1-(2,3-dideoxy-2,3-difluoro-5-O-trityl-β-D-ribofuranosyl)uracil | 127840-98-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-(2,3-dideoxy-2,3-difluoro-5-O-trityl-β-D-ribofuranosyl)uracil
• 英文别名: 5'-O-trityl-2',3'-dideoxy-2',3'-difluorouridine；1-[(2R,3S,4R,5R)-3,4-difluoro-5-(trityloxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 127840-98-6
• 化学式: C₂₈H₂₄F₂N₂O₄
• 分子量: 490.506
• InChiKey: HPFYJGFTKXOIBI-VNSJUHMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  73.32
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(2,3-dideoxy-2,3-difluoro-5-O-trityl-β-D-ribofuranosyl)uracil 在 吡啶 、 氨 、 溶剂黄146 、 trifluoromethanesulfonic acid anhydride 作用下， 反应 3.5h， 生成 2',3'-dideoxy-2',3'-difluorocytidine hydrochloride
  参考文献：
  名称：

  Aerschot, A. Van; Herdewijn, P., Bulletin des Societes Chimiques Belges, 1989, vol. 98, # 12, p. 937 - 942

  摘要：

  DOI：
• 作为产物：
  描述：

  2'-氟-2'-脱氧尿苷 在 吡啶 、 sodium hydroxide 、 二乙胺基三氟化硫 、 trifluoromethanesulfonic acid anhydride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 生成 1-(2,3-dideoxy-2,3-difluoro-5-O-trityl-β-D-ribofuranosyl)uracil
  参考文献：
  名称：

  Aerschot, A. Van; Herdewijn, P., Bulletin des Societes Chimiques Belges, 1989, vol. 98, # 12, p. 937 - 942

  摘要：

  DOI：

文献信息

• Synthesis and in vitro antiviral activities of 3′-fluoro (or chloro) and 2′,3′-difluoro 2′,3′-dideoxynucleoside analogs against hepatitis B and C viruses
  作者：Naveen C. Srivastav、Neeraj Shakya、Michelle Mak、Chao Liang、D. Lorne J. Tyrrell、Babita Agrawal、Rakesh Kumar

  DOI：10.1016/j.bmc.2010.08.048

  日期：2010.11

  Chronic infections with hepatitis B virus (HBV) and hepatitis C virus (HCV) lead to serious liver diseases worldwide. Co-infection with HBV and HCV is very common and is associated with increased risk of liver pathogenesis, liver cancer, and liver failure. Several 5-substituted 3'-fluoro (or chloro) (1-4, 6, 7, 17-19) and 2',3'-difluoro 2',3'-dideoxynucleosides (15 and 16) were synthesized and evaluated for in vitro antiviral activities against duck hepatitis B virus (DHBV), human hepatitis B virus, and hepatitis C virus. Of these compounds 4, 7, 17, and 19 demonstrated moderate anti-HBV activity, and 2, 4, 7, 8, and 19 were weak inhibitors of HCV. Although 5-iodo derivative (7) was most inhibitory against HCV, it exhibited a reduction in cellular RNA levels in Huh-7 cells. The 5-hydroxymethyl-3'-fluoro-2',3'-dideoxyuridine (4) and 1-(3-chloro-2,3-dideoxy-beta-D-erythro-pentofuranosyl)-5-fluorouracil (19) provided the most inhibition of both viruses without cytotoxicity. (C) 2010 Elsevier Ltd. All rights reserved.
• VAN, AERSCHOT A.;HERDEWIJN, P., BULL. SOC. CHIM. BELG., 98,(1989) N2, C. 937-941
  作者：VAN, AERSCHOT A.、HERDEWIJN, P.

  DOI：——

  日期：——