1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranose | 90580-88-4

• 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: 1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranose
• 英文别名: 1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-beta-d-ribofuranose；[(2S,4R,5S)-4,5-diacetyloxyoxolan-2-yl]methyl benzoate
• CAS: 90580-88-4
• 化学式: C₁₆H₁₈O₇
• 分子量: 322.315
• InChiKey: DPLPHOLDKAGPOZ-SQWLQELKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranose 在 氨 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 7-amino-5-chloro-3-(3-deoxy-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine
  参考文献：
  名称：

  3′-DEOXYRIBOFURANOSE DERIVATIVES OF 1-DEAZA AND 3-DEAZA-ADENOSINE AND THEIR ACTIVITY AS ADENOSINE DEAMINASE INHIBITORS

  摘要：

  2,6-Dichloro-1-deazapurine and 2,6-dichloro-3-deazapurine were coupled with 1,2-O-diacetyl-5-O-benzoyl-3-deoxy-beta -D-ribofuranose. Deprotection of the obtained compounds and reaction with liquid ammonia gave the desired 2-chloroadenine nucleosides, which were dechlorinated to afford the corresponding 1-deaza and 3-deazaadenosine derivatives. Biological studies performed on ADA from calf intestine showed that these new nucleosides are inhibitors of the enzyme.

  DOI：

  10.1081/ncn-100002486
• 作为产物：
  描述：

  、 乙酸酐 在 吡啶 作用下， 反应 1.0h， 以1.62 g的产率得到1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranose
  参考文献：
  名称：

  新型C5修饰的嘧啶核呋喃核苷作为潜在抗肿瘤药和/或抗病毒药的设计，合成和生物学评估。

  摘要：

  背景技术核苷类似物是众所周知的抗肿瘤剂，抗病毒剂和化学治疗剂。它们的糖和杂环部分的改变都可能导致其生物学活性和选择性毒性程度以及其理化性质发生重大变化。方法C5-芳基炔基-β-D-呋喃核苷3-6、3′-脱氧12-15、3′-脱氧-3′-C-甲基-β-D-呋喃呋喃核苷18-21和2′-脱氧-β-尿嘧啶的D-呋喃核糖核苷23-26，是在微波辐射下通过一步Sonogashira反应合成的，然后进行脱保护。结果测试了所有新合成的核苷的抗肿瘤或抗病毒活性。针对宫颈癌（HeLa）的中等细胞抑制活性，受保护的3′-脱氧衍生物12b，12c，12d和3′-脱氧-3′-甲基18a，18b，18c显示出鼠白血病（L1210）和人淋巴细胞（CEM）肿瘤细胞系。抗病毒评估显示，该化合物对3 Co-脱氧化合物12b，14和3΄-脱氧-3΄-甲基18a，18c具有明显的抗柯萨奇病毒B4，呼吸道合胞病毒，黄热病毒和人冠状病毒（229E）的活性，

  DOI：

  10.2174/1573406415666190225112950

文献信息

• TLR7 AGONISTS
  申请人：Primmune Therapeutics, Inc.

  公开号：US20190359613A1

  公开（公告）日：2019-11-28

  The present invention relates to TLR7 agonists according to Formula I and their use in the treatment of diseases such as cancer and infectious disease.

  本发明涉及按照式I的TLR7激动剂及其在治疗癌症和传染病等疾病中的应用。
• 5-Aza-7-deazapurine derivatives for treating Flaviviridae
  申请人：Gosselin Gilles

  公开号：US20060040944A1

  公开（公告）日：2006-02-23

  This invention is directed to a method for treating a host, especially a human, infected with hepatitis C, flavivirus and/or pestivirus, comprising administering to that host an effective amount of an anti-flavivirus or anti-pestivirus, biologically active compound has a 5-aza-7-deazapurine moiety. The 5-aza-7-deazapurine moiety may be substituted or unsubstituted, and may comprise a nucleoside analogue, or a salt or prodrug thereof. The compound of the present invention may be administered alone or in combination with another anti-hepatitis C, anti-flavivirus and/or anti-pestivirus agent.

  本发明涉及一种治疗宿主，特别是感染丙型肝炎、黄热病毒和/或瘟疫病毒的人类的方法，包括向该宿主施用有效量的具有5-aza-7-deazapurine基团的抗黄热病毒或抗瘟疫病毒生物活性化合物。5-aza-7-deazapurine基团可以是取代或未取代的，并且可以包括核苷类似物或其盐或前药。本发明的化合物可以单独或与另一种抗丙型肝炎、抗黄热病毒和/或抗瘟疫病毒药物组合使用。
• [EN] 5-AZA-7-DEAZAPURINE DERIVATIVES FOR TREATING INFECTIONS WITH FLAVIVIRIDAE<br/>[FR] DERIVES DE 5-AZA-7-DEAZAPURINE POUR LE TRAITEMENT DES FLAVIVIRIDAE
  申请人：IDENIX CAYMAN LTD

  公开号：WO2006000922A3

  公开（公告）日：2006-05-26
• Purine and deazapurine nucleosides: synthetic approaches, molecular modelling and biological activity
  作者：Gloria Cristalli、Stefano Costanzi、Catia Lambertucci、Sara Taffi、Sauro Vittori、Rosaria Volpini

  DOI：10.1016/s0014-827x(03)00019-3

  日期：2003.3

  A number of ligands for the adenosine binding sites has been obtained by using nucleoside convergent and divergent synthesis. Most of our nucleosides have been synthesized by coupling 2,6-dichloropurine (1), 2,6-dichloro-1-deazapurine (2), 2,6-dichloro-3-deazapurine (3) with ribose, 2- and 3-deoxyribose and 2,3-dideoxyribose derivatives. The use of these versatile synthons allowed the introduction of various substituents in 2- and/or 6-positions. The glycosylation site and the anomeric configuration of the obtained nucleosides were assigned on the basis of spectroscopic studies and confirmed by molecular models. A series of potent adenosine receptor ligands has been obtained by using divergent approaches, mostly starting from guanosine. Substitutions in 2, 6, 8, and 5' position of adenosine molecule led to ligands selective for the different adenosine receptor subtypes. Furthermore, we investigated the molecular bases of the different behavior of 2- and 8-alkynyl adenosines, by means of NMR experiments and molecular modeling studies. With docking experiments, we demonstrated that the two class of molecules should have different binding modes that explain their different degree of affinity and the shift of their activity from agonistic (2-substituted derivatives) to antagonistic (8-substituted derivatives).
• Synthesis and Adenosine Deaminase Inhibitory Activity of 3′-Deoxy-1-deazaadenosines
  作者：Rosaria Volpini、Stefano Costanzi、Sauro Vittori、Gloria Cristalli、Giulio Lupidi

  DOI：10.1002/(sici)1522-2675(19991215)82:12<2112::aid-hlca2112>3.0.co;2-2

  日期：1999.12.15