5-methyl-5'-O-(triphenylmethyl)uridine 2',3'-bis(methanesulfonate) | 124493-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5-methyl-5'-O-(triphenylmethyl)uridine 2',3'-bis(methanesulfonate)
• 英文别名: 1-(2,3-di-O-mesyl-5-O-trityl-β-D-ribofuranosyl)thymine；1-(2',3'-di-O-methylsulfonyl-5'-O-trityl-β-D-ribofuranosyl)thymine；5-Methyl-5'-O-(triphenylmethyl)uridine 2',3'-dimethansulfonate；1-(2,3-Di-O-mesyl-5-O-trityl-beta-D-ribofuranosyl)thymine；[(2R,3R,4R,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-4-methylsulfonyloxy-2-(trityloxymethyl)oxolan-3-yl] methanesulfonate
• CAS: 124493-84-1
• 化学式: C₃₁H₃₂N₂O₁₀S₂
• 分子量: 656.734
• InChiKey: YTPDEKJOKAGGQY-LTGLEFCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  171
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5-methyl-5'-O-(triphenylmethyl)uridine 2',3'-bis(methanesulfonate) 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 1-(3-deoxy-3-phenylseleno-β-D-arabinofuranosyl)thymine
  参考文献：
  名称：

  4'-氰基-2'，3'-二氢-3'-脱氧胸苷的合成及其抗HIV活性。

  摘要：

  通过对3'，4'-不饱和核苷14进行烯丙基取代，合成了一种新的抗HIV剂4'-cyano-2'，3'-didehydro-3'-脱氧胸苷（9）在氰化三甲基硅烷存在下，在SnCl4存在的情况下在α-位。对9的抗HIV活性的评估表明，该化合物的药效比最近报道的2'，3'-didehydro-3'-deoxy-4'-（ethynyl）thymidine（1）强得多。

  DOI：

  10.1081/ncn-120030721
• 作为产物：
  描述：

  5-甲基尿甙 在 吡啶 作用下， 反应 5.0h， 生成 5-methyl-5'-O-(triphenylmethyl)uridine 2',3'-bis(methanesulfonate)
  参考文献：
  名称：

  4'-氰基-2'，3'-二氢-3'-脱氧胸苷的合成及其抗HIV活性。

  摘要：

  通过对3'，4'-不饱和核苷14进行烯丙基取代，合成了一种新的抗HIV剂4'-cyano-2'，3'-didehydro-3'-脱氧胸苷（9）在氰化三甲基硅烷存在下，在SnCl4存在的情况下在α-位。对9的抗HIV活性的评估表明，该化合物的药效比最近报道的2'，3'-didehydro-3'-deoxy-4'-（ethynyl）thymidine（1）强得多。

  DOI：

  10.1081/ncn-120030721

文献信息

• Synthesis of 2‘,3‘-Didehydro-2‘,3‘-dideoxynucleosides by Reaction of 5‘-Protected Nucleoside 2‘,3‘-Dimesylates with Telluride Dianion:  A General Route from <i>Cis</i> Vicinal Diols to Olefins
  作者：Derrick L. J. Clive、Philip L. Wickens、Paulo W. M. Sgarbi

  DOI：10.1021/jo9610570

  日期：1996.1.1

  treatment with telluride dianion in the form of the sodium or lithium salt. The method is well-suited to the preparation of unsaturated nucleosides that can be converted into compounds that are believed to be useful in the treatment of AIDS. The deoxygenation is general for vicinal dimesylates that have, or may adopt, a synperiplanar conformation. With straight chain compounds the reaction is stereospecific

  通过用钠或锂盐形式的碲化物二价阴离子处理，将5'-保护的核苷的2'，3'-二甲磺酸酯转化为相应的2'，3'-二氢-2'，3'-二脱氧化合物。该方法非常适合于不饱和核苷的制备，该不饱和核苷可以转化为据信可用于治疗艾滋病的化合物。脱氧通常用于具有或可以采用间平面构象的邻近二甲基酯。对于直链化合物，反应是立体特异性的。在某些情况下，可以用硒化物二价阴离子进行类似但较慢的脱氧。
• Reaction of cis-vicinal dimethanesulfonates with Te^2–: a method for converting cis-vicinal diols into olefins and its use in the preparation of 2′,3′-didehydro-2′,3′-dideoxynucleosides
  作者：Derrick L. J. Clive、Philip L. Wickens

  DOI：10.1039/c39930000923

  日期：——

  cis-Vicinal dimethanesulfonates, prepared from the corresponding diols, are converted into olefins by treatment with alkali metal tellurides or selenides (M2Te or M2Se); the reaction has been used to make derivatives of 2′,3′-didehydro-2′,3′-dideoxynucleosides.

  由相应二醇制备的顺式邻二甲磺酸酯，通过与碱金属碲化物或硒化物（M2Te或M2Se）处理，可转化为烯烃；该反应已被用于制备2′,3′-二脱氢-2′,3′-二脱氧核苷的衍生物。
• Deoxygenation of cis vicinal diols to make didehydro dideoxy
  申请人：Terochem Laboratories Limited

  公开号：US05410033A1

  公开（公告）日：1995-04-25

  Cis vicinal diols are converted to olefins using tellurides or selenide reagents. The diol is reacted to convert the hydroxyl groups into good leaving groups for nucleophilic substitution. Alkyl and aryl sulfonate groups such as mesylate or tosylate are preferred. The product is then reacted with a source of Te.sup.2- or Se.sup.2- ions, preferably an alkali metal telluride or selenide, to form the desired olefin. The process is particularly useful for generating 2',3'-unsaturation in the sugar moiety of nucleosides. Novel intermediate mesylate, tosylate and olefin derivatives of nucleosides are also provided.

  顺式邻二醇可使用碲化物或硒化物试剂转化为烯烃。将二醇反应以将羟基转化为亲核取代的良好离去基团。烷基和芳基磺酸酯基团，如甲磺酸酯或对甲苯磺酸酯，是首选的。然后，将产物与Te.sup.2-或Se.sup.2-离子源反应，最好是碱金属碲化物或硒化物，形成所需的烯烃。该过程特别适用于在核苷的糖基中生成2'，3'-不饱和度。还提供了新颖的核苷中间体甲磺酸酯、对甲苯磺酸酯和烯烃衍生物。
• Fluorinated sugar analogs of potential anti-HIV-1 nucleosides
  作者：Jai Tung Huang、Ling Ching Chen、Liben Wang、Moon Hwan Kim、James A. Warshaw、Donald Armstrong、Qing Yu Zhu、Ting Chao Chou、Kyoichi A. Watanabe

  DOI：10.1021/jm00109a017

  日期：1991.5

  3'-dideoxy-5-methyluridine (31), and 2'3'-dideoxy-2' -fluoro-5-methyluridine (37). These new nucleosides were screened for their activity against HIV and feline TLV in vitro. None of the compounds showed significant activity. It is interesting to note that such a small modification in the sugar moiety of active anti-HIV nucleosides (i.e., displacement of hydrogen by fluorine) almost completely inactivate the agents

  为了获得具有优于AZT，FLT或D4T的治疗指数的药物，合成了抗HIV-1核苷的几种类似物。这些包括2'，3'-dideoxy-2'，3'-difluoro-5-methyluridine（13），其阿拉伯糖类似物19，arab-5--5-甲基胞嘧啶类似物21、3'-脱氧2'，3'-二氢-2'-氟胸苷（25），3'-叠氮基2'，3'-二脱氧基2'-氟-5-甲基尿苷（29），2'-叠氮基3'-氟-2'，3'-双脱氧-5-甲基尿苷（31）和2'3'-二脱氧-2'-氟-5-甲基尿苷（37）。对这些新核苷在体外针对HIV和猫TLV的活性进行了筛选。没有一种化合物显示出明显的活性。有趣的是，活性抗HIV核苷的糖部分有这么小的修饰（即
• 3′-Bromo Analogues of Pyrimidine Nucleosides as a New Class of Potent Inhibitors of<i>Mycobacterium tuberculosis</i>
  作者：Neeraj Shakya、Naveen C. Srivastav、Nancy Desroches、Babita Agrawal、Dennis Y. Kunimoto、Rakesh Kumar

  DOI：10.1021/jm100165w

  日期：2010.5.27

  Tuberculosis (TB) is a major health problem worldwide. We herein report a new class of pyrimidine nucleosides as potent inhibitors of Mycobacterium tuberculosis (M. tuberculosis). Various 2'- or 3'-halogeno derivatives of pyrimidine nucleosides containing uracil, 5-fluorouracil, and thymine bases were synthesized and evaluated for antimycobacterial activities. Among the compounds tested, 3'-bromo-3'-deoxy-arabinofuranosylthymine (3') was the most effective antituberculosis agent in the in vitro assays against wild-type M. tuberculosis strain (H37Ra) (MIC50 = 1 mu g/mL) as well as drug-resistant (H37Rv) (rifampicin-resistant and isoniazid-resistant) strains of M. tuberculosis (MIC50 = 1-2 mu g/mL). Compound 3' also inhibited intracellular M. tuberculosis in a human monocytic cell line infected with H37Ra, demonstrating higher activity against intramacrophagic mycobacteria (80% reduction at 10 mu g/mL concentration) than extracellular mycobacteria (75% reduction at 10 mu g/mL concentration). In contrast, pyrimidine nucleosides possessing 5-fluorouracil base were weak inhibitors of M. tuberculosis. No cytotoxicity was found up to the highest concentration of compounds tested (CC50 > 100-200 mu g/mL) against a human cell line. Overall, these encouraging results substantiate the potential of this new class of compounds as promising antituberculosis agents.