8-bromo-9-(β-D-arabinofuranosyl)adenine | 71203-25-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 8-bromo-9-(β-D-arabinofuranosyl)adenine
• 英文别名: 9-(β-D-arabinofuranosyl)-8-bromoadenine；8-bromo-9-(D-arabinofuranosyl)adenine；9FU2HA5Dxq；(2R,3S,4S,5R)-2-(6-amino-8-bromopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 71203-25-3
• 化学式: C₁₀H₁₂BrN₅O₄
• 分子量: 346.14
• InChiKey: VJUPMOPLUQHMLE-FJFJXFQQSA-N

物化性质

• 沸点：
  717.7±70.0 °C(Predicted)
• 密度：
  2.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  8-bromo-9-(β-D-arabinofuranosyl)adenine 生成 (10R,11S,12R,14R)-6-amino-12-(hydroxymethyl)-13-oxa-1,3,5,8-tetrazatetracyclo[7.5.0.02,7.010,14]tetradeca-2,4,6,8-tetraen-11-ol
  参考文献：
  名称：

  YAKOVLEVA, L. A.;AKULOV, G. P.;NAGORSKIJ, A. I.;PATOKINA, N. A.;KAMINSKIJ+, XIMIYA GETEROTSIKL. SOED.,(1988) N 1, 95-99

  摘要：

  DOI：
• 作为产物：
  描述：

  阿糖腺苷 在 溴 、 sodium acetate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以95.22 %的产率得到8-bromo-9-(β-D-arabinofuranosyl)adenine
  参考文献：
  名称：

  [EN] COMPOSITIONS FOR EDITING MECP2 TRANSCRIPTS AND METHODS THEREOF
  [FR] COMPOSITIONS POUR L'ÉDITION DE TRANSCRITS MECP2 ET PROCÉDÉS ASSOCIÉS

  摘要：

  Among other things, the present disclosure provides oligonucleotides, compositions and methods thereof that can bring about specific editing of a target adenosine in a target RNA molecule. Such oligonucleotides, compositions and methods are useful to treat, prevent, or ameliorate MECP2 associated disorders, diseases and syndromes that can benefit from adenosine modification.

  公开号：

  WO2023049477A2

文献信息

• Introduction of a tritium label into nucleoside analogs modified in their carbohydrate residues
  作者：L. A. Yakovleva、G. P. Akulov、A. I. Nagorskii、N. A. Patokina、Yu. L. Kaminskii、R. Z. Zhuk

  DOI：10.1007/bf00475575

  日期：1988.1
• Purine and 8-substituted purine arabinofuranosyl and ribofuranosyl nucleoside derivatives as potential inducers of the differentiation of the Friend erythroleukemia
  作者：Tai Shun Lin、Jia Chong Cheng、Kimiko Ishiguro、Alan C. Sartorelli

  DOI：10.1021/jm00148a018

  日期：1985.10

  Several antimetabolites have been demonstrated to have the capacity to initiate differentiation in vitro of a variety of leukemic cell lines. To explore the structural requirements for this activity, a series of purine and 8-substituted purine arabinofuranosyl and ribofuranosyl nucleoside derivatives were synthesized and tested as inducers of the differentiation of Friend murine erythroleukemia cells. 9-(beta-D-Arabinofuranosyl)hypoxanthine and 6-(hydroxyamino)-9-(beta-D-arabinofuranosyl)purine were effective inducers of maturation, producing 82% and 74% benzidine-positive cells, a measure of the number of cells synthesizing hemoglobin. 6-Mercapto-9-(beta-D-ribofuranosyl)purine and 6-(methylmercapto)-9-(beta-D-ribofuranosyl)purine and their corresponding beta-D-arabinofuranosyl derivatives were also effective initiators of maturation, causing approximately 50% of the cell population to assume a differentiated phenotype.
• Synthesis of 8-Substituted Analogues of 2′-Deoxy-2′-Fluoroadenosine
  作者：Tokumi Maruyama、Shigetada Kozai、Takako Manabe、Yuko Yazima、Yoshiko Satoh、Hiroshi Takaku

  DOI：10.1080/07328319908044618

  日期：1999.11

  After 3',5'-di-O-protection of 8-bromoadenosine, the product was converted to the arabinoside, which was successively treated with diethylaminosulfur trifluoride (DAST) and acid to afford 8-bromo-2'-deoxy-2'-fluoroadenosine. However, the formation of an 8,2'-anhydro compound was noted by treatment of the arabinoside with alkali. Finally, the 8-oxo analog was obtained from the 8-bromo congener.