3'-(acetylthio)-2',3'-dideoxythymidine | 115913-88-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3'-(acetylthio)-2',3'-dideoxythymidine
• 英文别名: 3'-Acetylthio-3'-deoxythymidine；S-[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] ethanethioate
• CAS: 115913-88-7
• 化学式: C₁₂H₁₆N₂O₅S
• 分子量: 300.335
• InChiKey: GQTPSSXMGAEGLR-KXUCPTDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3'-(acetylthio)-2',3'-dideoxythymidine 在 N-碘代丁二酰亚胺 、 过氧化苯甲酰 作用下， 生成 Thioacetic acid S-[(2R,3S,5R)-2-(diphenyl-phosphinoyloxymethoxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester
  参考文献：
  名称：

  含有3-硫代甲缩醛连接的五胸苷酸的寡核苷酸的合成和杂交性质。

  摘要：

  合成了完全被3'-硫代甲缩醛核苷间键取代的五甲基甲磺酸盐，随后将其掺入15mer寡核苷酸（ON）中。对与其互补RNA杂交的所得ON进行Tm分析。相对于对照磷酸二酯ON / RNA杂合体，该双链体显示出稍微改善的结合亲和力。

  DOI：

  10.1016/s0960-894x(98)00741-0
• 作为产物：
  描述：

  1-(3-甲磺酰氧代-5-三苯代甲基氧代甲基-2-D-苏呋喃基)胸苷 在 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.25h， 生成 3'-(acetylthio)-2',3'-dideoxythymidine
  参考文献：
  名称：

  Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides

  摘要：

  A series of base-modified pyrimidine 3'-azido-2',3'-dideoxynucleosides and 3'-substituted purine and pyrimidine 2',3'-dideoxynucleosides have been synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV) replication in MT-4 cells. The following pyrimidine derivatives emerged as the most potent and/or selective inhibitors of HIV-induced cytopathogenicity (in order of decreasing selectivity: 3'-azido-3'-deoxythymidine (AZT), 3'-azido-2',3'-dideoxyuridine (AzddUrd), 3'-azido-2',3'-dideoxy-5-methylcytidine (AzddMeCyd), 3'-fluoro-ddUrd (FddUrd), 3'-fluoro-ddThd (FddThd), the N4-hydroxylated derivative of AzddMeCyd and the N4-methylated derivative of AzddMeCyd. Among the purine 2',3'-dideoxynucleosides, 3'-azido-2',3'-dideoxyguanosine (AzddGuo), 3'-fluoro-ddGuo (FddGuo), and 3'-fluoro-2,6-diaminopurine 2',3'-dideoxynucleoside (FddDAPR) were the most selective inhibitors of HIV replication.

  DOI：

  10.1021/jm00118a033

文献信息

• RONCO, GINO LINO;VILLA, PIERRE JOSEPH;VILLE, GUY ANDRE
  作者：RONCO, GINO LINO、VILLA, PIERRE JOSEPH、VILLE, GUY ANDRE

  DOI：——

  日期：——
• HERDEWIJN, PIET;BALZARINI, JAN;BADA, MASANORI;PAUWELS, RUDI;VAN, AERSCHOT+, J. MED. CHEM., 31,(1988) N 10, C. 2040-2048
  作者：HERDEWIJN, PIET、BALZARINI, JAN、BADA, MASANORI、PAUWELS, RUDI、VAN, AERSCHOT+

  DOI：——

  日期：——
• Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides
  作者：Piet Herdewijn、Jan Balzarini、Masanori Baba、Rudi Pauwels、Arthur Van Aerschot、Gerard Janssen、Erik De Clercq

  DOI：10.1021/jm00118a033

  日期：1988.10

  A series of base-modified pyrimidine 3'-azido-2',3'-dideoxynucleosides and 3'-substituted purine and pyrimidine 2',3'-dideoxynucleosides have been synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV) replication in MT-4 cells. The following pyrimidine derivatives emerged as the most potent and/or selective inhibitors of HIV-induced cytopathogenicity (in order of decreasing selectivity: 3'-azido-3'-deoxythymidine (AZT), 3'-azido-2',3'-dideoxyuridine (AzddUrd), 3'-azido-2',3'-dideoxy-5-methylcytidine (AzddMeCyd), 3'-fluoro-ddUrd (FddUrd), 3'-fluoro-ddThd (FddThd), the N4-hydroxylated derivative of AzddMeCyd and the N4-methylated derivative of AzddMeCyd. Among the purine 2',3'-dideoxynucleosides, 3'-azido-2',3'-dideoxyguanosine (AzddGuo), 3'-fluoro-ddGuo (FddGuo), and 3'-fluoro-2,6-diaminopurine 2',3'-dideoxynucleoside (FddDAPR) were the most selective inhibitors of HIV replication.
• Synthesis and hybridization property of an oligonucleotide containing a 3′-thioformcetal linked pentathymidylate
  作者：Jiancun Zhang、Jared T. Shaw、Mark D. Matteucci

  DOI：10.1016/s0960-894x(98)00741-0

  日期：1999.2

  A pentathymidylate fully substituted with 3'-thioformacetal intemucleotidic linkages was synthesized and subsequently incorporated into an oligonucleotide (ON) 15mer. Tm analysis was performed on the resulting ON hybridized with its complementary RNA. This duplex demonstrated slightly improved binding affinity relative to the control phosphate diester ON/RNA hybrid.

  合成了完全被3'-硫代甲缩醛核苷间键取代的五甲基甲磺酸盐，随后将其掺入15mer寡核苷酸（ON）中。对与其互补RNA杂交的所得ON进行Tm分析。相对于对照磷酸二酯ON / RNA杂合体，该双链体显示出稍微改善的结合亲和力。