N-<(benzyloxy)carbonyl>-N'-(2-furoyl)-N'-methyl-1,6-hexanediamine | 116784-99-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-<(benzyloxy)carbonyl>-N'-(2-furoyl)-N'-methyl-1,6-hexanediamine
• 英文别名: benzyl N-[6-[furan-2-carbonyl(methyl)amino]hexyl]carbamate
• CAS: 116784-99-7
• 化学式: C₂₀H₂₆N₂O₄
• 分子量: 358.437
• InChiKey: JKMMLWDQYPNKRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  26.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  71.78
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-<(benzyloxy)carbonyl>-N'-(2-furoyl)-N'-methyl-1,6-hexanediamine 在 palladium on activated charcoal 环己烯 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以68%的产率得到N-(2-furoyl)-N-methyl-1,6-hexanediamine
  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：

  氯甲酸苄酯 在 吡啶 、 sodium hydroxide 、 碳酸氢钠 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 69.0h， 生成 N-<(benzyloxy)carbonyl>-N'-(2-furoyl)-N'-methyl-1,6-hexanediamine
  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

文献信息

• 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：——