2,6-二溴嘌呤 | 1196-41-4

• 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: 2,6-二溴嘌呤
• 英文名称: 2,6-dibromo-7(9)H-purine
• 英文别名: 2,6-Dibrom-7(9)H-purin；2,6-dibromo-1H-purine；2,6-dibromo-7H-purine
• CAS: 1196-41-4
• 化学式: C₅H₂Br₂N₄
• 分子量: 277.906
• InChiKey: YPFDNCJJFMAZPJ-UHFFFAOYSA-N

物化性质

• 沸点：
  285.2±50.0 °C(Predicted)
• 密度：
  2.78±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  2,6-二溴嘌呤 在 sodium hydrogensulfide 作用下， 以 乙醇 为溶剂， 反应 0.67h， 以76%的产率得到2-溴-6-巯基嘌呤
  参考文献：
  名称：

  Sodium salt glycosylation in the synthesis of purine 2'-deoxyribonucleosides: studies of isomer distribution

  摘要：

  A systematic study of 2-deoxyribonucleoside isomer distribution from the sodium salt glycosylation of substituted purines is reported. Reactions of 1-alpha-chloro-2-deoxy-3,5-di(p-toluyl)-erythro-pentofuranose with the sodium salts of purines in acetonitrile typically results in 9-beta and 7-beta regioisomers as major products in a ratio of about 4:1, results consistent with a S(N)2 reaction of base anion with the 1-alpha chlorosugar. However, the reaction with 2,6-dibromopurine (2) gave 9-beta and 9-alpha stereoisomers as major products in a 4:1 ratio. We have isolated and identified all nucleoside products from sodium salt glycosylations of several 2,6-disubstituted purines and 6-substituted purines. In addition to the major products, the 9-alpha and 7-alpha isomers were obtained in small yields in most cases. Rate studies showed that fastest glycosylations occurred with 2,6-bis(methylthio)purine (3). Glycosylations of 2,6-dichloropurine (1) and of 2 proceeded with nearly identical rates for the formation of the 9-beta isomers and with comparable rates for the formation of 7-beta and 9-alpha isomers, respectively. These observations indicate that the extent of sugar anomerization during glycosylation of 2 does not alone account for 9-alpha isomer formation, although, in a separate experiment, aging of chlorosugar solutions did increase the yield of 9-alpha product in the reaction. Studies of possible interconversion of isomers under the reaction conditions indicated that formation of the 9-alpha isomer from 2 was not the result of conversion of a kinetically favored (7-beta) isomer, nor was the 7-beta isomer from 1 derived from conversion of the 9-alpha isomer. We conclude that a combination of steric effect of the 6-bromo group and an as yet unidentified rate effect of the 2-bromo group is responsible for the significant yield of 9-alpha product from 2. The ability of substituents to enhance the rate and regioselectivity in the sodium salt glycosylation was evaluated with 2-bromo-6-(methylthio)purine (6). This base afforded the highest total nucleoside yield (86%) and the highest 9-beta isomer yield (68.3%) among all purines tested, suggesting a useful strategy to increase yield of intermediates that can be converted to biologically important purine 2'-deoxy-ribonucleosides.

  DOI：

  10.1021/jo00032a038
• 作为产物：
  描述：

  黄嘌呤 在 三溴氧磷 作用下， 生成 2,6-二溴嘌呤
  参考文献：
  名称：

  Studies on Condensed Pyrimidine Systems. XVII. Some Halogenopurines

  摘要：

  DOI：

  10.1021/ja01595a065

文献信息

• Synthesis and biological activity of 2'-fluoro-2-halo derivatives of 9-.beta.-D-arabinofuranosyladenine
  作者：John A. Montgomery、Anita T. Shortnacy-Fowler、Sarah D. Clayton、James M. Riordan、John A. Secrist

  DOI：10.1021/jm00080a029

  日期：1992.1

  The synthesis of 2-halo-9-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)adenines (4b and 4d) by coupling the 2,6-dihalopurine with 3-acetyl-5-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide (2) followed by replacement of the 6-halogen with concomitant removal of the acyl blocking groups is described. 2-Fluoroadenine derivative 4g had to be prepared by the diazotization-fluorination of 2-aminoadenine

  通过将2,6-二卤代嘌呤与3-乙酰基-5-苯甲酰基-2-脱氧偶合，合成2-卤代9-（2-脱氧-2-氟-β-D-阿拉伯呋喃糖基）ni啶（4b和4d）描述了-2-氟-D-阿拉伯呋喃糖基溴化物（2），然后取代6-卤素并同时去除了酰基保护基团。必须通过2-氨基腺嘌呤核苷4e的重氮化-氟化来制备2-氟鸟嘌呤衍生物4g。所有三种核苷均能使接种P388白血病的小鼠的寿命延长。当在白血病细胞植入后第1、5和9天每3h x 8给予化合物时，可获得最佳结果。通过4f脱乙酰基化并在4h脱氧后再去除5a的苯甲酰基制得的2'，3'-二脱氧核苷5b在细胞培养中对HIV具有轻微的活性。
• 2-fluoro-9-(2-deoxy-2-fluoro-.beta.-D-arabinofuranosyl) adenine
  申请人：Southern Research Institute

  公开号：US05034518A1

  公开（公告）日：1991-07-23

  There are disclosed nucleosides having Formula I: ##STR1## wherein R is H or acyl. These compounds have anticancer activity.

  公开了具有I式的核苷，其中R为H或酰基。这些化合物具有抗癌活性。
• Improved synthesis and antitumor activity of 2-bromo-2'-deoxyadenosine
  作者：Minchi Huang、Thomas L. Avery、Raymond L. Blakeley、John A. Secrist、John A. Montgomery

  DOI：10.1021/jm00372a017

  日期：1984.6

  A more convenient synthetic route to 2-bromo-2'-deoxyadenosine (5) is reported, and results indicating significant antitumor activity of 5 against three murine tumors (L1210 leukemia, B16 melanoma, and M5076 ovarian carcinoma) are presented. The antitumor activity is very schedule dependent, being much greater when the drug is given q 3 h (X8) every 3rd or 4th day than when given by single daily administration. Toxicity of 5 for the tumor-bearing host is also very schedule dependent. Thus, on the q 3 h schedule of administration, a greater cumulative dose is tolerated by the host, and the therapeutic effectiveness of 5 is enhanced accordingly.
• Convenient synthesis of 2-halo-2'-deoxyadenosines
  作者：George E. Wright、Catherine Hildebrand、Stephen Freese、Lech W. Dudycz、Zygmunt Kazimierczuk

  DOI：10.1021/jo00229a037

  日期：1987.10
• KAZIMIERCZUK, ZYGMUNT;VILPO, JUHANI;HILDEBRAND, CATHERINE;WRIGHT, GEORGE, J. MED. CHEM., 33,(1990) N, C. 1683-1687
  作者：KAZIMIERCZUK, ZYGMUNT、VILPO, JUHANI、HILDEBRAND, CATHERINE、WRIGHT, GEORGE

  DOI：——

  日期：——