3-甲氧基-2-苯基喹啉-4-羧酸 | 41957-64-6

• 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
• 中文名称: 3-甲氧基-2-苯基喹啉-4-羧酸
• 英文名称: 3-methoxy-2-phenylquinoline-4-carboxylic cid
• 英文别名: 3-methoxy-2-phenyl-quinoline-4-carboxylic acid；3-Methoxy-2-phenyl-chinolin-4-carbonsaeure；3-methyloxy-2-phenylquinoline-4-carboxylic acid；3-methoxy-2-phenylquinoline-4-carboxylic acid
• CAS: 41957-64-6
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: LOHMJODBCXKQCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  羟辛可芬	oxycinchophen	485-89-2	C16H11NO3	265.268
  ——	3-methyloxy-2-phenyl-4-quinolinecarbonyl chloride	174636-95-4	C17H12ClNO2	297.741
  ——	3-methyloxy-N',2-diphenyl-4-quinolinecarbohydrazide	746637-39-8	C23H19N3O2	369.423
  ——	(S)-N-(α-ethylbenzyl)-3-(2-hydroxyethoxy)-2-phenylquinoline-4-carboxamide	——	C27H26N2O3	426.515
  ——	N-(2-Amino-2-phenylbutyl)-3-methoxy-2-phenylquinoline-4-carboxamide	298689-35-7	C27H27N3O2	425.53
  ——	(S)-N-(α-ethylbenzyl)-3-(ethoxycarbonylmethoxy)-2-phenylquinoline-4-carboxamide	191796-72-2	C29H28N2O4	468.552
  ——	(S)-N-(α-ethylbenzyl)-3-(dimethylaminocarbonylmethoxy)-2-phenylquinoline-4-carboxamide	——	C29H29N3O3	467.568
  (-)-(S)-N-(alpha-乙基苄基)-3-羟基-2-苯基喹啉-4-羧酰胺	talnetant	174636-32-9	C25H22N2O2	382.462
  ——	(+/-)-Talnetant	——	C25H22N2O2	382.462
  ——	(S)-(-)-N-(α-ethylbenzyl)-3-hydroxy-2-phenyl-4-quinoline carboxamide	174636-33-0	C25H22N2O2	382.462

反应信息

• 作为反应物：
  描述：

  3-甲氧基-2-苯基喹啉-4-羧酸 在 氢溴酸 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 (-)-(S)-N-(alpha-乙基苄基)-3-羟基-2-苯基喹啉-4-羧酰胺
  参考文献：
  名称：

  2-Phenyl-4-quinolinecarboxamides：一类新型的有效和选择性的非肽类竞争性人类神经激肽3受体拮抗剂。

  摘要：

  DOI：

  10.1021/jm9602423
• 作为产物：
  描述：

  2-甲氧基苯乙酮 、 靛红 生成 3-甲氧基-2-苯基喹啉-4-羧酸
  参考文献：
  名称：

  Method for the Synthesis of Quinoline Derivatives

  摘要：

  本发明涉及新型中间体和制备药用活性喹啉化合物的过程，包括(−)-(S)-N-(α-乙基苯基)-3-羟基-2-苯基喹啉-4-羧酰胺。

  公开号：

  US20080194623A1

文献信息

• 4-substituted quinoline derivatives
  申请人：Neurogen Corporation

  公开号：US06413982B1

  公开（公告）日：2002-07-02

  Disclosed are compounds of the Formula where R1, R2, R3, R4, X, Y1, and Y2 are defined herein. These compounds bind with high affinity to NK-3 receptors and/or GABAA receptors. Also provided are pharmaceutical compositions comprising these compounds, and methods of treating patients suffering from various central nervous system and peripheral diseases or disorders with these pharmaceutical compositions. This invention also relates to the use of such compounds in combination with one or more other CNS agents to potentiate the effects of the other CNS agents. The compounds of this invention are also useful as probes for the localization of NK-3 receptors and GABAA receptors.

  揭示了具有以下式的化合物，其中R1、R2、R3、R4、X、Y1和Y2在此处被定义。这些化合物与NK-3受体和/或GABAA受体具有高亲和力结合。还提供了包括这些化合物的药物组合物，以及使用这些药物组合物治疗患有各种中枢神经系统和外周疾病或障碍的患者的方法。本发明还涉及将这些化合物与一个或多个其他中枢神经系统药剂结合以增强其他中枢神经系统药剂效果的用途。本发明的化合物还可用作定位NK-3受体和GABAA受体的探针。
• [EN] SUBSTITUTED QUINOLINE-4-CARBOXYLIC HYDRAZIDES AS NK-2/NK-3 RECEPTOR LIGANDS<br/>[FR] HYDRAZIDES D'ACIDE CARBOXYLIQUE DE 4-QUINOLEINE SUBSTITUES EN TANT QUE LIGANDS DU RECEPTEUR DE NK-2/NK-3
  申请人：MERCK SHARP & DOHME

  公开号：WO2004072045A1

  公开（公告）日：2004-08-26

  The present invention discloses a compound of formula (I): wherein: R1 is an aryl or heteroaryl ring; R2 is hydroxy, C1-6 alkoxy, C1-6 alkyl, amino, NR'R' or C1-6 alkyl-NR'R' where R' and R' are independently chosen from hydrogen and C1-4 alkyl and where R' and R', together with the nitrogen atom to which they are attached, form a saturated nitrogen-containing 3-7 membered heterocycle optionally containing a further nitrogen atom and optionally substituted by NR'R' as defined above or R2 is C1-6 alkoxy substituted by NR'R' as defined above; R3 is hydrogen or C1-6 alkyl; R4 is hydrogen, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C3-8 cycloalkyl, aryl or aryl C1-6 alkyl; R5 is hydrogen, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C3-8 cycloalkyl, aryl, aryl C1-6 alkyl or C1-6 alkoxycarbonyl; or R4 and R5, together with the nitrogen atom to which they are attached, form a C3-C10 mono- or bicyclic saturated ring; X and Y are independently chosen from hydrogen, hydroxy, nitro, amino, cyano, CF3, halogen and C1-4 alkyl; or a pharmaceutically acceptable salt thereof; as NK-2/NK-3 ligands for treating schizophrenia, COPD, asthma or irritable bowel syndrome.

  本发明公开了一种化合物，其化学式为（I）：其中：R1是芳基或杂环芳基；R2是羟基，C1-6烷氧基，C1-6烷基，氨基，NR'R'或C1-6烷基-NR'R'，其中R'和R'分别选择自氢和C1-4烷基，且R'和R'与它们连接的氮原子一起形成一个饱和的含氮3-7成员杂环，该杂环可以包含另一个氮原子，并且可以被上述定义的NR'R'取代，或者R2是被上述定义的NR'R'取代的C1-6烷氧基；R3是氢或C1-6烷基；R4是氢，C1-8烷基，C2-8烯基，C2-8炔基，C3-8环烷基，芳基或芳基C1-6烷基；R5是氢，C1-8烷基，C2-8烯基，C2-8炔基，C3-8环烷基，芳基，芳基C1-6烷基或C1-6烷氧羰基；或者R4和R5，与它们连接的氮原子一起形成一个C3-C10单环或双环饱和环；X和Y分别选择自氢，羟基，硝基，氨基，氰基，三氟甲基，卤素和C1-4烷基；或其药用盐；作为治疗精神分裂症、COPD、哮喘或肠易激综合征的NK-2/NK-3配体。
• Substituted quinoline-4-carboxylic hydrazides as nk-2/nk-3 receptor ligands
  申请人：Chambers Stuart Mark

  公开号：US20060089348A1

  公开（公告）日：2006-04-27

  The present invention discloses a compound of formula (I): wherein: R 1 is an aryl or heteroaryl ring; R 2 is hydroxy, C 1-6 alkoxy, C 1-6 alkyl, amino, NR′R″ or C 1-6 alkyl-NR′R″ where R′ and R″ are independently chosen from hydrogen and C 1-4 alkyl and where R′ and R″, together with the nitrogen atom to which they are attached, form a saturated nitrogen-containing 3-7 membered heterocycle optionally containing a further nitrogen atom and optionally substituted by NR′R″ as defined above or R 2 is C 1-6 alkoxy substituted by NR′R″ as defined above; R 3 is hydrogen or C 1-6 alkyl; R 4 is hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, C 3-8 cycloalkyl, aryl or aryl C 1-6 alkyl; R 5 is hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, C 3 -8 cycloalkyl, aryl, aryl C 1-6 alkyl or C 1-6 alkoxycarbonyl; or R 4 and R 5 , together with the nitrogen atom to which they are attached, form a C 3 -C 10 mono- or bicyclic saturated ring; X and Y are independently chosen from hydrogen, hydroxy, nitro, amino, cyano, CF 3 , halogen and C 1-4 alkyl; or a pharmaceutically acceptable salt thereof; as NK-2/NK-3 ligands for treating schizophrenia, COPD, asthma or irritable bowel syndrome.

  本发明揭示了一种化合物，其化学式为（I）：其中：R1为芳基或杂环芳基环；R2为羟基，C1-6烷氧基，C1-6烷基，氨基，NR′R″或C1-6烷基-NR′R″，其中R′和R″分别选择氢和C1-4烷基，且R′和R″与它们所连接的氮原子一起形成一个饱和的含氮3-7成员杂环，可选地含有进一步的氮原子，并可选地被上述定义的NR′R″或R2为C1-6烷氧基所取代；R3为氢或C1-6烷基；R4为氢，C1-8烷基，C2-8烯基，C2-8炔基，C3-8环烷基，芳基或芳基C1-6烷基；R5为氢，C1-8烷基，C2-8烯基，C2-8炔基，C3-8环烷基，芳基，芳基C1-6烷基或C1-6烷氧羰基；或R4和R5与它们所连接的氮原子一起形成C3-C10单环或双环饱和环；X和Y分别选择自氢，羟基，硝基，氨基，氰基，CF3，卤素和C1-4烷基；或其药学上可接受的盐；作为NK-2 / NK-3配体，用于治疗精神分裂症，慢性阻塞性肺疾病，哮喘或肠易激综合征。
• Amide Alkyl Pyridiyl Quinolines as Nk3 Receptor Modulators
  申请人：Albert Jeffrey S.

  公开号：US20080200504A1

  公开（公告）日：2008-08-21

  Compounds of Formula (I) wherein R 1 , A, R 2 , R 3 , R 4 , R 5 ,n, m and q are as described in the specification, pharmaceutically-acceptable salts, methods of making, pharmaceutical compositions containing and methods for using the same.

  化合物公式(I)的化合物，其中R1，A，R2，R3，R4，R5，n，m和q如规范中所述，药学上可接受的盐，制备方法，含有该化合物的制药组合物以及使用该组合物的方法。
• 4-Substituted quinoline derivatives
  申请人：Neurogen Corporation

  公开号：US06624175B2

  公开（公告）日：2003-09-23

  Disclosed are compounds of the Formula where R1, R2, R3, R4, X, Y1, and Y2 are defined herein. These compounds bind with high affinity to NK-3 receptors and/or GABAA receptors. Also provided are pharmaceutical compositions comprising these compounds, and methods of treating patients suffering from various central nervous system and peripheral diseases or disorders with these pharmaceutical compositions. This invention also relates to the use of such compounds in combination with one or more other CNS agents to potentiate the effects of the other CNS agents. The compounds of this invention are also useful as probes for the localization of NK-3 receptors and GABAA receptors.

  本发明涉及的化合物具有下列式中所定义的R1、R2、R3、R4、X、Y1和Y2。这些化合物与NK-3受体和/或GABAA受体结合亲和力高。本发明还提供了包含这些化合物的制药组合物以及使用这些制药组合物治疗患有各种中枢神经系统和周围疾病或疾病的患者的方法。本发明还涉及使用这种化合物与一个或多个其他中枢神经系统药物结合以增强其他中枢神经系统药物的效果。本发明所述的化合物还可用作定位NK-3受体和GABAA受体的探针。