8-bromo-9-(3-hydroxypropyl)-9H-adenine | 98411-75-7

• 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: 8-bromo-9-(3-hydroxypropyl)-9H-adenine
• 英文别名: 3-(6-amino-8-bromopurin-9-yl)propan-1-ol
• CAS: 98411-75-7
• 化学式: C₈H₁₀BrN₅O
• 分子量: 272.104
• InChiKey: MUZYIFHIQGFDMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-bromo-9-(3-hydroxypropyl)-9H-adenine 在 sodium hydride 作用下， 以 1,4-二氧六环 为溶剂， 生成 4'-O,8-anhydro-9-(3-hydroxypropyl)adenine
  参考文献：
  名称：

  Janeba, Zlatko; Holy, Antonin, Collection of Czechoslovak Chemical Communications, 1996, vol. 61, p. S116 - S117

  摘要：

  DOI：
• 作为产物：
  描述：

  Benzoic acid 3-(6-amino-purin-9-yl)-propyl ester 在 溴 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 生成 8-bromo-9-(3-hydroxypropyl)-9H-adenine
  参考文献：
  名称：

  Holy, Antonin; Kohoutova, Jitka; Merta, Ales, Collection of Czechoslovak Chemical Communications, 1986, vol. 51, # 2, p. 459 - 477

  摘要：

  DOI：

文献信息

• Synthesis of Acyclic Nucleoside and Nucleotide Analogs Derived from 6-Amino-7H-purine-8(9H)-thione and 8-(Methylsulfanyl)adenine
  作者：Zlatko Janeba、Antonín Holý、Milena Masojídková

  DOI：10.1135/cccc20001698

  日期：——

  Reaction of 8-bromoadenine derivatives1with thiourea in ethanol or butanol was used for the synthesis of the correspondingN⁹-substituted 6-amino-7H-purine-8(9H)-thiones2. 8-(Methylsulfanyl)adenine derivatives3were prepared by reaction of thiones2with iodomethane in 1 M sodium methoxide or in aqueous 1.5 M potassium hydroxide. Alkylation of 6-amino-7H-purine-8(9H)-thione (2a) proceeds preferentially on the sulfur atom. Under similar conditions, alkylation of 8-(methylsulfanyl)adenine (3a) with diverse alkylation agents affordedN⁹-substituted adenine derivatives3and6, andN³-substituted adenine derivatives5and7. 8,3'-S-Anhydro derivatives9were prepared in good yields by cyclization of 6-amino-7H-purine-8(9H)-thiones2dand2funder the Mitsunobu reaction conditions.

  8-溴腺嘌呤衍生物1与硫脲在乙醇或丁醇中的反应被用于合成相应的N⁹-取代的6-氨基-7H-嘌呤-8(9H)-硫酮2。通过硫酮2与碘甲烷在1 M甲醇钠或水溶性1.5 M氢氧化钾中的反应制备了8-(甲硫基)腺嘌呤衍生物3。6-氨基-7H-嘌呤-8(9H)-硫酮 (2a) 的烷基化优先在硫原子上进行。在类似条件下，8-(甲硫基)腺嘌呤 (3a) 与不同的烷基化试剂反应得到了N⁹-取代的腺嘌呤衍生物3和6，以及N³-取代的腺嘌呤衍生物5和7。通过6-氨基-7H-嘌呤-8(9H)-硫酮2d和2f在Mitsunobu反应条件下环化，制备了8,3'-S-缺水衍生物9，产率较高。
• 8-(2-Furyl)adenine derivatives as A2A adenosine receptor ligands
  作者：Diego Dal Ben、Michela Buccioni、Catia Lambertucci、Ajiroghene Thomas、Karl-Norbert Klotz、Stephanie Federico、Barbara Cacciari、Giampiero Spalluto、Rosaria Volpini

  DOI：10.1016/j.ejmech.2013.10.006

  日期：2013.12

  8-(2-furyl)adenine derivatives are reported. Results show that 8-(2-furyl)-9-methyladenine is endowed with high affinity at the A2A subtype. Further modification of this compound with introduction of arylacetyl or arylcarbamoyl groups in N6-position takes to different effects on the A2A affinity and in particular on the selectivity versus the other three adenosine receptor subtypes. A molecular modelling

  选择性腺苷受体调节剂是用于许多治疗应用的潜在工具，包括心血管，炎性和神经退行性疾病。在这项工作中，报道了一系列9-取代的8-（2-呋喃基）腺嘌呤衍生物的四种人腺苷受体亚型的合成和生物学评估。结果表明8-（2-呋喃基）-9-甲基腺嘌呤在A 2A亚型上具有高亲和力。通过在N 6位上引入芳基乙酰基或芳基氨基甲酰基基团对该化合物进行进一步修饰，对A 2A亲和力，特别是相对于其他三种腺苷受体亚型，对选择性具有不同的影响。三种不同的A 2A下的分子建模分析 受体晶体结构提供了对所获得的生物学结果的解释。
• 8-Bromo-9-alkyl adenine derivatives as tools for developing new adenosine A2A and A2B receptors ligands
  作者：Catia Lambertucci、Ippolito Antonini、Michela Buccioni、Diego Dal Ben、Dhuldeo D. Kachare、Rosaria Volpini、Karl-Norbert Klotz、Gloria Cristalli

  DOI：10.1016/j.bmc.2009.02.030

  日期：2009.4

  Importance of making available selective adenosine receptor antagonists is boosted by recent findings of adenosine involvement in many CNS dysfunctions. In the present work a series of 8-bromo-9-alkyl adenines are prepared and fully characterized in radioligand binding assays or functional cyclase experiments in respect to their interaction with all the four adenosine receptor subtypes. Results show that the presence of the bromine atom in 8-position of 9-substituted adenines promotes in general the interaction with the adenosine receptors, in particular at the A(2A) subtype. The present study also demonstrates that adenine derivatives could be a good starting point to obtain selective adenosine A(2B) receptor antagonists. (c) 2009 Elsevier Ltd. All rights reserved.