isopropyl (5-amino-2'-methyl-[1,1'-biphenyl]-2-carbonyl)-L-methioninate | 1334402-13-9

• 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: isopropyl (5-amino-2'-methyl-[1,1'-biphenyl]-2-carbonyl)-L-methioninate
• CAS: 1334402-13-9
• 化学式: C₂₂H₂₈N₂O₃S
• 分子量: 400.542
• InChiKey: MVEMLIKENBULMN-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  81.42
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  isopropyl (5-amino-2'-methyl-[1,1'-biphenyl]-2-carbonyl)-L-methioninate 在 甲酸 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 propan-2-yl (2S)-2-[[4-[3-(2-amino-1,3-thiazol-4-yl)propanoylamino]-2-(2-methylphenyl)benzoyl]amino]-4-methylsulfanylbutanoate
  参考文献：
  名称：

  Thiazole- and imidazole-containing peptidomimetic inhibitors of protein farnesyltransferase

  摘要：

  Mimetics of the C-terminal CAAX tetrapeptide of Ras protein were designed replacing internal dipeptide AA with 4-amino-2-phenylbenzoic acid and cysteine (C) with 2-amino-4-thiazolyl-, 2-mercapto-4-thiazolyl-, 2-mercapto-4-imidazolyl- and 2-methylmercapto-4-thiazolyl-acetic or propionic acid. The compound in which C is replaced by 2-amino-4-thiazolylacetic acid inhibited FTase activity in the low nanomolar range and showed antiproliferative effect on rat aortic smooth muscle cells interfering with Ras farnesylation. On the basis of these results, 2-aminothiazole can be considered as an alternative to heterocycles, such as pyridine and imidazole, normally used in FTase inhibitors designed as non-thiol CAAX mimetics. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.003
• 作为产物：
  描述：

  2'-methyl-5-nitro-biphenyl-2-carboxylic acid methyl ester 在 甲醇 、 palladium on activated charcoal 、 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 isopropyl (5-amino-2'-methyl-[1,1'-biphenyl]-2-carbonyl)-L-methioninate
  参考文献：
  名称：

  Thiazole- and imidazole-containing peptidomimetic inhibitors of protein farnesyltransferase

  摘要：

  Mimetics of the C-terminal CAAX tetrapeptide of Ras protein were designed replacing internal dipeptide AA with 4-amino-2-phenylbenzoic acid and cysteine (C) with 2-amino-4-thiazolyl-, 2-mercapto-4-thiazolyl-, 2-mercapto-4-imidazolyl- and 2-methylmercapto-4-thiazolyl-acetic or propionic acid. The compound in which C is replaced by 2-amino-4-thiazolylacetic acid inhibited FTase activity in the low nanomolar range and showed antiproliferative effect on rat aortic smooth muscle cells interfering with Ras farnesylation. On the basis of these results, 2-aminothiazole can be considered as an alternative to heterocycles, such as pyridine and imidazole, normally used in FTase inhibitors designed as non-thiol CAAX mimetics. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.003