Acetic acid (3R,4S,5R)-2-acetoxy-5-acetoxymethyl-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-3-yl ester | 892499-12-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (3R,4S,5R)-2-acetoxy-5-acetoxymethyl-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-3-yl ester
• 英文别名: [(2R,3S,4R)-4,5-diacetyloxy-3-(4-methylphenyl)sulfonyloxyoxolan-2-yl]methyl acetate
• CAS: 892499-12-6
• 化学式: C₁₈H₂₂O₁₀S
• 分子量: 430.433
• InChiKey: HFOJRDYKYSIJQN-SOABOVLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Acetic acid (3R,4S,5R)-2-acetoxy-5-acetoxymethyl-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-3-yl ester 在 氢溴酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 97.0h， 生成 Acetic acid (2R,3R,4S,5R)-5-acetoxymethyl-2-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Nucleosides. 116. 1-(.beta.-D-Xylofuranosyl)-5-fluorocytosines with a leaving group on the 3' position. Potential double-barreled masked precursors of anticancer nucleosides

  摘要：

  Syntheses of five pairs of cytosine and 5-fluorocytosinexylofuranosyl nucleosides in which the 3'-hydroxyl group is replaced by Cl, Br, OMs, or OTs are described. Those xylosyl nucleosides with a good leaving group at the 3' position exhibit good inhibitory activity against L5178Y and P815 mouse leukemic cells in vitro at rather low concentrations, and like that of ara-C this cytotoxicity is reversed by 2'-deoxycytidine but not by thymidine. Xylosylcytosines are not active against ara-C resistant lines of L5178Y and P815 cells; however, the corresponding 5-fluorocytosine analogues exhibit significant cytotoxicity against these ara-C resistant leukemic cell lines, and this activity is reversed by thmidine but not by deoxycytidine. These data support the "double-barreled" masked precursor hypothesis in that xylosyl-5-fluorocytosines substituted at the 3' position by a good leaving group exhibit activity akin to that of ara-C in the ara-C sensitive lines, while these nucleosides act as 5-fluoropyrimidines in the ara-C resistant lines.

  DOI：

  10.1021/jm00184a006

文献信息

• 3,5-Disubsitituted and 3,5,7-trisubstituted-3H-oxazolo and 3H-thiazolo[4,5-d]pyrimidin-2-one compounds and prodrugs thereof
  申请人：Webber E. Stephen

  公开号：US20060160830A1

  公开（公告）日：2006-07-20

  The invention is directed to 3,5-disubstituted and 3,5,7-trisubstituted-3H-oxazolo and 3H-thiazolo[4,5-d]pyrimidin-2-one compounds and prodrugs thereof that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and pharmaceutical compositions containing them, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds and prodrugs.

  本发明涉及具有免疫调节活性的3,5-二取代和3,5,7-三取代-3H-噁唑啉和3H-噻唑啉[4,5-d]嘧啶-2-酮化合物及其前药。本发明还涉及使用这些化合物和前药的治疗或预防用途，以及包含它们的制药组合物，以及通过给予这些化合物和前药的有效量来治疗所述疾病和障碍的方法。
• 3,5-DISUBSTITUTED AND 3,5,7-TRISUBSTITUTED-3H-OXAZOLO AND 3H-THIAZOLO[4,5-d]PYRIMIDIN-2-ONE COMPOUNDS AND PRODRUGS THEREOF
  申请人：Webber Stephen E.

  公开号：US20110275589A1

  公开（公告）日：2011-11-10

  The invention is directed to 3,5-disubstituted and 3,5,7-trisubstituted-3H-oxazolo and 3H-thiazolo[4,5-d]pyrimidin-2-one compounds and prodrugs thereof that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and pharmaceutical compositions containing them, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds and prodrugs.

  本发明涉及具有免疫调节活性的3,5-二取代和3,5,7-三取代-3H-噁唑并[4,5-d]嘧啶-2-酮化合物及其前药。本发明还涉及使用此类化合物及其前药的治疗或预防用途，以及含有它们的制药组合物和通过给予这些化合物和前药的有效量来治疗本文所述疾病和疾病的方法。
• 3,5-DISUBSTITUTED AND 3,5,7-TRISUBSTITUTED-3H-OXAZOLO AND 3H-THIAZOLO[4,5-D]PYRIMIDIN-2-ONE COMPOUNDS AND PRODRUGS THEREOF
  申请人：Webber Stephen E.

  公开号：US20120121541A1

  公开（公告）日：2012-05-17

  The invention is directed to 3,5-disubstituted and 3,5,7-trisubstituted-3H-oxazolo and 3H-thiazolo[4,5-d]pyrimidin-2-one compounds and prodrugs thereof that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and pharmaceutical compositions containing them, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds and prodrugs.

  本发明涉及具有免疫调节活性的3,5-二取代和3,5,7-三取代-3H-噁唑和3H-噻唑[4,5-d]嘧啶-2-酮化合物及其前药。本发明还涉及使用这些化合物和前药的治疗或预防用途，以及含有它们的制药组合物，并通过给予这些化合物和前药的有效剂量来治疗本文所述的疾病和障碍的方法。
• 3,5-Disubstituted and 3,5,7-Trisubstituted-3H-Oxazolo and 3H-Thiazolo[4,5-d]pyrimidin-2-one Compounds and Prodrugs Thereof
  申请人：Webber Stephen E.

  公开号：US20130259831A1

  公开（公告）日：2013-10-03

  The invention is directed to 3,5-disubstituted and 3,5,7-trisubstituted-3H-oxazolo and 3H-thiazolo[4,5-d]pyrimidin-2-one compounds and prodrugs thereof that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and pharmaceutical compositions containing them, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds and prodrugs.

  该发明涉及具有免疫调节活性的3,5-二取代和3,5,7-三取代-3H-噁唑并[4,5-d]嘧啶-2-酮化合物及其前药。该发明还涉及使用这些化合物的治疗或预防用途，以及含有它们的制药组合物，以及通过给予这些化合物和前药的有效量来治疗本文所述的疾病和障碍的方法。
• 3, 5-disubstituted and 3,5,7-trisubstituted-3H-oxazolo [4,5-d]pyrimidin-2-one compounds and prodrugs thereof
  申请人：Anadys Pharmaceuticals, Inc.

  公开号：EP2561872A1

  公开（公告）日：2013-02-27

  The present application concerns a compound selected from or a pharmaceutically acceptable salt thereof. The applications also concerns pharmaceutical uses of the compound or a pharmaceutically acceptable salt thereof

  本申请涉及一种选自或其药学上可接受的盐的化合物。 本申请还涉及该化合物或其药学上可接受的盐的药物用途