5,6,7,8-tetrahydro-6-(4-pentenyl)-1,6-naphthyridine | 75509-71-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5,6,7,8-tetrahydro-6-(4-pentenyl)-1,6-naphthyridine
• 英文别名: 6-pent-4-enyl-7,8-dihydro-5H-1,6-naphthyridine
• CAS: 75509-71-6
• 化学式: C₁₃H₁₈N₂
• 分子量: 202.299
• InChiKey: QLMGTKIQPNJTTF-UHFFFAOYSA-N

物化性质

• 沸点：
  304.9±30.0 °C(Predicted)
• 密度：
  0.997±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-Pent-4-enyl-[1,6]naphthyridin-6-ium 在 sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 以69%的产率得到5,6,7,8-tetrahydro-6-(4-pentenyl)-1,6-naphthyridine
  参考文献：
  名称：

  Antivertigo agents. II. Structure-activity relationships of 6-substituted 5,6,7,8-tetrahydro-1,6-naphthyridines.

  摘要：

  通过还原相应的 1，6-萘啶鎓盐，合成了一些 6-取代的 5，6，7，8-四氢-1，6-萘啶，它们被设计为 2-（2-甲基氨基乙基）吡啶的环状同系物。根据这些衍生物抑制猫自发性眼球震颤的能力，对其抗眩晕活性进行了评估。通过基于 6 位取代基亲油性（π）的回归分析，以及使用改进的忽略二原子重叠分子轨道法对相关化合物进行构象分析，研究了受试化合物的分子结构与其抗眩晕活性之间的关系。在这些化合物中，6-烯丙基和 6-环丙基甲基衍生物表现出极强的活性，同时大大降低了降压作用。

  DOI：

  10.1248/cpb.32.995

文献信息

• 1,6-Naphthyridine derivatives, and antidinic and cerebral circulation
  申请人：Nippon Kayaku Kabushiki Kaisha

  公开号：US04308273A1

  公开（公告）日：1981-12-29

  This invention relates to the novel 1,6-naphthyridine derivatives useful as antidinic and/or cerebral circulation improver, such novel derivatives being represented by the following general formula: ##STR1## (wherein R is a C.sub.2-10 alkyl which may have hydroxyl, lower alkylcarbonyl, lower alkyloxycarbonyl or phenoxy as a substituent; a C.sub.2-10 unsaturated aliphatic hydrocarbon group having unsaturated double bond(s); a phenyl-lower alkyl which may have halogen, lower alkyl, lower alkoxy or lower alkylthio as substituent(s) attached to the phenyl ring; a cinnamyl which may have halogen, nitro, lower alkyl or lower alkoxy as substituent(s) attached to the phenyl ring; propargyl; 1-naphthylmethyl; 2-thenyl; cyclohexenyl; a cycloalkyl-lower alkyl with a 3- to 6-membered ring; 1/2(C.sub.2-4 alkylene); 1/2(butenylene), or diphenylmethyl, and in case two alkoxyl groups are present attached to the phenyl ring, they may be bonded to form a ring) and salt thereof.

  本发明涉及一种新型的1,6-萘啶衍生物，可用作抗衰老和/或改善脑循环的药物。这种新型衍生物的一般结构式如下：##STR1##（其中R是C.sub.2-10烷基，可以具有羟基、低碳酰基、低氧代碳酰基或苯氧基作为取代基；C.sub.2-10不饱和脂肪烃基，具有不饱和双键；苯基-低烷基，可以具有卤素、低烷基、低氧代烷基或低硫代烷基作为苯环的取代基；肉桂基，可以具有卤素、硝基、低烷基或低氧代烷基作为苯环的取代基；丙炔基；1-萘甲基；2-噻吩基；环己烯基；具有3-至6-成员环的环烷基-低烷基；1/2(C.sub.2-4烷基)；1/2(丁烯基)，或二苯甲基，当有两个烷氧基取代基连接到苯环时，它们可以连接形成一个环，并且其盐。
• US4308273A
  申请人：——

  公开号：US4308273A

  公开（公告）日：1981-12-29
• Antivertigo agents. II. Structure-activity relationships of 6-substituted 5,6,7,8-tetrahydro-1,6-naphthyridines.
  作者：AKIRA SHIOZAWA、YUHICHIRO ICHIKAWA、MICHIO ISHIKAWA、YOSHIYA KOGO、SHUJI KURASHIGE、HIROSHI MIYAZAKI、HIROSHI YAMANAKA、TAKAO SAKAMOTO

  DOI：10.1248/cpb.32.995

  日期：——

  A number of 6-substituted 5, 6, 7, 8-tetrahydro-1, 6-naphthyridines designed as cyclic homologues of betahistine, 2-(2-methylaminoethyl) pyridine, were synthesized by the reduction of the corresponding 1, 6-naphthyridinium salts. The antivertigo activity of these derivatives was evaluated in terms of their ability to inhibit spontaneous nystagmus in cats. The relationships between the molecular structures of the test compounds and their antivertigo activities were investigated by a regression analysis based on the lipophilicity (π) of the substituents at the 6-position and by a conformational analysis of the compounds of interest using the modified neglect of diatomic overlap molecular orbital method. Among these compounds, the 6-allyl-and 6-cyclopropylmethyl derivatives exhibited extremely potent activity with greatly reduced hypotensive action.

  通过还原相应的 1，6-萘啶鎓盐，合成了一些 6-取代的 5，6，7，8-四氢-1，6-萘啶，它们被设计为 2-（2-甲基氨基乙基）吡啶的环状同系物。根据这些衍生物抑制猫自发性眼球震颤的能力，对其抗眩晕活性进行了评估。通过基于 6 位取代基亲油性（π）的回归分析，以及使用改进的忽略二原子重叠分子轨道法对相关化合物进行构象分析，研究了受试化合物的分子结构与其抗眩晕活性之间的关系。在这些化合物中，6-烯丙基和 6-环丙基甲基衍生物表现出极强的活性，同时大大降低了降压作用。