Fmoc-(2S,4R)-4-chlorocarbonateproline methyl ester | 556796-28-2

• 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-chlorocarbonateproline methyl ester
• 英文别名: 1-O-(9H-fluoren-9-ylmethyl) 2-O-methyl (2S,4R)-4-carbonochloridoyloxypyrrolidine-1,2-dicarboxylate
• CAS: 556796-28-2
• 化学式: C₂₂H₂₀ClNO₆
• 分子量: 429.857
• InChiKey: WBTZAUBRGMDYCV-YJYMSZOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Fmoc-(2S,4R)-4-chlorocarbonateproline methyl ester 在 4-二甲氨基吡啶 、 sodium hydroxide 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 19.0h， 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
• 作为产物：
  描述：

  反式-4-羟基-L-脯氨酸甲酯 在 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 Fmoc-(2S,4R)-4-chlorocarbonateproline methyl ester
  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.