2-氨基-7-苄基-1H-嘌呤-6(7H)-酮盐酸盐 | 20755-15-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 2-氨基-7-苄基-1H-嘌呤-6(7H)-酮盐酸盐
• 英文名称: 7-benzylguanine hydrochloride
• 英文别名: 2-Amino-7-benzyl-1,7-dihydro-6H-purin-6-one hydrochloride；2-amino-7-benzyl-1H-purin-6-one;hydrochloride
• CAS: 20755-15-1
• 化学式: C₁₂H₁₁N₅O*ClH
• 分子量: 277.713
• InChiKey: NFEPYUIHMLLXRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  85.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氨基-7-苄基-1H-嘌呤-6(7H)-酮盐酸盐 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 以68.8%的产率得到7-benzylxanthine
  参考文献：
  名称：

  Easy preparative scale syntheses of labelled xanthines: caffeine, theophylline and theobromine

  摘要：

  描述了几种易于准备的规模（0.5–1.5克）氘标记咖啡因、可可碱和茶碱的合成方法。开发了一些新的选择性合成可可碱和茶碱的方法。标记的黄嘌呤在定性或定量同位素稀释质谱中具有很大兴趣，并与气相色谱或液相色谱结合，目前在反兴奋剂和法医实验室中进行。版权 © 2007 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1154
• 作为产物：
  描述：

  鸟苷 在 盐酸 、 sodium acetate 、 sodium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 2-氨基-7-苄基-1H-嘌呤-6(7H)-酮盐酸盐
  参考文献：
  名称：

  Practical syntheses of penciclovir and famciclovir from N2-acetyl-7-benzylguanine

  摘要：

  We have established practical methods for the synthesis of penciclovir (PCV) and famciclovir (FCV) from readily available guanosine via N2-acetyl-7-benzylguanine. The alkylation of N2-acetyl-7-benzylguanine proceeded selectively at the N9 position to give the desired alkylated product in good yield in salt form. After conventional catalytic hydrogenolysis of the benzyl group and hydrolysis of the resulting acetate, pure PCV was obtained without the need for chromatography. As a side chain precursor, the mesylate was selected rather than a halide since the corresponding halides gave several impurities under the same reaction conditions. Two procedures for the synthesis of FCV from PCV and a derivative are also reported. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.080

文献信息

• [EN] XANTHINE CB1 INHIBITORS<br/>[FR] INHIBITEURS DE XANTHINE CB1
  申请人：GOLDFINCH BIO INC

  公开号：WO2021062089A1

  公开（公告）日：2021-04-01

  Disclosed are compounds having structural formula (I), and related pharmaceutical compositions. Also disclosed are therapeutic methods, e.g., of treating diseases such as diabetic kidney disease, diabetic nephropathy, obesity-related kidney disease, focal segmental glomerular sclerosis, IgA nephropathy, nephrotic syndrome, kidney fibrosis, Prader Willi syndrome, metabolic syndrome, gastrointestinal diseases, non-alcoholic liver disease, alcoholic liver disease, or non-alcoholic fatty liver disease, using the compounds of Formula (I).

  揭示了具有结构式（I）的化合物，以及相关的药物组合物。还揭示了治疗方法，例如治疗糖尿病肾病、糖尿病肾病、肥胖相关肾病、节段性肾小球硬化、IgA肾病、肾病综合征、肾脏纤维化、普拉德威利综合征、代谢综合征、胃肠疾病、非酒精性肝病、酒精性肝病或非酒精性脂肪肝病，使用式（I）的化合物。
• Use of theophylline derivatives for the treatment and prophylaxis of states of shock, novel xanthine compounds and processes for their preparation
  申请人：Hoechst Aktiengesellschaft

  公开号：US06214992B1

  公开（公告）日：2001-04-10

  Theophylline derivatives having at least one ether function in the structurally modified methyl radical in the 1-position that are useful in the treatment and prophylaxis of states of shock, new xanthine compounds having this substitution pattern, and processes for their preparation.

  在结构上改变的甲基自由基中至少具有一个醚功能的茶碱衍生物，可用于治疗和预防休克状态，具有这种取代模式的新黄嘌呤化合物，以及它们的制备方法。
• Process for producing purine derivatives
  申请人：Ajinomoto Co., Inc.

  公开号：US05942617A1

  公开（公告）日：1999-08-24

  A process for preparing 7-benzylpurine derivatives is provided. An acetylpurine nucleoside is reacted with a benzyl halide to benzylate the 7-position of the purine base, and an acid is then added to the reaction mixture to hydrolyze the glycoside bond. The 7-benzylpurines may be used to prepare 9-substituted purine derivatives.

  提供了一种制备7-苄基嘌呤衍生物的方法。将乙酰基嘌呤核苷与苄基卤化物反应，以苄基化嘌呤碱的7位，然后向反应混合物中加入酸以水解糖苷键。7-苄基嘌呤可用于制备9-取代嘌呤衍生物。
• A Regioselective Synthesis of Alkyl 2-(Guanin-9-yl)acetates as PNA Building Blocks from 7-(4-Nitrobenzyl)guanine Derivatives
  作者：Györgyi Ferenc、Péter Forgó、Zoltán Kele、Lajos Kovács

  DOI：10.1135/cccc20050085

  日期：——

  Guanine derivatives substituted at N⁷ with 4-R-benzyl groups (R = H, MeO, NO₂) have been evaluated in the regioselective N⁹-alkylation of guanine. Given the capricious removal of (substituted) benzyl groups from guanine derivatives and pent-4-enoylation of guaninium hydrochloride, an improved alternative approach has been elaborated consisting in the pent-4-enoylation and per-O-acetylation of guanosine (8), 4-nitrobenzylation at N⁷ followed by N-glycoside hydrolysis (10), N⁹-alkylation (13) and deprotection with sodium dithionite to afford the peptide nucleic acid building block tert-butyl [N²-(pent-4-enoyl)guanin-9-yl]- acetate (15) in 36% overall yield. This avoids N⁷ regioisomer formation, solubility problems and any chromatographic purification. A remarkable influence of the O- and/or N²-acyl groups on the stability of N-glycosidic bond and reactivity of 2-amino group was observed. The structure of a pyrimidine by-product 12 arising from the imidazole ring-opening of guaninium salt 4d in alkaline medium has been elucidated by 2D NMR.

  鸟嘌呤衍生物在N7位置被4-R-苄基基团（R = H，MeO，NO2）取代，已在鸟嘌呤的N9-烷基化中进行评估。鉴于从鸟嘌呤衍生物中（取代的）苄基基团的善变去除和鸟嘌呤盐酸盐的pent-4-烯酰化，已制定了一种改进的替代方法，包括pent-4-烯酰化和guanosine的per-O-乙酰化（8），N7位置的4-硝基苄基化，后接N-糖苷水解（10），N9-烷基化（13）和用亚硫酸钠去保护以得到肽核酸构建块tert-丁基[N2-(pent-4-烯酰)鸟嘌呤-9-基]-乙酸酯（15），总收率为36%。这避免了N7位置异构体的形成，溶解度问题和任何色谱纯化。观察到O-和/或N2-酰基对N-糖苷键的稳定性和2-氨基基团的反应性具有显著影响。通过2D NMR阐明了在碱性介质中由鸟嘌呤盐4d的咪唑环开环产生的嘧啶副产物12的结构。
• Improved Synthesis of 7‐(Alkyl/aralkyl)guanines
  作者：A. Vidal、I. Giraud、J.‐C. Madelmont

  DOI：10.1081/scc-200030585

  日期：2004.1.1

  Abstract A rapid and convenient preparation of 7‐(alkyl/aralkyl)guanines from guanosine is described. Using this method, a series of 7‐substituted guanines (compounds 2a–k) was synthesized in good yields (51%–97%).

  摘要描述了一种从鸟苷中快速方便地制备 7-（烷基/芳烷基）鸟嘌呤的方法。使用这种方法，以良好的产率 (51%–97%) 合成了一系列 7-取代鸟嘌呤（化合物 2a–k）。