tert-butyl (6-chloro-9-isopropyl-9H-purin-2-yl)carbamate | 1175562-17-0

• 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: tert-butyl (6-chloro-9-isopropyl-9H-purin-2-yl)carbamate
• 英文别名: N2-Boc-9-(iso-propyl)-6-chloro-9H-purin-2-ylamine；tert-butyl N-(6-chloro-9-propan-2-ylpurin-2-yl)carbamate
• CAS: 1175562-17-0
• 化学式: C₁₃H₁₈ClN₅O₂
• 分子量: 311.771
• InChiKey: XEQFBCLUKJNUKO-UHFFFAOYSA-N

物化性质

• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (6-chloro-9-isopropyl-9H-purin-2-yl)carbamate 在 甲酸 作用下， 以 水 为溶剂， 反应 2.0h， 以96%的产率得到2-amino-9-isopropyl-1H-purin-6(9H)-one
  参考文献：
  名称：

  Concise access to N9-mono-, N2-mono- and N2,N9-di-substituted guanines via efficient Mitsunobu reactions

  摘要：

  Guanine poses several problems to the synthetic chemist owing to its polyfunctional nature and poor solubility. Over the past few decades, synthetic guanines have found applications as anti-cancer and anti-viral agents. Coupled with the ever-growing interest in designer PNAs and G-quartets, simple and efficient synthetic routes to novel guanines would be of significant benefit. We herein report that, upon simple protection and/or activation step(s), the guanine precursor 2-amino-6-chloropurine is rendered an excellent substrate for Mitsunobu chemistry, furnishing, after subsequent hydrolytic dechlorination and appropriate deprotection step(s), the desired N9-mono-, N2-mono- or N2,N9-di-substituted guanines in excellent yields (>= 80%). Importantly, we demonstrate that N9-functionalization proceeds with very good N9/N7 regioselectivity and with complete inversion of stereochemistry. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.118
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 4-二甲氨基吡啶 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 tert-butyl (6-chloro-9-isopropyl-9H-purin-2-yl)carbamate
  参考文献：
  名称：

  走向更多类似药物的蛋白质模拟物：基于嘌呤支架的两面合成α-螺旋模拟物†

  摘要：

  模仿α-螺旋的两个面可能会产生更有效和更具选择性的异常螺旋介导的蛋白质-蛋白质相互作用（PPI）抑制剂。在本文中，我们证明了2,6,9-三取代嘌呤能够通过有效模仿Bak-BH3α-螺旋相对面上的关键残基来破坏Mcl-1-Bak-BH3 PPI。

  DOI：

  10.1039/c5ob00478k

文献信息

• Facile and efficient access to 2,6,9-tri-substituted purines through sequential N9, N2 Mitsunobu reactions
  作者：Steven Fletcher、Vijay M. Shahani、Patrick T. Gunning

  DOI：10.1016/j.tetlet.2009.04.137

  日期：2009.7

  both Mitsunobu reactions. Significantly, excellent chemoselectivity and N9-regioselectivity were observed for the first coupling, and reactions were complete within 15 min at room temperature. Our novel methodology may be readily adapted to furnish N9-mono- or N2,N9-di-functionalized guanine analogues, and the utility of our protocol is further demonstrated by the efficient synthesis of the CDK inhibitor

  提出了一种2,6,9-三取代嘌呤的简便，有效和温和的合成方法，从市售的2-氨基-6-氯嘌呤开始，其采用先后顺序的N9然后N2 Mitsunobu反应作为关键步骤。重要的是，我们对嘌呤核进行N2官能化的合成方法消除了用伯胺将2-卤基团进行传统亲核芳香取代所需要的苛刻条件。在两次光延反应中，苯甲酸，烯丙基，炔丙基和脂肪族醇的收率都非常好。显着地，对于第一次偶联观察到优异的化学选择性和N9-区域选择性，并且在室温下15分钟内反应完成。我们新颖的方法很容易适应提供N 9-单-或N2，N 9-二官能化的鸟嘌呤类似物，并且我们的方案的实用性通过CDK抑制剂波西米因的有效合成得到进一步证明。
• COMPOSITIONS FOR THE PREVENTION OF HEARING LOSS
  申请人：Ting Therapeutics LLC

  公开号：EP3310783B1

  公开（公告）日：2020-11-04
• EP3786164A1
  申请人：——

  公开号：EP3786164A1

  公开（公告）日：2021-03-03
• METHODS AND COMPOSITIONS FOR THE PREVENTION AND TREATMENT OF HEARING LOSS
  申请人：St. Jude Children's Research Hospital

  公开号：US20180161340A1

  公开（公告）日：2018-06-14

  In one aspect, pharmaceutical compositions comprising a CDK2 inhibitor and one or more of at least one agent known to treat a hearing impairment and at least one agent known to prevent a hearing impairment, and methods of treating and/or preventing hearing impairments or disorders using the compositions are disclosed. 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.
• [EN] METHODS AND COMPOSITIONS FOR THE PREVENTION AND TREATMENT OF HEARING LOSS<br/>[FR] PROCÉDÉS ET COMPOSITIONS DE PRÉVENTION ET DE TRAITEMENT DE LA PERTE D'AUDITION
  申请人：ST JUDE CHILDREN'S RES HOSPITAL

  公开号：WO2016205806A1

  公开（公告）日：2016-12-22

  In one aspect, pharmaceutical compositions comprising a CDK2 inhibitor and one or more of at least one agent known to treat a hearing impairment and at least one agent known to prevent a hearing impairment, and methods of treating and/or preventing hearing impairments or disorders using the compositions are disclosed. 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.