1,3-二氢吡咯并[3,4-b]喹啉-2-羧酸乙酯 | 26862-71-5

• 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
• 中文名称: 1,3-二氢吡咯并[3,4-b]喹啉-2-羧酸乙酯
• 英文名称: ethyl 2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-2-carboxylate
• 英文别名: N-carbethoxy-2,3-dihydro-1H-pyrrolo[3,4-b]quinoline；1,3-dihydro-pyrrolo[3,4-b]quinoline-2-carboxylic acid ethyl ester；Ethyl 1H-pyrrolo[3,4-b]quinoline-2(3H)-carboxylate；ethyl 1,3-dihydropyrrolo[3,4-b]quinoline-2-carboxylate
• CAS: 26862-71-5
• 化学式: C₁₄H₁₄N₂O₂
• 分子量: 242.277
• InChiKey: DPNXOZFTZHIWAF-UHFFFAOYSA-N

物化性质

• 沸点：
  408.2±45.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-二氢吡咯并[3,4-b]喹啉-2-羧酸乙酯 在 氢氧化钾 、 草酰氯 、 甲基丙烯酸 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Novel pyrrolo-quinoline derivatives as potent inhibitors for PI3-kinase related kinases

  摘要：

  Several pyrrolo-quinoline gamma -lactones were found as novel inhibitors for two members of the PI3-kinase related kinase (PIKK) family, Ataxia-Telangiectasia-mutated (ATM) protein and the mammalian Target of Rapamycin (mTOR). Preliminary structure-activity relationship studies indicated that an electrophilic exocyclic double bond conjugated to the carbonyl group of the gamma -lactone ring was crucial for the PIKK inhibitory potency. One of the best ATM inhibitors in this series, DK8G557, showed IC50 values of 0.6 and 7.0 muM for ATM and mTOR, respectively. This compound exhibited potent and selective growth inhibition activities in the NCI 60 human tumor cell line screen with a GI(50) MG-MID value of 2.69 muM. The best mTOR inhibitor in this series, HP9912, exhibited IC50 values of 0.5 and 6.5 muM for mTOR and ATM, respectively. These compounds suggest novel leads for the discovery of potent small molecule inhibitors of PIKKs as potential anticancer drugs, with therapeutic activities as either single, or as sensitizing agents to conventional radio-, or chemo-therapeutic strategies. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00260-7
• 作为产物：
  描述：

  2-iodoquinoline-3-carbaldehyde 在 盐酸 、 正丁基锂 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 、 正己烷 、 水 、 苯 为溶剂， 反应 13.0h， 生成 1,3-二氢吡咯并[3,4-b]喹啉-2-羧酸乙酯
  参考文献：
  名称：

  喜树碱及相关生物碱ABC环骨架的简便合成

  摘要：

  摘要 从廉价易得的化学试剂开始制备喜树碱和相关生物碱的 ABC 环的简便合成方法。

  DOI：

  10.1081/scc-200028560

文献信息

• A convergent total synthesis of mappicine ketone: A leading antiviral compound
  作者：J.S. Yadav、Sanjita Sarkar、S. Chandrasekhar

  DOI：10.1016/s0040-4020(99)00191-x

  日期：1999.4

  An efficient total synthesis of the naturally occuring mappicine ketone 1 and mappicine 2 are described. The approach is based on the assembly of tricyclic amine 5 with pseudo acid chloride 20. A Friedlander condensation is utilized for the construction of the ABC skeleton and a periselective Diels-Alder approach is utilized for the preparation of the pseudo acid chloride.

  描述了天然存在的马卡比汀酮1和马卡比汀2的有效的全合成。该方法基于三环胺5与假酰氯20的组装。利用弗里德兰德缩合法来构建ABC骨架，并使用过选择性的Diels-Alder方法来制备假酰氯。
• Plant antitumour agents: alkaloids: synthesis of a pentacyclic camptothecin precursor
  作者：M. C. Wani、J. A. Kepler、J. B. Thompson、Monroe E. Wall、S. G. Levine

  DOI：10.1039/c29700000404

  日期：——

  A pentacyclic product (VIII) suitable for conversion into camptothecin (I)2 has been synthesized.

  已经合成了适于转化为喜树碱（I）2的五环产物（VIII）。
• Microwave Assisted FriedläNder Condensation Catalyzed by Clay
  作者：Gowravaram Sabitha、R. Satheesh Babu、B. V. Subba Reddy、J. S. Yadav

  DOI：10.1080/00397919908086603

  日期：1999.12.1

  Clay catalyzed Friedlander condensation of 2-amino arylaldehyde or ketone with carbonyl compounds containing a-methylene group has been achieved in solvent free condition under microwave irradiation to give polycyclic quinoline derivatives.
• Facile Syntheses of ABC Ring Skeleton of Camptothecin and Related Alkaloids
  作者：Subhash P. Chavan、K. Pasupathy、R. Sivappa、M. S. Venkatraman

  DOI：10.1081/scc-200028560

  日期：2004.1

  Abstract Facile synthetic approaches toward the preparation of ABC ring of camptothecin and related alkaloids starting from cheaper and readily available chemical reagents.

  摘要 从廉价易得的化学试剂开始制备喜树碱和相关生物碱的 ABC 环的简便合成方法。
• Novel pyrrolo-quinoline derivatives as potent inhibitors for PI3-kinase related kinases
  作者：Hairuo Peng、Doeg-Il Kim、Jann N Sarkaria、Yong-Seo Cho、Robert T Abraham、Leon H Zalkow

  DOI：10.1016/s0968-0896(01)00260-7

  日期：2002.1

  Several pyrrolo-quinoline gamma -lactones were found as novel inhibitors for two members of the PI3-kinase related kinase (PIKK) family, Ataxia-Telangiectasia-mutated (ATM) protein and the mammalian Target of Rapamycin (mTOR). Preliminary structure-activity relationship studies indicated that an electrophilic exocyclic double bond conjugated to the carbonyl group of the gamma -lactone ring was crucial for the PIKK inhibitory potency. One of the best ATM inhibitors in this series, DK8G557, showed IC50 values of 0.6 and 7.0 muM for ATM and mTOR, respectively. This compound exhibited potent and selective growth inhibition activities in the NCI 60 human tumor cell line screen with a GI(50) MG-MID value of 2.69 muM. The best mTOR inhibitor in this series, HP9912, exhibited IC50 values of 0.5 and 6.5 muM for mTOR and ATM, respectively. These compounds suggest novel leads for the discovery of potent small molecule inhibitors of PIKKs as potential anticancer drugs, with therapeutic activities as either single, or as sensitizing agents to conventional radio-, or chemo-therapeutic strategies. (C) 2001 Elsevier Science Ltd. All rights reserved.