N-(4-(3-((3R,4R)-3,4-dihydroxypyrrolidin-1-yl)-3-oxopropyl)phenyl)-4-(trifluoromethyl)benzenesulfonamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-(3-((3R,4R)-3,4-dihydroxypyrrolidin-1-yl)-3-oxopropyl)phenyl)-4-(trifluoromethyl)benzenesulfonamide
• 英文别名: N-[4-[3-[(3R,4R)-3,4-dihydroxypyrrolidin-1-yl]-3-oxopropyl]phenyl]-4-(trifluoromethyl)benzenesulfonamide
• 化学式: C₂₀H₂₁F₃N₂O₅S
• 分子量: 458.458
• InChiKey: CZIIUBMPMGURTA-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  tert-butyl 4-(3-((3R,4R)-3,4-dihydroxypyrrolidin-1-yl)-3-oxopropyl)phenylcarbamate 在 吡啶 、 盐酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 20.08h， 生成 N-(4-(3-((3R,4R)-3,4-dihydroxypyrrolidin-1-yl)-3-oxopropyl)phenyl)-4-(trifluoromethyl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis and α-glucosidase inhibition activity of dihydroxy pyrrolidines

  摘要：

  A new series of Deacetylsarmentamide A and B derivatives, amides and sulfonamides of 3,4-dihydroxypyrrolidines as alpha-glucosidase inhibitors were designed and synthesized. The biological screening test against alpha-glucosidase showed that some of these compounds have the positive inhibitory activity against alpha-glucosidase. Saturated aliphatic amides were more potent than the olefinic amides. Among all the compounds, 5o/6o having polar -NH2 group, 10f/11f having polar -OH group on phenyl ring displayed 3-4-fold more potent than the standard drugs. Acarbose, Voglibose and Miglitol were used as standard references. The promising compounds 6i, 5o, 6o, 10a, 11a, 10f and 11f have been identified. Molecular docking simulations were done for compounds to identify important binding modes responsible for inhibition activity of alpha-glucosidase. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.04.078

文献信息

• Synthesis and α-glucosidase inhibition activity of dihydroxy pyrrolidines
  作者：Sivaprasad Kasturi、Sujatha Surarapu、Srinivas Uppalanchi、Jaya Shree Anireddy、Shubham Dwivedi、Hasitha Shilpa Anantaraju、Yogeeswari Perumal、Dilep Kumar Sigalapalli、Bathini Nagendra Babu、Krishna S. Ethiraj

  DOI：10.1016/j.bmcl.2017.04.078

  日期：2017.6

  A new series of Deacetylsarmentamide A and B derivatives, amides and sulfonamides of 3,4-dihydroxypyrrolidines as alpha-glucosidase inhibitors were designed and synthesized. The biological screening test against alpha-glucosidase showed that some of these compounds have the positive inhibitory activity against alpha-glucosidase. Saturated aliphatic amides were more potent than the olefinic amides. Among all the compounds, 5o/6o having polar -NH2 group, 10f/11f having polar -OH group on phenyl ring displayed 3-4-fold more potent than the standard drugs. Acarbose, Voglibose and Miglitol were used as standard references. The promising compounds 6i, 5o, 6o, 10a, 11a, 10f and 11f have been identified. Molecular docking simulations were done for compounds to identify important binding modes responsible for inhibition activity of alpha-glucosidase. (C) 2017 Elsevier Ltd. All rights reserved.