9-苄基-6-氯嘌呤-2-胺 | 6336-42-1

• 物质功能分类: 有机原料 - 氨基化合物 - 环烷胺、芳香单胺、芳香多胺及其衍生物和盐
• 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: 9-苄基-6-氯嘌呤-2-胺
• 英文名称: 2-amino-9-benzyl-6-chloro-9H-purine
• 英文别名: 2-amino-9-benzyl-6-chloropurine；9-Benzyl-6-chloro-9h-purin-2-amine；9-benzyl-6-chloropurin-2-amine
• CAS: 6336-42-1
• 化学式: C₁₂H₁₀ClN₅
• 分子量: 259.698
• InChiKey: XBAIDBLXRCQTCV-UHFFFAOYSA-N

物化性质

• 熔点：
  204 °C
• 沸点：
  543.0±60.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 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：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-苄基-6-氯嘌呤-2-胺 在 palladium on activated charcoal copper(l) iodide 、 二碘甲烷 、 氢气 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 25.0~60.0 ℃ 、344.74 kPa 条件下， 反应 7.0h， 生成 9-benzyl-2-iodo-9H-purine
  参考文献：
  名称：

  Addition and Cycloaddition to 2- and 8-Vinylpurines.

  摘要：

  The reactivity of purines carrying an alkenyl substituent in the 2- or 8-position in nucleophilic addition and cycloaddition reactions has been studied. A vinyl substituent situated at C-8 is highly electrophilic and readily participates as a Michael acceptor in nucleophilic additions and as a dienophile in Diels-Alder reactions. 2-Vinylpurines may also give addition and cycloaddition products. When benzenethiol was added to 9-benzyl-2-vinylpurine, both the simple adduct as well as 9-benzyl-2-(2-phenylthio-1-hydroxyethyl)-9H-purine were formed. The structure of the latter compound was determined by single-crystal X-ray methods.

  DOI：

  10.3891/acta.chem.scand.53-0269
• 作为产物：
  描述：

  鸟嘌呤 在 palladium on activated charcoal ammonium hydroxide 、 甲酸铵 、 三氯氧磷 作用下， 以 N-甲基吡咯烷酮 、 甲醇 、 乙腈 为溶剂， 生成 9-苄基-6-氯嘌呤-2-胺
  参考文献：
  名称：

  β-Diketo acids with purine nucleobase scaffolds: Novel, selective inhibitors of the strand transfer step of HIV integrase

  摘要：

  The HIV pol gene encodes three viral enzymes that are required for its replication. While drug discovery involving the viral targets, reverse transcriptase and protease, has resulted in useful therapeutic agents, such efforts on HIV integrase have not produced a single FDA-approved drug. In the work focused on the discovery of inhibitors of HIV integrase, we have synthesized new beta-diketo acids with purine nucleobase scaffolds that are potent inhibitors of the strand transfer steps of wild-type HIV-1 integrase. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.093

文献信息

• Regiochemistry in Stille couplings of 2,6-dihalopurines
  作者：Geir Langli、Lise-Lotte Gundersen、Frode Rise

  DOI：10.1016/0040-4020(96)00199-8

  日期：1996.4

  The regiochemistry in Stille couplings of 2,6-dihalopurines have been studied. 2,6-Dichloropurines react selectively in the 6-position, and 6-chloro-2-iodopurines and 2-bromo-6-chloropurines in the 2-position.

  已经研究了2，6-二卤代尿烷在Stille偶联中的区域化学。2,6-二氯嘌呤在6-位选择性反应，6-氯-2-碘嘌呤和2-溴-6-氯嘌呤在2-位选择性反应。
• Design, synthesis and structure–activity relationships of a series of 9-substituted adenine derivatives as selective phosphodiesterase type-4 inhibitors
  作者：Pierre Raboisson、Claire Lugnier、Christian Muller、Jean-Marie Reimund、Dominique Schultz、Guillaume Pinna、Alain Le Bec、Hélène Basaran、Laurent Desaubry、François Gaudiot、Mohamed Seloum、Jean-Jacques Bourguignon

  DOI：10.1016/s0223-5234(02)01446-0

  日期：2003.2

  Adenine derivatives substituted in position 9 have been demonstrated to have potent cyclic nucleotide phosphodiesterase (PDE) inhibition properties with high selectivity toward PDE-4. Starting from our initial lead compound 9-(2-fluorobenzyl)-N(6)-methyl-2-trifluoromethyladenine (4, NCS613), we designed and synthesized a new series of 9-substituted derivatives for developing structure-activity relationship

  已经证明在9位取代的腺嘌呤衍生物具有有效的环核苷酸磷酸二酯酶（PDE）抑制特性，并且对PDE-4具有高选择性。从我们最初的先导化合物9-（2-氟苄基）-N（6）-甲基-2-三氟甲基腺嘌呤（4，NCS613）开始，我们设计并合成了一系列新的9-取代衍生物，用于开展结构-活性关系研究。这一系列新的衍生物显示出更高的效价和更好的选择性。在腺嘌呤环的三个不同位置上并行完成结构修饰，并得到以下观察结果：（i）引入亲脂性取代基（如三氟甲基），C-2位的正丙基或碘对于PDE-4抑制活性和对其他同工酶的选择性都有利；（ii）用2-甲氧基取代基对N9苄基进行官能化，导致活性更高的化合物；（iii）用其他氨基取代N（6）-甲基氨基部分对活性是有害的。在所有制备的衍生物中，9-（2-甲氧基苄基）-N（6）-甲基-2-三氟甲基腺嘌呤（9r），9-（2-甲氧基苄基）-N（6）-甲基-2-n-丙基腺嘌呤（9s） ），
• Synthesis of radiolabeled O6-benzylguanine derivatives as new potential PET tumor imaging agents for the DNA repair protein O6-alkylguanine-DNA alkyltransferase
  作者：Qi-Huang Zheng、Xuan Liu、Xiangshu Fei、Ji-Quan Wang、David W. Ohannesian、Leonard C. Erickson、K. Lee Stone、Tanya D. Martinez、Kathy D. Miller、Gary D. Hutchins

  DOI：10.1002/jlcr.636

  日期：2002.12

  Novel radiolabeled O6-benzylguanine derivatives, 2-amino-6-O-[11C]-[(methoxymethyl)benzyloxy]-9-benzyl purines ([11C]p-O6-AMBP, 1a; [11C]m-O6-AMBP, 1b; [11C]o-O6-AMBP, 1c), have been synthesized for evaluation as new potential positron emission tomography (PET) tumor imaging agents for the DNA repair protein, O6-alkylguanine-DNA alkyltransferase (AGT). The appropriate precursors for radiolabeling were

  新型放射性标记的 O6-苄基鸟嘌呤衍生物，2-氨基-6-O-[11C]-[（甲氧基甲基）苄氧基]-9-苄基嘌呤（[11C]p-O6-AMBP，1a；[11C]m-O6-AMBP , 1b; [11C]o-O6-AMBP, 1c) 已合成用于评估作为 DNA 修复蛋白 O6-烷基鸟嘌呤-DNA 烷基转移酶 (AGT) 的新型潜在正电子发射断层扫描 (PET) 肿瘤成像剂。用于放射性标记的合适前体是从起始材料 2-氨基-6-氯嘌呤分三步获得的，化学产率中等至极好。示踪剂是通过使用 [11C] 三氟甲磺酸甲酯对羟甲基前体进行 O-[11C] 甲基化来制备的。纯目标化合物通过固相萃取 (SPE) 纯化程序以 45-60% 的放射化学产率（衰减校正到轰击结束）和 20-25 分钟的合成时间分离。版权所有 © 2002 John Wiley & Sons，
• Di-p-nitrobenzyl azodicarboxylate (DNAD): an alternative azo-reagent for the Mitsunobu reaction
  作者：Jianhai Yang、Liyan Dai、Xiaozhong Wang、Yingqi Chen

  DOI：10.1016/j.tet.2010.12.036

  日期：2011.2

  Di-p-nitrobenzyl azodicarboxylate is prepared in 83.6% yield in two steps as a bright yellow solid, which can be used as an azo-reagent in the Mitsunobu reaction. When a chiral secondary alcohol was used, sufficient configurational inversion of alcohol occurred under Mitsunobu conditions. That the hydrazine produced from DNAD is semisoluble in some solvents such as THF and CH2Cl2 makes it separated

  分两步制备呈亮黄色固体的二对硝基苄基偶氮二羧酸酯，产率为83.6％，可以用作Mitsunobu反应中的偶氮试剂。当使用手性仲醇时，在Mitsunobu条件下发生足够的构型醇转化。由DNAD产生的肼在某些溶剂（如THF和CH 2 Cl 2）中可半溶，因此仅通过过滤即可将其轻松从反应混合物中分离出来。然后可以将回收的肼化合物重新暴露于氧化剂以产生DNAD。由于DNAD在环境温度下比DIAD更稳定并且易于分离，因此它是Mitsunobu反应的良好替代偶氮试剂。
• Design and synthesis of a new generation of substituted purine hydroxamate analogs as histone deacetylase inhibitors
  作者：Renshuai Liu、Junhua Wang、Weiping Tang、Hao Fang

  DOI：10.1016/j.bmc.2016.02.005

  日期：2016.4

  Histone deacetylase inhibitors have been proved to be great potential for the treatment of cancer. Recently, we designed and modified a series of substituted purine hydroxamate analogs as potent HDAC inhibitors based on our previous studies. The target compounds were investigated for their in vitro HDAC inhibitory activities and anti-proliferative activities. Results indicated that these compounds

  组蛋白脱乙酰基酶抑制剂已被证明在治疗癌症方面具有巨大潜力。最近，我们根据先前的研究设计并修饰了一系列取代的嘌呤异羟肟酸酯类似物，作为有效的HDAC抑制剂。研究了目标化合物的体外HDAC抑制活性和抗增殖活性。结果表明，这些化合物可有效抑制HDAC，对肿瘤细胞具有明显的抗增殖活性。可能地，目标化合物4m和4n在酶抑制活性和细胞抗增殖活性测定方面均优于SAHA。