furan-2-carboxylic acid methyl-(6-methylamino-hexyl)-amide | 116784-90-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: furan-2-carboxylic acid methyl-(6-methylamino-hexyl)-amide
• 英文别名: N-methyl-N-[6-(methylamino)hexyl]furan-2-carboxamide
• CAS: 116784-90-8
• 化学式: C₁₃H₂₂N₂O₂
• 分子量: 238.33
• InChiKey: UVWYZTGAPYXVLK-UHFFFAOYSA-N

物化性质

• 沸点：
  366.6±22.0 °C(Predicted)
• 密度：
  1.012±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  furan-2-carboxylic acid methyl-(6-methylamino-hexyl)-amide 、 2-氯-4-氨基-6,7-二甲氧基喹唑啉 在 盐酸 作用下， 以 异戊醇 为溶剂， 反应 36.0h， 生成 N-[6-[(4-amino-6,7-dimethoxyquinazolin-2-yl)-methylamino]hexyl]-N-methylfuran-2-carboxamide;hydrochloride
  参考文献：
  名称：

  Structure-activity relationships in prazosin-related compounds. Effect of replacing a piperazine ring with an alkanediamine moiety on .alpha.1-adrenoreceptor blocking activity

  摘要：

  Several prazosin-related compounds were synthesized in which the piperazine ring of prazosin (1) was replaced by an alkanediamine chain and were evaluated for their blocking activity on alpha 1- and alpha 2-adrenoreceptors in isolated rat vas deferens. All the compounds investigated proved highly selective toward the alpha 1-adrenoreceptor owing to a very low affinity for alpha 2-adrenoreceptors. Furthermore, compounds 2, 9, and 13 were also investigated in vivo to determine their hypotensive effect on anesthetized rats, which were compared with that of prazosin (1). It was confirmed that the piperazine moiety of 1 is not essential for potency. However, optimum activity depends on two parameters: carbon-chain length of the alkanediamine moiety and N-methylation of both the amide and the 2-amino functions. In the desmethyl series, optimum activity was associated with the lower homologues (2-4) bearing a chain of two to four methylenes whereas in the N,N'-dimethyl series peak potency was observed with a six-carbon chain as in 13. Compound 13 proved the most active of the series and was more potent than prazosin (1) in both in vivo and in vitro assays. It is hypothesized that the alpha 1-adrenoreceptor incorporates a lipophilic area that is located between the binding sites for the quinazoline and the furoyl moieties and is able to accommodate a polymethylene chain.

  DOI：

  10.1021/jm00121a011
• 作为产物：
  描述：

  呋喃甲酰氯 、 N,N'-二甲基-1,6-己二胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 furan-2-carboxylic acid methyl-(6-methylamino-hexyl)-amide
  参考文献：
  名称：

  Oxazolone derivatives and uses thereof

  摘要：

  这项发明涉及一般为α1B-受体拮抗剂的化合物，其由式(I)所代表： 其中X、Y和R1如规范中所定义，或者是各个异构体或消旋或非消旋异构体的混合物，或其药学上可接受的盐或溶剂。该发明还涉及含有这种化合物的药物组合物，以及它们作为治疗剂的使用方法。

  公开号：

  US06355641B1

文献信息

• Oxazolone derivatives and uses thereof
  申请人：Syntex (U.S.A.) LLC

  公开号：US06355641B1

  公开（公告）日：2002-03-12

  This invention relates to compounds which are generally alpha1B-receptor antagonists, and which are represented by Formula (I): wherein X, Y, and R1 are as defined in the specification, or individual isomers or racemic or non-racemic mixtures of isomers, or pharmaceutically acceptable salts or solvates thereof. The invention further relates to pharmaceutical compositions containing such compounds, and methods for their use as therapeutic agents.

  这项发明涉及一般为α1B-受体拮抗剂的化合物，其由式(I)所代表： 其中X、Y和R1如规范中所定义，或者是各个异构体或消旋或非消旋异构体的混合物，或其药学上可接受的盐或溶剂。该发明还涉及含有这种化合物的药物组合物，以及它们作为治疗剂的使用方法。
• GIARDINA, DARIO;BRASILI, LIVIO;GREGORY, MAURIZIO;MASSI, MAURIZIO;PICCHIO,+, J. MED. CHEM., 32,(1989) N, C. 50-55
  作者：GIARDINA, DARIO、BRASILI, LIVIO、GREGORY, MAURIZIO、MASSI, MAURIZIO、PICCHIO,+

  DOI：——

  日期：——
• US6355641B1
  申请人：——

  公开号：US6355641B1

  公开（公告）日：2002-03-12
• [EN] OXAZOLONE DERIVATIVES AND THEIR USE AS ALPHA-1 ADRENORECEPTOR MODULATORS<br/>[FR] DERIVES D'OXAZOLONE ET UTILISATIONS DE CES DERNIERS EN TANT QUE MODULATEURS DU RECEPTEUR ADRENERGIQUE ALPHA-1
  申请人：HOFFMANN LA ROCHE

  公开号：WO2000055143A1

  公开（公告）日：2000-09-21

  Compounds of Formula (I) wherein X is Formula (A), (B) or (C): Z is CH or N; R1 is cycloalkyl, cycloalkenyl, heterocyclic, aryl or heteroaryl; are useful as alpha1- adrenoreceptor modulators, particularly antagonists.
• Structure-activity relationships in prazosin-related compounds. Effect of replacing a piperazine ring with an alkanediamine moiety on .alpha.1-adrenoreceptor blocking activity
  作者：Dario Giardina、Livio Brasili、Maurizio Gregori、Maurizio Massi、Maria T. Picchio、Wilma Quaglia、Carlo Melchiorre

  DOI：10.1021/jm00121a011

  日期：1989.1

  Several prazosin-related compounds were synthesized in which the piperazine ring of prazosin (1) was replaced by an alkanediamine chain and were evaluated for their blocking activity on alpha 1- and alpha 2-adrenoreceptors in isolated rat vas deferens. All the compounds investigated proved highly selective toward the alpha 1-adrenoreceptor owing to a very low affinity for alpha 2-adrenoreceptors. Furthermore, compounds 2, 9, and 13 were also investigated in vivo to determine their hypotensive effect on anesthetized rats, which were compared with that of prazosin (1). It was confirmed that the piperazine moiety of 1 is not essential for potency. However, optimum activity depends on two parameters: carbon-chain length of the alkanediamine moiety and N-methylation of both the amide and the 2-amino functions. In the desmethyl series, optimum activity was associated with the lower homologues (2-4) bearing a chain of two to four methylenes whereas in the N,N'-dimethyl series peak potency was observed with a six-carbon chain as in 13. Compound 13 proved the most active of the series and was more potent than prazosin (1) in both in vivo and in vitro assays. It is hypothesized that the alpha 1-adrenoreceptor incorporates a lipophilic area that is located between the binding sites for the quinazoline and the furoyl moieties and is able to accommodate a polymethylene chain.