(2S)-2-[[(4E,8E)-2-diethoxyphosphoryl-5,9,13-trimethyltetradeca-4,8,12-trienoyl]amino]-3-phenylpropanoic acid | 180088-03-3

• 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: (2S)-2-[[(4E,8E)-2-diethoxyphosphoryl-5,9,13-trimethyltetradeca-4,8,12-trienoyl]amino]-3-phenylpropanoic acid
• CAS: 180088-03-3
• 化学式: C₃₀H₄₆NO₆P
• 分子量: 547.672
• InChiKey: WGLQOVUCORDUIL-JNENEZIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  38
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S)-2-[[(4E,8E)-2-diethoxyphosphoryl-5,9,13-trimethyltetradeca-4,8,12-trienoyl]amino]-3-phenylpropanoic acid 在 2,3,5-三甲基吡啶 、 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到(2S)-3-phenyl-2-[[(4E,8E)-5,9,13-trimethyl-2-phosphonotetradeca-4,8,12-trienoyl]amino]propanoic acid
  参考文献：
  名称：

  Inhibition of farnesyl protein transferase by new farnesyl phosphonate derivatives of phenylalanine

  摘要：

  New farnesyl phosphonate derivatives of phenylalanine have been prepared as inhibitors of farnesyl-protein transferase (FPT). Enzyme inhibition studies with bovine brain FPT and rat liver squalene synthase show that compound <(3a)under bar> is a new, potent and selective FPT inhibitor. Moreover, structural modifications from <(3a)under bar> have provided some useful information concerning the key structural subunits necessary for optimum and selective FPT inhibition. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00238-7
• 作为产物：
  描述：

  反,反-法呢基溴 在 lithium hydroxide 、 正丁基锂 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 3-羟基-1,2,3-苯并三嗪-4(3H)-酮 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (2S)-2-[[(4E,8E)-2-diethoxyphosphoryl-5,9,13-trimethyltetradeca-4,8,12-trienoyl]amino]-3-phenylpropanoic acid
  参考文献：
  名称：

  Inhibition of farnesyl protein transferase by new farnesyl phosphonate derivatives of phenylalanine

  摘要：

  New farnesyl phosphonate derivatives of phenylalanine have been prepared as inhibitors of farnesyl-protein transferase (FPT). Enzyme inhibition studies with bovine brain FPT and rat liver squalene synthase show that compound <(3a)under bar> is a new, potent and selective FPT inhibitor. Moreover, structural modifications from <(3a)under bar> have provided some useful information concerning the key structural subunits necessary for optimum and selective FPT inhibition. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00238-7

文献信息

• [EN] NOVEL CARBOXAMIDE-DERIVED PHOSPHONATES, METHOD FOR MAKING SAME AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAID PHOSPHONATES<br/>[FR] NOUVEAUX PHOSPHONATES DERIVES DE CARBOXAMIDES, LEUR PROCEDE DE FABRICATION ET LES COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：PIERRE FABRE MEDICAMENT

  公开号：WO1996019484A1

  公开（公告）日：1996-06-27

  (EN) Compounds of general formula (I), wherein, in particular, R1 is a farnesyl residue, V1 is OH, and n, m, R2, R3, R4 and Y are as defined in the description; a method for making same; and their use for making drugs for treating or preventing cancer, hyperlipidaemia, hypercholesterolaemia, related cardio-vascular diseases, fungal skin diseases and other fungal infections.(FR) L'invention concerne des composés de formule générale (I) dans laquelle, en particulier, R1 représente un résidu farnésyle, V1 représente OH, n, m, R2, R3, R4 et Y étant définis dans la description, ainsi que leur procédé de fabrication et leur utilisation pour la fabrication de médicaments destinés au traitement ou à la prévention du cancer, de l'hyperlipidémie de l'hypercholestérolémie, des maladies cardio-vasculaires associées, des mycoses et autres infections d'origines fongiques.
• Inhibition of farnesyl protein transferase by new farnesyl phosphonate derivatives of phenylalanine
  作者：M. Lamothe、D. Perrin、D. Blotières、M. Leborgne、S. Gras、D. Bonnet、B.T. Hill、S. Halazy

  DOI：10.1016/0960-894x(96)00238-7

  日期：1996.6

  New farnesyl phosphonate derivatives of phenylalanine have been prepared as inhibitors of farnesyl-protein transferase (FPT). Enzyme inhibition studies with bovine brain FPT and rat liver squalene synthase show that compound <(3a)under bar> is a new, potent and selective FPT inhibitor. Moreover, structural modifications from <(3a)under bar> have provided some useful information concerning the key structural subunits necessary for optimum and selective FPT inhibition. Copyright (C) 1996 Elsevier Science Ltd