[(S)-1-(5-Bromo-pyridin-3-yloxymethyl)-2-naphthalen-1-yl-ethyl]-carbamic acid tert-butyl ester | 882169-88-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [(S)-1-(5-Bromo-pyridin-3-yloxymethyl)-2-naphthalen-1-yl-ethyl]-carbamic acid tert-butyl ester
• CAS: 882169-88-2
• 化学式: C₂₃H₂₅BrN₂O₃
• 分子量: 457.367
• InChiKey: BVRQKJWMNCRQHD-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  60.45
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [(S)-1-(5-Bromo-pyridin-3-yloxymethyl)-2-naphthalen-1-yl-ethyl]-carbamic acid tert-butyl ester 在 palladium diacetate 、 三(邻甲基苯基)磷 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 10.0h， 生成 (S)-2-Naphthalen-1-yl-1-[5-((E)-2-pyridin-4-yl-vinyl)-pyridin-3-yloxymethyl]-ethylamine
  参考文献：
  名称：

  Discovery of trans-3,4′-bispyridinylethylenes as potent and novel inhibitors of protein kinase B (PKB/Akt) for the treatment of cancer: Synthesis and biological evaluation

  摘要：

  A novel series of Akt/PKB inhibitors derived from a screening lead (1) has been prepared. The novel trans-3,4'-bispyridinylethylenes described herein are potent inhibitors of Akt/PKB with IC50 values in the low double-digit nanomolar range against Akt1. Compound 2q shows excellent selectivity against distinct families of kinases such as tyrosine kinases and CAMK, and displays poor to modest selectivity against closely related kinases in the AGC and CMGC families. The cellular activities including inhibition of cell growth and phosphorylation of downstream target GSK3 are also described. The X-ray structure of compound 2q complexed with PKA in the ATP binding site was determined. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.017
• 作为产物：
  描述：

  Boc-3-(1-萘基)-L-丙氨酸 在 三苯基膦 、 偶氮二甲酸二乙酯 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 生成 [(S)-1-(5-Bromo-pyridin-3-yloxymethyl)-2-naphthalen-1-yl-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Identification of a novel 3,5-disubstituted pyridine as a potent, selective, and orally active inhibitor of Akt1 kinase

  摘要：

  Based on lead compounds 2 and 3 a series of 3,5-disubstituted pyridines have been designed and evaluated for inhibition of AKT/PKB. Modifications at the 3 position of the pyridine ring led to a number of potent compounds with improved physical properties, resulting in the identification of 11g as a promising, orally active Akt inhibitor. The synthesis, structure-activity relationship studies, and pharmacokinetic data are presented in this paper. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.046