cis-2-hydroxymethyl-4-(2'-amino-purin-9'-yl)-1,3-dioxolane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: cis-2-hydroxymethyl-4-(2'-amino-purin-9'-yl)-1,3-dioxolane
• 英文别名: [(2S,4S)-4-(2-aminopurin-9-yl)-1,3-dioxolan-2-yl]methanol
• 化学式: C₉H₁₁N₅O₃
• 分子量: 237.218
• InChiKey: SXHGYAAPHCFGCV-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  cis-2-hydroxymethyl-4-(2'-amino-6'-chloro-purin-9'-yl)-1,3-dioxolane 生成 cis-2-hydroxymethyl-4-(2'-amino-purin-9'-yl)-1,3-dioxolane
  参考文献：
  名称：

  2-Substituted-4-substituted-1,3-dioxolanes and use thereof

  摘要：

  含有1,3-二氧杂环戊烷结构的核苷类似物是适用的抗病毒药物，特别适用于治疗哺乳动物，尤其是人类的HIV感染。核苷类似物的例子包括：顺式-2-乙酰氧甲基-4-(胸腺嘧啶-1'-基)-1,3-二氧杂环戊烷，顺式-2-羟甲基-4-(胸腺嘧啶-1'-基)-1,3-二氧杂环戊烷，顺式-2-苯甲酰氧甲基-4-(胞嘧啶-1'-基)-1,3-二氧杂环戊烷，以及顺式-2-羟甲基-4-(胞嘧啶-1'-基)-1,3-二氧杂环戊烷。这些化合物可以是它们的外消旋体或它们的单独对映体形式。

  公开号：

  US06350753B1

文献信息

• [EN] STEREOSELECTIVE SYNTHESIS OF NUCLEOSIDE ANALOGUES<br/>[FR] SYNTHESE STEREOSELECTIVE D'ANALOGUES DE NUCLEOSIDES
  申请人：IAF BIOCHEM INT

  公开号：WO2001058894A1

  公开（公告）日：2001-08-16

  The invention is a process for stereoselectively producing a dioxolane nucleoside analogue from an anomeric mixture of β and α anomers represented by formula (A) or formula (B), wherein R is selected from the group consisting of C1-6 alkyl and C6-15 aryl and Bz is benzoyl. The process comprises hydrolyzing said mixture with an enzyme selected from the group consisting of Protease N, Alcalase, Savinase, ChiroCLEC-BL, PS-30, and ChiroCLEC-PC to stereoselectively hydrolyze predominantly one anomer to form a product wherein R1 is replaced with H. The process also includes the step of separating the product from unhydrolyzed starting material. Additionally, the functional group at the C4 position is stereoselectively replaced with a purinyl or pyrimidinyl or derivative thereof.

  该发明涉及一种从β和α异构体混合物中立体选择性地生产二噁烷核苷类似物的方法，其由式（A）或式（B）表示，其中R选择自由基，包括C1-6烷基和C6-15芳基，Bz为苯甲酰基。该方法包括使用选自蛋白酶N、Alcalase、Savinase、ChiroCLEC-BL、PS-30和ChiroCLEC-PC的酶水解该混合物，以立体选择性地水解优选的一种异构体，形成一个产物，其中R1被替换为H。该方法还包括从未水解的起始物质中分离产物的步骤。此外，C4位置的功能基团被立体选择性地替换为嘌呤或嘧啶或其衍生物。
• [EN] STEREOSELECTIVE SYNTHESIS OF NUCLEOSIDE ANALOGUES<br/>[FR] SYNTHESE STEREOSELECTIVE D'ANALOGUES NUCLEOSIDIQUES
  申请人：IAF BIOCHEM INT

  公开号：WO2000047759A1

  公开（公告）日：2000-08-17

  The present invention provides a process for making stereochemically pure dioxolane nucleoside analogues. The process includes the use of hydrolytic enzymes for separating β and α anomers from an anomeric mixture represented by formula (A) or formula (B) wherein W is benzyl or benzoyl; R1 is selected from the group consisting of C1-6 alkyl and C6-15 aryl.

  本发明提供了一种制备立体化学纯的二氧兰嘧啶核苷类似物的方法。该方法包括使用水解酶从由式(A)或式(B)表示的异构混合物中分离β和α异构体，其中W为苯甲基或苯甲酰基；R1选自由C1-6烷基和C6-15芳基组成的群。
• Stereoselective synthesis of nucleoside analogues
  申请人：BioChem Pharma Inc.

  公开号：US20030187262A1

  公开（公告）日：2003-10-02

  The invention is a process for stereoselectively producing a dioxolane nucleoside analogue from an anomeric mixture of &bgr; and &agr; anomers represented by the following formula A or formula B: 1 wherein R is selected from the group consisting of C 1-6 alkyl and C 6 - 15 aryl and Bz is benzoyl. The process comprises hydrolyzing said mixture with an enzyme selected from the group consisting of Protease N, Alcalase, Savinase, ChiroCLEC-BL, PS-30, and ChiroCLEC-PC to stereoselectively hydrolyze predominantly one anomer to form a product wherein R 1 is replaced with H. The process also includes the step of separating the product from unhydrolyzed starting material. Additionally, the functional group at the C4 position is stereoselectively replaced with a purinyl or pyrimidinyl or derivative thereof.

  该发明是一种从由以下A或B式表示的β和α异构体的异构体混合物中立体选择性地生产二氧六环核苷类似物的过程：其中R选自由C1-6烷基和C6-15芳基组成的群，Bz为苯甲酰基。该过程包括使用从Protease N、Alcalase、Savinase、ChiroCLEC-BL、PS-30和ChiroCLEC-PC组成的酶中选择的酶水解该混合物，以立体选择性地水解优选的一个异构体，形成其中R1被H取代的产物。该过程还包括将产物与未水解的起始材料分离的步骤。此外，C4位置的官能团体立体选择性地被嘌呤基或嘧啶基或其衍生物取代。
• Substituted-1,3-oxathiolanes and substituted-1,3-dioxolanes with antiviral properties
  申请人：——

  公开号：US20040254201A1

  公开（公告）日：2004-12-16

  Disclosed are compounds of the formula wherein R 1 is hydrogen or an acyl group having 1 to 16 carbon atoms; R 2 is a purine or pyrimidine base or an analogue or derivative thereof; Z is O, S, S═O or SO 2 ; and pharmaceutically acceptable derivatives thereof. Also described are processes for and intermediates of use in their preparation, pharmaceutical compositions containing these compounds, and the use of these compounds in the antiviral treatment of mammals.

  本发明公开了下列化合物：其中R1为氢或1至16个碳原子的酰基基团；R2为嘌呤或嘧啶碱基或其类似物或衍生物；Z为O、S、S═O或SO2；以及其药学上可接受的衍生物。还公开了用于制备这些化合物的过程和中间体，含有这些化合物的制药组合物，以及在哺乳动物的抗病毒治疗中使用这些化合物的方法。
• Method for the treatment or prevention of Flaviviridea viral infection using nucleoside analogues
  申请人：BioChem Pharma Inc.

  公开号：US20030225037A1

  公开（公告）日：2003-12-04

  In accordance with the present invention there is provided a method for treating or preventing a Flaviviridea viral infection in a host comprising administering a therapeutically effective amount of at least one compound of formula (I) or (II) 1 or or a pharmaceutically acceptable salts thereof, wherein Ra, R, Z and Y are defined in the application.

  根据本发明，提供了一种用于治疗或预防宿主中的Flavivirideaviral感染的方法，包括给予至少一种式(I)或(II)1或它们的药学上可接受的盐的治疗有效量，其中Ra、R、Z和Y在申请中有定义。