2-benzoyloxymethyl-5-<2-methoxyethyloxy>-1,3-oxathiolane | 144897-15-4

• 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: 2-benzoyloxymethyl-5-<2-methoxyethyloxy>-1,3-oxathiolane
• 英文别名: [5-(2-Methoxyethoxy)-1,3-oxathiolan-2-yl]methyl benzoate
• CAS: 144897-15-4
• 化学式: C₁₄H₁₈O₅S
• 分子量: 298.36
• InChiKey: ZISSVJNOGHRHLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-benzoyloxymethyl-5-<2-methoxyethyloxy>-1,3-oxathiolane 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 trans-2-benzoyloxymethyl-5-(N'4-acetylcytosin-1'-yl)-1,3-oxathiolane
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a New N⁴-(N-Formyl Peptide)- 2′,3′-Dideoxy-3′-Thiacytidine as Anti-Hiv Prodrug

  摘要：

  The synthesis of a new analogue of 2,3'-dideoxy-3'-thiacytidine 9 covalently linked to an N-formyl methionyl leucyl phenylalanine peptide is described. This new prodrug analogue has been tested on the one hand as activator of human polymorphonuclear leukocytes (an EC50 value of 1.8 10(-5) M was determined from dose-response curve for superoxide production) and on the other hand as inhibitor Of the syncitium formation caused by HIV-1 in MT4-cells (IC50 = 8.0 +/- 0.8 muM). In so far as this new prodrug possesses these two biological properties, it represents a useful ''chemical-head' capable of targeting specific receptors located on leukocytes membranes.

  DOI：

  10.1080/07328319308019017
• 作为产物：
  描述：

  2-benzoyloxyacetaldehyde 、 2-mercaptoacetaldehyde di-(2-methoxyethyl) acetal 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以65%的产率得到2-benzoyloxymethyl-5-<2-methoxyethyloxy>-1,3-oxathiolane
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a New N⁴-(N-Formyl Peptide)- 2′,3′-Dideoxy-3′-Thiacytidine as Anti-Hiv Prodrug

  摘要：

  The synthesis of a new analogue of 2,3'-dideoxy-3'-thiacytidine 9 covalently linked to an N-formyl methionyl leucyl phenylalanine peptide is described. This new prodrug analogue has been tested on the one hand as activator of human polymorphonuclear leukocytes (an EC50 value of 1.8 10(-5) M was determined from dose-response curve for superoxide production) and on the other hand as inhibitor Of the syncitium formation caused by HIV-1 in MT4-cells (IC50 = 8.0 +/- 0.8 muM). In so far as this new prodrug possesses these two biological properties, it represents a useful ''chemical-head' capable of targeting specific receptors located on leukocytes membranes.

  DOI：

  10.1080/07328319308019017

文献信息

• 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。
• Synthesis of substituted 1,3-dioxolanes and substituted 1,3-oxathiolanes with antiviral properties
  申请人：BioChem Pharma Inc.

  公开号：US20030087918A1

  公开（公告）日：2003-05-08

  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.

  本发明涉及的化合物的通式为其中R1为氢或具有1至16个碳原子的酰基；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。本发明还描述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这些化合物在哺乳动物的抗病毒治疗中的使用。
• Substituted-1, 3-oxathiolanes and substituted-1, 3-dioxolanes with antiviral properties
  申请人：Belleau Bernard

  公开号：US20070037977A1

  公开（公告）日：2007-02-15

  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 process 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.

  本发明涉及的化合物的结构式如下：其中R1是氢或具有1至16个碳原子的酰基基团；R2是嘌呤或嘧啶碱基或其类似物或衍生物；Z是O、S、S═O或SO2；以及其药学上可接受的衍生物。还描述了用于制备这些化合物的过程和中间体，含有这些化合物的药物组合物，以及这些化合物在哺乳动物的抗病毒治疗中的使用。
• Substituted-1,3-oxathiolanes and substituted-1, 3-dioxolanes with antiviral properties
  申请人：Belleau Bernard

  公开号：US20070037975A1

  公开（公告）日：2007-02-15

  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.

  本发明涉及一种化合物，其化学式为：其中R1为氢或具有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。本发明还描述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。
• US6350753B1
  申请人：——

  公开号：US6350753B1

  公开（公告）日：2002-02-26