4-(4-hydroxyphenylmethyl)-5-isopropyl-1H-pyrazol-3-yl β-d-glucopyranoside | 1410808-04-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(4-hydroxyphenylmethyl)-5-isopropyl-1H-pyrazol-3-yl β-d-glucopyranoside
• 英文别名: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[4-[(4-hydroxyphenyl)methyl]-5-propan-2-yl-1H-pyrazol-3-yl]oxy]oxane-3,4,5-triol
• CAS: 1410808-04-6
• 化学式: C₁₉H₂₆N₂O₇
• 分子量: 394.425
• InChiKey: LZNSCJBZAOZHJT-YRHQEJDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  148
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-(4-benzyloxyphenylmethyl)-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one 在 甲醇 、 palladium 10% on activated carbon 、 氢气 、 sodium methylate 、 苄基三丁基氯化铵 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 21.0h， 生成 4-(4-hydroxyphenylmethyl)-5-isopropyl-1H-pyrazol-3-yl β-d-glucopyranoside
  参考文献：
  名称：

  Structure–activity relationship studies of 4-benzyl-1H-pyrazol-3-yl β-d-glucopyranoside derivatives as potent and selective sodium glucose co-transporter 1 (SGLT1) inhibitors with therapeutic activity on postprandial hyperglycemia

  摘要：

  Sodium glucose co-transporter 1 (SGLT1) plays a dominant role in the absorption of glucose in the gut and is considered a promising target in the development of treatments for postprandial hyperglycemia. A series of 4-benzyl-1H-pyrazol-3-yl beta-D-glucopyranoside derivatives have been synthesized, and its inhibitory activity toward SGLTs has been evaluated. By altering the substitution groups at the 5-position of the pyrazole ring, and every position of the phenyl ring, we studied the structure-activity relationship (SAR) profiles and identified a series of potent and selective SGLT1 inhibitors. Representative derivatives showed a dose-dependent suppressing effect on the escalation of blood glucose levels in oral mixed carbohydrate tolerance tests (OCTT) in streptozotocin-nicotinamide-induced diabetic rats (NA-STZ rats). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.037

文献信息

• Structure–activity relationship studies of 4-benzyl-1H-pyrazol-3-yl β-d-glucopyranoside derivatives as potent and selective sodium glucose co-transporter 1 (SGLT1) inhibitors with therapeutic activity on postprandial hyperglycemia
  作者：Nobuhiko Fushimi、Hideki Fujikura、Hiroaki Shiohara、Hirotaka Teranishi、Kazuo Shimizu、Shigeru Yonekubo、Kohsuke Ohno、Takashi Miyagi、Fumiaki Itoh、Toshihide Shibazaki、Masaki Tomae、Yukiko Ishikawa-Takemura、Takeshi Nakabayashi、Noboru Kamada、Tomonaga Ozawa、Susumu Kobayashi、Masayuki Isaji

  DOI：10.1016/j.bmc.2012.09.037

  日期：2012.11

  Sodium glucose co-transporter 1 (SGLT1) plays a dominant role in the absorption of glucose in the gut and is considered a promising target in the development of treatments for postprandial hyperglycemia. A series of 4-benzyl-1H-pyrazol-3-yl beta-D-glucopyranoside derivatives have been synthesized, and its inhibitory activity toward SGLTs has been evaluated. By altering the substitution groups at the 5-position of the pyrazole ring, and every position of the phenyl ring, we studied the structure-activity relationship (SAR) profiles and identified a series of potent and selective SGLT1 inhibitors. Representative derivatives showed a dose-dependent suppressing effect on the escalation of blood glucose levels in oral mixed carbohydrate tolerance tests (OCTT) in streptozotocin-nicotinamide-induced diabetic rats (NA-STZ rats). (C) 2012 Elsevier Ltd. All rights reserved.