4-formyl-2-methoxyphenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-formyl-2-methoxyphenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• 英文别名: 4-formyl-2-methoxyphenyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-beta-D-glucopyranoside；[(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-(4-formyl-2-methoxyphenoxy)oxan-2-yl]methyl acetate
• 化学式: C₂₂H₂₇NO₁₁
• 分子量: 481.456
• InChiKey: DWDIISAYNDWVDF-ZGJYDULXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-formyl-2-methoxyphenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 、 3,4-diamino-N-isopropylbenzamidine hydrochloride 在 对苯醌 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以80%的产率得到2-[4-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D‑glucopyranosyloxy)-3-methoxyphenyl]benzimidazole-5‑[N‑(isopropyl)carboxamidine] hydrochloride
  参考文献：
  名称：

  Synthesis and Antimicrobial Activity of Glycosylated 2-Aryl‑5‑amidinobenzimidazoles

  摘要：

  A series of new glycosylated 2-aryl-5-amidinobenzimidazoles derived from four different carbohydrates (D-glucose, D-galactose, N-acetyl-D-glucosamine and lactose) were synthesized by the condensation of the appropriate 4-formy1-3-methoxyphenyl glycoside with 4-amidino- or 4-N-isopropylamidino-ortho-phenylenediamine hydrochloride. All the compounds were properly characterized by high resolution mass spectrometry. uni- and bidimensional H-1 and C-13 nuclear magnetic resonance and then were evaluated for their antibacterial and antifungal potential. Considering the antifungal potential of them, two derivatives were active against Candida parapsilosis at 96.4 mu mol L-1 and another was active against this same strain at 83.5 mu mol L-1. In addition, one benzamidine showed activity against Candida glabrata at 97 mu mol L--(1). Considering the antibacterial potential of these compounds. six of them showed better activity against three different stains: three of them with IC50 of 96.4, 97 and 83.5 mu mol L-1 against Gram-positive Micrococcus luteus, the other two with IC50 96.5 and 96.4 mu mol L-1 against Gram-positive Enterococcus faecalis and one against Gram-negative Escherichia coli at 90.5 mu mol L-1. These findings suggest this structural pattern can be employed for design of more potent agents for discovery of new antimicrobial drug candidates.

  DOI：

  10.21577/0103-5053.20170227
• 作为产物：
  描述：

  香草醛 、 2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 15-冠醚-5 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 4.5h， 以86%的产率得到4-formyl-2-methoxyphenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  摘要：

  Glycosylation of various phenols with alpha -D-glucosaminyl chloride peracetate in a solid phase-liquid system catalyzed by crown compounds was studied. The highest yields of aryl beta -glycosides were observed at room temperature in acetonitrile using anhydrous potassium carbonate as a base. The optimum phenol-glycosyl donor-base-crown ether ratio was 1 : 1 : 1 : 0.2.

  DOI：

  10.1023/a:1012988719296

文献信息

• ——
  作者：V. O. Kur'yanov、T. A. Chupakhina、A. E. Zemlyakov、S. A. Kotlyar、G. L. Kamalov、V. Ya. Chirva

  DOI：10.1023/a:1012988719296

  日期：——

  Glycosylation of various phenols with alpha -D-glucosaminyl chloride peracetate in a solid phase-liquid system catalyzed by crown compounds was studied. The highest yields of aryl beta -glycosides were observed at room temperature in acetonitrile using anhydrous potassium carbonate as a base. The optimum phenol-glycosyl donor-base-crown ether ratio was 1 : 1 : 1 : 0.2.
• Synthesis and Antimicrobial Activity of Glycosylated 2-Aryl‑5‑amidinobenzimidazoles
  作者：Thiago de Souza、Josidel Oliver、Ana Paula Gomes、Cícero Flávio Aragão、Leandro Ferreira、Fernando Henrique Nogueira、Amanda Dias、Ricardo Alves

  DOI：10.21577/0103-5053.20170227

  日期：——

  A series of new glycosylated 2-aryl-5-amidinobenzimidazoles derived from four different carbohydrates (D-glucose, D-galactose, N-acetyl-D-glucosamine and lactose) were synthesized by the condensation of the appropriate 4-formy1-3-methoxyphenyl glycoside with 4-amidino- or 4-N-isopropylamidino-ortho-phenylenediamine hydrochloride. All the compounds were properly characterized by high resolution mass spectrometry. uni- and bidimensional H-1 and C-13 nuclear magnetic resonance and then were evaluated for their antibacterial and antifungal potential. Considering the antifungal potential of them, two derivatives were active against Candida parapsilosis at 96.4 mu mol L-1 and another was active against this same strain at 83.5 mu mol L-1. In addition, one benzamidine showed activity against Candida glabrata at 97 mu mol L--(1). Considering the antibacterial potential of these compounds. six of them showed better activity against three different stains: three of them with IC50 of 96.4, 97 and 83.5 mu mol L-1 against Gram-positive Micrococcus luteus, the other two with IC50 96.5 and 96.4 mu mol L-1 against Gram-positive Enterococcus faecalis and one against Gram-negative Escherichia coli at 90.5 mu mol L-1. These findings suggest this structural pattern can be employed for design of more potent agents for discovery of new antimicrobial drug candidates.