Cbz-Ahx-OH | 95484-20-1

• 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: Cbz-Ahx-OH
• 英文别名: benzyl N-(6-oxoheptyl)carbamate
• CAS: 95484-20-1
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: CTHCPTZAHKMCLP-UHFFFAOYSA-N

物化性质

• 沸点：
  438.4±38.0 °C(Predicted)
• 密度：
  1.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Cbz-Ahx-OH 在 氢溴酸 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 4-[2-(6-Amino-1-methyl-hexylamino)-1-hydroxy-ethyl]-benzene-1,2-diol; hydrochloride
  参考文献：
  名称：

  Conjugates of Catecholamines. 5. Synthesis and β-Adrenergic Activity of N-(Aminoalkyl)norepinephrine Derivatives

  摘要：

  A novel series of N-aminoalkyl congeners and model derivatives of norepinephrine has been synthesized. Compounds that were structurally related to epinephrine were prepared from fully protected intermediates. Alternatively, isoproterenol-related compounds were synthesized via reductive amination of preformed methyl ketone derivatives with norepinephrine. The beta-adrenergic activities of these new compounds were assessed through measurement of intracellular cyclic AMP accumulation in S49 mouse lymphoma cells and displacement of iodocyanopindolol (ICYP) from membrane preparations. Congeners that contained an underivatized primary amine function exhibited virtually no activity in these assays. However, when this amine function was acylated (e.g., to an amide, carbamate, urea, sulfonamide, etc.), the products exhibited generally increased beta-adrenergic activity, which was, however, strongly dependent on the nature of the acylating group and also the length of the spacer. In particular, a benzyl carbamate derivative containing a branched, seven-carbon spacer group was 40 times more potent than isoproterenol in the in vitro S49 assay.

  DOI：

  10.1021/jm50001a017
• 作为产物：
  描述：

  7-羰基辛酸 在 二苯基膦叠氮化物 、 三乙胺 作用下， 以 苯 为溶剂， 反应 17.75h， 生成 Cbz-Ahx-OH
  参考文献：
  名称：

  Conjugates of Catecholamines. 5. Synthesis and β-Adrenergic Activity of N-(Aminoalkyl)norepinephrine Derivatives

  摘要：

  A novel series of N-aminoalkyl congeners and model derivatives of norepinephrine has been synthesized. Compounds that were structurally related to epinephrine were prepared from fully protected intermediates. Alternatively, isoproterenol-related compounds were synthesized via reductive amination of preformed methyl ketone derivatives with norepinephrine. The beta-adrenergic activities of these new compounds were assessed through measurement of intracellular cyclic AMP accumulation in S49 mouse lymphoma cells and displacement of iodocyanopindolol (ICYP) from membrane preparations. Congeners that contained an underivatized primary amine function exhibited virtually no activity in these assays. However, when this amine function was acylated (e.g., to an amide, carbamate, urea, sulfonamide, etc.), the products exhibited generally increased beta-adrenergic activity, which was, however, strongly dependent on the nature of the acylating group and also the length of the spacer. In particular, a benzyl carbamate derivative containing a branched, seven-carbon spacer group was 40 times more potent than isoproterenol in the in vitro S49 assay.

  DOI：

  10.1021/jm50001a017

文献信息

• INOSITOL AND TREHALOSE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS FOR TREATING NEURODEGENERATIVE DISEASES COMPRISING THE SAME
  申请人：Chung Sung-Kee

  公开号：US20110224423A1

  公开（公告）日：2011-09-15

  The invented inositol and trehalose derivatives, prepared by introducing multiple units of the guanidine group to the backbone molecules, show excellent blood-brain barrier permeability, and accordingly, it can be easily transported to the brain tissues and utilized for the treatment of neurodegenerative diseases such as Alzheimer's disease and Huntington's disease.

  通过将多个胍基单元引入骨架分子，制备出的肌醇和海藻糖衍生物表现出优异的血脑屏障渗透性，因此可以轻松地运输到大脑组织并用于治疗神经退行性疾病，如阿尔茨海默病和亨廷顿病。
• [EN] COMPOSITION AND METHOD FOR NEW THERAPEUTIC AGENTS INCLUDING GUANIDINIUM-PRESENTING DENDRIMERS AND BRANCHED STRUCTURES<br/>[FR] COMPOSITION ET PROCÉDÉ POUR DE NOUVEAUX AGENTS THÉRAPEUTIQUES COMPRENANT DES DENDRIMÈRES DE PRÉSENTATION DE GUANIDINIUM ET DES STRUCTURES RAMIFIÉES
  申请人：UNIV LELAND STANFORD JUNIOR

  公开号：WO2021257723A9

  公开（公告）日：2022-03-10
• US9371350B2
  申请人：——

  公开号：US9371350B2

  公开（公告）日：2016-06-21
• Conjugates of Catecholamines. 5. Synthesis and β-Adrenergic Activity of N-(Aminoalkyl)norepinephrine Derivatives
  作者：Allen B. Reitz、Etienne Sonveaux、Roberto P. Rosenkranz、Michael S. Verlander、Kenneth L. Melmon、Brian B. Hoffman、Yasio Akita、Neal Castagnoli、Murray Goodman

  DOI：10.1021/jm50001a017

  日期：1985.5

  A novel series of N-aminoalkyl congeners and model derivatives of norepinephrine has been synthesized. Compounds that were structurally related to epinephrine were prepared from fully protected intermediates. Alternatively, isoproterenol-related compounds were synthesized via reductive amination of preformed methyl ketone derivatives with norepinephrine. The beta-adrenergic activities of these new compounds were assessed through measurement of intracellular cyclic AMP accumulation in S49 mouse lymphoma cells and displacement of iodocyanopindolol (ICYP) from membrane preparations. Congeners that contained an underivatized primary amine function exhibited virtually no activity in these assays. However, when this amine function was acylated (e.g., to an amide, carbamate, urea, sulfonamide, etc.), the products exhibited generally increased beta-adrenergic activity, which was, however, strongly dependent on the nature of the acylating group and also the length of the spacer. In particular, a benzyl carbamate derivative containing a branched, seven-carbon spacer group was 40 times more potent than isoproterenol in the in vitro S49 assay.