7-methyl-1-phenacyl-quinolinium bromide | 713077-23-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-methyl-1-phenacyl-quinolinium bromide
• 英文别名: 2-(7-methylquinolin-1-ium-1-yl)-1-phenylethanone;bromide
• CAS: 713077-23-7
• 化学式: Br*C₁₈H₁₆NO
• 分子量: 342.235
• InChiKey: NRKHWZRYDUIJBN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.32
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  21
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-methyl-1-phenacyl-quinolinium bromide 、 丙烯腈 以 N,N-二甲基甲酰胺 为溶剂， 以40%的产率得到1-benzoyl-3-cyano-8-methyl-pyrrolo[1,2-a]quinoline
  参考文献：
  名称：

  Substituted 1-benzoyl-3-cyano-pyrrolo [1,2-a] quinolines and analogs as activators of caspases and inducers of apoptosis

  摘要：

  本发明涉及取代的1-苯甲酰基-3-氰基-吡咯并[1,2-a]喹啉及其类似物，由通用式I表示： 其中R1-R8，L，Q，虚线和Ar在此定义。本发明还涉及发现具有式I的化合物是caspase的激活剂和凋亡诱导剂。因此，本发明的caspase激活剂和凋亡诱导剂可用于诱导在各种临床病况中发生未受控制的异常细胞生长和扩散的细胞死亡。

  公开号：

  US20050014759A1
• 作为产物：
  描述：

  7-甲基喹啉 、 2-溴苯乙酮 以 乙腈 为溶剂， 以69%的产率得到7-methyl-1-phenacyl-quinolinium bromide
  参考文献：
  名称：

  Substituted 1-benzoyl-3-cyano-pyrrolo [1,2-a] quinolines and analogs as activators of caspases and inducers of apoptosis

  摘要：

  本发明涉及取代的1-苯甲酰基-3-氰基-吡咯并[1,2-a]喹啉及其类似物，由通用式I表示： 其中R1-R8，L，Q，虚线和Ar在此定义。本发明还涉及发现具有式I的化合物是caspase的激活剂和凋亡诱导剂。因此，本发明的caspase激活剂和凋亡诱导剂可用于诱导在各种临床病况中发生未受控制的异常细胞生长和扩散的细胞死亡。

  公开号：

  US20050014759A1

文献信息

• Assembly of functionalized π-extended indolizine polycycles through dearomative [3+2] cycloaddition/oxidative decarbonylation
  作者：Shaojing Jin、Lele Wang、Huabin Han、Xiongli Liu、Zhanwei Bu、Qilin Wang

  DOI：10.1039/d0cc07116a

  日期：——

  Reported herein is an unexpected construction of functionalized π-extended indolizine polycycles through a one-pot two-step cascade process comprising the base-promoted dearomative [3+2] cycloaddition of quinilinium salts and 3-alkenyl oxindoles, followed by a DDQ-mediated oxidative decarbonylation. Moreover, we could achieve the substrate-controlled diverse synthesis of structurally strained cyclopropane

  本文报道的是通过一锅两步的级联过程意外地构建的功能化π延伸的吲哚嗪多环，该过程包括碱基促进的喹啉盐和3-烯基氧吲哚的脱芳香性[3 + 2]环加成，然后由DDQ介导氧化脱羰。此外，我们可以使用吡啶鎓盐作为起始原料，实现底物控制的结构应变环丙烷螺并吲哚的多样化合成。
• Discovery of 1-benzoyl-3-cyanopyrrolo[1,2-a]quinolines as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 2: Structure–activity relationships of the 4-, 5-, 6-, 7- and 8-positions
  作者：William Kemnitzer、Jared Kuemmerle、Songchun Jiang、Nilantha Sirisoma、Shailaja Kasibhatla、Candace Crogan-Grundy、Ben Tseng、John Drewe、Sui Xiong Cai

  DOI：10.1016/j.bmcl.2009.05.012

  日期：2009.7

  As a continuation of our efforts to discover and develop the apoptosis inducing 1-benzoyl-3-cyanopyrrolo[1,2-a] quinolines as potential anticancer agents, we explored substitutions at the 4-, 5-, 6-, 7- and 8-positions of pyrrolo[1,2-a] quinoline. SAR studies showed that substitution at the 6- position by a small group such as Cl resulted in potent compounds. Substitutions at the 5- and 8-positions were tolerated while substitutions at the 4- and 7- position led to inactive compounds. Several compounds, including 2c, 3a, 3b and 3f, were found to be highly active against human breast cancer cells T47D with EC50 values of 0.053-0.080 mu M, but much less active against human colon cancer cells HCT116 and hepatocellular carcinoma cancer cells SNU398 in the caspase activation assay. Compound 3f also was found to be highly active with a GI(50) value of 0.018 mu M against T47D cells in a growth inhibition assay. (C) 2009 Elsevier Ltd. All rights reserved.
• EP1578424A4
  申请人：——

  公开号：EP1578424A4

  公开（公告）日：2007-08-08
• SUBSTITUTED 1-BENZOYL-3-CYANO-PYRROLO 1,2-A] QUINOLINES AND ANALOGS AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS
  申请人：Cytovia, Inc.

  公开号：EP1578424A2

  公开（公告）日：2005-09-28
• US7135480B2
  申请人：——

  公开号：US7135480B2

  公开（公告）日：2006-11-14