methyl 5-benzyl-1-((1-methyl-1H-indol-2-yl)methyl)-1H-pyrrole-3-carboxylate | 1378942-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl 5-benzyl-1-((1-methyl-1H-indol-2-yl)methyl)-1H-pyrrole-3-carboxylate
• 英文别名: Methyl 5-benzyl-1-[(1-methylindol-2-yl)methyl]pyrrole-3-carboxylate
• CAS: 1378942-19-8
• 化学式: C₂₃H₂₂N₂O₂
• 分子量: 358.44
• InChiKey: OAGKOGPSVFVNHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  36.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 5-benzyl-1-((1-methyl-1H-indol-2-yl)methyl)-1H-pyrrole-3-carboxylate 、 3-甲基-1-苯基-1H-吡唑-4-甲醛 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 3-benzyl-6-methyl-11-(3-methyl-1-phenyl-1H-pyrazol-4-yl)-6,11-dihydro-5H-indolizino[6,7-b]indole-1-carboxylate
  参考文献：
  名称：

  A dihydroindolizino indole derivative selectively stabilizes G-quadruplex DNA and down-regulates c-MYC expression in human cancer cells

  摘要：

  Background: Telomeric and NHE III1 a c-MYC promoter region is abundant in guanine content and readily form G-quadruplex structures. Small molecules that stabilize G-quadruplex DNA were shown to reduce oncoprotein expression, initiate apoptosis and they may function as anticancer molecules.Methods: Electrospray ionization mass spectrometry, spectroscopy, isothermal titration calorimetry, Taq DNA polymerase stop assay, real time PCR and luciferase reporter assay. Cell migration assay to find out the effect of derivatives on normal as well as cancer cell proliferation.Results: Among three different dihydroindolizino indole derivatives, 4-cyanophenyl group attached derivative has shown maximum affinity, selective interaction and higher stability towards G-quadruplex DNA over dsDNA. Further, as a potential G-quadruplex DNA stabilizer, 4-cyanophenyl linked dihydroindolizino indole derivative was found to be more efficient in inhibiting in vitro DNA synthesis, c-MYC expression and cancer cell proliferation among human cancer cells.Conclusion: The present study reveals that dihydroindolizino indole derivative having 4-cyanophenyl group has potential to stabilize G-quadruplex DNA and exhibit anticancer activity.General significance: These studies are useful in the identification and synthesis of lead derivatives that will selectively stabilize G-quadruplex DNA and function as anticancer agents. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.bbagen.2014.10.004
• 作为产物：
  描述：

  (1-甲基-1H-吲哚-2-基)-甲醇 在 偶氮二甲酸二异丙酯 、 二苯基膦叠氮化物 、 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 25.0h， 生成 methyl 5-benzyl-1-((1-methyl-1H-indol-2-yl)methyl)-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  膦介导的叠氮化物与炔醛的MBH-乙酸盐与取代的吡咯的级联反应：易于获得N稠合的吡咯并杂环†

  摘要：

  描述了叠氮化物与炔属醛的森田-贝利斯-希尔曼乙酸盐的级联反应的一锅法合成取代的吡咯，该反应在室温下由三苯基膦有效地介导。叠氮化钠已成功用于提供N-未取代的吡咯，而烷基叠氮化物通过一系列烯丙基取代/叠氮化物还原/环异构化反应提供了相应的N-烷基化吡咯。所获得的产品为吲哚并吲哚，吡咯并异喹啉和8-氧代-5、6、7、8-四氢吲哚并嗪提供了新的入口。

  DOI：

  10.1039/c2ob25272d

文献信息

• A dihydroindolizino indole derivative selectively stabilizes G-quadruplex DNA and down-regulates c-MYC expression in human cancer cells
  作者：Narayana Nagesh、G. Raju、R. Srinivas、P. Ramesh、M. Damoder Reddy、Ch. Raji Reddy

  DOI：10.1016/j.bbagen.2014.10.004

  日期：2015.1

  Background: Telomeric and NHE III1 a c-MYC promoter region is abundant in guanine content and readily form G-quadruplex structures. Small molecules that stabilize G-quadruplex DNA were shown to reduce oncoprotein expression, initiate apoptosis and they may function as anticancer molecules.Methods: Electrospray ionization mass spectrometry, spectroscopy, isothermal titration calorimetry, Taq DNA polymerase stop assay, real time PCR and luciferase reporter assay. Cell migration assay to find out the effect of derivatives on normal as well as cancer cell proliferation.Results: Among three different dihydroindolizino indole derivatives, 4-cyanophenyl group attached derivative has shown maximum affinity, selective interaction and higher stability towards G-quadruplex DNA over dsDNA. Further, as a potential G-quadruplex DNA stabilizer, 4-cyanophenyl linked dihydroindolizino indole derivative was found to be more efficient in inhibiting in vitro DNA synthesis, c-MYC expression and cancer cell proliferation among human cancer cells.Conclusion: The present study reveals that dihydroindolizino indole derivative having 4-cyanophenyl group has potential to stabilize G-quadruplex DNA and exhibit anticancer activity.General significance: These studies are useful in the identification and synthesis of lead derivatives that will selectively stabilize G-quadruplex DNA and function as anticancer agents. (C) 2014 Elsevier B.V. All rights reserved.
• Phosphine-mediated cascade reaction of azides with MBH-acetates of acetylenic aldehydes to substituted pyrroles: a facile access to N-fused pyrrolo-heterocycles
  作者：Chada Raji Reddy、Motatipally Damoder Reddy、Boinapally Srikanth

  DOI：10.1039/c2ob25272d

  日期：——

  One-pot synthesis of substituted pyrroles by a cascade reaction of azides with Morita–Baylis–Hillman acetates of acetylenic aldehydes is described and the reaction is efficiently mediated by triphenyl phosphine at room temperature. Sodium azide is successfully used to provide N-unsubstituted pyrroles, while alkyl azides afforded the corresponding N-alkylated pyrroles through a sequence of allylic substitution/azide

  描述了叠氮化物与炔属醛的森田-贝利斯-希尔曼乙酸盐的级联反应的一锅法合成取代的吡咯，该反应在室温下由三苯基膦有效地介导。叠氮化钠已成功用于提供N-未取代的吡咯，而烷基叠氮化物通过一系列烯丙基取代/叠氮化物还原/环异构化反应提供了相应的N-烷基化吡咯。所获得的产品为吲哚并吲哚，吡咯并异喹啉和8-氧代-5、6、7、8-四氢吲哚并嗪提供了新的入口。