N-Cyclohexyl-N-methyl-4-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)butanamide | 69592-33-2

• 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: N-Cyclohexyl-N-methyl-4-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)butanamide
• 英文别名: N-cyclohexyl-N-methyl-4-[(2-oxo-3,4-dihydro-1H-quinolin-6-yl)oxy]butanamide
• CAS: 69592-33-2
• 化学式: C₂₀H₂₈N₂O₃
• 分子量: 344.454
• InChiKey: XSUBCFUQNASGMT-UHFFFAOYSA-N

物化性质

• 熔点：
  141-142 °C
• 沸点：
  585.0±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Cyclohexyl-N-methyl-4-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)butanamide 、 sodium hydroxide 、 氢气 、 碘甲烷 在 氯仿 、 potassium carbonate 、 水 、 Sodium sulfate-III 、 ligroin 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以to obtain 0.9 g of 1-methyl-6-[3-(N-cyclohexyl-N-methylaminocarbonyl)propoxy]-3,4-dihydrocarbostyril in the form of colorless needle-like crystals with melting point of 104.5°-106.5° C.的产率得到1-methyl-6-[3-(N-cyclohexyl)-N-methylaminocarbonylpropoxy]-3,4-dihydrocarbostyril
  参考文献：
  名称：

  Novel carbostyril derivatives

  摘要：

  具有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甲基苯基吡咯衍生物，可用于预防或治疗血栓、动脉硬化、高血压、哮喘等疾病，并可用作抗炎或抗溃疡剂，其化学式表示为：##STR1## 其中，R1为氢、C1-4烷基、C2-4烯基、苯基-C1-4烷基；R2为氢、卤素原子、羟基、苯基-C1-4烷氧基；R3为氢、羟基、C1-4烷基；R4为C3-8环烷基、取代或未取代苯基、C3-8环烷基-C1-4烷基、2-(3,4-二甲氧基苯基)-乙基、R5为氢、C1-8烷基、C2-4烯基、苯基、C3-8环烷基、苯基-C1-4烷基、C3-8环烷基-C1-4烷基，m为1-3的整数，l和n可以相同或不同，分别为0或1-7的整数，l和n的和不超过7，羧甲基苯基吡咯骨架的3-和4-位碳-碳键为单键或双键。

  公开号：

  US04298739A1
• 作为产物：
  描述：

  N-甲基环己胺 在 palladium on activated charcoal 吡啶 、 ammonium hydroxide 、 氢气 、 sodium carbonate 、 iron(II) sulfate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 4.25h， 生成 N-Cyclohexyl-N-methyl-4-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)butanamide
  参考文献：
  名称：

  Inhibitors of cyclic AMP phosphodiesterase. 1. Analogs of cilostamide and anagrelide

  摘要：

  Evaluation of a series of lactam heterocyclic analogues of cilostamide (2) as inhibitors of cyclic AMP phosphodiesterase derived from both human platelets and rat heart in comparison with their corresponding methoxy-substituted heterocycles has revealed that the N-cyclohexyl-N-methyl-4-oxybutyramide side chain of 2 is an important lipophilic and/or steric pharmacophore. Attachment of this side chain to the parent heterocycle of the potent cyclic AMP phosphodiesterase inhibitor anagrelide (3) afforded the hybrid structure RS-82856 (1), shown to be more potent than either of its progenitors as an inhibitor of cyclic AMP phosphodiesterase or of ADP-induced platelet aggregation. The available in vitro data suggest that 1 possesses potentially useful antithrombotic and cardiotonic properties.

  DOI：

  10.1021/jm00385a011

文献信息

• Discovery of a Thioxanthone–TfOH Complex as a Photoredox Catalyst for Hydrogenation of Alkenes Using <i>p</i> ‐Xylene as both Electron and Hydrogen Sources
  作者：Wen‐Jie Kang、Bo Li、Meng Duan、Guangxing Pan、Weiqiang Sun、Aishun Ding、Yanbin Zhang、K. N. Houk、Hao Guo

  DOI：10.1002/anie.202211562

  日期：2022.11.25

  novel organic photoredox catalyst was discovered by simply adding a catalytic amount of TfOH as a co-catalyst to readily available thioxanthone. The new catalyst, 9-HTXTF, shows a sufficiently long singlet lifetime and adequately strong oxidation potential, as well as relatively facile photoexcitation, with applications in the hydrogenation and deuteration of carbonylated alkenes.

  通过简单地将催化量的 TfOH 作为助催化剂添加到容易获得的噻吨酮中，发现了一种新型有机光氧化还原催化剂。新型催化剂9-HTXTF具有足够长的单线态寿命和足够强的氧化电位，以及相对容易的光激发，可用于羰基化烯烃的氢化和氘化。
• JONES G. H.; VENUTI M. C.; ALVAREZ R.; BRUNO J. J.; BERKS A. H.; PRINCE A+, J. MED. CHEM., 30,(1987) N 2, 295-303
  作者：JONES G. H.、 VENUTI M. C.、 ALVAREZ R.、 BRUNO J. J.、 BERKS A. H.、 PRINCE A+

  DOI：——

  日期：——
• US4298739A
  申请人：——

  公开号：US4298739A

  公开（公告）日：1981-11-03
• Inhibitors of cyclic AMP phosphodiesterase. 1. Analogs of cilostamide and anagrelide
  作者：Gordon H. Jones、Michael C. Venuti、Robert Alvarez、John J. Bruno、Andrew H. Berks、Anthony Prince

  DOI：10.1021/jm00385a011

  日期：1987.2

  Evaluation of a series of lactam heterocyclic analogues of cilostamide (2) as inhibitors of cyclic AMP phosphodiesterase derived from both human platelets and rat heart in comparison with their corresponding methoxy-substituted heterocycles has revealed that the N-cyclohexyl-N-methyl-4-oxybutyramide side chain of 2 is an important lipophilic and/or steric pharmacophore. Attachment of this side chain to the parent heterocycle of the potent cyclic AMP phosphodiesterase inhibitor anagrelide (3) afforded the hybrid structure RS-82856 (1), shown to be more potent than either of its progenitors as an inhibitor of cyclic AMP phosphodiesterase or of ADP-induced platelet aggregation. The available in vitro data suggest that 1 possesses potentially useful antithrombotic and cardiotonic properties.
• 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甲基苯基吡咯衍生物，可用于预防或治疗血栓、动脉硬化、高血压、哮喘等疾病，并可用作抗炎或抗溃疡剂，其化学式表示为：##STR1## 其中，R1为氢、C1-4烷基、C2-4烯基、苯基-C1-4烷基；R2为氢、卤素原子、羟基、苯基-C1-4烷氧基；R3为氢、羟基、C1-4烷基；R4为C3-8环烷基、取代或未取代苯基、C3-8环烷基-C1-4烷基、2-(3,4-二甲氧基苯基)-乙基、R5为氢、C1-8烷基、C2-4烯基、苯基、C3-8环烷基、苯基-C1-4烷基、C3-8环烷基-C1-4烷基，m为1-3的整数，l和n可以相同或不同，分别为0或1-7的整数，l和n的和不超过7，羧甲基苯基吡咯骨架的3-和4-位碳-碳键为单键或双键。