N-((5-bromo-1H-indol-3-yl)methyl)(3-(4-methoxyphenyl)isoxazol-5-yl)methanamine hydrochloride

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-((5-bromo-1H-indol-3-yl)methyl)(3-(4-methoxyphenyl)isoxazol-5-yl)methanamine hydrochloride
• 英文别名: N-[(5-bromo-1H-indol-3-yl)methyl]-1-[3-(4-methoxyphenyl)-1,2-oxazol-5-yl]methanamine;hydrochloride
• 化学式: C₂₀H₁₈BrN₃O₂*ClH
• 分子量: 448.747
• InChiKey: RYVRAXFWWWMZFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  63.1
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对甲氧基苯甲醛肟 在 sodium azide 、 chloroamine-T 、 溶剂黄146 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 N-((5-bromo-1H-indol-3-yl)methyl)(3-(4-methoxyphenyl)isoxazol-5-yl)methanamine hydrochloride
  参考文献：
  名称：

  Synthesis of new secretory phospholipase A2-inhibitory indole containing isoxazole derivatives as anti-inflammatory and anticancer agents

  摘要：

  Secretory phospholipase A(2) (sPLA(2)) is an important enzyme that plays a key role in various inflammatory diseases including cancer and its inhibitors have been developed as preventive or therapeutic agents. In the present study, a series of new indole containing isoxazole derivatives (10a-10o) is synthesized and evaluated for their sPLA(2) inhibitory activities. All compounds (10a-10o) showed significant sPLA(2) inhibition activities both in vitro and in vivo studies which is substantiated in in silico studies. Among all the tested compounds, 100 showed potent sPLA(2) inhibition activity, that is comparable or more to ursolic acid (positive control). Further studies demonstrated that 100 showed in vitro antiproliferative activity when tested against MCF-7 breast and DU145 prostate cancer cells. Furthermore, compounds 10a-10o obeyed lipinsky's rule of 5 and suggesting druggable properties. The in vitro, in vivo and in silico results are encouraging and warrant pre-clinical studies to develop sPLA(2)-inhibitory compound 10o as novel therapeutic agent for various inflammatory disorders and several malignancies. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.02.025

文献信息

• Synthesis of new secretory phospholipase A2-inhibitory indole containing isoxazole derivatives as anti-inflammatory and anticancer agents
  作者：Srinivasa Rao Pedada、Nagendra Sastry Yarla、Pawan J. Tambade、Bhadrapura Lakkappa Dhananjaya、Anupam Bishayee、Kalle M. Arunasree、Gundala Harold Philip、Gangappa Dharmapuri、Gjumrach Aliev、Swathi Putta、Gururaja Rangaiah

  DOI：10.1016/j.ejmech.2016.02.025

  日期：2016.4

  Secretory phospholipase A(2) (sPLA(2)) is an important enzyme that plays a key role in various inflammatory diseases including cancer and its inhibitors have been developed as preventive or therapeutic agents. In the present study, a series of new indole containing isoxazole derivatives (10a-10o) is synthesized and evaluated for their sPLA(2) inhibitory activities. All compounds (10a-10o) showed significant sPLA(2) inhibition activities both in vitro and in vivo studies which is substantiated in in silico studies. Among all the tested compounds, 100 showed potent sPLA(2) inhibition activity, that is comparable or more to ursolic acid (positive control). Further studies demonstrated that 100 showed in vitro antiproliferative activity when tested against MCF-7 breast and DU145 prostate cancer cells. Furthermore, compounds 10a-10o obeyed lipinsky's rule of 5 and suggesting druggable properties. The in vitro, in vivo and in silico results are encouraging and warrant pre-clinical studies to develop sPLA(2)-inhibitory compound 10o as novel therapeutic agent for various inflammatory disorders and several malignancies. (C) 2016 Elsevier Masson SAS. All rights reserved.