(2S,3R,4R,5R)-5-(azidomethyl)tetrahydrofuran-2,3,4-triyl triacetate | 78031-48-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5R)-5-(azidomethyl)tetrahydrofuran-2,3,4-triyl triacetate
• 英文别名: [(2R,3R,4R,5S)-4,5-diacetyloxy-2-(azidomethyl)oxolan-3-yl] acetate
• CAS: 78031-48-8
• 化学式: C₁₁H₁₅N₃O₇
• 分子量: 301.256
• InChiKey: ZAFHUFUBCYMYLP-GWOFURMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5R)-5-(azidomethyl)tetrahydrofuran-2,3,4-triyl triacetate 在 甲醇 、 sodium methylate 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 1-[(2R,4S,5R)-5-((2R,3R,4S,5R)-5-Azidomethyl-3,4-dihydroxy-tetrahydro-furan-2-yloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of analogues of the O-β-d-Ribofuranosyl nucleoside moiety of liposidomycins. Part 2: role of the hydroxyl groups upon the inhibition of MraY

  摘要：

  O-beta -D-Ribofuranosyl nucleoside I is the minimal structural entity of liposidomycins that maintains enzyme inhibitory activity on MraY. A set of compounds with hydroxyl patterns different from I has been synthesized. The presence of a hydroxyl group in the 3 " position is essential for the activity. The 3'-deoxy derivative (IV), however, shows a 5-fold improved potency. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00714-9
• 作为产物：
  描述：

  四乙酰核糖 在 咪唑 、 sodium azide 、 Candida rugosa lipase (Type VII) 、 碘 、 三苯基膦 作用下， 以 aq. phosphate buffer 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 35.0h， 生成 (2S,3R,4R,5R)-5-(azidomethyl)tetrahydrofuran-2,3,4-triyl triacetate
  参考文献：
  名称：

  用于追踪组蛋白核糖糖化中酮胺加合物的叠氮核糖探针

  摘要：

  反应性细胞代谢物可以修饰大分子并形成加合物，称为非酶共价修饰 (NECM)。由于所形成的加合物的性质复杂且常常不明确，剖析 NECM（例如糖化）的机制、调节和后果一直具有挑战性。直接追踪关键靶标修饰的形成以揭示其潜在的生理重要性需要特定的化学工具。在这里，我们介绍活性叠氮基修饰核糖类似物 5-叠氮核糖 (5-AR) 以及无活性对照衍生物 1-叠氮核糖 (1-AR) 的新型化学酶合成方法及其在理解蛋白质核糖糖化方面的应用体外和纤维素中。通过这些新探针，我们发现，与 MGO 糖化类似，核糖糖化特异性地积聚在组蛋白上。除了荧光标记之外，我们还展示了探针在富集修饰靶标方面的实用性，这些靶标是通过无标记定量蛋白质组学和高分辨率 MS/MS 工作流程进行识别的。最后，我们确定已知的癌蛋白和己糖脱糖酶、果糖胺 3-激酶 (FN3K) 能够识别并促进活细胞中 5-AR 糖基化加合物的去除，支持核糖糖基化的动态调节，并验证探针作为监测

  DOI：

  10.1021/jacs.0c01325

文献信息

• Uridine derivatives as antibiotics
  申请人：——

  公开号：US20030130227A1

  公开（公告）日：2003-07-10

  The invention concerns compounds of formula (I) wherein: R 2 is hydrogen, halogen, alkyl, alkenyl or alkynyl, a OH, O-alkyl, OCO-alkyl radical, an O-aryl or OCO-aryl radical; R 4 is CH 2 NH 2 ; CH 2 NHalkyl, CH 2 N(alkyl1)(alkyl2), CH 2 -guanidine, CH 2 -amidine optionally substituted; R 5 represents in particular (a) or (b) or (c) or (d), a CH 2 N 3 radical (e); R 8 is hydrogen or alkyl; R 9 is alkyl, aryl or heteroaryl, R 8 and R 9 capable of forming a heterocycle, or R 5 represents a CH 2 alkyl, CH 2 Oalkyl or CO 2 alkyl, CH 2 Salkyl radical; R 6 is hydrogen or halogen, OH, Oalkyl, OCOalkyl, S-alkyl or S-aryl; R 7 is hydrogen or OH. The compounds of formula (I) exhibit antibiotic properties.

  本发明涉及式（I）的化合物，其中：R2是氢、卤素、烷基、烯基或炔基、羟基、O-烷基、OCO-烷基基团、O-芳基或OCO-芳基基团；R4是CH2NH2；CH2NH烷基、CH2N（烷基1）（烷基2）、CH2-鸟氨酸、CH2-脒可选地取代；R5特别代表（a）或（b）或（c）或（d）、CH2N3基团（e）；R8是氢或烷基；R9是烷基、芳基或杂环芳基，R8和R9能够形成杂环，或R5代表CH2烷基、CH2O烷基或CO2烷基、CH2S烷基基团；R6是氢或卤素、羟基、O烷基、OCO烷基、S-烷基或S-芳基；R7是氢或羟基。式（I）的化合物具有抗生素特性。
• 5'-SUBSTITUTED-RIBOFURANOSYL BENZIMIDAZOLES AS ANTIVIRAL AGENTS
  申请人：——

  公开号：US20010011075A1

  公开（公告）日：2001-08-02

  The present invention relates to polysubstituted benzimidazoles, having the following formula: 1 wherein Q is a substituted benzimidazole group attached at the benzimidazole 1-position; R is a halogen of atomic number 9 to 53, inclusive (i.e., —F, —Cl, —Br, or —I); azido (i.e., —N 3 ); or —X—R 1 , wherein X is a chalcogen of atomic number 8 to 16, inclusive (i.e., —O— or —S—), and R 1 may be straight or branched chain alkyl of 1 to 8 carbon atoms; and R 2 and R 3 may be the same or different and are separately —O—C(═O)CH 3 (i.e., —OAc) or hydroxy (i.e., —OH); and pharmaceutically acceptable salts and operative combinations thereof. Also provided by this invention are compositions comprising a polysubstituted benzimidazole as defined above and methods of use thereof.

  本发明涉及具有下式的多取代苯并咪唑： 1 其中 Q 是连接在苯并咪唑 1 位上的取代苯并咪唑基团；R 是原子序数为 9 至 53（含）的卤素（即 -F、-Cl、-Br 或 -I）；叠氮（即 -N 3 ）；或 -X-R 1 其中 X 是原子序数为 8 至 16（包括 8 和 16）的缩醛（即 -O- 或 -S-），而 R 1 可以是 1 至 8 个碳原子的直链或支链烷基；以及 R 2 和 R 3 可以相同或不同，并分别为-O-C(═O)CH 3 (即-OAc)或羟基(即-OH)；以及药学上可接受的盐及其作用组合。本发明还提供了包含如上定义的多取代苯并咪唑的组合物及其使用方法。
• Glucose isomerase catalysed isomerisation reactions of (2R,3R)-configured aldofuranoses into the corresponding open-chain 2-ketoses
  作者：Michael Ebner、Arnold E. Stütz

  DOI：10.1016/s0008-6215(97)00206-1

  日期：1997.12

  Immobilised glucose isomerase (EC 5.3.1.5) accepted various (2R,3R)-configured aldofuranoses such as D-erythrose, as well as homologous C-5-modified D-ribose derivatives, as substrates. In the case of D-erythrose, quantitative conversion into D-glycero-tetrulose took place. D-Ribofuranoses were converted into the corresponding open-chain 2-ketoses in isolated yields of 65%. Surprisingly, L-erythrose also turned out to be a substrate of this enzyme. (C) 1998 Elsevier Science Ltd.
• Trimethylsilyl bromide as a mild, stereoselective anomeric brominating agent
  作者：John W Gillard、Mervyn Israel

  DOI：10.1016/s0040-4039(01)90142-x

  日期：——
• Synthesis and Antiviral Activity of Certain 5‘-Modified Analogs of 2,5,6-Trichloro-1-(β-<scp>d</scp>-ribofuranosyl)benzimidazole
  作者：Kristjan S. Gudmundsson、John C. Drach、Linda L. Wotring、Leroy B. Townsend

  DOI：10.1021/jm9604888

  日期：1997.2.1

  A series of 5'-modified 2,5,6-trichlorobenzimidazole ribonucleosides has been synthesized and tested for activity against two human herpesviruses and for cytotoxicity. The 5'-methoxy, 5'-ethoxy, and 5'-butoxy analogs of 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole (TCRB) were prepared by coupling the appropriate 5-O-alkyl-1,2,3-tri-O-acetyl-beta-D-ribose derivatives with 2,5,6-trichlorobenzimidazole followed by removal of the protecting groups. The 5'-deoxy-5'-fluoro, -5'-chloro, -5'-bromo, -5'-iodo, -5'-azido, and -5'-thiomethyl derivatives were synthesized in a similar fashion. All of these 5'-modified derivatives had significant activity against HCMV in plaque and yield reduction assays (IC50's = 0.5-14.2 mu M) but had little activity (IC50's > 100 mu M) against HSV-1. This pattern is similar to the antiviral activity profile observed for TCRB. The 5'-halogenated derivatives were more active than the other 5'-modified derivatives with antiviral activity well separated from cytotoxicity. In general, cytotoxicity of all the 5'-modified derivatives was greater in human foreskin fibroblasts (HFF cells) than in L1210 or K-B tumor cells. These results indicate that the viral target tolerates significant modifications of TCRB at the 5'-position without adversely affecting activity against HCMV, whereas the 5'-modifications increased cytotoxicity in human diploid cells.