摩熵化学
数据库官网
小程序
打开微信扫一扫
首页 分子通 化学资讯 化学百科 反应查询 关于我们
请输入关键词

4-chloro-8-methoxy-3-quinolinecarboxylic acid chloride | 142782-01-2

中文名称
——
中文别名
——
英文名称
4-chloro-8-methoxy-3-quinolinecarboxylic acid chloride
英文别名
4-chloro-8-methoxy quinoline-3-carboxylic acid chloride;4-Chloro-8-methoxyquinoline-3-carbonyl chloride
4-chloro-8-methoxy-3-quinolinecarboxylic acid chloride化学式
CAS
142782-01-2
化学式
C11H7Cl2NO2
mdl
——
分子量
256.088
InChiKey
DHVVUOMPHRRYQE-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    3.3
  • 重原子数:
    16
  • 可旋转键数:
    2
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.09
  • 拓扑面积:
    39.2
  • 氢给体数:
    0
  • 氢受体数:
    3

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    参考文献:
    名称:
    Reversible inhibitors of the gastric (H+/K+)-ATPase. 3. 3-Substituted-4-(phenylamino)quinolines
    摘要:
    Previously, gastric (H+/K+)-ATPase inhibitors such as 2 have been prepared as analogues of 1a on the presumption that the 3-carbethoxy substituent plays a key role in establishing the orientation of the 4-arylamino group. In this paper we explore further the contribution made to activity by the quinoline 3-substituent. We show th bearing such a substituent, only a particular combination of properties provides high activity, both in as inhibitors of gastric acid secretion in vivo. The ability of the substituent to affect activity by restricting rotation about the C(quin)-N bond through a combination of both a pi-electron withdrawal and hydrogen bonding is supported by the current study. However, high activity is only achieved if the effect of this group on the quinoline pK(a) is kept to a minimum. 3-Acyl substituents provide an optimum combination of electronic properties. From this series, compound 17c (SK&F 96067) was shown to be a potent inhibitor of histamine-stimulated gastric acid secretion oral dosing in the Heidenhain pouch dog and was selected for further development and evaluation in man.
    DOI:
    10.1021/jm00096a018
  • 作为产物:
    描述:
    8-methoxy-4-oxoquinoline-3-carboxylic acid 在 氯化亚砜N,N-二甲基甲酰胺 作用下, 反应 4.0h, 以85%的产率得到4-chloro-8-methoxy-3-quinolinecarboxylic acid chloride
    参考文献:
    名称:
    Reversible inhibitors of the gastric (H+/K+)-ATPase. 3. 3-Substituted-4-(phenylamino)quinolines
    摘要:
    Previously, gastric (H+/K+)-ATPase inhibitors such as 2 have been prepared as analogues of 1a on the presumption that the 3-carbethoxy substituent plays a key role in establishing the orientation of the 4-arylamino group. In this paper we explore further the contribution made to activity by the quinoline 3-substituent. We show th bearing such a substituent, only a particular combination of properties provides high activity, both in as inhibitors of gastric acid secretion in vivo. The ability of the substituent to affect activity by restricting rotation about the C(quin)-N bond through a combination of both a pi-electron withdrawal and hydrogen bonding is supported by the current study. However, high activity is only achieved if the effect of this group on the quinoline pK(a) is kept to a minimum. 3-Acyl substituents provide an optimum combination of electronic properties. From this series, compound 17c (SK&F 96067) was shown to be a potent inhibitor of histamine-stimulated gastric acid secretion oral dosing in the Heidenhain pouch dog and was selected for further development and evaluation in man.
    DOI:
    10.1021/jm00096a018
点击查看最新优质反应信息

文献信息

  • 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。
  • Quinoline derivative and antiulcer agent containing said quinoline
    申请人:Otsuka Pharmaceutical Co., Ltd.
    公开号:US05215999A1
    公开(公告)日:1993-06-01
    The present invention discloses a quinoline derivative and salt thereof of the following general formula: ##STR1## (wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and n have the same meanings as defined above). Such a derivative is useful as an antiulcer agent.
    本发明公开了一种喹啉衍生物及其盐,其一般式如下:##STR1##(其中R.sup.1、R.sup.2、R.sup.3、R.sup.4和n的含义与上述定义相同)。这种衍生物可用作抗溃疡剂。
  • QUINOLINE DERIVATIVE, ANTIULCER DRUG CONTAINING THE SAME, AND PRODUCTION OF SAID DERIVATIVE
    申请人:OTSUKA PHARMACEUTICAL CO., LTD.
    公开号:EP0480052A1
    公开(公告)日:1992-04-15
    A quinoline derivative of general formula (I) and its salt, useful as an antiulcer drug, wherein R¹ represents lower alkoxy, halogen, lower alkyl, lower alkylthio, lower alkanoyloxy-substituted lower alkyl, halogenated lower alkyl or hydroxylated lower alkyl; R² and R³ may be the same or different from each other and each represents hydrogen, loweralkyl, halogenated lower alkyl, C₃ to C₈ cycloalkyl, cycloalkyl-substituted lower alkyl, lower alkenyloxy, lower alkenyl, lower alkoxy-substituted lower alkyl, phenyl-substituted lower alkyl, lower alkynyl, lower alkylphenyl or hydroxylated lower alkyl; R⁴ represents phenyl, tetrahydronaphthyl or naphthyl which may be each substituted with one or two members selected from the group consisting of lower alkyl, halogen, lower alkoxy, lower alkylthio, lower alkanoyl, phenyl, cyano, lower alkynylsulfinyl, lower alkoxycarbonyl, lower alkenylthio, phenyl-substituted lower alkylthio, benzoyl, hydroxylated lower alkyl, lower alkanoyloxy-substituted lower alkyl, lower alkanoyloxy and hydroxyl; and n is 0, 1 or 2.
    一种通式(I)的喹啉衍生物及其盐,可用作抗溃疡药物,其中 R¹ 代表低级烷氧基、卤素、低级烷基、低级烷硫基、低级烷酰氧基取代的低级烷基、卤代低级烷基或羟基低级烷基;R² 和 R³ 可以相同或互不相同,各自代表氢、低级烷基、卤代低级烷基、C₃ 至 C₈ 环烷基、环烷基取代的低级烷基、低级烯酰氧基、低级烯基、低级烷氧基取代的低级烷基、苯基取代的低级烷基、低级炔基、低级烷基苯基或羟基化低级烷基;R⁴ 代表苯基、四氢萘基或萘基,可分别被一个或两个成员取代,这 些成员选自由低级烷基、卤素、低级烷氧基、低级烷硫基、低级烷酰基、苯基、氰基、 低级炔硫基、低级烷氧基羰基、低级烯硫基、苯基取代的低级烷硫基、苯甲酰基、 羟基化低级烷基、低级烷酰氧基取代的低级烷基、低级烷酰氧基和羟基组成的组;n 为 0、1 或 2。
  • US5215999A
    申请人:——
    公开号:US5215999A
    公开(公告)日:1993-06-01
  • Reversible inhibitors of the gastric (H+/K+)-ATPase. 3. 3-Substituted-4-(phenylamino)quinolines
    作者:Robert J. Ife、Thomas H. Brown、David J. Keeling、Colin A. Leach、Malcolm L. Meeson、Michael E. Parsons、David R. Reavill、Colin J. Theobald、Kenneth J. Wiggall
    DOI:10.1021/jm00096a018
    日期:1992.9
    Previously, gastric (H+/K+)-ATPase inhibitors such as 2 have been prepared as analogues of 1a on the presumption that the 3-carbethoxy substituent plays a key role in establishing the orientation of the 4-arylamino group. In this paper we explore further the contribution made to activity by the quinoline 3-substituent. We show th bearing such a substituent, only a particular combination of properties provides high activity, both in as inhibitors of gastric acid secretion in vivo. The ability of the substituent to affect activity by restricting rotation about the C(quin)-N bond through a combination of both a pi-electron withdrawal and hydrogen bonding is supported by the current study. However, high activity is only achieved if the effect of this group on the quinoline pK(a) is kept to a minimum. 3-Acyl substituents provide an optimum combination of electronic properties. From this series, compound 17c (SK&F 96067) was shown to be a potent inhibitor of histamine-stimulated gastric acid secretion oral dosing in the Heidenhain pouch dog and was selected for further development and evaluation in man.
查看更多