1-[2'-hydroxy-4'-(2''',3''',4''',6'''-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl]-3-(2''-chloro phenyl)-propane-1,3-dione | 1294456-81-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: 1-[2'-hydroxy-4'-(2''',3''',4''',6'''-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl]-3-(2''-chloro phenyl)-propane-1,3-dione
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[4-[3-(2-chlorophenyl)-3-oxopropanoyl]-3-hydroxyphenoxy]oxan-2-yl]methyl acetate
• CAS: 1294456-81-7
• 化学式: C₂₉H₂₉ClO₁₃
• 分子量: 620.994
• InChiKey: GXWZFYAGVJUNFO-XYPQWYOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  178
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  1-[2'-hydroxy-4'-(2''',3''',4''',6'''-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl]-3-(2''-chloro phenyl)-propane-1,3-dione 在 甲醇 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以73%的产率得到1-(4'-β-D-glucopyranosyloxy-2'-hydroxyphenyl)-3-(2''-chlorophenyl)-propane-1,3-dione
  参考文献：
  名称：

  Synthesis, biopharmaceutical characterization, antimicrobial and antioxidant activities of 1-(4′-O-β-d-glucopyranosyloxy-2′-hydroxyphenyl)-3-aryl-propane-1,3-diones

  摘要：

  This research communication is toward the investigation of the antibacterial, antifungal and antioxidant activities of the synthesized compounds 1-(4'-O-beta-D-glucopyranosyloxy-2'-hydroxyphenyl)-3-aryl-propane-1,3-diones (5a)-(5h). These compounds have been obtained by the interaction of alpha-acetobromoglucose with 1-(2',4'-dihydroxyphenyl)-3-aryl-propane-1,3-diones (3a)-(3h) under anhydrous condition and at lower temperature. The structures of these newly synthesized O-beta-D-glucopyranosides were established on the basis of chemical, elemental, and spectral analyses. Further, the compounds (5b), (5c), (5d) and (5g) showed potent antibacterial and antifungal activity. A good correlation was obtained between the theoretical predictions of bioavailability using Lipinski's rule-of-five and experimental verification. (c) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.068
• 作为产物：
  描述：

  1-(2',4'-dihydroxyphenyl)-3-(2''-chlorophenyl)-propane-1,3-dione 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以70%的产率得到1-[2'-hydroxy-4'-(2''',3''',4''',6'''-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl]-3-(2''-chloro phenyl)-propane-1,3-dione
  参考文献：
  名称：

  Synthesis, biopharmaceutical characterization, antimicrobial and antioxidant activities of 1-(4′-O-β-d-glucopyranosyloxy-2′-hydroxyphenyl)-3-aryl-propane-1,3-diones

  摘要：

  This research communication is toward the investigation of the antibacterial, antifungal and antioxidant activities of the synthesized compounds 1-(4'-O-beta-D-glucopyranosyloxy-2'-hydroxyphenyl)-3-aryl-propane-1,3-diones (5a)-(5h). These compounds have been obtained by the interaction of alpha-acetobromoglucose with 1-(2',4'-dihydroxyphenyl)-3-aryl-propane-1,3-diones (3a)-(3h) under anhydrous condition and at lower temperature. The structures of these newly synthesized O-beta-D-glucopyranosides were established on the basis of chemical, elemental, and spectral analyses. Further, the compounds (5b), (5c), (5d) and (5g) showed potent antibacterial and antifungal activity. A good correlation was obtained between the theoretical predictions of bioavailability using Lipinski's rule-of-five and experimental verification. (c) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.068