2-(oxiran-2-ylmethyl)-1H-pyrrolo[3,4-b]quinolin-3(2H)-one | 1309889-86-8

• 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-(oxiran-2-ylmethyl)-1H-pyrrolo[3,4-b]quinolin-3(2H)-one
• 英文别名: 2-(oxiran-2-ylmethyl)-1H-pyrrolo[3,4-b]quinolin-3-one
• CAS: 1309889-86-8
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: CFIPZYGWXVGBOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  45.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(oxiran-2-ylmethyl)-1H-pyrrolo[3,4-b]quinolin-3(2H)-one 在 immobilized Candida antarctica lipase B 作用下， 以 甲醇 为溶剂， 反应 60.0h， 生成 2-[(2S)-2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3,4-b]quinolin-3-one 、 [(2R)-1-(3-oxo-1H-pyrrolo[3,4-b]quinolin-2-yl)-3-(4-phenylpiperazin-1-yl)propan-2-yl] acetate
  参考文献：
  名称：

  Chemoenzymatic synthesis with lipase catalyzed resolution and evaluation of antitumor activity of (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3,4-b]quinolin-3(2H)-one

  摘要：

  Synthesis, characterization, resolution and evaluation of novel (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3,4-b]quinolin-3(2H)-one derivatives are described. Enantiomerically pure compounds were isolated in good to excellent yield with high enantiomeric excess under mild reaction conditions by using Candida antarctica B (CAL-B) and Candida rugosa (CRL) Lipases. Newly synthesized and resolved compounds were screened for their antitumor activity against cancer cells such as human neuroblastoma SK-N-SH and human lung carcinoma A549 cell line in vitro. The results have shown that the compound 1 S-(-) alcohol was more effective in inhibiting the tumor cell growth. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.069
• 作为产物：
  描述：

  3-(烯丙基氨基)丙酸乙酯 在 盐酸 、 原乙酸三甲酯 、 三甲基氯硅烷 、 AD-mix-β 、 水 、 sodium methylate 、 对甲苯磺酸 作用下， 以 乙醚 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 39.0h， 生成 2-(oxiran-2-ylmethyl)-1H-pyrrolo[3,4-b]quinolin-3(2H)-one
  参考文献：
  名称：

  Chemoenzymatic synthesis with lipase catalyzed resolution and evaluation of antitumor activity of (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3,4-b]quinolin-3(2H)-one

  摘要：

  Synthesis, characterization, resolution and evaluation of novel (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3,4-b]quinolin-3(2H)-one derivatives are described. Enantiomerically pure compounds were isolated in good to excellent yield with high enantiomeric excess under mild reaction conditions by using Candida antarctica B (CAL-B) and Candida rugosa (CRL) Lipases. Newly synthesized and resolved compounds were screened for their antitumor activity against cancer cells such as human neuroblastoma SK-N-SH and human lung carcinoma A549 cell line in vitro. The results have shown that the compound 1 S-(-) alcohol was more effective in inhibiting the tumor cell growth. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.069

文献信息

• Chemoenzymatic synthesis with lipase catalyzed resolution and evaluation of antitumor activity of (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3,4-b]quinolin-3(2H)-one
  作者：Lingaiah Nagarapu、Hanmant K. Gaikwad、Rajashaker Bantu、Sheeba Rani Manikonda

  DOI：10.1016/j.ejmech.2011.02.069

  日期：2011.6

  Synthesis, characterization, resolution and evaluation of novel (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3,4-b]quinolin-3(2H)-one derivatives are described. Enantiomerically pure compounds were isolated in good to excellent yield with high enantiomeric excess under mild reaction conditions by using Candida antarctica B (CAL-B) and Candida rugosa (CRL) Lipases. Newly synthesized and resolved compounds were screened for their antitumor activity against cancer cells such as human neuroblastoma SK-N-SH and human lung carcinoma A549 cell line in vitro. The results have shown that the compound 1 S-(-) alcohol was more effective in inhibiting the tumor cell growth. (C) 2011 Elsevier Masson SAS. All rights reserved.