4-amino-6-bromo-7-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine-5-carbonitrile | 162019-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 4-amino-6-bromo-7-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine-5-carbonitrile
• 英文别名: 4-amino-6-bromo-7-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile；4-amino-6-bromo-7-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile
• CAS: 162019-41-2
• 化学式: C₁₂H₁₁BrFN₅O₃
• 分子量: 372.153
• InChiKey: BDPJWRZJFZYRCG-ADVRJHOBSA-N

物化性质

• 沸点：
  724.6±60.0 °C(predicted)
• 密度：
  2.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-amino-6-bromo-7-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine-5-carbonitrile 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 magnesium oxide 作用下， 以 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， -25.0 ℃ 、275.79 kPa 条件下， 反应 3.0h， 生成 4-amino-7-(3',5'-di-O-acetyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Total synthesis of 2′-deoxy-2′-arafluorotoyocamycin and related nucleosides

  摘要：

  以 5-溴-2-乙氧基亚甲基氨基吡咯-3,4-二甲腈 4 为起点，首次完成了玩具霉素 11、红霉素 12 和硫代红霉素 13 的 2â²-脱氧-2â²-阿拉氟类似物的全合成。

  DOI：

  10.1039/c39950000115
• 作为产物：
  描述：

  2-氨基-5-溴-1H-吡咯-3,4-二甲腈 在 氨 、 sodium hydride 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 18.0h， 生成 4-amino-6-bromo-7-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Total synthesis of 2′-deoxy-2′-arafluorotoyocamycin and related nucleosides

  摘要：

  以 5-溴-2-乙氧基亚甲基氨基吡咯-3,4-二甲腈 4 为起点，首次完成了玩具霉素 11、红霉素 12 和硫代红霉素 13 的 2â²-脱氧-2â²-阿拉氟类似物的全合成。

  DOI：

  10.1039/c39950000115

文献信息

• Bhattacharya, Birendra K.; Rao, T. Sudhakar; Revankar, Ganapathi R., Journal of the Chemical Society. Perkin transactions I, 1995, # 12, p. 1543 - 1550
  作者：Bhattacharya, Birendra K.、Rao, T. Sudhakar、Revankar, Ganapathi R.

  DOI：——

  日期：——
• Synthesis and Antiproliferative and Antiviral Activity of 2'-Deoxy-2'-fluoroarabinofuranosyl Analogs of the Nucleoside Antibiotics Toyocamycin and Sangivamycin
  作者：Steven H. Krawczyk、M. Reza Nassiri、Louis S. Kucera、Earl R. Kern、Roger G. Ptak、Linda L. Wotring、John C. Drach、Leory B. Townsend

  DOI：10.1021/jm00020a026

  日期：1995.9

  The glycosylation of 3,4-dicyano-2-[(ethoxymethylene)amino]py (7) with 2-deoxy-2-fluoro-alpha-D-erythro-pentofuranosyl bromide (2) furnished an anomeric mixture of nucleosides (8a,b). This mixture was separated, and the individual anomers were treated with methanolic ammonia to effect a concomitant deblocking and ring closure. This furnished both anomers of 2'-deoxy-2'-fluoro-ara-toyocamycin (9a,b). The cyano moiety of 9b was converted to the carboxamide moiety to furnish 2'-deoxy-2'-fluoro-ara-sangivamycin (10) and to the thiocarboxamide moiety to furnish 2'-deoxy-2'-fluoro-ara-thiosangivamycin (11). The target compounds 10 and 11 showed similar antiproliferative activity against L1210 cells in vitro, with IC50's Of 3 and 5 mu M. Antiviral evaluation revealed a somewhat different pattern of activity. All analogs, both alpha and beta anomers, were active against human cytomegalovirus (HCMV), albeit the beta anomers were most active. The beta anomers also were active against herpes simplex virus type 1 (HSV-1) and human immunodeficiency virus (HIV). Compound 10 was most active in the series, ca. 10-fold more potent than 11; IC50's for 10 ranged from 4 to 25 nM for HCMV, HIV, and varicella tester virus (VZV) and from 30 to 500 nM for HSV-1. Even though compound 10 was cytotoxic, which will probably preclude its use as an antiviral drug (IC50's = 0.2-5.5 mu M), the difference between cytotoxicity and activity against HCMV, HIV, and VZV was sufficient to indicate specific activity against-a viral target.
• Total synthesis of 2′-deoxy-2′-arafluorotoyocamycin and related nucleosides
  作者：Birendra K. Bhattacharya、Ganapathi R. Revankar

  DOI：10.1039/c39950000115

  日期：——

  Total synthesis of 2′-deoxy-2′-arafluoro analogues of toyocamycin 11, sangivamycin 12 and thiosangivamycin 13, starting from 5-bromo-2-ethoxymethyleneaminopyrrole-3,4-dicarbonitrile 4 has been accomplished for the first time.

  以 5-溴-2-乙氧基亚甲基氨基吡咯-3,4-二甲腈 4 为起点，首次完成了玩具霉素 11、红霉素 12 和硫代红霉素 13 的 2â²-脱氧-2â²-阿拉氟类似物的全合成。