6-(4-chlorobutanoyl)-3,4-dihydroquinolin-2(1H)-one | 80834-82-8

• 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: 6-(4-chlorobutanoyl)-3,4-dihydroquinolin-2(1H)-one
• 英文别名: 6-(4-chloro-1-oxobutyl)-3,4-dihydrocarbostyril；6-(4-chlorobutyryl)-3,4-dihydrocarbostyril；6-(4-chlorobutanoyl)-3,4-dihydro-1H-quinolin-2-one
• CAS: 80834-82-8
• 化学式: C₁₃H₁₄ClNO₂
• 分子量: 251.713
• InChiKey: MOCQEWYNVLOSBY-UHFFFAOYSA-N

物化性质

• 沸点：
  499.6±45.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(4-chlorobutanoyl)-3,4-dihydroquinolin-2(1H)-one 在 sodium borohydrid 作用下， 以 甲醇 为溶剂， 生成 6-(1-hydroxy-4-chlorobutyl)-3,4-dihydrocarbostyril
  参考文献：
  名称：

  Carbostyril derivatives and pharmaceutical composition containing the

  摘要：

  新型的羰基喹啉衍生物及其盐具有抗组胺效应和中枢神经系统控制效应，其一般公式如下：其中R.sup.1为氢原子、较低的烷基基团、苯基较低的烷基基团、较低的烯基基团、较低的炔基基团；A为下列式的基团：(其中R.sup.2为氢原子或较低的烷基基团)；B为较低的烷基烯基基团；当A为下列式的基团时，l为1：或当A为下列式的基团时，l为0或1：Z为下列式的基团：或(其中R.sup.3、R.sup.4和R.sup.5如上所定义)。

  公开号：

  US04455422A1
• 作为产物：
  描述：

  3,4-二氢-2(1H)-喹啉酮 在 aluminium chloride 作用下， 以 二硫化碳 为溶剂， 生成 6-(4-chlorobutanoyl)-3,4-dihydroquinolin-2(1H)-one
  参考文献：
  名称：

  Carbostyril derivatives and pharmaceutical composition containing the

  摘要：

  新型的羰基喹啉衍生物及其盐具有抗组胺效应和中枢神经系统控制效应，其一般公式如下：其中R.sup.1为氢原子、较低的烷基基团、苯基较低的烷基基团、较低的烯基基团、较低的炔基基团；A为下列式的基团：(其中R.sup.2为氢原子或较低的烷基基团)；B为较低的烷基烯基基团；当A为下列式的基团时，l为1：或当A为下列式的基团时，l为0或1：Z为下列式的基团：或(其中R.sup.3、R.sup.4和R.sup.5如上所定义)。

  公开号：

  US04455422A1

文献信息

• New dual 5-HT1A and 5-HT7 receptor ligands derived from SYA16263
  作者：Edward Ofori、Edem K. Onyameh、Uma M. Gonela、Chandrashekhar Voshavar、Barbara Bricker、Tracy L. Swanson、Amy J. Eshleman、Jennifer L. Schmachtenberg、Shelley H. Bloom、Aaron J. Janowsky、Seth Y. Ablordeppey

  DOI：10.1016/j.ejmech.2021.113243

  日期：2021.3

  nM). Thus, it was of interest to exploit its pharmacophore elements in designing new dual receptor ligands. Using SYA16263 as the lead molecule, we have conducted a limited structure-affinity relationship (SAFIR) study by modifying various structural elements in the arylalkyl moiety, resulting in the identification of a new dual 5-HT1AR and 5-HT7R ligand, 6-chloro-2-methyl-2-(3-(4-(pyridin-2-yl)piperazin-1-yl)propyl)-2

  我们之前曾报道，双重 5-HT 1A和 5-HT 7受体配体可能会发现作为各种 CNS 相关疾病（包括认知和抗焦虑障碍）的治疗选择。我们最近还报道了 SYA16263 具有抗精神病药样特性，在动物模型中没有僵直症，这归因于其将 β-抑制蛋白募集到 D 2受体的能力。然而，SYA16263 也以非常高的亲和力与 5-HT 1A R ( Ki = 1.1 nM) 结合，在 5-HT 7 R ( Ki= 90纳米）。因此，在设计新的双受体配体中利用其药效团元素是有意义的。使用 SYA16263 作为先导分子，我们通过修饰芳烷基部分中的各种结构元素进行了有限结构亲和关系 (SAFIR) 研究，从而鉴定出新的双 5-HT 1A R 和 5-HT 7 R 配体, 6-chloro-2-methyl-2-(3-(4-(pyridin-2-yl)piperazin-1-yl)propyl)-2,3-dihydro-1H-inden-1-one
• Carbostyril derivatives and salts thereof and pharmaceutical
  申请人：Otsuka Pharmaceutical Co. Ltd.

  公开号：US05434164A1

  公开（公告）日：1995-07-18

  Carbostyril derivatives and salts thereof represented by the general formula (1a), including some known compounds, possess activities for inhibiting adhesion of thrombocytes. ##STR1## Z, A, X, R, R.sup.1 and R.sup.2 are defined in the specification. Some carbostyril derivatives having chemical structural formulas similar to those of carbostyril derivatives and salts thereof represented by the general formula (1a) have been known in prior art references, however the above-mentioned pharmacological activities have not been known to the present date.

  通式（1a）所表示的羧基苯基咪唑衍生物及其盐，包括一些已知化合物，具有抑制血小板粘附活性。其中，Z、A、X、R、R.sup.1和R.sup.2在说明书中有定义。先前的文献中已知一些具有与通式（1a）所表示的羧基苯基咪唑衍生物及其盐相似的化学结构式的羧基苯基咪唑衍生物，但上述药理活性直到现在才被发现。
• Carbostyril derivatives, and central nervous system controlling agents
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US04460593A1

  公开（公告）日：1984-07-17

  Novel carbostyril derivatives and their salts are useful as antihistaminic agents and central nervous system controlling agents, represented by the general formula (1), ##STR1## wherein R.sup.1 is a hydrogen atom, a lower alkyl group, a phenyl-lower alkyl group, a lower alkenyl group, a lower alkynyl group; A is a group of the formula ##STR2## or a group of the formula ##STR3## (wherein R.sup.2 is a hydrogen atom or a lower alkyl group); B is a lower alkylene group; l is 1 when A is a group of the formula ##STR4## or l is 0 or 1 when A is a group of the formula ##STR5## Z is a group of the formula >N--R.sup.3 or ##STR6## (wherein R.sup.3, R.sup.4 and R.sup.5 are as defined herein).

  新型的羧基苯基吡啶衍生物及其盐作为抗组胺药和中枢神经系统控制药物，其通式表示为（1），其中R1是氢原子、较低的烷基、苯基-较低的烷基、较低的烯基、较低的炔基；A是式子的基团或式子的基团（其中R2是氢原子或较低的烷基）；B是较低的亚烷基基团；当A是式子的基团时，l为1，当A是式子的基团时，l为0或1；Z是式子或式子的基团（其中R3、R4和R5如上定义）。
• Carbostyril derivatives and salts thereof and pharmaceutical composition
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US05008274A1

  公开（公告）日：1991-04-16

  A carbostyril derivative or pharmaceutically acceptable salt thereof represented by the following general formula: ##STR1## wherein Z, A, XN, R, R.sup.1, and R.sup.2 are as defined in the specification. These carbostyril derivatives are useful in pharmaceutical compositions for inhibiting adhesion of thrombocytes.

  以下是一种由碳基喹啉衍生物或其药学上可接受的盐所表示的通式：##STR1## 其中Z，A，XN，R，R.sup.1和R.sup.2在说明书中定义。这些碳基喹啉衍生物在制备用于抑制血小板粘附的药物组合物中有用。
• Carbostyril derivatives and antihistaminic agents containing the
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US04567187A1

  公开（公告）日：1986-01-28

  Novel carbostyril derivatives and their salts having antihistaminic effect and central nervous system controlling effect and are useful as antihistaminic agents and central nervous system controlling agents, represented by the general formula (1), ##STR1## wherein R.sup.1 is a hydrogen atom, a lower alkyl group, a phenyl-lower alkyl group, a lower alkenyl group, a lower alkynyl group; A is a group of the formula ##STR2## or a group of the formula ##STR3## (wherein R.sup.2 is a hydrogen atom or a lower alkyl group); B is a lower alkylene group; l is 1 when A is a group of the formula ##STR4## or l is 0 or 1 when A is a group of the formula ##STR5## Z is a group of the formula ##STR6## (wherein R.sup.3 is a substituted-phenyl group having 1 to 3 substituents, on the phenyl ring, selected from the group consisting of a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy-carbonyl group, a carboxyl group, a lower alkylthio group, a lower alkanoyl group, a hydroxyl group, a nitro group, an amino group and a cyano group; or R.sup.3 is a substituted-phenyl group having a lower alkylenedioxy group as the substituent, a phenyl-lower alkyl group or a 1,2,3,4-tetrahydronaphthyl group; R.sup.4 is a substituted-phenyl group having 1 to 3 substituents, on the phenyl group, selected from the group consisting of a halogen atom, a lower alkyl group and a lower alkoxy group; or R.sup.4 is a substituted-phenyl group having a lower alkylenedioxy group as the substituent, a phenyl-lower alkyl group, a 1,2,3,4-tetrahydronaphthyl group or a group of the formula ##STR7## R.sup.5 is a hydrogen atom, a hydroxyl group or a lower alkanoyl group; or when R.sup.5 is a hydrogen atom the carbon-carbon bond between 3- and 4-positions in the piperidine ring is a double bond which is dehydrogenated the hydrogen atoms bonded at 3- and 4-positions of piperidine ring; the carbon-carbon bond between 3- and 4-positions in the carbostyril skeleton is a single or double bond. The carbostyril derivatives of the present invention have antihistaminic effects and central nervous system controlling effects and are useful for antihistaminic agents and central nervous system controlling agents.

  具有抗组胺作用和中枢神经系统调节作用的新型羧基苯基吡啶衍生物及其盐，可用作抗组胺剂和中枢神经系统调节剂，其一般式表示为（1），其中R1是氢原子、较低的烷基、苯基较低的烷基、较低的烯基、较低的炔基；A是公式（2）的基团或公式（3）的基团（其中R2是氢原子或较低的烷基）；B是较低的烷基链；当A为公式（4）的基团时，l为1，或当A为公式（5）的基团时，l为0或1；Z是公式（6）的基团（其中R3是苯环上具有1至3个取代基的取代苯基，所述取代基从卤原子、较低的烷基、较低的烷氧基、较低的烷氧羰基、羧基、较低的烷硫基、较低的烷酰基、羟基、硝基、氨基和氰基中选择；或R3是具有较低的烷基二氧基基团的取代苯基、苯基较低的烷基或1,2,3,4-四氢萘基；R4是苯基上具有1至3个取代基的取代苯基，所述取代基从卤原子、较低的烷基和较低的烷氧基中选择；或R4是具有较低的烷基二氧基基团的取代苯基、苯基较低的烷基、1,2,3,4-四氢萘基或公式（7）的基团；R5是氢原子、羟基或较低的烷酰基；或当R5是氢原子时，哌啶环上3-和4-位置之间的碳-碳键为脱氢的双键，3-和4-位置的氢原子脱离；在羧基苯基吡啶骨架中3-和4-位置之间的碳-碳键为单键或双键。本发明的羧基苯基吡啶衍生物具有抗组胺作用和中枢神经系统调节作用，并可用作抗组胺剂和中枢神经系统调节剂。