α(S)-amino-4-hydroxy-2,6-dimethyl-N-<1(R)-methyl-2-<(3-phenylpropyl)amino>ethyl>benzenepropanamide dihydrochloride | 137650-33-0

• 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: α(S)-amino-4-hydroxy-2,6-dimethyl-N-<1(R)-methyl-2-<(3-phenylpropyl)amino>ethyl>benzenepropanamide dihydrochloride
• CAS: 137650-33-0
• 化学式: C₂₃H₃₃N₃O₂*2ClH
• 分子量: 456.456
• InChiKey: RRKCRYKHPVIEFI-MYXGOWFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  29.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  87.38
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  {(S)-2-(4-Hydroxy-2,6-dimethyl-phenyl)-1-[(R)-1-methyl-2-(3-phenyl-propylamino)-ethylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 在 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 α(S)-amino-4-hydroxy-2,6-dimethyl-N-<1(R)-methyl-2-<(3-phenylpropyl)amino>ethyl>benzenepropanamide dihydrochloride
  参考文献：
  名称：

  Preparation and opioid activity of analogs of the analgesic dipeptide 2,6-dimethyl-L-tyrosyl-N-(3-phenylpropyl)-D-alaninamide

  摘要：

  A number of analogues of the recently disclosed analgesic dipeptide 2,6-dimethyl-L-tyrosyl-D-alanine-phenylpropylamide (SC-39566,2) were prepared. These analogues contained oxymethylene, aminomethylene, ketomethylene, bismethylene, and trans double bond (including vinyl fluoride) isosteric replacements for the amide bond between the D-alanine and phenylpropylamine units in 2. These compounds were tested in opioid binding assays and in the mouse writhing assay for analgesic activity. Though not as potent as 2, the oxymethylene, and trans double bond isosteres showed analgesic activity. The aminomethylene analogues also showed binding activity in subnanomolar concentrations at the mu-receptor. The amide bond between 2,6-dimethyl-L-tyrosine and D-alanine units seems to be critical for opioid activity.

  DOI：

  10.1021/jm00080a005