9-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)-9H-purine | 109304-16-7

• 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: 9-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)-9H-purine
• 英文别名: 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)purine；(2R,3R,4S,5R)-4-Fluoro-2-(hydroxymethyl)-5-(9H-purin-9-yl)tetrahydrofuran-3-ol；(2R,3R,4S,5R)-4-fluoro-2-(hydroxymethyl)-5-purin-9-yloxolan-3-ol
• CAS: 109304-16-7
• 化学式: C₁₀H₁₁FN₄O₃
• 分子量: 254.221
• InChiKey: HLBLWLNFMONEHG-IBCQBUCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 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：
  93.3
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide 在 镍 甲醇 、 Celite 、 氨 、 硫脲 作用下， 以 乙醇 、 水 为溶剂， 反应 74.0h， 生成 9-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)-9H-purine
  参考文献：
  名称：

  核苷。CXXXV。一些9-（2-脱氧-2-氟-β-D-阿拉伯呋喃糖基）-9H-嘌呤的合成及其生物学活性。

  摘要：

  合成了含有2'-脱氧-2'-氟-β-D-阿拉伯呋喃糖基部分的七个嘌呤核苷，并测试了它们的抗肿瘤活性。3-O-乙酰基-5-O-苯甲酰基-2-脱氧-2-氟-D-阿拉伯呋喃糖基溴化物（1）与N6-苯甲酰腺嘌呤在CH2Cl2中的直接缩合，然后将产物皂化，得到腺嘌呤核苷（I，2 -F-ara-A）。用HOAc中的NaNO 2脱除I，得到次黄嘌呤类似物（II，2'-F-ara-H）。通过汞法将1与6-氯嘌呤缩合，然后进行硫脲处理和产物皂化，制备6-硫嘌呤核苷（III，2'-F-ara-6MP）。III的甲基化得到6-SCH3类似物（IV）。III的阮内镍脱硫得到未取代的嘌呤核苷（V，2'-F-ara-P）。通过甲硅烷基方法将1-与2-乙酰氨基-6-氯嘌呤缩合，得到被保护的2-乙酰氨基-6-氯嘌呤核苷，其可用作鸟嘌呤和6-硫代鸟嘌呤核苷的前体（VI，2'-F-ara- G和VII，分别为2'-F-ara

  DOI：

  10.1248/cpb.37.336

文献信息

• Potential anti-AIDS drugs. Lipophilic, adenosine deaminase-activated prodrugs
  作者：Joseph J. Barchi、Victor E. Marquez、John S. Driscoll、Harry Ford、Hiroaki Mitsuya、Takuma Shirasaka、Shizuko Aoki、James A. Kelley

  DOI：10.1021/jm00109a018

  日期：1991.5

  Selected acid-stable (2'-fluoro-2',3'-dideoxyarabinofuranosyl)adenine nucleosides containing methyl groups and other lipophilic functions at various positions in the adenine ring were prepared and evaluated as anti-HIV agents. The N6-methyl (1f), N6-benzoyl (1g), and 6-chloro (li) analogues had modest activity, giving 30-50% protection to ATH8 cells infected with HIV. 2-Methyl (1d), 8-methyl (1h), and 2,N6-dimethyl (1e) substitution, as well as N1-oxide (21) formation, abolished the activity of the parent compound (1a). Several of these compounds, originally designed as agents for treating HIV in the central nervous system, were further investigated as substrates for adenosine deaminase (ADA). Kinetic experiments showed that ADA catalyzed the formation of the anti-HIV active inosine compound 1b from the N6-methyl analogue 1f in a quantitative manner. The anti-HIV activity of 1f and 1i was abolished when the ADA inhibitor, 2'-deoxycoformycin, was added to the test mixture. In contrast, the activity of 1f was significantly enhanced when ADA was added to the test system. These data indicate that 1f and 1i are prodrug forms of 1b in systems containing ADA.
• CHU, CHUNG K.;MATULIC-ADAMIC, JASENKA;HUANG, JAI-TUNG;CHOU, TING-CHAO;BUR+, CHEM. AND PHARM. BULL., 37,(1989) N, C. 336-339
  作者：CHU, CHUNG K.、MATULIC-ADAMIC, JASENKA、HUANG, JAI-TUNG、CHOU, TING-CHAO、BUR+

  DOI：——

  日期：——
• WATANABE, KYOICHI A.;CHU, CHUNG K.;FOX, JACK J.
  作者：WATANABE, KYOICHI A.、CHU, CHUNG K.、FOX, JACK J.

  DOI：——

  日期：——
• PROCESSES AND INTERMEDIATES FOR PREPARING ANTI-HIV AGENTS
  申请人：Gilead Sciences, Inc.

  公开号：US20150203525A1

  公开（公告）日：2015-07-23

  The invention provides synthetic processes and synthetic intermediates that can be used to prepare compounds having useful anti-HIV properties.
• US9296779B2
  申请人：——

  公开号：US9296779B2

  公开（公告）日：2016-03-29