Fmoc-(2S,4R)-(4-OCO-NH-CH2-CH2-NH2)-Pro-OH | 556796-31-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-(2S,4R)-(4-OCO-NH-CH2-CH2-NH2)-Pro-OH
• 英文别名: (2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-(((2-aminoethyl)carbamoyl)oxy)pyrrolidine-2-carboxylic acid；(2S,4R)-4-(2-aminoethylcarbamoyloxy)-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid
• CAS: 556796-31-7
• 化学式: C₂₃H₂₅N₃O₆
• 分子量: 439.468
• InChiKey: FRBBWMSBMUHUOQ-VLIAUNLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 Fmoc-(2S,4R)-(4-OCO-NH-CH2-CH2-NH2)-Pro-OH 在 sodium cyanoborohydride 作用下， 反应 1.0h， 以89%的产率得到Fmoc-(2S,4R)-(4-OCO-NH-CH2-CH2-NMe2)-Pro-OH
  参考文献：
  名称：

  A Novel Somatostatin Mimic with Broad Somatotropin Release Inhibitory Factor Receptor Binding and Superior Therapeutic Potential

  摘要：

  A rational drug design approach, capitalizing on structure-activity relationships and involving transposition of functional groups from somatotropin release inhibitory factor (SRIF) into a reduced size cyclohexapeptide template, has led to the discovery of SOM230 (25), a novel, stable cyclohexapeptide somatostatin mimic that exhibits unique high-affinity binding to human somatostatin receptors (subtypes sst1-sst5). SOM230 has potent, long-lasting inhibitory effects on growth hormone and insulin-like growth factor-1 release and is a promising development candidate currently under evaluation in phase I clinical trials.

  DOI：

  10.1021/jm021093t
• 作为产物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 4-二甲氨基吡啶 、 sodium hydroxide 、 sodium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 22.0h， 生成 Fmoc-(2S,4R)-(4-OCO-NH-CH2-CH2-NH2)-Pro-OH
  参考文献：
  名称：

  A Novel Somatostatin Mimic with Broad Somatotropin Release Inhibitory Factor Receptor Binding and Superior Therapeutic Potential

  摘要：

  A rational drug design approach, capitalizing on structure-activity relationships and involving transposition of functional groups from somatotropin release inhibitory factor (SRIF) into a reduced size cyclohexapeptide template, has led to the discovery of SOM230 (25), a novel, stable cyclohexapeptide somatostatin mimic that exhibits unique high-affinity binding to human somatostatin receptors (subtypes sst1-sst5). SOM230 has potent, long-lasting inhibitory effects on growth hormone and insulin-like growth factor-1 release and is a promising development candidate currently under evaluation in phase I clinical trials.

  DOI：

  10.1021/jm021093t

文献信息

• A Novel Somatostatin Mimic with Broad Somatotropin Release Inhibitory Factor Receptor Binding and Superior Therapeutic Potential
  作者：Ian Lewis、Wilfried Bauer、Rainer Albert、Nagarajan Chandramouli、Janos Pless、Gisbert Weckbecker、Christian Bruns

  DOI：10.1021/jm021093t

  日期：2003.6.1

  A rational drug design approach, capitalizing on structure-activity relationships and involving transposition of functional groups from somatotropin release inhibitory factor (SRIF) into a reduced size cyclohexapeptide template, has led to the discovery of SOM230 (25), a novel, stable cyclohexapeptide somatostatin mimic that exhibits unique high-affinity binding to human somatostatin receptors (subtypes sst1-sst5). SOM230 has potent, long-lasting inhibitory effects on growth hormone and insulin-like growth factor-1 release and is a promising development candidate currently under evaluation in phase I clinical trials.