4-[(2-氧代-1H-喹啉-6-基)氧基]丁酸 | 58899-33-5

• 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: 4-[(2-氧代-1H-喹啉-6-基)氧基]丁酸
• 英文名称: 4-(1,2-dihydro-2-oxo-6-quinolyloxy)butyric acid
• 英文别名: 4-((2-oxo-1,2-dihydroquinolin-6-yl)oxy)butanoic acid；4-(2-oxo-1,2-dihydro-quinolin-6-yloxy)-butyric acid；4-(1,2-dihydro-2-oxoquinolin-6-yloxy)butanoic acid；6-(3-carboxypropoxy)carbostyril；4-(2-oxo-6-hydroquinolyloxy)butyric acid；4-(2-oxo-6-hydroquinolyl)butyric acid；4-[(2-oxo-1H-quinolin-6-yl)oxy]butanoic acid
• CAS: 58899-33-5
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: FHJRNXFGMHYZDW-UHFFFAOYSA-N

物化性质

• 熔点：
  265 °C(Solv: N,N-dimethylformamide (68-12-2); water (7732-18-5))
• 沸点：
  567.4±50.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[(2-氧代-1H-喹啉-6-基)氧基]丁酸 在 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 氯甲酸异丁酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 N-cyclohexyl-N-methyl-4-(1,2-dihydro-1-methyl-2-oxo-6-quinolyloxy)butyramide
  参考文献：
  名称：

  Studies on 2-oxoquinoline derivatives as blood platelet aggregation inhibitors. III. N-Cyclohexyl-N-(2-hydroxyethyl)-4-(1,2-dihydro-2-oxo-6-quinolyloxy)butyramide and related compounds.

  摘要：

  合成了一系列 N,N-取代的ω-(1, 2-二氢-2-氧羟喹啉氧基)烷基氨基酸酰胺，并对其在体外对胶原和ADP诱导的兔血小板聚集的抑制活性进行了测试。这些化合物是通过ω-(1, 2-二氢-2-氧羟喹啉氧基)烷酸与各种胺反应，采用混合酸酐法制备的。其中，N-环己基-N-(2-羟乙基)-4-(1, 2-二氢-2-氧-6-喹啉氧基)丁酰胺（IVa1）被发现具有最强的抑制活性。文中讨论了结构-活性关系。

  DOI：

  10.1248/cpb.31.852
• 作为产物：
  描述：

  4-(2-oxo-1,2,3,4-tetrahydro-6-quinolyloxy)butyric acid 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 15.0h， 以85%的产率得到4-[(2-氧代-1H-喹啉-6-基)氧基]丁酸
  参考文献：
  名称：

  2-氧代喹啉衍生物作为血小板聚集抑制剂的研究。I.4-（2-氧代-1,2,3,4-四氢-6-喹啉基氧基）丁酸酯和相关化合物。

  摘要：

  合成并测试了许多烷基4-(2-氧代-1, 2, 3, 4-四氢-6-喹啉氧基)丁酸酯及相关化合物对体外血小板聚集的抑制活性。其中，乙基4-(2-氧代-1, 2, 3, 4-四氢-6-喹啉氧基)丁酸酯显示出最强的抑制活性。讨论了构效关系。

  DOI：

  10.1248/cpb.31.798

文献信息

• Carbostyril derivatives
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US04435404A1

  公开（公告）日：1984-03-06

  Novel carbostyril derivative and its salt represented by the general formula (1), ##STR1## wherein R.sup.1 is a hydrogen atom, a lower alkyl group, a lower alkenyl group or a phenyl-lower alkyl group; R.sup.2 is a hydrogen atom, a lower alkyl group or a group of the formula ##STR2## wherein A is a lower alkylene group; R.sup.3 is a lower alkyl group, a hydroxy lower alkyl group, a lower alkoxy-lower alkyl group, a lower alkanoyloxy-lower alkyl group or a benzoyloxy-lower alkyl group; and R.sup.4 is a C.sub.3-10 -cycloalkyl group which may have at least one hydroxyl group as the substituent(s) in the cycloalkyl ring, a C.sub.3-10 -cycloalkyl-lower alkyl group, a phenyl group, a phenyl-lower alkyl group which may have at least one lower alkoxy group as the substituent(s) in the phenyl ring, a lower alkyl group which may have at least one hydroxyl group as the substituent(s), a heterocyclic ring residue or a lower alkyl group having one heterocyclic ring residue as the substituent; further, R.sup.3, R.sup.4 and the adjacent nitrogen atom, as well as with or without another nitrogen atom, may form a group of the formula ##STR3## (wherein R.sup.5 is a phenyl group, a C.sub.3-10 -cycloalkyl group or a phenyl-lower alkyl group; and B is a methine group or a nitrogen atom); the carbon-carbon bond between the 3- and 4-positions in the carbostyril skeleton is a single or double bond; the substituted position of the group of the formula ##STR4## is any one of 5-, 6-, 7- or 8-position in the carbostyril skeleton; when the group of the formula ##STR5## is substituted at 5-, 6-, 7- or 8-position in the carbostyril skeleton, then R.sup.2 is a hydrogen atom or a lower alkyl group; alternatively, when R.sup.2 is a group of the formula ##STR6## then 5-, 6-, 7- and 8-positions in the carbostyril skeleton are hydrogen atoms and are not substituted with groups of the formula ##STR7## and when R.sup.3 is a lower alkyl group, then R.sup.4 should be neither of a C.sub.3-10 -cycloalkyl group, a C.sub.3-10 -cycloalkyl-lower alkyl group nor a lower alkyl group, having effects for preventing and treating thrombosis and embolism.

  新型的羧基喹啉衍生物及其盐由通式（1）表示，其中R.sup.1是氢原子，低碳基团，低烯基团或苯基-低碳基团；R.sup.2是氢原子，低碳基团或式##STR2##的基团，其中A是低碳烷基团；R.sup.3是低碳基团，羟基低碳基团，低烷氧基-低碳基团，低烷酰氧基-低碳基团或苯甲酰氧基-低碳基团；R.sup.4是C.sub.3-10-环烷基团，该环烷基团可能至少有一个羟基作为环烷基环上的取代基，C.sub.3-10-环烷基-低碳基团，苯基，苯基-低碳基团，该苯基环上可能至少有一个低烷氧基作为取代基，低碳基，该低碳基可能至少有一个羟基作为取代基，杂环环残基或具有一个杂环环残基作为取代基的低碳基；此外，R.sup.3，R.sup.4和相邻的氮原子，以及有或没有另一个氮原子，可能形成式##STR3##的基团（其中R.sup.5是苯基，C.sub.3-10-环烷基团或苯基-低碳基团；B是亚甲基基团或氮原子）；羧基喹啉骨架中3-和4-位置之间的碳-碳键是单键或双键；式##STR4##的基团的取代位置是羧基喹啉骨架中的5-，6-，7-或8-位置中的任意一个；当式##STR5##的基团在羧基喹啉骨架的5-，6-，7-或8-位置取代时，R.sup.2是氢原子或低碳基团；或者，当R.sup.2是式##STR6##的基团时，羧基喹啉骨架的5-，6-，7-和8-位置是氢原子，并且未被式##STR7##的基团取代；当R.sup.3是低碳基团时，R.sup.4不应是C.sub.3-10-环烷基团，C.sub.3-10-环烷基-低碳基团或低碳基团，具有预防和治疗血栓形成和栓塞的作用。
• [EN] DIHYDROPYRIDINE COMPOUNDS HAVING SIMULTANEOUS ABILITY TO BLOCK L-TYPE CALCIUM CHANNELS AND TO INHIBIT PHOSPHODIESTERASE TYPE 3 ACTIVITY<br/>[FR] COMPOSES DE DIHYDROPYRIDINE PRESENTANT A LA FOIS LA CAPACITE DE BLOQUER DES CANAUX CALCIQUES DE TYPE L ET LA CAPACITE D'INHIBER L'ACTIVITE DE TYPE 3 DE LA PHOSPHODIESTERASE
  申请人：ARTESIAN THERAPEUTICS INC

  公开号：WO2004033444A1

  公开（公告）日：2004-04-22

  The present invention provides compounds that possess inhibitory activity against PDE-3 and L-type calcium channels. The present invention further provides pharmaceutical compositions comprising such compounds and methods of using such compounds for treating cardiovascular disease, stroke, epilepsy, ophthalmic disorder or migraine.

  本发明提供了具有对PDE-3和L型钙通道具有抑制活性的化合物。本发明还提供了包含这些化合物的药物组合物以及使用这些化合物治疗心血管疾病、中风、癫痫、眼科疾病或偏头痛的方法。
• [EN] PIPERIDINE-PYRIDAZONES AND PHTHALAZONES AS PDE4 INHIBITORS<br/>[FR] PIPERIDINE-PYRIDAZONES ET PHTHALAZONES EN TANT QU'INHIBITEURS DE PDE4
  申请人：ALTANA PHARMA AG

  公开号：WO2004017974A1

  公开（公告）日：2004-03-04

  The compounds of a certain formula 1, in which the given substituents have the meanings as indicated in the description, are novel effective PDE4 inhibitors.

  某种化学式为1的化合物，其中给定的取代基具有描述中所示的含义，是新颖有效的PDE4抑制剂。
• Novel carbostyril derivatives
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US04298739A1

  公开（公告）日：1981-11-03

  Novel carbostyril derivatives having platelet aggregation inhibitory action, antiinflamatory action, antiulcer action, vasodilatory action and phosphodiesterase inhibitory action and are useful for preventing or curing thrombus, arteriosclerosis, hypertension, asthma and other like diseases, and also useful as an antiinflamatory or anti-ulcer agent, represented by the formula ##STR1## wherein R.sup.1 is hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, phenyl-C.sub.1-4 alkyl-; R.sup.2 is hydrogen, a halogen atom, hydroxy, phenyl-C.sub.1-4 alkoxy; R.sup.3 is hydrogen, hydroxy, C.sub.1-4 alkyl; R.sup.4 is C.sub.3-8 cycloalkyl, substituted or unsubstituted phenyl, C.sub.3-8 cycloalkyl-C.sub.1-4 alkyl, 2-(3,4-dimethoxyphenyl)-ethyl, R.sup.5 is hydrogen, C.sub.1-8 alkyl, C.sub.2-4 alkenyl, phenyl, C.sub.3-8 cycloalkyl, phenyl-C.sub.1-4 alkyl, C.sub.3-8 cycloalkyl-C.sub.1-4 alkyl, m is an integer of 1 - 3, l and n which may be same or different, and are respectively 0 or an integer of 1 - 7 and the sum of l and n is not exceeding 7, the carbon-carbon bond at 3- and 4-positions in the carbostyril skelton is either single or double bond.

  具有抗血小板聚集抑制作用、抗炎作用、抗溃疡作用、扩血管作用和磷酸二酯酶抑制作用的新型羧基吲哚衍生物，用于预防或治疗血栓、动脉硬化、高血压、哮喘等疾病，同时也可用作抗炎或抗溃疡剂，其结构式如下：其中R.sup.1为氢、C.sub.1-4烷基、C.sub.2-4烯基、苯基-C.sub.1-4烷基-；R.sup.2为氢、卤素原子、羟基、苯基-C.sub.1-4烷氧基；R.sup.3为氢、羟基、C.sub.1-4烷基；R.sup.4为C.sub.3-8环烷基、取代或未取代苯基、C.sub.3-8环烷基-C.sub.1-4烷基、2-(3,4-二甲氧基苯基)-乙基；R.sup.5为氢、C.sub.1-8烷基、C.sub.2-4烯基、苯基、C.sub.3-8环烷基、苯基-C.sub.1-4烷基、C.sub.3-8环烷基-C.sub.1-4烷基；m为1-3的整数，l和n可以相同也可以不同，分别为0或1-7的整数，且l和n的和不超过7，在羧基吲哚骨架的3-和4-位置的碳-碳键为单键或双键。
• Piperidine-pyridazones and phthalazones as pde4 inhibitors
  申请人：Sterk Geert Jan

  公开号：US20060094710A1

  公开（公告）日：2006-05-04

  The compounds of a certain formula 1, in which the given substituents have the meanings as indicated in the description, are novel effective PDE4 inhibitors.

  某种化学式为1的化合物，其中给定的取代基具有描述中指定的含义，是新颖有效的PDE4抑制剂。