(S)-(+)-γ-bromometilen-γ-butirrolattolo | 211037-98-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (S)-(+)-γ-bromometilen-γ-butirrolattolo
• 英文别名: (S)-(+)-5-bromomethyl-1-tetrahydrofuranol；(5S)-5-(Bromomethyl)-2-Hydroxy-Tetrahydrofuran；(5S)-5-(bromomethyl)oxolan-2-ol
• CAS: 211037-98-8
• 化学式: C₅H₉BrO₂
• 分子量: 181.029
• InChiKey: YCWGUHNTCUOMTQ-ROLXFIACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(+)-γ-bromometilen-γ-butirrolattolo 在 吡啶 、 4-二甲氨基吡啶 、 四氯化钛 、 caesium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (+)-(2S,5S)-5-(2'-amino-6'-chloropurin-9'-ylmethyl)-2-diethoxyphosphinoyl-tetrahydrofuran
  参考文献：
  名称：

  Identification of novel nucleotide phosphonate analogs with potent anti-HCMV activity

  摘要：

  We have recently described the discovery of new leads in the area of anti-HCMV research. Further structure - activity relationship studies have allowed us to identify potent and selective anti-HCMV nucleotide analogs. The synthesis as well as structure - activity relationship studies are described. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00649-0
• 作为产物：
  描述：

  (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 在 四溴化碳 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 甲苯 、 乙腈 为溶剂， 生成 (S)-(+)-γ-bromometilen-γ-butirrolattolo
  参考文献：
  名称：

  Design and SAR Study of a Novel Class of Nucleotide Analogues as Potent Anti-HCMV Agents

  摘要：

  We have developed a novel class of 2-phosphonate 1,3-dioxolane nucleotide analogues, from which the guanine derivative displayed weak anti-HCMV activity. Further SAR studies led to the identification of both cis and trans guanine derivatives of tetrahydrofuran analogues as potent anti-HCMV agents, both in vitro and in vivo, compared to ganciclovir and HPMPC.

  DOI：

  10.1080/15257779908041570

文献信息

• Anti-viral compounds
  申请人：——

  公开号：US05789394A1

  公开（公告）日：1998-08-04

  Nucleotide analogues having the general formula (I) and pharmaceutically acceptable derivatives: ##STR1## wherein n is 0 or an integer; X is O or S, CH.sub.2, CH-halogen, CH--N.sub.3, or C.dbd.CH.sub.2 ; Q and U are independently selected from: O, S, and CH(R.sub.a) wherein R.sub.a is hydrogen, OH, halogen, N.sub.3, NH.sub.2, SH, carboxyl, C.sub.1-6 alkyl or R.sub.a is CH.sub.2 (R.sub.b) wherein R.sub.b is hydrogen, OH, SH, NH.sub.2, C.sub.1-6 alkyl or carboxyl; or both Q and U are CH when Q and U are linked by a double bond; Z is selected from: O, a C.sub.1-6 alkoxy, a C.sub.1-6 thioalkyl, a C.sub.1-6 aminoalkyl, (CH.sub.2).sub.m wherein m is 0 or an integer, and N(R.sub.c).sub.2 wherein both R.sub.c are independently hydrogen or a C.sub.1-6, alkyl; and R2 is a purine or pyrimidine base or an analogue or derivative thereof are disclosed. Members of this series of analogues possess anti-viral activity.

  核苷酸类似物具有一般式(I)和药用可接受衍生物：##STR1##其中n为0或整数；X为O或S，CH.sub.2，CH-卤素，CH--N.sub.3，或C.dbd.CH.sub.2；Q和U分别选自：O，S和CH(R.sub.a)，其中R.sub.a为氢，OH，卤素，N.sub.3，NH.sub.2，SH，羧基，C.sub.1-6烷基或R.sub.a为CH.sub.2(R.sub.b)，其中R.sub.b为氢，OH，SH，NH.sub.2，C.sub.1-6烷基或羧基；或当Q和U由双键连接时，Q和U均为CH；Z选自：O，C.sub.1-6烷氧基，C.sub.1-6硫代烷基，C.sub.1-6氨基烷基，(CH.sub.2).sub.m，其中m为0或整数，和N(R.sub.c).sub.2，其中两个R.sub.c独立地为氢或C.sub.1-6烷基；和R2为嘌呤或嘧啶碱基或其类似物或衍生物。该类类似物系列的成员具有抗病毒活性。
• Identification of novel nucleotide phosphonate analogs with potent anti-HCMV activity
  作者：Paul Nguyen-Ba、Nathalie Turcotte、Leonard Yuen、Jean Bédard、Miguel Quimpère、Laval Chan

  DOI：10.1016/s0960-894x(98)00649-0

  日期：1998.12

  We have recently described the discovery of new leads in the area of anti-HCMV research. Further structure - activity relationship studies have allowed us to identify potent and selective anti-HCMV nucleotide analogs. The synthesis as well as structure - activity relationship studies are described. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Pirillo d.; Portaluppi; Di Giacomo, Farmaco, Edizione Scientifica, 1987, vol. 42, # 8, p. 603 - 610
  作者：Pirillo d.、Portaluppi、Di Giacomo、Azzolina、Vercesi、Traverso

  DOI：——

  日期：——
• Pirillo, D.; Malamidis, A.; Vercesi, D., Farmaco, Edizione Scientifica, 1987, vol. 42, # 2, p. 101 - 110
  作者：Pirillo, D.、Malamidis, A.、Vercesi, D.、Azzolina, O.、Portaluppi, L.、Traverso, G.

  DOI：——

  日期：——
• Design and SAR Study of a Novel Class of Nucleotide Analogues as Potent Anti-HCMV Agents
  作者：N. Nguyen-ba、L. Chan、M. Quimpère、N. Turcotte、N. Lee、H. Mitchell、J. Bédard

  DOI：10.1080/15257779908041570

  日期：1999.4

  We have developed a novel class of 2-phosphonate 1,3-dioxolane nucleotide analogues, from which the guanine derivative displayed weak anti-HCMV activity. Further SAR studies led to the identification of both cis and trans guanine derivatives of tetrahydrofuran analogues as potent anti-HCMV agents, both in vitro and in vivo, compared to ganciclovir and HPMPC.