[(3S,4S)-4-acetyloxypyrrolidin-1-ium-3-yl] acetate;2,2,2-trifluoroacetate | 1428671-14-0

• 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: [(3S,4S)-4-acetyloxypyrrolidin-1-ium-3-yl] acetate;2,2,2-trifluoroacetate
• CAS: 1428671-14-0
• 化学式: C₂HF₃O₂*C₈H₁₃NO₄
• 分子量: 301.219
• InChiKey: BRAWOMUZNZGMJW-WSZWBAFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.09
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (3S,4S)-1-(tert-butoxycarbonyl)-3,4-pyrrolidinediyl diacetate 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 1.5h， 以98%的产率得到[(3S,4S)-4-acetyloxypyrrolidin-1-ium-3-yl] acetate;2,2,2-trifluoroacetate
  参考文献：
  名称：

  Five-membered iminocyclitol α-glucosidase inhibitors: Synthetic, biological screening and in silico studies

  摘要：

  The design and synthesis of a small library of pyrrolidine iminocyclitol inhibitors with a structural similarity to 1,4-dideoxy-1,4-imino-D-arabitol (DAB-1) is reported. This library was specifically designed to gain a better insight into the mechanism of inhibition of glycosidases by polyhydroxylated pyrrolidines or iminocyclitols. Pyrrolidine-3,4-diol 15a and pyrrolidine-3,4-diol diacetate 15b had emerged as the most potent alpha-glucosidase inhibitors in the series. Docking studies performed with an homology model of alpha-glucosidase disclosed binding poses for compounds 15a, 15b, 16a, and 16a' occupying the same region as the NH group of the terminal ring of acarbose and suggest a closer and stronger binding of compound 15a and 15b with the enzyme active site residues. Our studies indicate that 2 or 5-hydroxyl substituents appear to be vital for high inhibitory activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.030

文献信息

• Five-membered iminocyclitol α-glucosidase inhibitors: Synthetic, biological screening and in silico studies
  作者：Luis R. Guerreiro、Elisabete P. Carreiro、Luis Fernandes、Teresa A.F. Cardote、Rui Moreira、Ana T. Caldeira、Rita C. Guedes、A.J. Burke

  DOI：10.1016/j.bmc.2013.01.030

  日期：2013.4

  The design and synthesis of a small library of pyrrolidine iminocyclitol inhibitors with a structural similarity to 1,4-dideoxy-1,4-imino-D-arabitol (DAB-1) is reported. This library was specifically designed to gain a better insight into the mechanism of inhibition of glycosidases by polyhydroxylated pyrrolidines or iminocyclitols. Pyrrolidine-3,4-diol 15a and pyrrolidine-3,4-diol diacetate 15b had emerged as the most potent alpha-glucosidase inhibitors in the series. Docking studies performed with an homology model of alpha-glucosidase disclosed binding poses for compounds 15a, 15b, 16a, and 16a' occupying the same region as the NH group of the terminal ring of acarbose and suggest a closer and stronger binding of compound 15a and 15b with the enzyme active site residues. Our studies indicate that 2 or 5-hydroxyl substituents appear to be vital for high inhibitory activity. (C) 2013 Elsevier Ltd. All rights reserved.