4-Chloro-8-methylquinoline-3-carbonyl chloride | 1027904-81-9

• 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: 4-Chloro-8-methylquinoline-3-carbonyl chloride
• CAS: 1027904-81-9
• 化学式: C₁₁H₇Cl₂NO
• 分子量: 240.089
• InChiKey: PBCKSDSKTHNLRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Chloro-8-methylquinoline-3-carbonyl chloride 在 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 6.0h， 生成 4-(2-Ethyl-phenylamino)-8-methyl-quinoline-3-carboxylic acid allylamide
  参考文献：
  名称：

  作为一类新型的胃H + / K + -ATPase抑制剂，合成了4-（苯基氨基）喹啉-3-羧酰胺。

  摘要：

  为了寻找胃H + / K + -ATP酶的抑制剂，合成了4-（苯氨基）喹啉-3-羧酰胺并评估了其对组胺诱导的大鼠胃酸分泌的抗分泌活性。这些化合物是通过将苯胺衍生物与N-取代的4-氯喹啉-3-羧酰胺缩合而合成的，后者是由亚硫酰氯处理4（1H）-喹啉酮-3-羧酸而获得的。大多数化合物抑制大鼠中组胺诱导的胃酸分泌。其中，N-烯丙基-4-（2-乙基苯基氨基）喹啉-3-羧酰胺（4h）是最有效的抑制剂，并且作为候选抗溃疡药的分布最佳。该化合物显示出可逆的K +竞争性胃H + / K + -ATPase抑制活性。

  DOI：

  10.1248/cpb.43.693
• 作为产物：
  描述：

  2-(邻甲苯氨基亚甲基)丙二酸二乙酯 在 sodium hydroxide 、 草酰氯 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 乙二醇二甲醚 、 1,2-二氯乙烷 、 xylene 为溶剂， 反应 16.67h， 生成 4-Chloro-8-methylquinoline-3-carbonyl chloride
  参考文献：
  名称：

  N-Arylpiperazinyl-N‘-propylamino Derivatives of Heteroaryl Amides as Functional Uroselective α₁-Adrenoceptor Antagonists

  摘要：

  Novel arylpiperazines were identified as alpha(1)-adrenoceptor(BR) subtype-selective antagonists by functional in vitro screening. 3-[4-(ortho-Substituted phenyl)piperazin-1-yl]propylamines were derivatized with N,N-dimethyl anthranilamides, nicotinamides,;as well as carboxamides of quinoline, I,8-naphthyridine, pyrazolo[3,4-b]pyridine, isoxazolo[3,4-b]pyridine, imidazo[4,5-b]pyridine, and pyrazolo[1,5-a]pyrimidines. Strips of rabbit bladder neck were employed as a predictive assay for antagonism in the human lower tract. Rings of rat aorta;a were used as a ''negative screen'' for the test antagonists. Binding to alpha(1)-ARs was relatively sensitive to size and electronic features of the arylpiperazine portion of the antagonists and permissive to these features on the heteroaryl carboxamide side. These structure-affinity findings were exploited to produce nicotinamides (e.g, 13ii and 25x) and pyrazolo[3,4-b]pyridines (e.g. 37f and 37y) ligands with nanomolar affinity at the alpha(1)-AR subtype prevalent in the human lower urinary tract (pA(2) values: 8.8, 10.7, 9.3, and 9.9, respectively) and displaying 2-3 orders of magnitude selectivity over the alpha(1D)-AR.

  DOI：

  10.1021/jm970166j

文献信息

• Design, synthesis, and biological evaluation of novel quinoline derivatives as HIV-1 Tat–TAR interaction inhibitors
  作者：Shuguang Chen、Ran Chen、Meizi He、Ruifang Pang、Zhiwu Tan、Ming Yang

  DOI：10.1016/j.bmc.2009.01.038

  日期：2009.3

  Thirty-two quinoline derivatives were designed and synthesized as HIV-1 Tat–TAR interaction inhibitors. All the compounds showed high antiviral activities in inhibiting the formation of SIV-induced syncytium in CEM174 cells. Nine of them with low cytotoxicities were evaluated by Tat dependent HIV-1 LTR-driven CAT gene expression colorimetric enzyme assay in human 293T cells, indicating effective inhibitory

  设计并合成了32种喹啉衍生物作为HIV-1 Tat-TAR相互作用抑制剂。所有这些化合物在抑制CEM174细胞中SIV诱导的合胞体形成方面均表现出很高的抗病毒活性。在人的293T细胞中，通过Tat依赖HIV-1 LTR驱动的CAT基因表达比色酶分析评估了其中9种低细胞毒性，表明它们具有有效的抑制Tat-TAR相互作用的抑制活性。分子模拟实验表明，这些化合物可能通过与Tat蛋白而非TAR RNA结合而抑制Tat-TAR相互作用。
• <i>N-</i>Arylpiperazinyl-<i>N</i>‘<i>-</i>propylamino Derivatives of Heteroaryl Amides as Functional Uroselective α₁-Adrenoceptor Antagonists
  作者：Todd R. Elworthy、Anthony P. D. W. Ford、Gary W. Bantle、David J. Morgans,、Rachel S. Ozer、Wylie S. Palmer、David B. Repke、Magarita Romero、Leticia Sandoval、Eric B. Sjogren、Francisco X. Talamás、Alfredo Vazquez、Helen Wu、Nicolas F. Arredondo、David R. Blue,、Andrea DeSousa、Lisa M. Gross、M. Shannon Kava、John D. Lesnick、Rachel L. Vimont、Timothy J. Williams、Quan-Ming Zhu、Jürg R. Pfister、David E. Clarke

  DOI：10.1021/jm970166j

  日期：1997.8.1

  Novel arylpiperazines were identified as alpha(1)-adrenoceptor(BR) subtype-selective antagonists by functional in vitro screening. 3-[4-(ortho-Substituted phenyl)piperazin-1-yl]propylamines were derivatized with N,N-dimethyl anthranilamides, nicotinamides,;as well as carboxamides of quinoline, I,8-naphthyridine, pyrazolo[3,4-b]pyridine, isoxazolo[3,4-b]pyridine, imidazo[4,5-b]pyridine, and pyrazolo[1,5-a]pyrimidines. Strips of rabbit bladder neck were employed as a predictive assay for antagonism in the human lower tract. Rings of rat aorta;a were used as a ''negative screen'' for the test antagonists. Binding to alpha(1)-ARs was relatively sensitive to size and electronic features of the arylpiperazine portion of the antagonists and permissive to these features on the heteroaryl carboxamide side. These structure-affinity findings were exploited to produce nicotinamides (e.g, 13ii and 25x) and pyrazolo[3,4-b]pyridines (e.g. 37f and 37y) ligands with nanomolar affinity at the alpha(1)-AR subtype prevalent in the human lower urinary tract (pA(2) values: 8.8, 10.7, 9.3, and 9.9, respectively) and displaying 2-3 orders of magnitude selectivity over the alpha(1D)-AR.
• Synthesis of 4-(Phenylamino)quinoline-3-carboxamides as a Novel Class of Gastric H+/K+-ATPase Inhibitors.
  作者：Minoru UCHIDA、Kenji OTSUBO、Jun MATSUBARA、Tadaaki OHTANI、Seiji MORITA、Katsuya YAMASAKI

  DOI：10.1248/cpb.43.693

  日期：——

  In search for inhibitors of gastric H+/K+-ATPase, 4-(phenylamino)quinoline-3-carboxamides were synthesized and evaluated for antisecretory activity against histamine-induced gastric acid secretion in rats. These compounds were synthesized by condensation of aniline derivatives with N-substituted 4-chloroquinoline-3-carboxamides, which were obtained from treatment of 4(1H)-quinolinone-3-carboxylic acid

  为了寻找胃H + / K + -ATP酶的抑制剂，合成了4-（苯氨基）喹啉-3-羧酰胺并评估了其对组胺诱导的大鼠胃酸分泌的抗分泌活性。这些化合物是通过将苯胺衍生物与N-取代的4-氯喹啉-3-羧酰胺缩合而合成的，后者是由亚硫酰氯处理4（1H）-喹啉酮-3-羧酸而获得的。大多数化合物抑制大鼠中组胺诱导的胃酸分泌。其中，N-烯丙基-4-（2-乙基苯基氨基）喹啉-3-羧酰胺（4h）是最有效的抑制剂，并且作为候选抗溃疡药的分布最佳。该化合物显示出可逆的K +竞争性胃H + / K + -ATPase抑制活性。