1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranose | 84025-00-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranose
• 英文别名: [(2R,3R,4S)-3,5-diacetyloxy-4-fluorooxolan-2-yl]methyl benzoate
• CAS: 84025-00-3
• 化学式: C₁₆H₁₇FO₇
• 分子量: 340.305
• InChiKey: LIIIPIJVTZRNMK-MHRDGSLOSA-N

物化性质

• 沸点：
  422.9±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranose 在 咪唑 、 sodium hydroxide 、 偶氮二异丁腈 、 (dimethylamido)pyridine 、 四丁基氟化铵 、 苄基三乙基氯化铵 、 氨 、 氢溴酸 、 三正丁基氢锡 、 溶剂黄146 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 108.18h， 生成 9-[(2R,3S,5S)-3-氟-5-(羟基甲基)四氢呋喃-2-基]-3H-嘌呤-6-酮
  参考文献：
  名称：

  Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV

  摘要：

  2',3'-Dideoxy purine nucleosides have anti-HIV activity in vitro and the inosine analogue is being clinically evaluated. The instability of these compounds toward acidic conditions complicates oral administration. The effect of the addition of a fluorine atom to the 2'-position was investigated by preparing the fluorine-containing 2'-erythro and 2'-threo isomers of ddA and the threo isomer of ddI. All fluorine-containing compounds were indefinitely stable to acidic conditions which completely decomposed ddI (1) and ddA (2) in minutes. While the fluorine-containing erythro isomer, 5, was inactive, the threo isomers, 2'-F-dd-ara-A (3) and 2'-F-dd-ara-I (4), were just as potent and active in protecting CD4+ ATH8 cells from the cytopathogenic effects of HIV-1 as the parent drugs. Exposure to pH 1 at 37 degrees C prior to testing destroyed the activity of ddA and ddI but left the anti-HIV properties of 3 and 4 unchanged. The fluorinated analogues also protected cells exposed to HIV-2 and inhibited gag gene product expression but not as effectively as the parent compounds. The fluorine-containing analogues appear to be somewhat more toxic in vitro to the antigen- and mitogen-driven proliferation of immunocompetent cells than their corresponding parent compounds.

  DOI：

  10.1021/jm00165a015
• 作为产物：
  描述：

  3-deoxy-1,2;5,6-di-O-isopropylidene-3-fluoro-α-D-glucofuranose 生成 1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranose
  参考文献：
  名称：

  MARQUEZ, VICTOR E.;TSENG, CHRISTOPHER K. -H.;MITSUYA, HIROAKI;AOKI, SHIZU+, J. MED. CHEM., 33,(1990) N, C. 978-985

  摘要：

  DOI：

文献信息

• Nucleosides. 123. Synthesis of antiviral nucleosides: 5-substituted 1-(2-deoxy-2-halogeno-.beta.-D-arabinofuranosyl)cytosines and -uracils. Some structure-activity relationships
  作者：Kyoichi A. Watanabe、Tsann Long Su、Robert S. Klein、Chung K. Chu、Akira Matsuda、Moon Woo Chun、Carlos Lopez、Jack J. Fox

  DOI：10.1021/jm00356a007

  日期：1983.2

  2'-"up" (arabino) configuration for enhancement of antiviral effectiveness is demonstrated by the superior activity of 2'-fluoro-5-iodo-ara-C [3a, FIAC] to that of 2'-fluoro-5-iodo-ribo-C. Of all the nucleosides tested herein, FIAC exhibited the most potent in vitro activity against HSV. 2'-Chloro-5-iodo- and -5-methyl-ara-C (3b and 4b) were 37 to greater than 500 times more effective in vitro against HSV

  描述了几种2'-卤素-5-取代-阿拉伯呋喃糖基胞嘧啶和-尿嘧啶的合成，并研究了结构与体外抗疱疹病毒活性的关系。与2'-溴类似物的2'-氯相比，那些含有2'-氟功能的阿拉伯核苷通常表现出更有效的抗疱疹病毒（HSV）活性。2'-氟-5-碘-ara-C [3a，FIAC]优于2'-氟-5-碘-ara-C [3a，FIAC]的活性证明了氟在2'-“ up”（阿拉伯糖）构型中增强抗病毒效力的重要性。 '-氟-5-碘-核糖-C。在本文测试的所有核苷中，FIAC表现出最强的抗HSV体外活性。2'
• [EN] METHODS FOR SYNTHESIZING 2-CHLORO-9-(2-DEOXY-2-FLUORO- beta -D-ARABINOFURANOSYL)-9H-PURIN-6-AMINE<br/>[FR] PROCEDES DE SYNTHESE DE 2-CHLORO-9-(2-DEOXY-2-FLUORO- DOLLAR G(B)-D-ARABINOFURANOSYL)-9H-PURINE-6-AMINE
  申请人：SOUTHERN RES INST

  公开号：WO2001060383A1

  公开（公告）日：2001-08-23

  2-Chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purin-9-amine is synthesized by reacting a 2-chloro-6-substituted purine with a protected and activated 2-deoxy-2-fluoro-D-arabinofuranose; and reacting with a base such as ammonia to provide 2-chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purin-6-amine. When the purine reactant is substituted in the 6 position with a halogen, a reaction step with an alkoxide is carried out prior to the reaction with ammonia.

  2-氯-9-(2-去氧-2-氟-β-D-阿拉伯糖呋喃核苷基)-9H-嘌呤-9-胺是通过将2-氯-6-取代嘌呤与受保护和活化的2-去氧-2-氟-D-阿拉伯糖呋喃糖反应，并与氨等碱基反应而合成的。当嘌呤反应物在6位被卤素取代时，必须在与氨反应之前进行一步与碱金属醇反应的反应步骤。
• Method for synthesizing 2-chloro-9-(2-fluoro-β-D-arabinofuranosyl)-9H-purin-6-amine
  申请人：Montgomery John A.

  公开号：US06949640B2

  公开（公告）日：2005-09-27

  2-Chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purin-9-amine is synthesized by reacting a 2-chloro-6-substituted purine with a protected and activated 2-deoxy-2-fluoro-D-arabinofuranose; and reacting with a base such as ammonia to provide 2-chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purin-6-amine. When the purine reactant is substituted in the 6 position with a halogen, a reaction step with an alkoxide is carried out prior to the reaction with ammonia.

  2-氯-9-(2-去氧-2-氟-β-D-阿拉伯糖呋喃核苷基)-9H-嘌呤-9-胺是通过将2-氯-6-取代嘌呤与受保护和活化的2-去氧-2-氟-D-阿拉伯糖呋喃糖进行反应，并与氨等碱基反应而合成的。当嘌呤反应物在6位取代卤素时，需要在与氨反应之前进行碱金属醇反应步骤。
• [EN] 2-HALO-9-(2-DEOXY-2-FLUORO-B-D-ARABINOFURANOSYL) ADENINE NUCLEOSIDE DERIVATIVES
  申请人：SOUTHERN RESEARCH INSTITUTE

  公开号：WO1990014352A1

  公开（公告）日：1990-11-29

  (EN) There are disclosed nucleosides having formula (I), wherein Z is F, Cl or Br and R is H or aryl. These compounds have anticancer activity.(FR) l'invention concerne des nucléosides ayant la forme (I) dans laquelle Z représente F, Cl ou Br et R représente H ou aryle. Ces composés présentent une activité anticancéreuse.

  （中）公开了具有式（I）的核苷，其中Z为F，Cl或Br，R为H或芳基。这些化合物具有抗癌活性。
• 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：##STR1## 其中R为H或酰基。这些化合物具有抗癌活性。