4-azidomethyl-2(1H)-quinolinone | 1432579-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-azidomethyl-2(1H)-quinolinone
• 英文别名: 4-(azidomethyl)quinolin-2(1H)-one；4-(azidomethyl)-1H-quinolin-2-one
• CAS: 1432579-06-0
• 化学式: C₁₀H₈N₄O
• 分子量: 200.2
• InChiKey: BBTGEZUUTOSVFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  81.62
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-azidomethyl-2(1H)-quinolinone 、 吉帕孟 在 copper(ll) sulfate pentahydrate 、 sodium carbonate 、 维生素 C 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.25h， 生成 4-((4-(((4-methyl-2-oxo-2H-chromen-7-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)quinolin-2(1H)-one
  参考文献：
  名称：

  铜（I）催化卤代香豆素和1-氮杂-香豆素的一锅SN点击反应

  摘要：

  一锅三组分，铜催化的叠氮化物-炔烃环加成反应已经用于合成双-coumarinyl三唑（甲- d）使用4-氯，4-溴甲基，3-溴乙酰和4-溴甲基- 1-氮杂-香豆素（I – IV），叠氮化钠和香豆素炔丙基醚（V – IX）产量适中。

  DOI：

  10.1002/jhet.3090
• 作为产物：
  描述：

  4-溴-3-氧代-N-苯基丁酰胺 在 sodium azide 、 硫酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 4-azidomethyl-2(1H)-quinolinone
  参考文献：
  名称：

  单击化学方法区域选择性合成iso-indoline-1,3-dione-linked 1,4 and 1,5 coumarinyl 1,2,3-triazoles 及其光物理性质

  摘要：

  摘要 在点击化学条件下，N-炔丙基异吲哚啉-1,3-二酮和 4-叠氮甲基香豆素/4-叠氮甲基-1-氮杂香豆素在铜催化下反应得到 1,4-二取代 1,2,3-三唑，而钌催化产生异构的 1,5-二取代的 1,2,3-三唑。两种区域异构体已通过 NOE 研究区分开来。一对给定异构体的紫外吸收显示出相似的趋势，而荧光测量显示出相当大的差异。还对叠氮化物与铜和钌的相互作用进行了光物理研究。图形概要

  DOI：

  10.1080/00397911.2017.1283524

文献信息

• Triazole–Dithiocarbamate Based Selective Lysine Specific Demethylase 1 (LSD1) Inactivators Inhibit Gastric Cancer Cell Growth, Invasion, and Migration
  作者：Yi-Chao Zheng、Ying-Chao Duan、Jin-Lian Ma、Rui-Min Xu、Xiaolin Zi、Wen-Lei Lv、Meng-Meng Wang、Xian-Wei Ye、Shun Zhu、David Mobley、Yan-Yan Zhu、Jun-Wei Wang、Jin-Feng Li、Zhi-Ru Wang、Wen Zhao、Hong-Min Liu

  DOI：10.1021/jm401002r

  日期：2013.11.14

  Lysine specific demethylase 1 (LSD1), the first identified histone demethylase, plays an important role in epigenetic regulation of gene activation and repression. The up-regulated LSD l's expression has been reported in several malignant tumors. In the current study, we designed and synthesized five series of 1,2,3-triazole-dithiocarbamate hybrids and screened their inhibitory activity toward LSD1. We found that some of these compounds, especially compound 26, exhibited the most specific and robust inhibition of LSD1. Interestingly, compound 26 also showed potent and selective cytotoxicity against LSD1 overexpressing gastric cancer cell lines MGC-803 and HGC-27, as well as marked inhibition of cell migration and invasion, compared to 2-PCPA. Furthermore, compound 26 effectively reduced the tumor growth bared by human gastric cancer cells in vivo with no signs of adverse side effects. These findings suggested that compound 26 deserves further investigation as a lead compound in the treatment of LSD1 overexpressing gastric cancer.
• Novel VEGFR-2 kinase inhibitors identified by the back-to-front approach
  作者：Kingkan Sanphanya、Suvara K. Wattanapitayakul、Suwadee Phowichit、Valery V. Fokin、Opa Vajragupta

  DOI：10.1016/j.bmcl.2013.03.042

  日期：2013.5

  We report a novel VEGFR-2 inhibitor, developed by the back-to-front approach. Docking experiments indicated that the 3-chloromethylphenylurea motif of the lead compound occupied the back pocket of VEGFR-2 kinase. An attempt was made to enhance the binding affinity of 1 by expanding the structure to access the front pocket using a triazole linker. A library of 1,4-(disubstituted)-1H-1,2,3-triazoles were screened in silico, and one compound (VH02) was identified with an IC50 against VEGFR-2 of 0.56 mu M. VH02 showed antiangiogenic effects, inhibiting tube formation in HUVEC cells (EA.hy926) at 0.3 mu M, 13 times lower than its cytotoxic dose. These enzymatic and cellular activities suggest that VH02 has potential as a lead for further optimization. (C) 2013 Elsevier Ltd. All rights reserved.
• A click chemistry approach for the synthesis of cyclic ureido tethered coumarinyl and 1-aza coumarinyl 1,2,3-triazoles as inhibitors of Mycobacterium tuberculosis H37Rv and their in silico studies
  作者：Netravati Khanapurmath、Manohar V. Kulkarni、Shrinivas D. Joshi、G.N. Anil Kumar

  DOI：10.1016/j.bmc.2019.115054

  日期：2019.10

  Nucleoside bases like uracil, pharmacophoric triazoles and benzimidazolones have been used during the present study to design molecular matrices for antitubercular activity, employing Click Chemistry. Click triazoles 4/7/10 have been obtained by the reaction of 4-(Azidomethyl)-2H-chromen-2-ones/quinolin-2(1H)-ones 3 and propargyl ethers 2/6/9 derived from theophylline/6-methyl uracil/2-benzimidazolone respectively. In addition to spectral data structures have been confirmed by single crystal X-ray diffraction studies in case of uracil bis alkyne (6) and theophylline mono triazole (4c). Theophylline linked mono triazoles, 4(a-d) and 6-methyl uracil linked bis triazoles, 7(a-e) have been found to inhibit Mycobacterium tuberculosis H37Rv with MIC values in the range 55.62-115.62 mu M. Benzimidazolone bis triazoles, 10(a-n) showed better activity with MIC in the range 2.33-18.34 mu M. Molecular modeling studies using Surflex-Dock algorithm supported our results.