2-(2-hydroxyethylamino)-6-benzylaminopurine | 70608-06-9

• 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-hydroxyethylamino)-6-benzylaminopurine
• 英文别名: 2-(6-benzylamino-7(9)H-purin-2-ylamino)-ethanol；2-((6-(Benzylamino)-1H-purin-2-yl)amino)ethanol；2-[[6-(benzylamino)-7H-purin-2-yl]amino]ethanol
• CAS: 70608-06-9
• 化学式: C₁₄H₁₆N₆O
• 分子量: 284.321
• InChiKey: HKQJWWBMRPTWIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  98.8
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,6-二氯嘌呤 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 2-(2-hydroxyethylamino)-6-benzylaminopurine
  参考文献：
  名称：

  Solution-phase synthesis of 2,6,9-trisubstituted purines

  摘要：

  A simple three-step method for the solution-phase combinatorial synthesis of 2,6,9-trisubstituted purines from 2,6-dichloropurine is described. The synthesis exploits the use of resin capture to remove excess reagent used in the final step. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00098-7

文献信息

• TNP Analogues Inhibit the Virulence Promoting IP3-4 Kinase Arg1 in the Fungal Pathogen Cryptococcus neoformans
  作者：Desmarini Desmarini、Daniel Truong、Lorna Wilkinson-White、Chandrika Desphande、Mario Torrado、Joel P. Mackay、Jacqueline M. Matthews、Tania C. Sorrell、Sophie Lev、Philip E. Thompson、Julianne Teresa Djordjevic

  DOI：10.3390/biom12101526

  日期：——

  New antifungals with unique modes of action are urgently needed to treat the increasing global burden of invasive fungal infections. The fungal inositol polyphosphate kinase (IPK) pathway, comprised of IPKs that convert IP3 to IP8, provides a promising new target due to its impact on multiple, critical cellular functions and, unlike in mammalian cells, its lack of redundancy. Nearly all IPKs in the fungal pathway are essential for virulence, with IP3-4 kinase (IP3-4K) the most critical. The dibenzylaminopurine compound, N2-(m-trifluorobenzylamino)-N6-(p-nitrobenzylamino)purine (TNP), is a commercially available inhibitor of mammalian IPKs. The ability of TNP to be adapted as an inhibitor of fungal IP3-4K has not been investigated. We purified IP3-4K from the human pathogens, Cryptococcus neoformans and Candida albicans, and optimised enzyme and surface plasmon resonance (SPR) assays to determine the half inhibitory concentration (IC50) and binding affinity (KD), respectively, of TNP and 38 analogues. A novel chemical route was developed to efficiently prepare TNP analogues. TNP and its analogues demonstrated inhibition of recombinant IP3-4K from C. neoformans (CnArg1) at low µM IC50s, but not IP3-4K from C. albicans (CaIpk2) and many analogues exhibited selectivity for CnArg1 over the human equivalent, HsIPMK. Our results provide a foundation for improving potency and selectivity of the TNP series for fungal IP3-4K.

  目前急需具有独特作用模式的新型抗真菌药物来治疗全球日益严重的侵袭性真菌感染。真菌肌醇多磷酸激酶（IPK）通路由将 IP3 转化为 IP8 的 IPK 组成，它对多种关键细胞功能都有影响，而且与哺乳动物细胞不同，它缺乏冗余性，因此是一个很有前景的新靶点。真菌途径中的几乎所有 IPK 都对毒力至关重要，其中 IP3-4 激酶（IP3-4K）最为关键。二苄基氨基嘌呤化合物 N2-（间三氟苄基氨基）-N6-（对硝基苄基氨基）嘌呤（TNP）是哺乳动物 IPK 的一种市售抑制剂。目前尚未研究 TNP 作为真菌 IP3-4K 抑制剂的适应能力。我们从人类病原体新型隐球菌和白色念珠菌中纯化了 IP3-4K，并优化了酶和表面等离子体共振（SPR）测定，以分别确定 TNP 和 38 种类似物的半数抑制浓度（IC50）和结合亲和力（KD）。研究人员开发了一种新的化学方法来高效制备 TNP 类似物。TNP 及其类似物以低 µM 的 IC50 抑制了来自新酵母菌（CnArg1）的重组 IP3-4K，但没有抑制来自白僵菌（CaIpk2）的 IP3-4K。我们的研究结果为提高 TNP 系列对真菌 IP3-4K 的效力和选择性奠定了基础。
• Facile Preparation of 2,6-Disubstituted Purines Using Solid-Phase Chemistry
  作者：David A. Nugiel、Lyndon A. M. Cornelius、Jeffrey W. Corbett

  DOI：10.1021/jo961909w

  日期：1997.1.1
• [EN] METHOD TO IDENTIFY REGULATORS OF CDK ACTIVITY<br/>[FR] PROCEDES D'IDENTIFICATION DE REGULATEURS DE L'ACTIVITE DE KINASES DEPENDANTES DES CYCLINES
  申请人：CROPDESIGN NV

  公开号：WO2000033657A1

  公开（公告）日：2000-06-15

  Provided are methods for the identification and isolation of active CDK/cyclin complexes and the constituents thereof and their use for screening of herbicides and plant growth regulators. Furthermore, methods for screening, identifying and obtaining novel plant growth regulators such as activators and inhibitors of plant growth are described. In particular, compounds are provided that are specific for A- and B-type CDKs, respectfully. Such compounds are useful as plant growth regulators and herbicides in agriculture and plant cell and tissue culture.
• Solution-phase synthesis of 2,6,9-trisubstituted purines
  作者：Maria T. Fiorini、Chris Abell

  DOI：10.1016/s0040-4039(98)00098-7

  日期：1998.3

  A simple three-step method for the solution-phase combinatorial synthesis of 2,6,9-trisubstituted purines from 2,6-dichloropurine is described. The synthesis exploits the use of resin capture to remove excess reagent used in the final step. (C) 1998 Elsevier Science Ltd. All rights reserved.