4-(2-benzyloxyphenylmethyl)-1,2-dihydro-5-methyl-3H-pyrazol-3-one | 1410807-08-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(2-benzyloxyphenylmethyl)-1,2-dihydro-5-methyl-3H-pyrazol-3-one
• CAS: 1410807-08-7
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: UJTFIPLOGHKRRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.88
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-(2-benzyloxyphenylmethyl)-1,2-dihydro-5-methyl-3H-pyrazol-3-one 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 苄基三丁基氯化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 以23%的产率得到4-(2-benzyloxyphenylmethyl)-5-methyl-1H-pyrazol-3-yl 2,3,4,6-tetra-O-acetyl-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
• 作为产物：
  描述：

  (2-benzyloxyphenyl)methyl mesylate 在 sodium hydride 、 一水合肼 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 反应 18.08h， 生成 4-(2-benzyloxyphenylmethyl)-1,2-dihydro-5-methyl-3H-pyrazol-3-one
  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