b-D-半乳吡喃糖,1,6-脱水-,3-乙酸酯2-[二(苯基甲基)磷酸酯](9CI) | 222631-12-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: b-D-半乳吡喃糖,1,6-脱水-,3-乙酸酯2-[二(苯基甲基)磷酸酯](9CI)
• 英文名称: (1S)-1-(3-amino-N-benzyloxycarbonyl-2-ethoxycarbonylpyrrol-4-yl)-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol
• 英文别名: 1-benzyl 2-ethyl 3-amino-4-((3aS,4S,6R,6aR)-5-(tert-butoxycarbonyl)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo [4,5-c]pyrrol-4-yl)-1H-pyrrole-1,2-dicarboxylate；(1S)-1-C-[3-amino-1-N-benzyloxycarbonyl-2-ethoxycarbonyl-4-pyrrolyl]-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol；1-benzyl 2-ethyl 3-amino-4-((3aS,4S,6R,6aR)-5-(tert-butoxycarbonyl)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-1H-pyrrole-1,2-dicarboxylate；1-O-benzyl 2-O-ethyl 4-[(3aS,4S,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-3-aminopyrrole-1,2-dicarboxylate
• CAS: 222631-12-1
• 化学式: C₃₄H₅₁N₃O₉Si
• 分子量: 673.879
• InChiKey: UASCRKNGKVFBCR-VVDBAWRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.63
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  b-D-半乳吡喃糖,1,6-脱水-,3-乙酸酯2-[二(苯基甲基)磷酸酯](9CI) 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 19.0h， 生成 7-[(2S,3S,4R,5R)-3,4-二羟基-5-(羟甲基)-2-吡咯烷基]-3,5-二氢-4H-吡咯并[3,2-D]嘧啶-4-酮
  参考文献：
  名称：

  Synthesis of Transition State Analogue Inhibitors for Purine Nucleoside Phosphorylase and N-Riboside Hydrolases

  摘要：

  Syntheses of the 'Immucillins', potent aza-C-nncleoside inhibitors of purine nucleoside phosphorylase are reported as well as those of 5-deoxy-, 5-deoxyfluoro- and 2-deoxy- analogues and others having modified bases. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00194-0
• 作为产物：
  描述：

  2,3-O-异亚丙基-D-核糖酸 gamma-内酯 在 吡啶 、 咪唑 、 甲醇 、 4-二甲氨基吡啶 、 selenium(IV) oxide 、 sodium tetrahydroborate 、 正丁基锂 、 palladium on activated charcoal 、 水 、 氢气 、 双氧水 、 sodium acetate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 potassium hydroxide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， -78.0~70.0 ℃ 、551.59 kPa 条件下， 反应 144.5h， 生成 b-D-半乳吡喃糖,1,6-脱水-,3-乙酸酯2-[二(苯基甲基)磷酸酯](9CI)
  参考文献：
  名称：

  [EN] ANTIVIRAL AZASUGAR-CONTAINING NUCLEOSIDES
  [FR] NUCLÉOSIDES ANTIVIRAUX CONTENANT DE L'AZASUCRE

  摘要：

  公开号：

  WO2014078778A3

文献信息

• Inhibitors of nucleoside metabolism
  申请人：Albert Einstein College of Medicine of Yeshiva University

  公开号：US06066722A1

  公开（公告）日：2000-05-23

  The present invention provides compounds having the formula: ##STR1## wherein A is CH or N; B is chosen from OH, NH.sub.2, NHR, H or halogen; D is chosen from OH, NH.sub.2, NHR, H, halogen or SCH.sub.3 ; R is an optionally substituted alkyl, aralkyl or aryl group; and X and Y are independently selected from H, OH or halogen except that when one of X and Y is hydroxy or halogen, the other is hydrogen; and Z is OH or, when X is hydroxy, Z is selected from hydrogen, halogen, hydroxy, SQ or OQ, Q is an optionally substituted alkyl, aralkyl or aryl group; or a tautomer thereof; or a pharmaceutically acceptable salt thereof; or an ester thereof; or a prodrug thereof; and compounds having the formula: ##STR2## wherein A, X, Y, Z and R are defined for compounds of formula (I) where first shown above; E is chosen from CO.sub.2 H or a corresponding salt form, CO.sub.2 R, CN, CONH.sub.2, CONHR or CONR.sub.2 ; and G is chosen from NH.sub.2, NHCOR, NHCONHR or NHCSNHR; or a tautomer thereof, or a pharmaceutically acceptable salt thereof, or an ester thereof, or a prodrug thereof. The present invention also provides the use of the above compounds as pharmaceuticals, pharmaceutical compositions containing the compounds and processes for preparing the compounds.

  本发明提供具有以下结构式的化合物：##STR1## 其中A为CH或N; B选择自OH、NH.sub.2、NHR、H或卤素; D选择自OH、NH.sub.2、NHR、H、卤素或SCH.sub.3; R为可选取的取代烷基、芳基烷基或芳基基团; X和Y独立选择自H、OH或卤素，但当X和Y中的一个为羟基或卤素时，另一个为氢; Z为OH，或当X为羟基时，Z选择自氢、卤素、羟基、SQ或OQ，Q为可选取的取代烷基、芳基烷基或芳基基团; 或其互变异构体; 或其药学上可接受的盐; 或其酯; 或其前药。还提供具有以下结构式的化合物：##STR2## 其中A、X、Y、Z和R在上述第一个式子中已定义; E选择自CO.sub.2H或相应的盐形式、CO.sub.2R、CN、CONH.sub.2、CONHR或CONR.sub.2; G选择自NH.sub.2、NHCOR、NHCONHR或NHCSNHR; 或其互变异构体，或其药学上可接受的盐，或其酯，或其前药。本发明还提供上述化合物作为药物的用途，含有上述化合物的药物组合物以及制备上述化合物的方法。
• ANTIVIRAL AZASUGAR-CONTAINING NUCLEOSIDES
  申请人：BIOCRYST PHARMACEUTICALS, INC.

  公开号：US20150291596A1

  公开（公告）日：2015-10-15

  Disclosed are compounds comprising an azasugar attached to a heterocyclic base, including pharmaceutically acceptable salts thereof, suitable for use in inhibiting viral RNA polymerase activity or viral replication, and treating viral infections. The compounds are characterized, in part, by favorable pharmacokinetics for the active pharmaceutical ingredient, particularly in conjunction with enteral administration, including, in particular, oral administration. Also disclosed are pharmaceutical compositions comprising one or more compounds mentioned above, or pharmaceutically acceptable salts thereof, as well as methods for preparing same. Also provided are methods for inhibiting viral RNA polymerase activity, viral replication, and treating viral infections.

  本发明涉及一种含有偶氮糖与杂环碱基结合的化合物，包括其药学上可接受的盐，适用于抑制病毒RNA聚合酶活性或病毒复制，并用于治疗病毒感染。该化合物的特点之一是具有良好的药代动力学，特别是在肠道给药的情况下，包括口服给药。本发明还涉及含有上述一种或多种化合物或其药学上可接受的盐的制药组合物，以及制备它们的方法。本发明还提供了抑制病毒RNA聚合酶活性、病毒复制和治疗病毒感染的方法。
• [EN] ANTIVIRAL AZASUGAR-CONTAINING NUCLEOSIDES<br/>[FR] NUCLÉOSIDES ANTIVIRAUX CONTENANT DE L'AZASUCRE
  申请人：BIOCRYST PHARM INC

  公开号：WO2014078778A3

  公开（公告）日：2014-10-09
• Synthesis of Transition State Analogue Inhibitors for Purine Nucleoside Phosphorylase and N-Riboside Hydrolases
  作者：Gary B. Evans、Richard H. Furneaux、Graeme J. Gainsford、Vern L. Schramm、Peter C. Tyler

  DOI：10.1016/s0040-4020(00)00194-0

  日期：2000.5

  Syntheses of the 'Immucillins', potent aza-C-nncleoside inhibitors of purine nucleoside phosphorylase are reported as well as those of 5-deoxy-, 5-deoxyfluoro- and 2-deoxy- analogues and others having modified bases. (C) 2000 Elsevier Science Ltd. All rights reserved.