(S)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-3-[(S)-2-[(S)-3-(1H-indol-3-yl)-2-isobutoxycarbonylamino-propionylamino]-6-(3-o-tolyl-ureido)-hexanoylamino]-N-methyl-succinamic acid

• 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)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-3-[(S)-2-[(S)-3-(1H-indol-3-yl)-2-isobutoxycarbonylamino-propionylamino]-6-(3-o-tolyl-ureido)-hexanoylamino]-N-methyl-succinamic acid
• 英文别名: (S)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-3-[(S)-2-((S)-3-1H-indol-3-yl-2-isobutoxycarbonylamino-propionylamino)-6-(3-o-tolyl-ureido)-hexanoylamino]-N-methyl-succinamic acid；(3S)-4-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]-methylamino]-3-[[(2S)-2-[[(2S)-3-(1H-indol-3-yl)-2-(2-methylpropoxycarbonylamino)propanoyl]amino]-6-[(2-methylphenyl)carbamoylamino]hexanoyl]amino]-4-oxobutanoic acid
• 化学式: C₄₄H₅₆N₈O₉
• 分子量: 840.977
• InChiKey: ZTESUZUASFFSGQ-BQYLNSIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  61
• 可旋转键数：
  23
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  254
• 氢给体数：
  8
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (S)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-3-[(S)-2-[(S)-3-(1H-indol-3-yl)-2-isobutoxycarbonylamino-propionylamino]-6-(3-o-tolyl-ureido)-hexanoylamino]-N-methyl-succinamic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 (S)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-3-[(S)-2-[(S)-3-(1H-indol-3-yl)-2-isobutoxycarbonylamino-propionylamino]-6-(3-o-tolyl-ureido)-hexanoylamino]-N-methyl-succinamic acid
  参考文献：
  名称：

  Tetrapeptide CCK agonists: structure-activity studies on modifications at the N-terminus

  摘要：

  We had reported earlier(1) on a novel series of potent and selective tetrapeptide cholecystokinin-A (CCK-A) agonists of the general structure Boc-Trp-Lys[epsilon-Y]-Asp-N(R)PheNH(2) [Y = amides, ureas; R = H, Me] that were potent anorectic agents in rats. In an effort to optimize the potency, selectivity, stability, and efficacy of our lead candidate A-71623 [R = Me, Y = o-tolylaminocarbonyl; Tac] toward-development of a clinical candidate; we have explored a series of analogues in which the N-terminal Boc functionality was systematically replaced with various amides, ureas, carbamates, and sulfonamides of differing size, hydrophobicity; and stereoelectronic properties. In;general, these analogues maintained good potency and selectivity for the CCK-A receptor (guinea pig pancreas), as well as potent anorectic activity in rats. Those analogues exhibiting equal or superior activity compared to A-71623 but differing physicochemical properties may represent superior drug candidates.

  DOI：

  10.1021/jm00028a015

文献信息

• Tetrapeptide CCK agonists: structure-activity studies on modifications at the N-terminus
  作者：Richard L. Elliott、Hana Kopecka、Michael J. Bennett、Youe Kong Shue、Richard Craig、Chun Wel Lin、Bruce R. Bianchi、Thomas R. Miller、David G. Witte

  DOI：10.1021/jm00028a015

  日期：1994.1

  We had reported earlier(1) on a novel series of potent and selective tetrapeptide cholecystokinin-A (CCK-A) agonists of the general structure Boc-Trp-Lys[epsilon-Y]-Asp-N(R)PheNH(2) [Y = amides, ureas; R = H, Me] that were potent anorectic agents in rats. In an effort to optimize the potency, selectivity, stability, and efficacy of our lead candidate A-71623 [R = Me, Y = o-tolylaminocarbonyl; Tac] toward-development of a clinical candidate; we have explored a series of analogues in which the N-terminal Boc functionality was systematically replaced with various amides, ureas, carbamates, and sulfonamides of differing size, hydrophobicity; and stereoelectronic properties. In;general, these analogues maintained good potency and selectivity for the CCK-A receptor (guinea pig pancreas), as well as potent anorectic activity in rats. Those analogues exhibiting equal or superior activity compared to A-71623 but differing physicochemical properties may represent superior drug candidates.