2-(2-((tert-butoxycarbonyl)(4-cyclohexylbenzyl)amino)-6-(isopentylamino)-9H-purin-9-yl)acetic acid | 1255653-18-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2-(2-((tert-butoxycarbonyl)(4-cyclohexylbenzyl)amino)-6-(isopentylamino)-9H-purin-9-yl)acetic acid
• 英文别名: 2-{2-[(4-cyclohexylbenzyl)amino]-6-(isopentylamino)-9H-purin-9-yl}acetic acid；S3I-V3-32；2-(2-((4-cyclohexylbenzyl)amino)-6-(isopentylamino)-9H-purin-9-yl)acetic acid；2-[2-[(4-cyclohexylphenyl)methylamino]-6-(3-methylbutylamino)purin-9-yl]acetic acid
• CAS: 1255653-18-9
• 化学式: C₂₅H₃₄N₆O₂
• 分子量: 450.584
• InChiKey: AHDIPWZACXRIMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  溴甲基乙酸酯 、 2-(2-((tert-butoxycarbonyl)(4-cyclohexylbenzyl)amino)-6-(isopentylamino)-9H-purin-9-yl)acetic acid 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 acetoxymethyl 2-{2-[(4-cyclohexylbenzyl)amino]-6-(isopentylamino)-9H-purin-9-yl}acetate
  参考文献：
  名称：

  A 2,6,9-hetero-trisubstituted purine inhibitor exhibits potent biological effects against multiple myeloma cells

  摘要：

  A focused library of hetero-trisubstituted purines was developed for improving the cell penetrating and biological efficacy of a series of anti-Stat3 protein inhibitors. From this SAR study, lead agent 22e was identified as being a promising inhibitor of MM tumour cells (IC50's <5 mu M). Surprisingly, biophysical and biochemical characterization proved that 22e was not a Stat3 inhibitor. Initial screening against the kinome, prompted by the purine scaffold's history for targeting ATP binding pockets, suggests possible targeting of the JAK family kinases, as well for ABL1 (nonphosphorylated F317L) and AAK1. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.080
• 作为产物：
  描述：

  ethyl 2-{2-[(tert-butoxycarbonyl)(4-cyclohexylbenzyl)amino]-6-chloro-9H-purin-9-yl}acetate 在 水 、 N,N-二异丙基乙胺 、 三氟乙酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 2-(2-((tert-butoxycarbonyl)(4-cyclohexylbenzyl)amino)-6-(isopentylamino)-9H-purin-9-yl)acetic acid
  参考文献：
  名称：

  A 2,6,9-hetero-trisubstituted purine inhibitor exhibits potent biological effects against multiple myeloma cells

  摘要：

  A focused library of hetero-trisubstituted purines was developed for improving the cell penetrating and biological efficacy of a series of anti-Stat3 protein inhibitors. From this SAR study, lead agent 22e was identified as being a promising inhibitor of MM tumour cells (IC50's <5 mu M). Surprisingly, biophysical and biochemical characterization proved that 22e was not a Stat3 inhibitor. Initial screening against the kinome, prompted by the purine scaffold's history for targeting ATP binding pockets, suggests possible targeting of the JAK family kinases, as well for ABL1 (nonphosphorylated F317L) and AAK1. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.080

文献信息

• [EN] SUBSTITUTED 2-(9H-PURIN-9-YL) ACETIC ACID ANALOGUES AS INHIBITORS OF STAT3<br/>[FR] ANALOGUES D'ACIDE 2-(9H-PURIN-9-YL)ACÉTIQUE SUBSTITUÉS EN TANT QU'INHIBITEURS DE STAT3
  申请人：UNIV CENTRAL FLORIDA RES FOUND

  公开号：WO2011163424A2

  公开（公告）日：2011-12-29

  In one aspect, the invention relates to substituted purine analogs, derivatives thereof, and related compounds, which are useful as inhibitors of STAT protein activity; synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating disorders of uncontrolled cellular proliferation associated with a STAT protein activity dysfunction using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
• A 2,6,9-hetero-trisubstituted purine inhibitor exhibits potent biological effects against multiple myeloma cells
  作者：Vijay M. Shahani、Daniel P. Ball、Allan V. Ramos、Zhihua Li、Paul A. Spagnuolo、Sina Haftchenary、Aaron D. Schimmer、Suzanne Trudel、Patrick T. Gunning

  DOI：10.1016/j.bmc.2013.04.080

  日期：2013.9

  A focused library of hetero-trisubstituted purines was developed for improving the cell penetrating and biological efficacy of a series of anti-Stat3 protein inhibitors. From this SAR study, lead agent 22e was identified as being a promising inhibitor of MM tumour cells (IC50's <5 mu M). Surprisingly, biophysical and biochemical characterization proved that 22e was not a Stat3 inhibitor. Initial screening against the kinome, prompted by the purine scaffold's history for targeting ATP binding pockets, suggests possible targeting of the JAK family kinases, as well for ABL1 (nonphosphorylated F317L) and AAK1. (C) 2013 Elsevier Ltd. All rights reserved.