2-Acetylamino-2-(5-benzyloxy-pyridin-2-ylmethyl)-malonic acid diethyl ester | 219638-16-1

• 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: 2-Acetylamino-2-(5-benzyloxy-pyridin-2-ylmethyl)-malonic acid diethyl ester
• 英文别名: Diethyl 2-acetamido-2-[(5-phenylmethoxypyridin-2-yl)methyl]propanedioate
• CAS: 219638-16-1
• 化学式: C₂₂H₂₆N₂O₆
• 分子量: 414.458
• InChiKey: UXGSDLBILYBSRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-Acetylamino-2-(5-benzyloxy-pyridin-2-ylmethyl)-malonic acid diethyl ester 在 硫酸 、 sodium carbonate 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 [2-(5-benzyloxy-pyridin-2-yl)-1-cyclopropylcarbamoyl-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Selective cytotoxicity of azatyrosinamides against ras-transformed NIH 3T3 cells

  摘要：

  This study aims to develop novel azatyrosinamide compounds structurally modified from ras-specific antioncogenic azatyrosine. Analogues 4-15 were prepared and their inhibition on the growth of wild-type and ras-transformed NIH 3T3 cell lines was compared. Compound 12 was found to be the most active with IC50 16.5 +/- 2.2 mu M which is 458-fold more potent than that of azatyrosine. The selective toxicity, defined as IC50 (wild-type)/IC50 (ras-transformed) for this compound was 138.5. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.048
• 作为产物：
  描述：

  5-(苄氧基)-2-(氯甲基)吡啶 、 乙酰氨基丙二酸二乙酯 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以93%的产率得到2-Acetylamino-2-(5-benzyloxy-pyridin-2-ylmethyl)-malonic acid diethyl ester
  参考文献：
  名称：

  Selective cytotoxicity of azatyrosinamides against ras-transformed NIH 3T3 cells

  摘要：

  This study aims to develop novel azatyrosinamide compounds structurally modified from ras-specific antioncogenic azatyrosine. Analogues 4-15 were prepared and their inhibition on the growth of wild-type and ras-transformed NIH 3T3 cell lines was compared. Compound 12 was found to be the most active with IC50 16.5 +/- 2.2 mu M which is 458-fold more potent than that of azatyrosine. The selective toxicity, defined as IC50 (wild-type)/IC50 (ras-transformed) for this compound was 138.5. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.048

文献信息

• US5869507A
  申请人：——

  公开号：US5869507A

  公开（公告）日：1999-02-09
• [EN] NOVEL AZATYROSINE ANALOGUES AND PROCESS OF PREPARATION THEREOF<br/>[FR] NOUVEAUX ANALOGUES D'AZATYROSINE ET PROCEDE DE PREPARATION
  申请人：TSAI, Hansen

  公开号：WO1999004792A1

  公开（公告）日：1999-02-04

  (EN) A novel anti-oncogenic azatyrosine analogues of formula (I) wherein R1 is C1-6 alkyl, C1-6 haloalkyl, benzyl, or (C1-6 alkyl)carbonyl; R2 is C1-6 alkyl, C1-6 haloalkyl, or C1-6 alkoxyl; and R3 is CONR4R5, CONHNR4R5, or COOR6, wherein each R4 and R5 independently is a hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, or C3-6 cycloalkyl, or R4 and R5 taken together with the nitrogen attached thereto form a C3-8 heterocyclic group; R6 is C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, or benzyl. Also disclosed is a method of preparing such a novel anti-oncogenic azatyrosine analogues, as well as a pharmaceutical composition containing a compound of formula (I).(FR) L'invention concerne de nouveaux analogues d'azatyrosine anti-oncogènes de formule (I), dans laquelle R1 désigne alkyle en C1-C6, benzyle, ou (alkyle en C1-C6)carbonyle; R2 désigne alkyle en C1-C6, haloalkyle en C1-C6, ou alcoxy en C1-C6; et R3 désigne CONR4R5, CONHNR4R5 ou COOR6 où chaque R4 et R5 pris indépendamment désigne un hydrogène, alkyle en C1-C6, alcényle en C2-C6, alkynyle en C2-C6, ou cycloalkyle en C3-C6,ou R4 et R5 pris ensemble avec l'azote fixé à ceux-ci forment un groupe hétérocyclique en C3-C8; R6 désigne un alkyle en C1-C6, haloalkyle en C1-C6, alcényle en C2-C6, alkynyle en C2-C6, cycloalkyle en C3-C6, ou benzyle. Un procédé de préparation de ces nouveaux analogues d'azatyrosine anti-oncogènes, ainsi qu'une composition pharmaceutique renfermant un composé de formule (I) font aussi l'objet de cette invention.
• Selective cytotoxicity of azatyrosinamides against ras-transformed NIH 3T3 cells
  作者：H.P. Wang、T.L. Hwang、On Lee、Y.J. Tseng、C.Y. Shu、S.J. Lee

  DOI：10.1016/j.bmcl.2005.06.048

  日期：2005.10

  This study aims to develop novel azatyrosinamide compounds structurally modified from ras-specific antioncogenic azatyrosine. Analogues 4-15 were prepared and their inhibition on the growth of wild-type and ras-transformed NIH 3T3 cell lines was compared. Compound 12 was found to be the most active with IC50 16.5 +/- 2.2 mu M which is 458-fold more potent than that of azatyrosine. The selective toxicity, defined as IC50 (wild-type)/IC50 (ras-transformed) for this compound was 138.5. (c) 2005 Elsevier Ltd. All rights reserved.