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nicotinoyl-Pro-Ala-Tyr-Lys(Boc) cholesteryl ester | 214596-57-3

中文名称
——
中文别名
——
英文名称
nicotinoyl-Pro-Ala-Tyr-Lys(Boc) cholesteryl ester
英文别名
[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (2S)-2-[[(2S)-3-(4-hydroxyphenyl)-2-[[(2S)-2-[[(2S)-1-(pyridine-3-carbonyl)pyrrolidine-2-carbonyl]amino]propanoyl]amino]propanoyl]amino]-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
nicotinoyl-Pro-Ala-Tyr-Lys(Boc) cholesteryl ester化学式
CAS
214596-57-3
化学式
C61H90N6O9
mdl
——
分子量
1051.42
InChiKey
YHGAWSKJUZJJNP-KDOPRQQVSA-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):
    11.6
  • 重原子数:
    76
  • 可旋转键数:
    24
  • 环数:
    7.0
  • sp3杂化的碳原子比例:
    0.69
  • 拓扑面积:
    205
  • 氢给体数:
    5
  • 氢受体数:
    10

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    硫酸二甲酯nicotinoyl-Pro-Ala-Tyr-Lys(Boc) cholesteryl ester乙醚 为溶剂, 以91.76%的产率得到trigonellyl-Pro-Ala-Tyr-Lys(Boc) cholesteryl ester
    参考文献:
    名称:
    Strategies To Target Kyotorphin Analogues to the Brain
    摘要:
    The design, synthesis, and pharmacological evaluation of brain-targeted chemical delivery systems (CDS) for a kyotorphin analogue (Tyr-Lys) are described. The brain-targeted compound contains the active peptide in a packaged, disguised form, flanked between the lipophilic cholesteryl ester on the C-terminus and the 1,4-dihydrotrigonellyl redox targetor, attached to the N-terminus through strategically selected L-amino acid(s) spacer. It was found that for successful brain targeting, the epsilon-amine of Lys needs to be also converted to a Lipophilic function. Through sequential enzymatic bioactivation, the Tyr-Lys dipeptide is released in a sustained manner, producing significant and prolonged analgesic activity as demonstrated by the rat tail latency test. An alternate strategy was also employed. Lys was replaced by a redox amino acid pair, Nys(+) <-> Nys, the nicotinamide <-> 1,4-dihydronicotinamide analogues of Lys (Nys(+) is 2-amino-6-(3-carbamoyl-1-pyridiniumyl)hexanoic acid). The Nys form is lipophilic and facilitates delivery in addition to the C- and N-terminal lipophilic functions, Enzymatic oxidation to Nys(+) provides the lock-in, followed by removal;of the lipophilic groups, releasing Tyr-Nys(+) from the brain-targeted analogue (BTRA). Nys(+) was shown to be an effective substitution for Arg or Lys. The activities of the CDS and BTRA, respectively,were antagonized by naloxone, supporting the designed brain-targeted processes. The mst potent compound is the two-proline spacer containing CDS (CDS-PP), followed by the BTRA.
    DOI:
    10.1021/jm970715l
  • 作为产物:
    参考文献:
    名称:
    Strategies To Target Kyotorphin Analogues to the Brain
    摘要:
    The design, synthesis, and pharmacological evaluation of brain-targeted chemical delivery systems (CDS) for a kyotorphin analogue (Tyr-Lys) are described. The brain-targeted compound contains the active peptide in a packaged, disguised form, flanked between the lipophilic cholesteryl ester on the C-terminus and the 1,4-dihydrotrigonellyl redox targetor, attached to the N-terminus through strategically selected L-amino acid(s) spacer. It was found that for successful brain targeting, the epsilon-amine of Lys needs to be also converted to a Lipophilic function. Through sequential enzymatic bioactivation, the Tyr-Lys dipeptide is released in a sustained manner, producing significant and prolonged analgesic activity as demonstrated by the rat tail latency test. An alternate strategy was also employed. Lys was replaced by a redox amino acid pair, Nys(+) <-> Nys, the nicotinamide <-> 1,4-dihydronicotinamide analogues of Lys (Nys(+) is 2-amino-6-(3-carbamoyl-1-pyridiniumyl)hexanoic acid). The Nys form is lipophilic and facilitates delivery in addition to the C- and N-terminal lipophilic functions, Enzymatic oxidation to Nys(+) provides the lock-in, followed by removal;of the lipophilic groups, releasing Tyr-Nys(+) from the brain-targeted analogue (BTRA). Nys(+) was shown to be an effective substitution for Arg or Lys. The activities of the CDS and BTRA, respectively,were antagonized by naloxone, supporting the designed brain-targeted processes. The mst potent compound is the two-proline spacer containing CDS (CDS-PP), followed by the BTRA.
    DOI:
    10.1021/jm970715l
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