tert-butyl N-[(2S,3R)-4-amino-3-methylbutan-2-yl]carbamate | 1330556-15-4

• 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: tert-butyl N-[(2S,3R)-4-amino-3-methylbutan-2-yl]carbamate
• CAS: 1330556-15-4
• 化学式: C₁₀H₂₂N₂O₂
• 分子量: 202.297
• InChiKey: IYYJVFGIIPQWNL-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S,3R)-4-amino-3-methylbutan-2-yl]carbamate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 乙醇 、 双氧水 、 三乙酰氧基硼氢化钠 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三氟乙酸 、 sodium hydroxide 、 sodium t-butanolate 作用下， 以 二氯甲烷 、 二甲基亚砜 、 1,2-二氯乙烷 、 甲苯 为溶剂， 生成 (15R,16S)-5,5,9,15,16-pentamethyl-7-oxo-2,13,17-triazatetracyclo[16.3.1.02,10.03,8]docosa-1(22),3(8),9,18,20-pentaene-19-carboxamide
  参考文献：
  名称：

  Discovery of a stable macrocyclic o-aminobenzamide Hsp90 inhibitor which significantly decreases tumor volume in a mouse xenograft model

  摘要：

  An extension of our previously reported series of macrocyclic ortho-aminobenzamide Hsp90 inhibitors is reported. Addition of a second methyl group to the tether provided analogs that show increased potency in binding as well as cell-proliferation assays and, more importantly, are stable toward microsomes. We wish to disclose the discovery of a macrocycle which showed impressive biomarker activity 24-h post dosing and which demonstrated prolonged exposure in tumors. When studied in a lung cancer xenograft model, the compound demonstrated significant tumor size reduction. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.102
• 作为产物：
  描述：

  (2S,3S)-3-amino-2-methyl butyric acid 在 N-甲基吗啉 、 ammonium hydroxide 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 tert-butyl N-[(2S,3R)-4-amino-3-methylbutan-2-yl]carbamate
  参考文献：
  名称：

  Discovery of a stable macrocyclic o-aminobenzamide Hsp90 inhibitor which significantly decreases tumor volume in a mouse xenograft model

  摘要：

  An extension of our previously reported series of macrocyclic ortho-aminobenzamide Hsp90 inhibitors is reported. Addition of a second methyl group to the tether provided analogs that show increased potency in binding as well as cell-proliferation assays and, more importantly, are stable toward microsomes. We wish to disclose the discovery of a macrocycle which showed impressive biomarker activity 24-h post dosing and which demonstrated prolonged exposure in tumors. When studied in a lung cancer xenograft model, the compound demonstrated significant tumor size reduction. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.102