5-(6-methoxynaphthalen-2-yl)-1-(3-methoxyphenyl)-1-(5-methylisoxazol-3-ylamino)pentan-3-one | 1365842-66-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(6-methoxynaphthalen-2-yl)-1-(3-methoxyphenyl)-1-(5-methylisoxazol-3-ylamino)pentan-3-one
• 英文别名: 5-(6-Methoxynaphthalen-2-yl)-1-(3-methoxyphenyl)-1-[(5-methyl-1,2-oxazol-3-yl)amino]pentan-3-one
• CAS: 1365842-66-5
• 化学式: C₂₇H₂₈N₂O₄
• 分子量: 444.53
• InChiKey: FBEGFEZFIQFIRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  73.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-甲氧基苯甲醛 在 盐酸 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 生成 5-(6-methoxynaphthalen-2-yl)-1-(3-methoxyphenyl)-1-(5-methylisoxazol-3-ylamino)pentan-3-one
  参考文献：
  名称：

  Synthesis and antidiabetic performance of β-amino ketone containing nabumetone moiety

  摘要：

  We wish to report the further design and improved synthesis that resulted in two series of target molecules, TM-1 and TM-2, with remarkably simplified structures containing beta-amino ketone of discrete nabumetone moiety. These were obtained via a 'one-pot, two-step, three-component' protocol of Mannich reaction with yield up to 97%. A total of 28 out of 31 new compounds were characterized using H-1 NMR, C-13 NMR, ESI MS and HRMS techniques. Studies on their antidiabetic activities, screened in vitro at 10 mu g mL (1) level, indicate that TM-2 possesses peroxisome proliferator-activated receptor activation and alpha-glucosidase inhibition activity significantly stronger than that of TM-1, and also that of the series B compounds that were previously synthesized by the group. Analysis of the structure-activity relationship points to the sulfanilamide unit as the most probable potent group of b-amino ketone and, on the basis of which, a tangible strategy is presented for the development of new antidiabetic drugs. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.028

文献信息

• Synthesis and antidiabetic performance of β-amino ketone containing nabumetone moiety
  作者：Hang Wang、Ju-fang Yan、Xiao-li Song、Li Fan、Jin Xu、Guang-ming Zhou、Li Jiang、Da-cheng Yang

  DOI：10.1016/j.bmc.2012.01.028

  日期：2012.3

  We wish to report the further design and improved synthesis that resulted in two series of target molecules, TM-1 and TM-2, with remarkably simplified structures containing beta-amino ketone of discrete nabumetone moiety. These were obtained via a 'one-pot, two-step, three-component' protocol of Mannich reaction with yield up to 97%. A total of 28 out of 31 new compounds were characterized using H-1 NMR, C-13 NMR, ESI MS and HRMS techniques. Studies on their antidiabetic activities, screened in vitro at 10 mu g mL (1) level, indicate that TM-2 possesses peroxisome proliferator-activated receptor activation and alpha-glucosidase inhibition activity significantly stronger than that of TM-1, and also that of the series B compounds that were previously synthesized by the group. Analysis of the structure-activity relationship points to the sulfanilamide unit as the most probable potent group of b-amino ketone and, on the basis of which, a tangible strategy is presented for the development of new antidiabetic drugs. (C) 2012 Elsevier Ltd. All rights reserved.