2-[(3-Ethenyl-1-propylpiperidin-4-yl)methyl]-1-quinolin-4-ylprop-2-en-1-one | 1396189-70-0

• 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: 2-[(3-Ethenyl-1-propylpiperidin-4-yl)methyl]-1-quinolin-4-ylprop-2-en-1-one
• 英文别名: 2-[(3-ethenyl-1-propylpiperidin-4-yl)methyl]-1-quinolin-4-ylprop-2-en-1-one
• CAS: 1396189-70-0
• 化学式: C₂₃H₂₈N₂O
• 分子量: 348.488
• InChiKey: JZUFIGBKFMGYHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  D-酒石酸 、 2-[(3-Ethenyl-1-propylpiperidin-4-yl)methyl]-1-quinolin-4-ylprop-2-en-1-one 以 乙醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis of 3-(1-alkyl/aminoalkyl-3-vinyl-piperidin-4-yl)-1-(quinolin-4-yl)-propan-1-ones and their 2-methylene derivatives as potential spermicidal and microbicidal agents

  摘要：

  A series of twenty two derivatives of 3-(1-alkyl/aminoalkyl-3-vinyl-piperidin-4-yl)-1-(quinolin-4-yl)-propan-1-one and their 2-methylene derivatives were synthesized from naturally abundant cinchonine (I). Tartarate salts of these compounds were prepared and evaluated for spermicidal activity. The most active compounds (24, 27, 34, 36, and 38) showing potent spermicidal activity were further evaluated against different strains of Trichomonas vaginalis, for antimicrobial activity, in HeLa cell lines for cytotoxicity and against Lactobacillus jensenii for eco-safety. The tartarate of 3-(1-pentyl-3-vinyl-piperidin-4-yl)-1-(quinolin-4-yl)-propan-1-one (27) was found to be more active than N-9 in spermicidal activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.062
• 作为产物：
  描述：

  quinolin-4-yl((1S,2S,4S,5R)-5-vinyl-quinuclidin-2-yl)methanol 在 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 24.25h， 生成 2-[(3-Ethenyl-1-propylpiperidin-4-yl)methyl]-1-quinolin-4-ylprop-2-en-1-one
  参考文献：
  名称：

  Synthesis of 3-(1-alkyl/aminoalkyl-3-vinyl-piperidin-4-yl)-1-(quinolin-4-yl)-propan-1-ones and their 2-methylene derivatives as potential spermicidal and microbicidal agents

  摘要：

  A series of twenty two derivatives of 3-(1-alkyl/aminoalkyl-3-vinyl-piperidin-4-yl)-1-(quinolin-4-yl)-propan-1-one and their 2-methylene derivatives were synthesized from naturally abundant cinchonine (I). Tartarate salts of these compounds were prepared and evaluated for spermicidal activity. The most active compounds (24, 27, 34, 36, and 38) showing potent spermicidal activity were further evaluated against different strains of Trichomonas vaginalis, for antimicrobial activity, in HeLa cell lines for cytotoxicity and against Lactobacillus jensenii for eco-safety. The tartarate of 3-(1-pentyl-3-vinyl-piperidin-4-yl)-1-(quinolin-4-yl)-propan-1-one (27) was found to be more active than N-9 in spermicidal activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.062

文献信息

• Synthesis of 3-(1-alkyl/aminoalkyl-3-vinyl-piperidin-4-yl)-1-(quinolin-4-yl)-propan-1-ones and their 2-methylene derivatives as potential spermicidal and microbicidal agents
  作者：Rishi Ranjan Pandey、Akansha Srivastava、Richa Malasoni、Arshi Naqvi、Ashish Jain、Jagdamba Prasad Maikhuri、Sarvesh Paliwal、Gopal Gupta、Anil Kumar Dwivedi

  DOI：10.1016/j.bmcl.2012.06.062

  日期：2012.9

  A series of twenty two derivatives of 3-(1-alkyl/aminoalkyl-3-vinyl-piperidin-4-yl)-1-(quinolin-4-yl)-propan-1-one and their 2-methylene derivatives were synthesized from naturally abundant cinchonine (I). Tartarate salts of these compounds were prepared and evaluated for spermicidal activity. The most active compounds (24, 27, 34, 36, and 38) showing potent spermicidal activity were further evaluated against different strains of Trichomonas vaginalis, for antimicrobial activity, in HeLa cell lines for cytotoxicity and against Lactobacillus jensenii for eco-safety. The tartarate of 3-(1-pentyl-3-vinyl-piperidin-4-yl)-1-(quinolin-4-yl)-propan-1-one (27) was found to be more active than N-9 in spermicidal activity. (C) 2012 Elsevier Ltd. All rights reserved.