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(S)-6-((3-(2-methylamino)propyl)phenoxy)-N-(2-(tritylthio)ethyl)hexanamide | 1313762-89-8

中文名称
——
中文别名
——
英文名称
(S)-6-((3-(2-methylamino)propyl)phenoxy)-N-(2-(tritylthio)ethyl)hexanamide
英文别名
6-[3-[(2S)-2-(methylamino)propyl]phenoxy]-N-(2-tritylsulfanylethyl)hexanamide
(S)-6-((3-(2-methylamino)propyl)phenoxy)-N-(2-(tritylthio)ethyl)hexanamide化学式
CAS
1313762-89-8
化学式
C37H44N2O2S
mdl
——
分子量
580.835
InChiKey
RDQXHIGCOMXILG-PMERELPUSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    7.8
  • 重原子数:
    42
  • 可旋转键数:
    17
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.32
  • 拓扑面积:
    75.7
  • 氢给体数:
    2
  • 氢受体数:
    4

反应信息

  • 作为反应物:
    描述:
    L-酒石酸(S)-6-((3-(2-methylamino)propyl)phenoxy)-N-(2-(tritylthio)ethyl)hexanamidemercury(II) diacetate硫化氢 作用下, 以 乙醇 为溶剂, 反应 2.0h, 以87%的产率得到(S)-N-(2-mercaptoethyl)-6-(3-(2-(methylamino)propyl)phenoxy)hexanamide tartrate
    参考文献:
    名称:
    Synthesis of Mercapto-(+)-methamphetamine Haptens and Their Use for Obtaining Improved Epitope Density on (+)-Methamphetamine Conjugate Vaccines
    摘要:
    This study reports the synthesis of the mercapto-hapten (S)-N-(2-(mercaptoethyl)-6-(3-(2-(methylamino)propyl)phenoxy)hexanamide [3, (+)-METH HSMO9] and its use to prepare METH-conjugated vaccines (MCV) from maleimide-activated proteins. MALDI-TOF mass spectrometry analysis of the MCV synthesized using 3 showed there was a high and controllable epitope density on two different carrier proteins. In addition, the MCV produced a substantially greater immunological response in mice than previous METH haptens, and a monoclonal antibody generated from this MCV in mice showed a very high affinity for (+)-METH (K(D) = 6.8 nM). The efficient covalent coupling of (+)-METH HSMO9 to the activated carrier proteins suggests that this approach could be cost-effective for large-scale production of MCV. In addition, the general methods described for the synthesis of (+)-METH HSMO9 (3) and its use to synthesize MCV will be applicable for conjugated vaccines of small molecules and other substances of abuse such as morphine, nicotine, and cocaine.
    DOI:
    10.1021/jm2004943
  • 作为产物:
    参考文献:
    名称:
    Synthesis of Mercapto-(+)-methamphetamine Haptens and Their Use for Obtaining Improved Epitope Density on (+)-Methamphetamine Conjugate Vaccines
    摘要:
    This study reports the synthesis of the mercapto-hapten (S)-N-(2-(mercaptoethyl)-6-(3-(2-(methylamino)propyl)phenoxy)hexanamide [3, (+)-METH HSMO9] and its use to prepare METH-conjugated vaccines (MCV) from maleimide-activated proteins. MALDI-TOF mass spectrometry analysis of the MCV synthesized using 3 showed there was a high and controllable epitope density on two different carrier proteins. In addition, the MCV produced a substantially greater immunological response in mice than previous METH haptens, and a monoclonal antibody generated from this MCV in mice showed a very high affinity for (+)-METH (K(D) = 6.8 nM). The efficient covalent coupling of (+)-METH HSMO9 to the activated carrier proteins suggests that this approach could be cost-effective for large-scale production of MCV. In addition, the general methods described for the synthesis of (+)-METH HSMO9 (3) and its use to synthesize MCV will be applicable for conjugated vaccines of small molecules and other substances of abuse such as morphine, nicotine, and cocaine.
    DOI:
    10.1021/jm2004943
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文献信息

  • Synthesis of Mercapto-(+)-methamphetamine Haptens and Their Use for Obtaining Improved Epitope Density on (+)-Methamphetamine Conjugate Vaccines
    作者:F. Ivy Carroll、Bruce E. Blough、Ramakrishna R. Pidaparthi、Philip Abraham、Paul K. Gong、Liu Deng、Xiaodong Huang、Melinda Gunnell、Jackson O. Lay、Eric C. Peterson、S. Michael Owens
    DOI:10.1021/jm2004943
    日期:2011.7.28
    This study reports the synthesis of the mercapto-hapten (S)-N-(2-(mercaptoethyl)-6-(3-(2-(methylamino)propyl)phenoxy)hexanamide [3, (+)-METH HSMO9] and its use to prepare METH-conjugated vaccines (MCV) from maleimide-activated proteins. MALDI-TOF mass spectrometry analysis of the MCV synthesized using 3 showed there was a high and controllable epitope density on two different carrier proteins. In addition, the MCV produced a substantially greater immunological response in mice than previous METH haptens, and a monoclonal antibody generated from this MCV in mice showed a very high affinity for (+)-METH (K(D) = 6.8 nM). The efficient covalent coupling of (+)-METH HSMO9 to the activated carrier proteins suggests that this approach could be cost-effective for large-scale production of MCV. In addition, the general methods described for the synthesis of (+)-METH HSMO9 (3) and its use to synthesize MCV will be applicable for conjugated vaccines of small molecules and other substances of abuse such as morphine, nicotine, and cocaine.
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