4,5-dichloro-7-<2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-7H-pyrrolo<2,3-d>pyrimidine | 157666-30-3

• 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: 4,5-dichloro-7-<2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-7H-pyrrolo<2,3-d>pyrimidine
• 英文别名: (2R,3S,5R)-5-(4,5-dichloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate；4,5-dichloro-7-[2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine；[(2R,3S,5R)-5-(4,5-dichloropyrrolo[2,3-d]pyrimidin-7-yl)-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 157666-30-3
• 化学式: C₂₇H₂₃Cl₂N₃O₅
• 分子量: 540.403
• InChiKey: FAMSXHOJVFKOLH-BHDDXSALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  92.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,5-dichloro-7-<2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-7H-pyrrolo<2,3-d>pyrimidine 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 5.0h， 生成 5-chloro-7-(2-deoxy-β-D-erythro-pentofuranosyl)-3,7-dihydro-4H-pyrrolo<2,3-d>pyrimidin-4-one
  参考文献：
  名称：

  7-Halogenated 7-Deaza-2′-deoxyinosines

  摘要：

  The synthesis of the 7-deaza-2'-deoxyinosine derivatives 3a-c with chloro, bromo, and iodo substituents at position 7 is described. Glycosylation of the 7-halogenated 6-chloro-7-deazapurines 4a-c or of the 7-halogenated 6-chloro-7-deaza-2-(methylthio)purines 9a-c with 2-deoxy-3,5-di-O-(4-toluoyl)-alpha-D-erythro-pento-furanosyl chloride (5) furnished the intermediates 7a-c and 11a-c, respectively, which gave, upon deprotection, the desired nucleosides 3a-c.

  DOI：

  10.1002/(sici)1522-2675(19990113)82:1<12::aid-hlca12>3.0.co;2-l
• 作为产物：
  描述：

  甲基-2-脱氧-D-核糖 在 盐酸 、 sodium hydride 作用下， 以 吡啶 、 乙醚 、 乙腈 、 mineral oil 为溶剂， 反应 19.17h， 生成 4,5-dichloro-7-<2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-7H-pyrrolo<2,3-d>pyrimidine
  参考文献：
  名称：

  [EN] 4'-SUBSTITUTED NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS
  [FR] INHIBITEURS NUCLÉOSIDIQUES SUBSTITUÉS EN 4' DE LA TRANSCRIPTASE INVERSE

  摘要：

  提供了Formula I的4'-取代核苷衍生物及其在抑制HIV逆转录酶、预防HIV感染、治疗HIV感染以及预防、治疗和延迟AIDS和/或ARC的发病或进展中的用途。

  公开号：

  WO2015143712A1

文献信息

• Synthesis of Certain 5-Substituted 2?-Deoxytubercidin Derivatives
  作者：Frank Seela、Horst Thomas

  DOI：10.1002/hlca.19940770403

  日期：1994.6.29

  The synthesis of the 7-deaza-2′-deoxy-adenine derivatives 7b–3 with chloro, bromo, or methyl substituents at C(5) is described. Glycosylation of the 5-substituted 4-chloropyrrolo[2,3-d]pyrimidines 4b–d with 2-deoxy-3,5-di-O-(4-toluoyl)-α-D-erythro-pentofuranosyl chloride (3) gave the β-D-nucleosides 5b–d, exclusively. They were deblocked (6b–d) and converted into the tubercidin derivatives 7b–d.

  描述了在C（5）处带有氯，溴或甲基取代基的7-deaza-2'-deoxy-腺嘌呤衍生物7b-3的合成。5-取代的4-氯吡咯并[2,3- d ]嘧啶4b-d与2-脱氧-3,5-二-O-（4-甲苯甲酰基）-α-D-赤型-戊呋喃糖酰氯的糖基化作用（3）仅给出了β-D-核苷5b–d。将它们解封（6b–d）并转化为结核菌素衍生物7b–d。
• 4'-SUBSTITUTED NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20150274767A1

  公开（公告）日：2015-10-01

  The present invention is directed to 4′-substituted nucleoside derivatives of Formula I and their use in the inhibition of HIV reverse transcriptase, the prophylaxis of infection by HIV, the treatment of infection by HIV, and the prophylaxis, treatment, and delay in the onset or progression of AIDS and/or ARC.

  本发明涉及式I的4'-取代核苷衍生物及其在抑制HIV逆转录酶、预防HIV感染、治疗HIV感染以及预防、治疗和延缓AIDS和/或ARC的发病或进展中的应用。
• US9777035B2
  申请人：——

  公开号：US9777035B2

  公开（公告）日：2017-10-03
• [EN] 4'-SUBSTITUTED NUCLEOSIDE-DERIVATIVES AS HIV REVERSE TRANSCRIPTASE INHIBITORS<br/>[FR] DÉRIVÉS NUCLÉOSIDIQUES 4'-SUBSTITUÉS UTILISÉS COMME INHIBITEURS DE LA TRANSCRIPTASE INVERSE DU VIH
  申请人：MERCK SHARP & DOHME

  公开号：WO2015148746A1

  公开（公告）日：2015-10-01

  The present invention is directed to 4'-substituted nucleoside derivatives of Formula I (Formula I), and their use in the inhibition of HIV reverse transcriptase, the prophylaxis of infection by HIV, the treatment of infection by HIV, and the prophylaxis, treatment, and delay in the onset or progression of AIDS and/or ARC.