N-(3-(4aR,7S,7aR,12bS)-7,9-dihydroxy-4,4a,7,7a-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-3(2H)-yl)butyl-3-mercaptopropanamide | 1313816-43-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: N-(3-(4aR,7S,7aR,12bS)-7,9-dihydroxy-4,4a,7,7a-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-3(2H)-yl)butyl-3-mercaptopropanamide
• 英文别名: N-[4-[(4R,4aR,7S,7aR,12bS)-7,9-dihydroxy-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-3-yl]butyl]-3-sulfanylpropanamide
• CAS: 1313816-43-1
• 化学式: C₂₃H₃₀N₂O₄S
• 分子量: 430.568
• InChiKey: KAXRNJGHLJFXLG-YRRUUWTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  83
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  盐酸海洛因 在 三异丙基硅烷 、 水 、 三乙酰氧基硼氢化钠 、 碳酸氢钠 、 溶剂黄146 、 三乙胺 、 三氟乙酸 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 10.75h， 生成 N-(3-(4aR,7S,7aR,12bS)-7,9-dihydroxy-4,4a,7,7a-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-3(2H)-yl)butyl-3-mercaptopropanamide
  参考文献：
  名称：

  A Vaccine Strategy that Induces Protective Immunity against Heroin

  摘要：

  Heroin addiction is a wide-reaching problem with a spectrum of damaging social consequences. A vaccine capable of blocking heroin's effects could provide a long-lasting and sustainable adjunct to heroin addiction therapy. Heroin, however, presents a particularly challenging immunotherapeutic target, as it is metabolized to multiple psychoactive molecules. To reconcile this dilemma, we examined the idea of a singular vaccine with the potential to display multiple drug-like antigens; thus two haptens were synthesized, one heroin-like and another morphine-like in chemical structure. A key feature in this approach is that immunopresentation with the heroin-like hapten is thought to be immunochemically dynamic such that multiple haptens are simultaneously presented to the immune system. We demonstrate the significance of this approach through the extremely rapid generation of robust polyclonal antibody titers with remarkable specificity. Importantly, both the antinociceptive effects of heroin and acquisition of heroin self-administration were blocked in rats vaccinated using the heroin-like hapten.

  DOI：

  10.1021/jm200461m

文献信息

• A Vaccine Strategy that Induces Protective Immunity against Heroin
  作者：G. Neil Stowe、Leandro F. Vendruscolo、Scott Edwards、Joel E. Schlosburg、Kaushik K. Misra、Gery Schulteis、Alexander V. Mayorov、Joseph S. Zakhari、George F. Koob、Kim D. Janda

  DOI：10.1021/jm200461m

  日期：2011.7.28

  Heroin addiction is a wide-reaching problem with a spectrum of damaging social consequences. A vaccine capable of blocking heroin's effects could provide a long-lasting and sustainable adjunct to heroin addiction therapy. Heroin, however, presents a particularly challenging immunotherapeutic target, as it is metabolized to multiple psychoactive molecules. To reconcile this dilemma, we examined the idea of a singular vaccine with the potential to display multiple drug-like antigens; thus two haptens were synthesized, one heroin-like and another morphine-like in chemical structure. A key feature in this approach is that immunopresentation with the heroin-like hapten is thought to be immunochemically dynamic such that multiple haptens are simultaneously presented to the immune system. We demonstrate the significance of this approach through the extremely rapid generation of robust polyclonal antibody titers with remarkable specificity. Importantly, both the antinociceptive effects of heroin and acquisition of heroin self-administration were blocked in rats vaccinated using the heroin-like hapten.