N-<(benzyloxy)carbonyl>-N'-methyl-1,6-hexanediamine | 116784-98-6

• 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'-methyl-1,6-hexanediamine
• 英文别名: Benzyl (6-(methylamino)hexyl)carbamate；benzyl N-[6-(methylamino)hexyl]carbamate
• CAS: 116784-98-6
• 化学式: C₁₅H₂₄N₂O₂
• 分子量: 264.368
• InChiKey: NBQLPCSVDWPHAR-UHFFFAOYSA-N

物化性质

• 沸点：
  411.0±38.0 °C(Predicted)
• 密度：
  1.021±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-<(benzyloxy)carbonyl>-N'-methyl-1,6-hexanediamine 在 palladium on activated charcoal 吡啶 、 盐酸 、 环己烯 作用下， 以 甲醇 、 异戊醇 、 苯 为溶剂， 反应 57.0h， 生成 Furan-2-carboxylic acid [6-(4-amino-6,7-dimethoxy-quinazolin-2-ylamino)-hexyl]-methyl-amide; 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：

  6-溴己基胺盐酸盐 在 sodium hydroxide 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 49.0h， 生成 N-<(benzyloxy)carbonyl>-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：——
• MULTIVALENT AGONISTS, PARTIAL AGONISTS AND ANTAGONISTS OF THE GABA RECEPTORS
  申请人：Advanced Medicine, Inc.

  公开号：EP1085870A2

  公开（公告）日：2001-03-28
• METHODS FOR PURIFICATION OF SERINE PROTEASES
  申请人：Portola Pharmaceuticals, Inc.

  公开号：EP2938596B1

  公开（公告）日：2017-11-01
• [EN] MULTIVALENT AGONISTS, PARTIAL AGONISTS AND ANTAGONISTS OF THE GABA RECEPTORS<br/>[FR] AGONISTES POLYVALENTS, AGONISTES ET ANTAGONISTES PARTIELS DES RECEPTEURS DE GABA
  申请人：ADVANCED MEDICINE, INC.

  公开号：WO1999063933A2

  公开（公告）日：1999-12-16

  (EN) Disclosed are multibinding compounds which are agonists, partial agonists, inverse agonists, partial inverse agonist or antagonists of the GABA receptors, which are involved in neurological disorders. The multibinding compounds of this invention containing from 2 to 10 ligands covalently attached to one or more linkers. Each ligand is an agonist, partial agonist, inverse agonist, partial inverse agonist or antagonist of the GABA receptors. The multibinding compounds of this invention are useful in the treatment of neurological disorders such as anxiety, depression, sleep and seizure disorders, emesis and overdoses of benzodiazepine-type drugs, and producing sedation, hypnosis, retrograde amnesia, and enhancing alertness and the like.(FR) L'invention concerne des composés de liaison multiple, lesquels constituent des agonistes, des agonistes partiels, des agonistes inverses, des agonistes ou antagonistes partiels inverses des récepteurs de GABA (acide $g(g)-amino-butyrique) impliqués dans des troubles neurologiques. Les composés de liaison multiple de l'invention contiennent 2 à 10 ligands, liés de manière covalente à un ou plusieurs segments de liaison. Chaque ligand constitue un agoniste, un agoniste partiel, un agoniste inverse, un agoniste ou antagoniste partiel inverse des récepteurs de GABA. Les composés de liaison multiple de l'invention sont utiles dans le traitement de troubles neurologiques tels que l'anxiété, la dépression, les troubles du sommeil et les crises d'épilepsie, les vomissements et overdoses de médicaments du type benzodiazépines; ils sont également utiles pour produire la sédation et l'hypnose, l'amnésie rétrograde, et pour accroître la vigilance et analogue.
• 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.