1-benzyl-5-methyl-1H-[1,2,3]triazole-4-carboxylic acid 3-(1,2:5,6-di-O-isopropylidene)-α-D-allofuranose ester | 1119518-72-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-benzyl-5-methyl-1H-[1,2,3]triazole-4-carboxylic acid 3-(1,2:5,6-di-O-isopropylidene)-α-D-allofuranose ester
• 英文别名: [(3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] 1-benzyl-5-methyltriazole-4-carboxylate
• CAS: 1119518-72-7
• 化学式: C₂₃H₂₉N₃O₇
• 分子量: 459.499
• InChiKey: XCMWMLFQJMACCH-POVPESKVSA-N

物化性质

• 熔点：
  97-98 °C
• 沸点：
  579.3±60.0 °C(predicted)
• 密度：
  1.42±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  1-benzyl-5-methyl-1H-[1,2,3]triazole-4-carboxylic acid 3-(1,2:5,6-di-O-isopropylidene)-α-D-allofuranose ester 在 水 、 三氟乙酸 作用下， 反应 48.0h， 生成 1-benzyl-5-methyl-1H-[1,2,3]triazole-4-carboxylic acid 3-D-allopyranose ester
  参考文献：
  名称：

  Synthesis, HIV-RT inhibitory activity and SAR of 1-benzyl-1H-1,2,3-triazole derivatives of carbohydrates

  摘要：

  This paper describes the synthesis of several 1-benzyl-1H-1,2,3-triazoles attached to different carbohydrate templates and their in vitro inhibitory profile against HIV-1 reverse transcriptase. In addition a theoretical comparison of the most active compounds with other classical antivirals was also performed. Our results showed 2a, 2d and 2g as the most active compounds that inhibited the HIV-1 reverse transcriptase catalytic activity with cytotoxicity lower than AZT and SI higher than DDC and DDI. The overall theoretical analysis of the molecular descriptors of 2a, 2d and 2g revealed that their HOMO energy is similar to other antivirals in use (AZT, DDC, DDI and 3TC) and together with the volume may contribute for the biological profile as they may allow new interactions with the target. In fact the 1,2,3-triazole compounds presented more lipophilicity and higher molecular volume and weight than the antivirals studied, which suggested that these features might not only contribute for new interactions with the HIV-RT but also influence the specificity and consequently the low cytoxicity profile of these compounds. Thus these data point them as promising leading compounds for generating new anti-HIV-RT compounds. (C) 2008 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2008.02.047
• 作为产物：
  描述：

  3-(benzylamino)but-2-enoic acid 3-(1,2:5,6-di-O-isopropylidene)-α-D-allofuranose ester 、 甲烷磺酰基叠氮化物 在 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以50%的产率得到1-benzyl-5-methyl-1H-[1,2,3]triazole-4-carboxylic acid 3-(1,2:5,6-di-O-isopropylidene)-α-D-allofuranose ester
  参考文献：
  名称：

  Synthesis, HIV-RT inhibitory activity and SAR of 1-benzyl-1H-1,2,3-triazole derivatives of carbohydrates

  摘要：

  This paper describes the synthesis of several 1-benzyl-1H-1,2,3-triazoles attached to different carbohydrate templates and their in vitro inhibitory profile against HIV-1 reverse transcriptase. In addition a theoretical comparison of the most active compounds with other classical antivirals was also performed. Our results showed 2a, 2d and 2g as the most active compounds that inhibited the HIV-1 reverse transcriptase catalytic activity with cytotoxicity lower than AZT and SI higher than DDC and DDI. The overall theoretical analysis of the molecular descriptors of 2a, 2d and 2g revealed that their HOMO energy is similar to other antivirals in use (AZT, DDC, DDI and 3TC) and together with the volume may contribute for the biological profile as they may allow new interactions with the target. In fact the 1,2,3-triazole compounds presented more lipophilicity and higher molecular volume and weight than the antivirals studied, which suggested that these features might not only contribute for new interactions with the HIV-RT but also influence the specificity and consequently the low cytoxicity profile of these compounds. Thus these data point them as promising leading compounds for generating new anti-HIV-RT compounds. (C) 2008 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2008.02.047

文献信息

• Synthesis, HIV-RT inhibitory activity and SAR of 1-benzyl-1H-1,2,3-triazole derivatives of carbohydrates
  作者：Fernando de C. da Silva、Maria Cecilia B.V. de Souza、Izabel I.P. Frugulhetti、Helena C. Castro、Silmara L. de O. Souza、Thiago Moreno L. de Souza、Diego Q. Rodrigues、Alessandra M.T. Souza、Paula A. Abreu、Fabiana Passamani

  DOI：10.1016/j.ejmech.2008.02.047

  日期：2009.1

  This paper describes the synthesis of several 1-benzyl-1H-1,2,3-triazoles attached to different carbohydrate templates and their in vitro inhibitory profile against HIV-1 reverse transcriptase. In addition a theoretical comparison of the most active compounds with other classical antivirals was also performed. Our results showed 2a, 2d and 2g as the most active compounds that inhibited the HIV-1 reverse transcriptase catalytic activity with cytotoxicity lower than AZT and SI higher than DDC and DDI. The overall theoretical analysis of the molecular descriptors of 2a, 2d and 2g revealed that their HOMO energy is similar to other antivirals in use (AZT, DDC, DDI and 3TC) and together with the volume may contribute for the biological profile as they may allow new interactions with the target. In fact the 1,2,3-triazole compounds presented more lipophilicity and higher molecular volume and weight than the antivirals studied, which suggested that these features might not only contribute for new interactions with the HIV-RT but also influence the specificity and consequently the low cytoxicity profile of these compounds. Thus these data point them as promising leading compounds for generating new anti-HIV-RT compounds. (C) 2008 Published by Elsevier Masson SAS.