| 1346232-54-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• CAS: 1346232-54-9
• 化学式: C₁₃H₂₀NO₃P*ClH
• 分子量: 305.741
• InChiKey: PEYBEOXZAOCOSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.55
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  、 N-苄氧羰基-L-苯丙氨酸 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以52%的产率得到benzyl (S)-(1-((3-(diethoxyphosphoryl)-1-phenylprop-1-en-1-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate
  参考文献：
  名称：

  Design, synthesis and biological evaluation of peptidyl-vinylaminophosphonates as novel cysteine protease inhibitors

  摘要：

  We report herein, design and synthesis of vinylaminophosphonates, a novel class of compounds as possible cysteine protease inhibitors. The synthesis of vinylaminophosphonates has been accomplished employing Tsuji-Trost reaction as a key step. The synthesized compounds were assayed against papain, a model cysteine protease and some of our synthesized compounds showed IC50 values in the range of 30-54 mu M thereby suggesting that these chemical entities thus could constitute an interesting template for the design of potential novel protease inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.058
• 作为产物：
  描述：

  在 三氯异氰尿酸 、 硫酸 、 potassium hydroxide 、 盐酸 作用下， 以 水 、 乙腈 、 乙酸乙酯 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Design, synthesis and biological evaluation of peptidyl-vinylaminophosphonates as novel cysteine protease inhibitors

  摘要：

  We report herein, design and synthesis of vinylaminophosphonates, a novel class of compounds as possible cysteine protease inhibitors. The synthesis of vinylaminophosphonates has been accomplished employing Tsuji-Trost reaction as a key step. The synthesized compounds were assayed against papain, a model cysteine protease and some of our synthesized compounds showed IC50 values in the range of 30-54 mu M thereby suggesting that these chemical entities thus could constitute an interesting template for the design of potential novel protease inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.058

文献信息

• The arginine mimicking β-amino acid β3hPhe(3-H2N-CH2) as S1 ligand in cyclotheonamide-based β-tryptase inhibitors
  作者：Dennis Janke、Christian P. Sommerhoff、Norbert Schaschke

  DOI：10.1016/j.bmc.2011.09.050

  日期：2011.12

  β-Tryptase, a mast-cell specific serine protease with trypsin-like activity, has emerged in the last years as a promising novel therapeutic target in the field of allergic inflammation. Recently, we have developed a potent and selective β-tryptase inhibitor based on the natural product cyclotheonamide E4 by implementing a basic P3 residue that addresses the determinants of the extended substrate specificity

  近年来，β-胰蛋白酶是一种具有胰蛋白酶样活性的肥大细胞特异性丝氨酸蛋白酶，已成为变应性炎症领域中一种有希望的新型治疗靶标。最近，我们通过实施碱性P3残基开发了一种基于天然产物环乙酰胺E4的有效且选择性的β-胰蛋白酶抑制剂，该残基解决了β-胰蛋白酶扩展底物特异性的决定因素。为了进一步改善该前导结构的亲和力/选择性，我们现在研究了β-高-3-氨基甲基苯基丙氨酸作为S1配体。与衍生自赖氨酸或精氨酸的相应β-高氨基酸相反，我们证明该特定的碱性β-高氨基酸是开发β-胰蛋白酶抑制剂的优先S1配体。除了亲和力，选择性和降低的碱性外，