(S)-4-[(2-Allyloxycarbonylamino-ethyl)-methyl-carbamoyl]-2-decanoylamino-butyric acid benzyl ester | 188403-11-4

• 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)-4-[(2-Allyloxycarbonylamino-ethyl)-methyl-carbamoyl]-2-decanoylamino-butyric acid benzyl ester
• CAS: 188403-11-4
• 化学式: C₂₉H₄₅N₃O₆
• 分子量: 531.693
• InChiKey: ZSKNHLXOKIQOFZ-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  38.0
• 可旋转键数：
  20.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  114.04
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-4-[(2-Allyloxycarbonylamino-ethyl)-methyl-carbamoyl]-2-decanoylamino-butyric acid benzyl ester 在 四(三苯基膦)钯 、 三正丁基氢锡 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.58h， 生成 (S)-2-Decanoylamino-4-(methyl-{2-[(5-methyl-2-phenyl-oxazole-4-carbonyl)-amino]-ethyl}-carbamoyl)-butyric acid benzyl ester
  参考文献：
  名称：

  Combinatorial synthesis and biological evaluation of Library of small-molecule Ser/Thr-protein phosphatase inhibitors

  摘要：

  In eukaryotes, phosphorylation of serine, threonine, and tyrosine residues on proteins is a fundamental posttranslational regulatory process for such functions as signal transduction, gene transcription, RNA splicing, cellular adhesion, apoptosis, and cell cycle control. Based on functional groups present in natural product serine/threonine protein phosphatase (PSTPase) inhibitors, we have designed pharmacophore model 1 and demonstrated the feasibility of a combinatorial chemistry approach for the preparation of functional analogues of 1. preliminary biological testing of 18 structural variants of 1 has identified two compounds with growth inhibitory activity against cultured human breast cancer cells. In vitro inhibition of the PSTPase PP2A was demonstrated with compound 1d. Using flow cytometry we observed that compound If caused prominent inhibition in the G1 phase of the cell cycle. Thus, the combinatorial modifications of the minimal pharmacophore 1 can generate biologically interesting antiproliferative agents. Copyright (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00199-x
• 作为产物：
  描述：

  癸酰氯 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 三正丁基氢锡 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 26.5h， 生成 (S)-4-[(2-Allyloxycarbonylamino-ethyl)-methyl-carbamoyl]-2-decanoylamino-butyric acid benzyl ester
  参考文献：
  名称：

  Combinatorial synthesis and biological evaluation of Library of small-molecule Ser/Thr-protein phosphatase inhibitors

  摘要：

  In eukaryotes, phosphorylation of serine, threonine, and tyrosine residues on proteins is a fundamental posttranslational regulatory process for such functions as signal transduction, gene transcription, RNA splicing, cellular adhesion, apoptosis, and cell cycle control. Based on functional groups present in natural product serine/threonine protein phosphatase (PSTPase) inhibitors, we have designed pharmacophore model 1 and demonstrated the feasibility of a combinatorial chemistry approach for the preparation of functional analogues of 1. preliminary biological testing of 18 structural variants of 1 has identified two compounds with growth inhibitory activity against cultured human breast cancer cells. In vitro inhibition of the PSTPase PP2A was demonstrated with compound 1d. Using flow cytometry we observed that compound If caused prominent inhibition in the G1 phase of the cell cycle. Thus, the combinatorial modifications of the minimal pharmacophore 1 can generate biologically interesting antiproliferative agents. Copyright (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00199-x