N-[(4-bromophenyl)methyl]-2-chloro-7H-purin-6-amine | 294647-87-3

• 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: N-[(4-bromophenyl)methyl]-2-chloro-7H-purin-6-amine
• CAS: 294647-87-3
• 化学式: C₁₂H₉BrClN₅
• mdl: MFCD27271051
• 分子量: 338.594
• InChiKey: GCQRCTKEYZUTNF-UHFFFAOYSA-N

物化性质

• 密度：
  1.783±0.06 g/cm3(Predicted)
• pKa：
  9.80±0.10 (Predicted,Most Acidic Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(4-bromophenyl)methyl]-2-chloro-7H-purin-6-amine 在 N-甲基吡咯烷酮 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-[[6-(4-Bromo-benzylamino)-9-isopropyl-9H-purin-2-yl]-(2-hydroxy-ethyl)-amino]-ethanol
  参考文献：
  名称：

  Synthesis and activity of 2,6,9-trisubstituted purines

  摘要：

  The preparation of a series of 2,6,9-trisubstituted purines and the structure-activity data for the inhibition of cyclin dependent kinase, CDK2 are presented. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10076-2
• 作为产物：
  描述：

  对溴苄胺 、 2,6-二氯嘌呤 在 N,N-二异丙基乙胺 作用下， 以 乙醇 、 水 为溶剂， 生成 N-[(4-bromophenyl)methyl]-2-chloro-7H-purin-6-amine
  参考文献：
  名称：

  Biaryl purine derivatives as potent antiproliferative agents: Inhibitors of cyclin dependent kinases. Part I

  摘要：

  The introduction of an aryl ring onto the 4-position of the C-6 benzyl amino group of the Cdk inhibitor roscovitine (2), maintained the potent Cdk inhibition demonstrated by roscovitine (2) as well as greatly improving the antiproliferative activity. A series of C-6 biarylmethylamino derivatives was prepared addressing modifications on the C-6 biaryl rings, N-9 and C-2 positions to provide compounds that displayed potent cytotoxic activity against tumor cell lines. In particular, derivative 21h demonstrated a >750-fold improvement in the growth inhibition of HeLa cells compared to roscovitine (2). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.025

文献信息

• Development of Potent Purine-Derived Nitrile Inhibitors of the Trypanosomal Protease TbcatB
  作者：Jeremy P. Mallari、Anang A. Shelat、Terri Obrien、Conor R. Caffrey、Aaron Kosinski、Michele Connelly、Michael Harbut、Doron Greenbaum、James H. McKerrow、R. Kiplin Guy

  DOI：10.1021/jm070760l

  日期：2008.2.1

  Human African trypanosomiasis (HAT), a major health concern in sub-Saharan Africa, is caused by the protozoan parasite Trypanosoma brucei. Recent studies have shown that a cathepsin B like protease, TbcatB, is essential to the survival of T brucei in vitro (Mackey, Z. B.; O'Brien, T. C.; Greenbaum, D. C.; Blank, R. B.; McKerrow, J. H. J. Biol. Chem. 2004, 279, 48426-48433). Herein, we describe the first inhibitors of TbcatB, a series of purine nitriles. The compounds are potent trypanocides, killing the parasite with a high degree of selectivity over a panel of three human cell lines. In addition, a predictive model of trypanocidal activity was developed on the basis of potency against TbcatB and various calculated physical property descriptors.
• [EN] 6-SUBSTITUTED BIARYL PURINE DERIVATIVES AS POTENT CYCLIN/CDK INHIBITORS AND ANTIPROLIFERATIVE AGENTS<br/>[FR] DERIVES DE PURINE DIARYLE SUBSTITUEE EN 6 UTILISES COMME INHIBITEURS PUISSANTS DE KINASE DEPENDANTE DES CYCLINES ET COMME AGENTS ANTIPROLIFERATIFS
  申请人：ALBANY MOLECULAR RES INC

  公开号：WO2000055161A1

  公开（公告）日：2000-09-21

  The present invention is directed to 2,6,9-trisubstituted purines cellular proliferation. Processes of preparing such compounds are also disclosed.
• [EN] NITROGEN SUBSTITUTED BIARYL PURINE DERIVATIVES AS POTENT ANTIPROLIFERATIVE AGENTS<br/>[FR] DERIVES DE PURINE BIARYLE A SUBSTITUTION AZOTE UTILES EN TANT QUE PUISSANTS AGENTS ANTIPROLIFERATIFS
  申请人：ALBANY MOLECULAR RES INC

  公开号：WO2003022219A2

  公开（公告）日：2003-03-20

  The compounds of the present invention are 2,6,9-trisubstituted purine derivatives which are inhibitors of cyclin/cdk complexes. The compounds of the current invention also are potent inhibitors of human cellular proliferation. As such, the compounds of the present invention constitute pharmaceutical compositions with a pharmaceutically acceptable carrier. Such compounds are useful in treating a disorder mediated by elevated levels of cell proliferation in a mammal compared to a healthy mammal by administering to such mammal an effective amount of the compound. Examples of the compounds of the present invention are represented by the following chemical structures; with X, Y, D, Q, V, A, R1, R2, R3, R4, and n1 defined herein.
• [EN] HETEROCYCLE SUBSTITUTED PURINE DERIVATIVES AS POTENT ANTIPROLIFERATIVE AGENTS<br/>[FR] DERIVES DE PURINE A SUBSTITUTION HETEROCYCLE UTILES EN TANT QUE PUISSANTS AGENTS ANTIPROLIFERATIFS
  申请人：ALBANY MOLECULAR RES INC

  公开号：WO2003022805A2

  公开（公告）日：2003-03-20

  The compounds of the present invention are 2,6,9-trisubstituted purine derivatives which are inhibitors of cyclin/cdk complexes. The compounds of the current invention also are potent inhibitors of human cellular proliferation. As such, the compounds of the present invention constitute pharmaceutical compositions with a pharmaceutically acceptable carrier. Such compounds are useful in treating a disorder mediated by elevated levels of cell proliferation in a mammal compared to a healthy mammal by administering to such mammal an effective amount of the compound. Examples of the compounds of the present invention are represented by the following chemical structures (I) and (II) with Y, V, A, R1, R2, R3, R4, R7, and n1 defined herein.
• Synthesis and activity of 2,6,9-trisubstituted purines
  作者：Steven R. Schow、Richard L. Mackman、Cheri L. Blum、Eric Brooks、Amy G. Horsma、Alison Joly、Suresh S. Kerwar、Gavin Lee、Dov Shiffman、Marek G. Nelson、Xingbo Wang、Michael M. Wick、Xiaoming Zhang、Robert T. Lum

  DOI：10.1016/s0960-894x(97)10076-2

  日期：1997.11

  The preparation of a series of 2,6,9-trisubstituted purines and the structure-activity data for the inhibition of cyclin dependent kinase, CDK2 are presented. (C) 1997 Elsevier Science Ltd.