2,3,5-tri-O-acetyl-α-D-arabinofuranosyl bromide | 55057-33-5

• 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: 2,3,5-tri-O-acetyl-α-D-arabinofuranosyl bromide
• 英文别名: 1-bromo-2,3,5-tri-O-acetyl-α-D-arabinofuranose
• CAS: 55057-33-5
• 化学式: C₁₁H₁₅BrO₇
• 分子量: 339.14
• InChiKey: WIDXXHUKKJXPEP-ZNSHCXBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.53
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-acetyl-α-D-arabinofuranosyl bromide 、 6-acetyl-3-amino-5-methyl-2-sulfanylidene-1H-thieno[2,3-d]pyrimidin-4-one 在 potassium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 24.0h， 以85%的产率得到3-amino-6-acetyl-5-methyl-2-(2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl-thio)-thieno[2,3-d]pyrimidin-4-one
  参考文献：
  名称：

  Synthesis, biological and medicinal significance of S-glycosido-thieno[2,3-d]-pyrimidines as new anti-inflammatory and analgesic agents

  摘要：

  Several 2-thioglycosides were prepared. Glycosylation of 2-thioxo-thieno[2,3-d]-pyrimidines 5a,b with 1-bromo-2,3,5-tri-O-acetyl-alpha-D-arabinofuranosyle 7, 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl and galacto-pyranosyl bromide 8a,b gave the protected beta-n-nuclosides 10a,b and 13a-d in high yields, which were transformed to deacetylated derivatives 14a,b and 15a-d. The structures of the compounds were elucidated by spectral and elemental analysis. Anti-inflammatory and Analgesic activities screening of the new compounds (at a dose of 100 mg/kg body weight) utilizing in vivo acute carrageenan-induced paw oedema standard method exhibited that the deacetylated derivatives 14a,b and 15a-d possess highly promising activities. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.056
• 作为产物：
  描述：

  D-arabinofuranose 、 乙酸酐 在 乙酰溴 作用下， 以 甲醇 为溶剂， 生成 2,3,5-tri-O-acetyl-α-D-arabinofuranosyl bromide
  参考文献：
  名称：

  新的齐墩果酸一氧化氮释放糖基衍生物的 合成及抗人肝癌活性†

  摘要：

  一系列 一氧化氮 （NO）释放 糖基的导数（2–14）齐墩果酸合成以改善母体化合物1的水溶性和细胞毒性。衍生物3对人肝细胞癌具有更好的溶解性和较强的细胞毒性（肝癌）体外。此外，3对小鼠的急性毒性较低，并显着抑制了小鼠的生长。肝癌体内肿瘤，表明3可能是治疗人类的有前途的候选药物肝癌。

  DOI：

  10.1039/b918846k

文献信息

• One-Pot Microwave Synthesis of Pyrimido[4,5-b]quinoline and its C- and S-Glycosides with Anti-Inflammatory and Anticancer Activities
  作者：Hend N. Hafez、Sami A. Al-Hussain、Abdel-Rhman B. A. El-Gazzar

  DOI：10.5562/cca2912

  日期：——

  An efficient one-pot synthesis of 2-thioxopyrimido[4,5-b]quinoline 3a,b has been accomplished from a three-component reaction of 6-aminothiouracil, cyclohexanone and aromatic aldehyde under microwave irradiation. Compound 3a,b was used as a key intermediate for the synthesis of Sand C-nucleoside analogs of types, 5-(4-fluorophenyl / 4-anisyl)-2-S-(-D-ribofuranosyl / arabinofuranosyl)-6,7,8,9-tetrahydro-3Hpyrimido[4

  由6-氨基硫氧嘧啶，环己酮和芳香醛在微波辐射下的三组分反应已完成2-硫氧嘧啶基[4,5-b]喹啉3a，b的有效一锅合成。化合物3a，b用作合成5-（4-氟苯基/ 4-茴香基）-2-S-（-D-呋喃呋喃糖基/阿拉伯呋喃呋喃糖基）-6型Sand C-核苷类似物的关键中间体， 7,8,9-四氢-3嘧啶基[4,5-b]喹啉-4-酮（6a–d）和5-（4-氟苯基/ 4-茴香基）-2-S-（-D-葡萄糖/ galactopyranosyl）-6,7,8,9-tetrahydro-3H-pyrimido [4,5b] quinolin-4-one（8a–d）。还。2-肼基化合物9a，b用于合成3-（糖基）-6-（4-取代的苯基）-7,8,9,10四氢[1,2,4]三唑[4'，3' ：1,2] pyrimido [4,5-b] quinoline-5-（1H）-one（11a–d和13a–d）。研究了
• Synthesis of substituted thieno[2,3-d]pyrimidine-2,4-dithiones and their S-glycoside analogues as potential antiviral and antibacterial agents
  作者：Hend N. Hafez、Hoda A.R. Hussein、Abdel-Rahman B.A. El-Gazzar

  DOI：10.1016/j.ejmech.2010.05.060

  日期：2010.9

  as potential anti-HIV-1 and antimicrobial agents. Also, from the literature, S-substituted pyrimidin-4-ones A and B exhibited interesting anti-HIV-1 activity. To further investigate the synthesis, tools and biological activities, we synthesized several new thienopyrimidine derivatives derived from thieno[2,3-d]-pyrimidine-2,4-dithione (3a,b) The compounds were designed to comprise the heterocyclic substituents

  以前，我们合成并评估了几种噻吩并嘧啶衍生物，它们含有通过2至4个原子的间隔基与C-2处的嘧啶-2-硫酮核连接的杂环取代基，作为潜在的抗HIV-1和抗菌剂。同样，从文献中，S-取代的嘧啶-4-酮A和B表现出令人感兴趣的抗HIV-1活性。为了进一步研究其合成，工具和生物学活性，我们合成了几种新的衍生自噻吩并[2,3- d ]-嘧啶-2,4-二硫酮（3a，b）这些化合物被设计为包含在C-2处直接连接至噻吩并嘧啶核的杂环取代基。此外，还制备了衍生自2-硫代噻吩并嘧啶的各种相关的三唑并[4，3- a ]苯并噻吩并[2，3- d ]嘧啶作为等排物。中合成的衍生物3 - 18，化合物3a中，图8A，图10A，13A和14A分别示出了在128毫克/毫升或更少完全抑制。
• <p>Novel purine thioglycoside analogs: synthesis, nanoformulation and biological evaluation in in vitro human liver and breast cancer models</p>
  作者：Mamdouh A. Abu-Zaied、Samah A Loutfy、Ashraf E. Hassan、Galal H Elgemeie

  DOI：10.2147/dddt.s201249

  日期：——

  Background: A series of novel pyrazolopyrimidine and pyrazololpyridine thioglycosides were synthesized and confirmed via their spectral analyses.Purpose: To evaluate the effect of these anti-metabolic compounds against proliferation of Huh-7 and Mcf-7 as in vitro models of human liver and breast cancers, respectively. Vero cells were used as an example of normal green monkey kidney cells.Methods: The most promising compound was subjected to a nanoformulation by its encapsulation into chitosan nanoparticles to increase its anti-cancerous activity. Nanoformulation was confirmed by TEM and FT-IR to ensure encapsulation and screened for their cytotoxicity against Huh-7 and Mcf-7 cells using MTT colorimetric assay and morphological examination. Genotoxic effect was performed by cellular DNA fragmentation assay. Simulated CompuSyn software (linear interaction effect) was conducted to predict the possible synergistic effect of nanocomposite as anticancerous activity. Apoptotic effect was further analyzed by detection of apoptotic proteins using ELISA assay.Results: The nano preparation was successfully prepared by encapsulation of compound 14 into chitosan nanoparticles, controlled to a size at 105 nm and zeta charges at 40.2 mV. Treatment of Huh-7 and Mcf-7 showed that compound 14 was the most cytotoxic compound on both cancer cell lines where IC50 was 24.59 (9.836 mu g/mL) and 12.203 (4.8812 mu g/mL) on Huh-7 and Mcf-7 respectively. But IC50 of the nano preparation was 37.19 and 30.68 mu g/mL on Huh-7 and Mcf-7, respectively, indicating its aggressiveness on human breast cancer cells as confirmed by DNA fragmentation assay and theoretically by CompuSyn tool.Conclusion: A novel series of pyrazolopyrimidine thioglycosides and pyrazolopyridine thioglycosides were synthesized. Nanoformulation of compound 14 into chitosan nanoparticles demonstrated anticancer activity and can be used as a drug delivery system, but further studies are still required.