[(S)-1-[3-(5-{4-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionylamino]-butyl}-3-methyl-6-oxo-1,6-dihydro-pyrazin-2-yl)-propylcarbamoyl]-2-(4-hydroxy-2,6-dimethyl-phenyl)-ethyl]-carbamic acid tert-butyl ester | 915766-60-8

• 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: [(S)-1-[3-(5-{4-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionylamino]-butyl}-3-methyl-6-oxo-1,6-dihydro-pyrazin-2-yl)-propylcarbamoyl]-2-(4-hydroxy-2,6-dimethyl-phenyl)-ethyl]-carbamic acid tert-butyl ester
• CAS: 915766-60-8
• 化学式: C₄₄H₆₄N₆O₉
• 分子量: 821.027
• InChiKey: OKMIOILTTFRAIZ-BCRBLDSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  59.0
• 可旋转键数：
  17.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  221.07
• 氢给体数：
  7.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  [(S)-1-[3-(5-{4-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionylamino]-butyl}-3-methyl-6-oxo-1,6-dihydro-pyrazin-2-yl)-propylcarbamoyl]-2-(4-hydroxy-2,6-dimethyl-phenyl)-ethyl]-carbamic acid tert-butyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以7.0 mg的产率得到(S)-2-Amino-N-[3-(5-{4-[(S)-2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionylamino]-butyl}-3-methyl-6-oxo-1,6-dihydro-pyrazin-2-yl)-propyl]-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionamide; compound with GENERIC INORGANIC NEUTRAL COMPONENT
  参考文献：
  名称：

  Synthesis of 3,6-bis[H-Tyr/H-Dmt-NH(CH2)m,n]-2(1H)pyrazinone derivatives: Function of alkyl chain length on opioid activity

  摘要：

  Dimeric opioid analogues linked to a pyrazinone platform, 3-[Tyr/Dmt-NH(CH2)(m)]-6-[Tyr/Dmt-NH(CH2)(n)]-2(1H)-pyrazinone (m, n = 3 or 4), were synthesized. The Tyr-containing compound (m = 4, n = 3) exhibited mu-receptor affinity (K-i mu; 7.58 nM) comparable to that of morphine, while the Dmt derivatives exhibited considerably higher affinity (K-i mu; 0.021-0.051 nM) with corresponding agonism (IC50 = 1.79-4.93 nM). Interestingly one compound (m = 4, n = 3) revealed modest delta-opioid agonism; the converse analogue (m = 3, n = 4), however, was inactive in MVD assay. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.079
• 作为产物：
  描述：

  [(S)-4-((S)-2-Amino-6-benzyloxycarbonylamino-hexanoylamino)-6-chloro-5-oxo-hexyl]-carbamic acid benzyl ester; hydrochloride 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢溴酸 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 [(S)-1-[3-(5-{4-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionylamino]-butyl}-3-methyl-6-oxo-1,6-dihydro-pyrazin-2-yl)-propylcarbamoyl]-2-(4-hydroxy-2,6-dimethyl-phenyl)-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of 3,6-bis[H-Tyr/H-Dmt-NH(CH2)m,n]-2(1H)pyrazinone derivatives: Function of alkyl chain length on opioid activity

  摘要：

  Dimeric opioid analogues linked to a pyrazinone platform, 3-[Tyr/Dmt-NH(CH2)(m)]-6-[Tyr/Dmt-NH(CH2)(n)]-2(1H)-pyrazinone (m, n = 3 or 4), were synthesized. The Tyr-containing compound (m = 4, n = 3) exhibited mu-receptor affinity (K-i mu; 7.58 nM) comparable to that of morphine, while the Dmt derivatives exhibited considerably higher affinity (K-i mu; 0.021-0.051 nM) with corresponding agonism (IC50 = 1.79-4.93 nM). Interestingly one compound (m = 4, n = 3) revealed modest delta-opioid agonism; the converse analogue (m = 3, n = 4), however, was inactive in MVD assay. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.079