2-allyl-1H-pyrrolo[3,4-b]quinolin-3(2H)-one | 440084-40-2

• 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-allyl-1H-pyrrolo[3,4-b]quinolin-3(2H)-one
• 英文别名: N-allyl-1H-pyrrolo[3,4-b]quinolin-3(2H)-one；2-prop-2-enyl-1H-pyrrolo[3,4-b]quinolin-3-one
• CAS: 440084-40-2
• 化学式: C₁₄H₁₂N₂O
• 分子量: 224.262
• InChiKey: PVRUBYOVDCAKAM-UHFFFAOYSA-N

物化性质

• 熔点：
  153-155 °C
• 沸点：
  430.9±45.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-allyl-1H-pyrrolo[3,4-b]quinolin-3(2H)-one 在 palladium dichloride 盐酸 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 色氨酸A
  参考文献：
  名称：

  A new synthesis of the cytotoxic alkaloid Luotonine A

  摘要：

  A convenient synthesis of the cytotoxic alkaloid Luotonine A has been achieved using cheap and readily accessible reagents. The key intermediate in the synthesis is the tricyclic Compound 2,3-dihydro[1H]-pyrrolo[3,4-b]quinolin-3-one (5). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00140-5
• 作为产物：
  描述：

  3-(烯丙基氨基)丙酸乙酯 在 盐酸 、 水 、 sodium methylate 、 对甲苯磺酸 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 16.0h， 生成 2-allyl-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

• Synthesis of novel building blocks of 1H-pyrrolo[3,4-b]quinolin-3(2H)-one and evaluation of their antitumor activity
  作者：Lingaiah Nagarapua、Hanmant K. Gaikwad、Sheeba Rani Manikonda、Rajashaker Bantu、Krishna Madhuri Manda、Shasi Vardhan Kalivendi

  DOI：10.1007/s00044-012-0018-x

  日期：2013.1

  A series of new building blocks consisting of 1H-pyrrolo[3,4-b]quinolin-3(2H)-one with potential as selective antitumor agents is described. Compounds were synthesized by using Heck reaction of N-allyl-1H-pyrrolo[3,4-b]quinolin-3(2H)-one with p-bromophenyl acetic acid followed by formation of amide (1a-h, 2a-d) by reaction with several secondary amines in good yields. The cytotoxicity of these compounds was evaluated against human cancer cell lines in vitro (SK-N-NH, A549). Studies suggest that most of these compounds were effective in inhibiting neuroblastoma cell growth, compound 1d was the most potent one (% IC50 = 8.62 mu M).
• Lewis acid-assisted olefin cross-metathesis reaction: an efficient approach for the synthesis of glycosidic-pyrroloquinolinone based novel building blocks of camptothecin and evaluation of their antitumor activity
  作者：Lingaiah Nagarapu、Hanmant K. Gaikwad、Rajashaker Bantu、Sheeba Rani Manikonda、C. Ganesh Kumar、Sujitha Pombala

  DOI：10.1016/j.tetlet.2012.01.001

  日期：2012.3

  A series of glycosidic-pyrroloquinolinone based novel building blocks of camptothecin (2a-g) were synthesized via Lewis acid-assisted olefin cross-metathesis reaction using Ti((OPr)-Pr-i)(4) 30 mol % and 10 mol % of Grubb's second generation catalyst with good to excellent yields. Most of these compounds exhibited significant growth inhibitory effects on all the tested cancer cell lines and three compounds (2c, 2d and ze) showed potent cytotoxic activity. (C) 2012 Elsevier Ltd. All rights reserved.
• 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.
• A new synthesis of the cytotoxic alkaloid Luotonine A
  作者：Sabrina Dallavalle、Lucio Merlini

  DOI：10.1016/s0040-4039(02)00140-5

  日期：2002.3

  A convenient synthesis of the cytotoxic alkaloid Luotonine A has been achieved using cheap and readily accessible reagents. The key intermediate in the synthesis is the tricyclic Compound 2,3-dihydro[1H]-pyrrolo[3,4-b]quinolin-3-one (5). (C) 2002 Elsevier Science Ltd. All rights reserved.