3,4-dibenzyloxy-5-(2-hydroxyethylidene)-2(5H)-furanone | 136767-82-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 3,4-dibenzyloxy-5-(2-hydroxyethylidene)-2(5H)-furanone
• 英文别名: 2,3-di-O-benzyl-4,5-didehydro-L-ascorbic acid；3,4-Bis(benzyloxy)-5-(2-hydroxyethylidene)furan-2(5H)-one；5-(2-hydroxyethylidene)-3,4-bis(phenylmethoxy)furan-2-one
• CAS: 136767-82-3
• 化学式: C₂₀H₁₈O₅
• 分子量: 338.36
• InChiKey: WOIRSMPSDUXFPK-UHFFFAOYSA-N

物化性质

• 沸点：
  620.5±55.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-dibenzyloxy-5-(2-hydroxyethylidene)-2(5H)-furanone 在 ammonium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 25.0h， 生成 3,4-di-O-benzyl-5-hydroxy-5-(2-(3H-pyrrolo[3,2-d]pyrimidine-4(5H)-one-1-yl)ethyl)-1H-pyrrolo-2(5H)-one
  参考文献：
  名称：

  Novel halogenated 3-deazapurine, 7-deazapurine and alkylated 9-deazapurine derivatives of l-ascorbic or imino-l-ascorbic acid: Synthesis, antitumour and antiviral activity evaluations

  摘要：

  Keeping the potential synergy of biological activity of synthetic anomalous derivatives of deazapurines and L-ascorbic acid (L-AA) in mind, we have synthesized new 3-, 7- and 9-deazapurine derivatives of L-ascorbic (1-4, 8-10, 13-15) and imino-L-ascorbic acid (5-7, 11, 12, 16-19). These novel compounds were evaluated for their cytostatic and antiviral activity in vitro against a panel of human malignant tumour cell lines and normal murine fibroblasts (3T3). Among all evaluated compounds, the 9-deazapurine derivative of L-AA (13) exerted the most potent inhibitory activity on the growth of CEM/0 cells (IC50 = 4.1 +/- 1.8 mu M) and strong antiproliferative effect against L1210/0 (IC50 = 4.7 +/- 0.1 mu M) while the 9-deazahypoxanthine derivative of L-AA (15) showed the best effect against HeLa cells (IC50 = 5.6 +/- 1.3 mu M) and prominent effect on L1210/0 (IC50 = 4.5 +/- 0.5 mu M). Furthermore, the 9-deazapurine derivative disubstituted with two imino-L-AA moieties (18) showed the best activity against L1210/0 tumour cells (IC50 = 4.4 +/- 0.3 mu M) and the most pronounced antiproliferative effects against MiaPaCa-2 cells (IC50 = 5.7 +/- 0.2 mu M). All these compounds showed selective cytostatic effect on tumour cell lines in comparison with embryonal murine fibroblasts (3T3). When evaluating their antiviral activity, the 3-deazapurine derivative of L-AA (3) exhibited the highest activity against both laboratory-adapted strains of human cytomegalovirus (HCMV) (AD-169 and Davis) with EC50 values comparable to those of the well-known anti-HCMV drug ganciclovir and without cytotoxic effects on normal human embryonal lung (HEL) cells. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.08.008
• 作为产物：
  描述：

  D-异抗坏血酸 在 三异丁基铝 、 potassium carbonate 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 195.0h， 生成 3,4-dibenzyloxy-5-(2-hydroxyethylidene)-2(5H)-furanone
  参考文献：
  名称：

  有机铝烷介导的抗坏血酸和异抗坏血酸衍生物的异构化

  摘要：

  当用三异丁基铝处理时，l-抗坏血酸2a和d-异抗坏血酸2b的衍生物部分发生差向异构化，生成l-异抗坏血酸ent - 2b，ent -10b或d-抗坏血酸ent - 2a ，ent -11a分别。保护基的完全除去是通过对亚甲基缩醛ent -10和ent- 11a进行氢解来实现的。该反应导致d抗坏血酸ENT -1a或1-异抗坏血酸ENT分别-1b。此外，四种丙酮化物2被臭氧分解，酯交换，最后催化氢化转化为苏糖醛和赤藓酸缩酮9。

  DOI：

  10.1016/0957-4166(96)00427-2

文献信息

• Cyclic polyethers derived from 5,6- O -isopropylidene- l -ascorbic acid
  作者：Alan H. Haines、Dina Katrania

  DOI：10.1016/0008-6215(92)84188-x

  日期：1992.9
• Novel halogenated 3-deazapurine, 7-deazapurine and alkylated 9-deazapurine derivatives of l-ascorbic or imino-l-ascorbic acid: Synthesis, antitumour and antiviral activity evaluations
  作者：Maja Stipković Babić、Damjan Makuc、Janez Plavec、Tamara Martinović、Sandra Kraljević Pavelić、Krešimir Pavelić、Robert Snoeck、Graciela Andrei、Dominique Schols、Karlo Wittine、Mladen Mintas

  DOI：10.1016/j.ejmech.2015.08.008

  日期：2015.9

  Keeping the potential synergy of biological activity of synthetic anomalous derivatives of deazapurines and L-ascorbic acid (L-AA) in mind, we have synthesized new 3-, 7- and 9-deazapurine derivatives of L-ascorbic (1-4, 8-10, 13-15) and imino-L-ascorbic acid (5-7, 11, 12, 16-19). These novel compounds were evaluated for their cytostatic and antiviral activity in vitro against a panel of human malignant tumour cell lines and normal murine fibroblasts (3T3). Among all evaluated compounds, the 9-deazapurine derivative of L-AA (13) exerted the most potent inhibitory activity on the growth of CEM/0 cells (IC50 = 4.1 +/- 1.8 mu M) and strong antiproliferative effect against L1210/0 (IC50 = 4.7 +/- 0.1 mu M) while the 9-deazahypoxanthine derivative of L-AA (15) showed the best effect against HeLa cells (IC50 = 5.6 +/- 1.3 mu M) and prominent effect on L1210/0 (IC50 = 4.5 +/- 0.5 mu M). Furthermore, the 9-deazapurine derivative disubstituted with two imino-L-AA moieties (18) showed the best activity against L1210/0 tumour cells (IC50 = 4.4 +/- 0.3 mu M) and the most pronounced antiproliferative effects against MiaPaCa-2 cells (IC50 = 5.7 +/- 0.2 mu M). All these compounds showed selective cytostatic effect on tumour cell lines in comparison with embryonal murine fibroblasts (3T3). When evaluating their antiviral activity, the 3-deazapurine derivative of L-AA (3) exhibited the highest activity against both laboratory-adapted strains of human cytomegalovirus (HCMV) (AD-169 and Davis) with EC50 values comparable to those of the well-known anti-HCMV drug ganciclovir and without cytotoxic effects on normal human embryonal lung (HEL) cells. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Organoalane-mediated isomerization of ascorbic and isoascorbic acid derivatives
  作者：Josef Schachtner、Hans-Dietrich Stachel

  DOI：10.1016/0957-4166(96)00427-2

  日期：1996.11

  removal of the protecting groups is effected by hydrogenolysis of the benzylidene acetals ent-10 and ent-11a. This reaction leads to d-ascorbic acid ent-1a or l-isoascorbic acid ent-1b, respectively. Furthermore, the four acetonides 2 were converted by ozonolysis, transesterification and finally catalytic hydrogenation to the threonic and erythronic acid ketals 9.

  当用三异丁基铝处理时，l-抗坏血酸2a和d-异抗坏血酸2b的衍生物部分发生差向异构化，生成l-异抗坏血酸ent - 2b，ent -10b或d-抗坏血酸ent - 2a ，ent -11a分别。保护基的完全除去是通过对亚甲基缩醛ent -10和ent- 11a进行氢解来实现的。该反应导致d抗坏血酸ENT -1a或1-异抗坏血酸ENT分别-1b。此外，四种丙酮化物2被臭氧分解，酯交换，最后催化氢化转化为苏糖醛和赤藓酸缩酮9。