂的绿色反应条件以及易于纯化。
• MUKHERJEE, ANITA;AKHTAR, MOHAMMAD S.;SHARMA, VISHNU L.;SETH, MANJU;BHADUR+, J. MED. CHEM., 32,(1989) N0, C. 2297-2300
  作者：MUKHERJEE, ANITA、AKHTAR, MOHAMMAD S.、SHARMA, VISHNU L.、SETH, MANJU、BHADUR+

  DOI：——

  日期：——
• Syntheses and bioevaluation of substituted dihydropyridines for pregnancy-interceptive activity in hamsters
  作者：Anita Mukherjee、Mohammad S. Akhtar、Vishnu L. Sharma、Manju Seth、Amiya P. Bhaduri、Anila Agnihotri、Purshottam K. Mehrotra、Ved Prakash Kamboj

  DOI：10.1021/jm00130a012

  日期：1989.10

  A number of 2,6-dimethyl-3,5-bis(methoxycarbonyl)-4-substituted-1,4- dihydropyridines were synthesized and evaluated for pregnancy-interceptive activity in mated hamsters. Out of 24 compounds, 12, 15, 21, 22, 28, and 34 caused a marked reduction in the number of implantations when administered on days 3-8 postcoitum. In an in vitro competition assay, none of the compounds exhibited noticeable binding affinity for uterine progesterone receptors. The results reported here have helped to identify new leads for developing pregnancy-interceptive agents and the active compounds do not seem to elicit their interceptive effect through receptor-mediated inhibition of progesterone action in hamster uterus.