5-amino-2-(p-methylbenzyl)benzoxazole | 959958-62-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 5-amino-2-(p-methylbenzyl)benzoxazole
• 英文别名: 2-(4-methylbenzyl)-5-aminobenzoxazole；2-[(4-methylphenyl)methyl]-1,3-benzoxazol-5-amine
• CAS: 959958-62-4
• 化学式: C₁₅H₁₄N₂O
• mdl: MFCD11104389
• 分子量: 238.289
• InChiKey: DBAPLEDIKZLDIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  52
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-amino-2-(p-methylbenzyl)benzoxazole 在 碳酸氢钠 、 三乙胺 作用下， 以 乙醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-(p-methylbenzyl)-5-[3-[4-(p-chlorophenyl)piperazin-1-yl]propionamido]benzoxazole
  参考文献：
  名称：

  Arisoy, Mustafa; Temiz-Arpaci, Ozlem; Kaynak-Onurdag, Fatma, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016, vol. 55B, # 2, p. 240 - 247

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(p-methylbenzyl)-5-nitrobenzoxazole 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 生成 5-amino-2-(p-methylbenzyl)benzoxazole
  参考文献：
  名称：

  Synthesis, biological evaluation and 2D-QSAR analysis of benzoxazoles as antimicrobial agents

  摘要：

  A new series of 5(or 6)-nitro/amino-2-(substituted phenyl/benzyl)benzoxazole derivatives (1a-1m, 2a-21) were synthesized and evaluated for antibacterial and antifungal activities against Staphylococcus aureus, Bacillus subtilis, Klebsiella pneumoniae, Pseudomonas aeruginosa, Escherichia coli, Candida albicans and their drug-resistant isolate. Microbiological results indicated that the synthesized compounds possessed a broad spectrum of activity against the tested microorganisms at MIC values between >400 and 12.5 mu g/ml. The results against B. subtilis, P. aeruginosa, drug-resistant B. subtilis, drug-resistant E. coli, and C. albicans isolate for these kinds of structures are quite encouraging. The 2D-QSAR analysis of a set of newly and previously synthesized benzoxazoles tested for growth inhibitory activity against B. subtilis ATCC 6633 was performed by using the multivariable regression analysis. The activity contributions for substituent effects of these compounds were determined from the correlation equation for predictions of the lead optimization. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.04.001

文献信息

• Synthesis, antimicrobial activity, pharmacophore analysis of some new 2-(substitutedphenyl/benzyl)-5-[(2-benzofuryl)carboxamido]benzoxazoles
  作者：Sabiha Alper-Hayta、Mustafa Arisoy、Özlem Temiz-Arpaci、Ilkay Yildiz、Esin Aki、Semiha Özkan、Fatma Kaynak

  DOI：10.1016/j.ejmech.2007.12.019

  日期：2008.11

  The synthesis and antimicrobial activity of a new series of 2-(substitutedphenyl/benzyl)-5-[(2-benzofuryl)carboxamido]benzoxazole derivatives 3-12 were described. The in vitro antimicrobial activity of the compounds was determined against some Gram-positive, Gram-negative bacteria and fungi and their drug-resistant isolates in comparison with standard drugs. Antimicrobial results indicated that the

  描述了一系列新的2-（取代的苯基/苄基）-5-[（2-苯并呋喃基）羧酰胺基]苯并恶唑衍生物3-12的合成和抗菌活性。与标准药物相比，确定了该化合物对某些革兰氏阳性，革兰氏阴性细菌和真菌及其耐药分离株的体外抗菌活性。抗菌结果表明，合成的化合物具有广谱的活性，MIC值为500-15.625 microg / ml。在该系列中，对克鲁斯假丝酵母和白色念珠菌分离物最有活性的化合物是8，MIC值为31.25 microg / ml。但是，它的稀释度比氟康唑的稀释度低。某些筛选的化合物表现出显着的活性，在铜绿假单胞菌中具有与利福平相同的活性，MIC值为31.25 microg / ml。
• Synthesis, molecular docking and antimicrobial evaluation of novel benzoxazole derivatives
  作者：Tugba Ertan-Bolelli、İlkay Yildiz、Selda Ozgen-Ozgacar

  DOI：10.1007/s00044-015-1499-1

  日期：2016.4

  research, previously and newly synthesized 5-amino-2-(4-substitutedphenyl/benzyl)benzoxazoles (3a–3l) and 2-substituted-5-(4-nitro/aminophenylsulfonamido)benzoxazoles (5a–5l, 6a–6l) were evaluated for their antimicrobial activities against Pseudomonas aeruginosa ATCC 27853, Staphylococcus aureus ATCC 29213, Escherichia coli ATCC 25922, Enterococcus faecalis ATCC 29212 and Mycobacterium tuberculosis H37RV

  在这项研究中，以前和新合成的5-氨基-2-（4-取代的苯基/苄基）苯并恶唑（3a - 3l）和2-取代的5-（4-硝基/氨基苯基磺酰胺基）苯并恶唑（5a - 5l，6a - 6l）它们对抗菌活性进行了评价铜绿假单胞菌ATCC 27853，金黄色葡萄球菌ATCC 29213，大肠杆菌ATCC 25922，粪肠球菌ATCC 29212和结核分枝杆菌H37RV ATCC 27294及其耐药株白色念珠菌ATCC 10231和克柔念珠菌ATCC 6258.通过IR，1 H NMR，13 C NMR，LC-MS和元素分析对新合成化合物的化学结构进行了表征。微生物学结果表明，该化合物在256至8 µg / mL的最低抑菌浓度（MIC）值下具有广泛的针对被测微生物的活性。化合物3a，3c和3f表现出显着的抗分枝杆菌活性，对两种M的MIC值为8 µg / mL 。结核病及其耐药分离株。InhA，来自M的烯酰
• Biological activity and ADME/Tox prediction of some 2-substituted benzoxazole derivatives
  作者：Fatma Zilifdar Foto、Egemen Foto、Tugba Ertan-Bolelli、Ilkay Yildiz

  DOI：10.1016/j.bioorg.2022.105756

  日期：2022.6

  some in vitro biological activities of a series of (5 or 6)-amino-2- (substituted phenyl and benzyl) benzoxazole derivatives. For this purpose, we tested cytotoxic and genotoxic activities of them on cancer cell lines and their topoisomerase inhibitory activities. We also tested their cytotoxic and genotoxic activities on non-cancerous cells (L929) and their mutagenic activities by Ames test to evaluate

  在这项研究中，我们主要关注一系列（5或6）-氨基-2-（取代的苯基和苄基）苯并恶唑衍生物的一些体外生物活性。为此，我们测试了它们对癌细胞系的细胞毒性和基因毒性活性及其拓扑异构酶抑制活性。我们还通过 Ames 测试测试了它们对非癌细胞 (L929) 的细胞毒性和基因毒性活性以及它们的诱变活性，以评估它们对健康细胞的影响。在所有测试的癌细胞系中，仅发现TD5具有细胞毒性，并且对健康细胞没有表现出细胞毒性或基因毒性活性，而TD1、TD2、TD3和TD7仅对 HeLa 细胞具有更强的细胞毒性。仅TD4被发现是诱变衍生物。没有一种化合物具有任何拓扑异构酶抑制活性，但是它们中的一些引起了对拓扑异构酶II活性的抑制。此外，我们使用计算机模型来预测它们的类药物特性，以评估它们对 QikProp 特性预测的生物利用度。所有计算的属性都在允许的范围内。根据生物活性研究的数据，可以得出结论，苯并恶唑环2位的亚甲
• A study on the genotoxic activities of some new benzoxazoles
  作者：Emine Oksuzoglu、Ozlem Temiz-Arpaci、Betul Tekiner-Gulbas、Hatice Eroglu、Gulseren Sen、Sabiha Alper、Ilkay Yildiz、Nuran Diril、Esin Aki-Sener、Ismail Yalcin

  DOI：10.1007/s00044-007-9005-z

  日期：2008.1

  The Bacillus subtilis rec assay has been specially developed to detect DNA-damaging potential in chemicals, with the rationale based on the relative difference of survival of a DNA repair combination proficient strains and its deficient strain, which is interpreted as genotoxicity. The genotoxic activities of newly (1-6) and previously (7-18) synthesized various benzoxazoles and benzimidazoles were analyzed via the B. subtilis rec assay. Newly obtained benzoxazole and benzimidazole derivatives (1-6) were synthesized in the presence of polyphosphoric acid (PPA) and 6 N HCl, respectively to detect their DNA-damaging activities. Among the tested compounds, 6-methyl-2-(o-chlorophenyl)benzoxazole (9), 5-amino-2-(p-methylbenzyl)benzoxazole (4), 5-(p-fluorobenzamido)-2-phenylbenzoxazole (13), and 2-(p-methylaminophenyl)benzoxazole (18) showed genotoxic activities having ReC50 values of 1.85, 1.74, 1.60, and 1.50 or S-probit values of 0.534, 0.482, 0.460, and 0.357, respectively. On the other hand, 2-(p-bromobenzyl)5-methylbenzimidazole (6) and 2-benzyl-5-(p-fluorophenylacetamido)-benzoxazole (15) were exhibited a reverse effect that displayed a bacterial growth in the rec strains while there was no any bacterial growth in rec(+) strains at the same concentration.
• Synthesis, Antimicrobial Activities of New Sulfonamidobenzoxazoles and Molecular Docking Studies on Escherichia coli TEM-1 β-Lactamase
  作者：Tugba Ertan-Bolelli、Kayhan Bolelli、Suzan Okten、Fatma Kaynak-Onurdag、Esin Aki-Yalcin、Ismail Yalcin

  DOI：10.5562/cca3111

  日期：——

  beta-Lactam antibiotics are frequently used for treatment of multi-drug resistant microbial infections and the most common mechanism of resistance against these antibiotics is bacterial beta-lactamase production. Herein, we reported the design, synthesis and in vitro antimicrobial activities of some new 2-substituted-5-(2,4-dinitrophenylsulfonamido) benzoxazole derivatives. Compounds TN1, TN2, and TN3 were found to be significantly active against E. coli isolate which contains extended spectrum beta-lactamase enzyme at the MIC value of 8 mu g mL(-1) and that is 4-fold higher than the reference drug ampicillin. We performed molecular docking studies into active site of Escherichia coli TEM-1 beta-lactamase enzyme in order to predict the protein-ligand interactions. According to the docking results, compounds TN1, TN2, and TN3 showed strong interactions between the important active site residues which are responsible for the catalytic mechanism of TEM-1 beta-lactamase enzyme and a good correlation is found with the experimental data.