4-(azidomethyl)-1-methoxy-2-nitrobenzene | 1152843-97-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(azidomethyl)-1-methoxy-2-nitrobenzene
• CAS: 1152843-97-4
• 化学式: C₈H₈N₄O₃
• 分子量: 208.177
• InChiKey: WNERLMMSXBXTLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3.4.5-三甲氧基苯乙炔 、 4-(azidomethyl)-1-methoxy-2-nitrobenzene 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 以96%的产率得到1-(4-methoxy-3-nitrobenzyl)-4-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  1,2,3-Triazole analogs of combretastatin A-4 as potential microtubule-binding agents

  摘要：

  A series of cis-restricted 1,4- and 1,5-disubstituted 1,2,3-triazole analogs of combretastatin A-4 (1) have been prepared. Cytotoxicity and tubulin inhibition studies showed that 2-methoxy-5-((5-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazol-1-yl)methyl)aniline (5e) and 2-methoxy-5-(1-(3,4,5-trimethoxybenzyl)-1H-1,2,3-triazol-5-yl)aniline (6e) were two of the most active compounds. Molecular modeling studies revealed that the N-2 and N-3 atoms in the triazole rings in 5e and 6e did not form hydrogen bonds with the amino acids in the anticipated pharmacophore. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.032
• 作为产物：
  描述：

  3-硝基-4-甲氧基苯甲醛 在 sodium tetrahydroborate 、 sodium azide 、 三溴化磷 作用下， 以 甲醇 、 乙醚 、 二甲基亚砜 为溶剂， 反应 14.5h， 生成 4-(azidomethyl)-1-methoxy-2-nitrobenzene
  参考文献：
  名称：

  1,2,3-三唑系吡唑啉和查尔酮衍生物的合成及生物学评价。

  摘要：

  合成了一系列吡唑啉衍生物及其相应的查耳酮中间体，这些中间体具有与Combretastatin-A4（CA-4）相同的取代基，并与三唑核共轭，并评估了它们的抗癌潜力。Sulforhodamine B（SRB）分析表明，化合物12c是该系列中针对人类肝癌细胞HepG2的GI50值为6.7μM的最具活性的化合物。有趣的是，中间体11c表现出更有希望的细胞毒性，表明针对前列腺癌细胞系DU145的GI50值为1.3μM。化合物11c和12c引起细胞在G2 / M期的积累并抑制微管蛋白聚合。此外，这些化合物降低线粒体膜电位并激活胱天蛋白酶3和9，从而表明它们触发细胞凋亡的能力。本文受版权保护。

  DOI：

  10.1111/cbdd.12738

文献信息

• Anti-tubercular agents. Part 8: Synthesis, antibacterial and antitubercular activity of 5-nitrofuran based 1,2,3-triazoles
  作者：Ahmed Kamal、Syed Mohammed Ali Hussaini、Shaikh Faazil、Y. Poornachandra、G. Narender Reddy、C. Ganesh Kumar、Vikrant Singh Rajput、Chitra Rani、Rashmi Sharma、Inshad Ali Khan、N. Jagadeesh Babu

  DOI：10.1016/j.bmcl.2013.10.010

  日期：2013.12

  A series of 5-nitrofuran-triazole conjugates were synthesized and evaluated for their antimicrobial activity against both Gram-positive and Gram-negative bacterial strains. All the compounds exhibited promising inhibition towards Gram-positive pathogenic strains, while mild inhibitory effects were observed towards Gram-negative bacterial strains. Some of the compounds 8a, 8b, 8e, 8f, 8h are most active among the series exhibiting MIC value of 1.17 mu g/ml against different bacterial strains. The bactericidal activity is found to be in accordance with the bacterial growth inhibition data. Compound 8e was found to be equipotent to the standard drug Ciprofloxacin displaying MBC value of 1.17 mu g/ml against the bacterial strain Bacillus subtilis. The compounds have also demonstrated promising antibacterial activity against the resistant strain MRSA and were found to be effective inhibitors of biofilm formation. The compound 8b exhibited excellent anti-biofilm activity with IC50 value as low as 0.8 mu g/ml. These conjugates were also screened for antitubercular activity against Mycobacterium tuberculosis H(37)Rv strain. Compound 8e showed promising antitubercular activity with MIC value of 0.25 mu g/ml. Most of these compounds are less toxic to normal mammalian cells than the widely used antibacterial drug Ciprofloxacin. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Evaluation of 1,2,3-triazole tethered Pyrazoline and Chalcone Derivatives
  作者：Syed Mohammed Ali Hussaini、Poornachandra Yedla、Korrapati Suresh Babu、Thokhir B. Shaik、Ganesh Kumar Chityal、Ahmed Kamal

  DOI：10.1111/cbdd.12738

  日期：2016.7

  A series of pyrazoline derivatives and corresponding chalcone intermediates with substituents same asCombretastatin-A4(CA-4) conjugated with triazole nucleus has been synthesized and evaluated for their anticancer potential. Sulforhodamine B(SRB) assay indicated ccompound 12cto be the most active compound from the series with GI50 value of 6.7 muM against the human liver carcinoma cell line HepG2.

  合成了一系列吡唑啉衍生物及其相应的查耳酮中间体，这些中间体具有与Combretastatin-A4（CA-4）相同的取代基，并与三唑核共轭，并评估了它们的抗癌潜力。Sulforhodamine B（SRB）分析表明，化合物12c是该系列中针对人类肝癌细胞HepG2的GI50值为6.7μM的最具活性的化合物。有趣的是，中间体11c表现出更有希望的细胞毒性，表明针对前列腺癌细胞系DU145的GI50值为1.3μM。化合物11c和12c引起细胞在G2 / M期的积累并抑制微管蛋白聚合。此外，这些化合物降低线粒体膜电位并激活胱天蛋白酶3和9，从而表明它们触发细胞凋亡的能力。本文受版权保护。
• 1,2,3-Triazole analogs of combretastatin A-4 as potential microtubule-binding agents
  作者：Kristin Odlo、Jérémie Fournier-Dit-Chabert、Sylvie Ducki、Osman A.B.S.M. Gani、Ingebrigt Sylte、Trond Vidar Hansen

  DOI：10.1016/j.bmc.2010.07.032

  日期：2010.9

  A series of cis-restricted 1,4- and 1,5-disubstituted 1,2,3-triazole analogs of combretastatin A-4 (1) have been prepared. Cytotoxicity and tubulin inhibition studies showed that 2-methoxy-5-((5-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazol-1-yl)methyl)aniline (5e) and 2-methoxy-5-(1-(3,4,5-trimethoxybenzyl)-1H-1,2,3-triazol-5-yl)aniline (6e) were two of the most active compounds. Molecular modeling studies revealed that the N-2 and N-3 atoms in the triazole rings in 5e and 6e did not form hydrogen bonds with the amino acids in the anticipated pharmacophore. (C) 2010 Elsevier Ltd. All rights reserved.