(R)-4-((E)-3-Bromo-propenyl)-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester | 245420-31-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (R)-4-((E)-3-Bromo-propenyl)-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester
• CAS: 245420-31-9
• 化学式: C₁₃H₂₂BrNO₂S
• 分子量: 336.293
• InChiKey: FTXYJWJIBGZPJZ-VQCYPWCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-4-((E)-3-Bromo-propenyl)-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 四(三苯基膦)钯 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and evaluation of hydroxyproline-derived isoprenyltransferase inhibitors

  摘要：

  A series of peptidomimetics based on a hydroxyproline scaffold was prepared and evaluated for inhibition of farnesyltransferase and geranylgeranyltransferase I in both enzymatic and cell-based assays. A number of analogs were potent and selective inhibitors of FTase, while one compound (22) was nonselective in the enzymatic assays but eight-fold selective for inhibition of GGTase in the cellular assay (IC50 = 0.39 mu M) (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00342-x
• 作为产物：
  描述：

  在 四溴化碳 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-4-((E)-3-Bromo-propenyl)-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and evaluation of hydroxyproline-derived isoprenyltransferase inhibitors

  摘要：

  A series of peptidomimetics based on a hydroxyproline scaffold was prepared and evaluated for inhibition of farnesyltransferase and geranylgeranyltransferase I in both enzymatic and cell-based assays. A number of analogs were potent and selective inhibitors of FTase, while one compound (22) was nonselective in the enzymatic assays but eight-fold selective for inhibition of GGTase in the cellular assay (IC50 = 0.39 mu M) (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00342-x

文献信息

• Synthesis and Evaluation of Some Hydroxyproline-Derived Peptidomimetics as Isoprenyltransferase Inhibitors.
  作者：Celeste E. O'CONNELL、Ceryl A. ROWELL、Karen ACKERMANN、Ana Maria GARCIA、Michael D. LEWIS、James J. KOWALCZYK

  DOI：10.1248/cpb.48.740

  日期：——

  CA1A2X peptidomimetics containing a modified proline at position A2 were prepared and evaluated for their ability to inhibit farnesyltransferase (FTase) and geranylgeranyltransferase I (GGTase I) in enzymatic and cellbased assays. These compounds inhibited farnesylation of H-ras in vitro in the high nanomolar to low micromolar IC50 range.

  含有位置A2处修饰脯氨酸的CA1A2X肽模拟物被制备并评估了它们抑制法尼基转移酶（FTase）和香叶香叶基转移酶I（GGTase I）的能力，通过酶学和细胞基础检测。这些化合物在体外抑制H-ras的法尼基化，IC50值在高达数百纳摩尔至低微摩尔范围内。