5-(6-氯己基)嘧啶 | 88940-79-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-(6-氯己基)嘧啶
• 中文别名: 嘧啶,5-(6-氯己基)-
• 英文名称: 6-(5-pyrimidinyl)hexylchloride
• 英文别名: 5-(6-chlorohexyl)pyrimidine
• CAS: 88940-79-8
• 化学式: C₁₀H₁₅ClN₂
• 分子量: 198.695
• InChiKey: SFRDOTKHIUHPAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(6-氯己基)嘧啶 在 一水合肼 、 potassium iodide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 5-pyrimidinehexanamine
  参考文献：
  名称：

  Pyrido[2,1-b]quinazolinecarboxamide derivatives as platelet activating factor antagonists

  摘要：

  A series of N-[(heteroaryl)alkyl]pyrido[2,1-b]quinazolines were evaluated for their ability to inhibit the binding of radiolabeled platelet activating factor (PAF) to its receptor on dog platelets. The most potent compounds in this series were found to be pyrido[2,1-b]quinazoline-8-carboxamides possessing a four- or six-carbon chain between the carboxamide nitrogen atom and a 3-pyridinyl or 5-pyrimidinyl moiety. Since earlier metabolism studies with pyridoquinazolinecarboxamides suggest that the carboxamide moiety is labile to hydrolysis in vivo, attempts were made to find isosteric replacements for this group. The substitutions examined led to a loss of activity; however, insertion of a methyl group on the carbon atom alpha to the carboxamide nitrogen led to an enantioselective enhancement of potency. (R)-2-(1-Methylethyl)-N-[1-methyl-4-(3-pyridinyl)butyl]-11-oxo-11H- pyrido[2,1-b]quinazoline-8-carboxamide (34) was more potent than the corresponding S enantiomer in the PAF binding assay and was also shown to be more resistant to degradation by amidases present in whole liver homogenates obtained from guinea pig, dog, and squirrel monkey. The corresponding rac-2-(1-methylethyl)-N-[1-methyl-4-(3-pyridinyl)butyl]-11-oxo-11H- pyrido[2,1-b]quinazoline-8-carboxamide (33) was found to inhibit transient PAF-induced thrombocytopenia and decreases in blood pressure in guinea pigs after intravenous or oral administration and to have a duration of action of greater than 5 h after an oral dose of 200 mg/kg. Compound 33 thus represents the prototype of a new class of orally active PAF antagonists.

  DOI：

  10.1021/jm00397a034
• 作为产物：
  描述：

  5-己炔-1-醇 在 palladium on activated charcoal bis-triphenylphosphine-palladium(II) chloride 、 氯化亚砜 、 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 5-(6-氯己基)嘧啶
  参考文献：
  名称：

  Pyrido[2,1-b]quinazolinecarboxamide derivatives as platelet activating factor antagonists

  摘要：

  A series of N-[(heteroaryl)alkyl]pyrido[2,1-b]quinazolines were evaluated for their ability to inhibit the binding of radiolabeled platelet activating factor (PAF) to its receptor on dog platelets. The most potent compounds in this series were found to be pyrido[2,1-b]quinazoline-8-carboxamides possessing a four- or six-carbon chain between the carboxamide nitrogen atom and a 3-pyridinyl or 5-pyrimidinyl moiety. Since earlier metabolism studies with pyridoquinazolinecarboxamides suggest that the carboxamide moiety is labile to hydrolysis in vivo, attempts were made to find isosteric replacements for this group. The substitutions examined led to a loss of activity; however, insertion of a methyl group on the carbon atom alpha to the carboxamide nitrogen led to an enantioselective enhancement of potency. (R)-2-(1-Methylethyl)-N-[1-methyl-4-(3-pyridinyl)butyl]-11-oxo-11H- pyrido[2,1-b]quinazoline-8-carboxamide (34) was more potent than the corresponding S enantiomer in the PAF binding assay and was also shown to be more resistant to degradation by amidases present in whole liver homogenates obtained from guinea pig, dog, and squirrel monkey. The corresponding rac-2-(1-methylethyl)-N-[1-methyl-4-(3-pyridinyl)butyl]-11-oxo-11H- pyrido[2,1-b]quinazoline-8-carboxamide (33) was found to inhibit transient PAF-induced thrombocytopenia and decreases in blood pressure in guinea pigs after intravenous or oral administration and to have a duration of action of greater than 5 h after an oral dose of 200 mg/kg. Compound 33 thus represents the prototype of a new class of orally active PAF antagonists.

  DOI：

  10.1021/jm00397a034

文献信息

• Pyrido[2,1-b]quinazoline derivatives useful as agents for treatment of
  申请人：Hoffmann-La Roche Inc.

  公开号：US04551460A1

  公开（公告）日：1985-11-05

  Pyrido[2,1-b]quinazoline derivatives of the formulas ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are as hereinafter set forth, are described. The compounds of formulas I and II are useful as agents for the treatment of allergic conditions as well as for the treatment of vascular disorders involving thrombosis.

  该文描述了化合物的结构公式为##STR1##其中R.sub.1、R.sub.2和R.sub.3如下所述的吡啶[2,1-b]喹唑啉衍生物。公式I和II的化合物可用作治疗过敏症状的药物，也可用于治疗涉及血栓形成的血管疾病。
• N-substituted diphenylpiperidines and antiobesity use thereof
  申请人：Hoffmann-La Roche Inc.

  公开号：US04632925A1

  公开（公告）日：1986-12-30

  Compounds of the formula ##STR1## wherein R.sub.1 is ##STR2## the asterisk denotes the specific bonding orientation to the piperidine moiety; R.sub.2 is alkylene or --CO--(CH.sub.2).sub.n -- wherein n is 0 to 11; R.sub.3 and R.sub.4, independently, are hydrogen, halogen or lower alkoxy; and HET is pyridinyl, pyrimidinyl or imidazolyl, and salts thereof with pharmaceutically acceptable acids, are described. The compounds of formula I exhibit insulin lowering activity and are useful as antiobesity agents.

  该化合物的公式为##STR1##其中R.sub.1是##STR2##星号表示与哌啶基团的特定配位取向；R.sub.2是烷基或--CO--(CH.sub.2).sub.n--其中n为0至11；R.sub.3和R.sub.4，独立地，是氢、卤素或低碳氧基；HET是吡啶基、嘧啶基或咪唑基，以及其与药用可接受酸的盐。公式I的化合物表现出降血糖活性，并可用作抗肥胖剂。
• TILLEY, JEFFERSON W.;BURGHARD, BARBARA;BURGHARDT, CHARLES;MOWLES, THOMAS +, J. MED. CHEM., 31,(1988) N 2, 466-472
  作者：TILLEY, JEFFERSON W.、BURGHARD, BARBARA、BURGHARDT, CHARLES、MOWLES, THOMAS +

  DOI：——

  日期：——
• Pyrido(2,1-b)chinazolinderivate
  申请人：F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft

  公开号：EP0094080B1

  公开（公告）日：1987-09-09
• N-substituierte Diphenylpiperidine
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0221376B1

  公开（公告）日：1990-06-20