2-chloro-4-(m-tolyloxy)quinazoline | 64778-46-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-chloro-4-(m-tolyloxy)quinazoline
• 英文别名: 2-Chloro-4-(3-methylphenoxy)quinazoline
• CAS: 64778-46-7
• 化学式: C₁₅H₁₁ClN₂O
• mdl: MFCD17980939
• 分子量: 270.718
• InChiKey: QAZWDZJUPFEBAO-UHFFFAOYSA-N

物化性质

• 熔点：
  134.2-134.6 °C(Solv: N,N-dimethylformamide (68-12-2))
• 沸点：
  380.5±24.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-4-(m-tolyloxy)quinazoline 在 四(三苯基膦)钯 、 sodium carbonate 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 丙酮 为溶剂， 反应 24.0h， 生成 N-(6-acetamidobenzo[d]thiazol-2-yl)-2-((4-(4-(m-tolyloxy)quinazolin-2-yl)phenyl)amino)acetamide
  参考文献：
  名称：

  新型苯并噻唑取代喹唑啉作为潜在抗菌剂的设计，合成和计算研究

  摘要：

  已经合成了一些新颖的N-（苯并[d]噻唑-2-基）-2-（（4-（4-（间甲苯基氧基）喹唑啉-2基）苯基）氨基）乙酰胺类似物（7a-j）。该合成方法利用了基于对喹唑啉环的铃木偶联反应的合并方案。测试了类似物对八种细菌（金黄色葡萄球菌MTCC 96，蜡状芽孢杆菌MTCC 619，大肠杆菌MTCC 739，铜绿假单胞菌MTCC 741，肺炎克雷伯菌肺炎MTCC 109，鼠伤寒沙门氏菌MTCC MTCC 733，变形杆菌1寻常型）的微生物活性。 ）和四种真菌（黑曲霉MTCC 282，烟曲霉MTCC 343，克拉维曲霉MTCC 1323和白色念珠菌MTCC 183）。与标准品（MIC：6.25-25μg/ mL）相比，某些合成的类似物已显示出优异的抗菌活性（MIC：3.12-25μg/ mL）。在B3LYP / 6-31G（d，p）水平进行密度泛函理论（DFT）计算以预测类似物的分子结构和电子性质

  DOI：

  10.2174/15701808113109990025
• 作为产物：
  描述：

  2,4-二氯喹唑啉 、 间甲酚 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 12.08h， 以81%的产率得到2-chloro-4-(m-tolyloxy)quinazoline
  参考文献：
  名称：

  新型苯并噻唑取代喹唑啉作为潜在抗菌剂的设计，合成和计算研究

  摘要：

  已经合成了一些新颖的N-（苯并[d]噻唑-2-基）-2-（（4-（4-（间甲苯基氧基）喹唑啉-2基）苯基）氨基）乙酰胺类似物（7a-j）。该合成方法利用了基于对喹唑啉环的铃木偶联反应的合并方案。测试了类似物对八种细菌（金黄色葡萄球菌MTCC 96，蜡状芽孢杆菌MTCC 619，大肠杆菌MTCC 739，铜绿假单胞菌MTCC 741，肺炎克雷伯菌肺炎MTCC 109，鼠伤寒沙门氏菌MTCC MTCC 733，变形杆菌1寻常型）的微生物活性。 ）和四种真菌（黑曲霉MTCC 282，烟曲霉MTCC 343，克拉维曲霉MTCC 1323和白色念珠菌MTCC 183）。与标准品（MIC：6.25-25μg/ mL）相比，某些合成的类似物已显示出优异的抗菌活性（MIC：3.12-25μg/ mL）。在B3LYP / 6-31G（d，p）水平进行密度泛函理论（DFT）计算以预测类似物的分子结构和电子性质

  DOI：

  10.2174/15701808113109990025

文献信息

• Synthesis and Evaluation on Anticonvulsant and Antidepressant Activities of 5-Alkoxy-tetrazolo[1,5-<i>a</i>]quinazolines
  作者：Huo-Jian Wang、Cheng-Xi Wei、Xian-Qing Deng、Fu-Lan Li、Zhe-Shan Quan

  DOI：10.1002/ardp.200900119

  日期：2009.11

  compounds displayed weak anticonvulsant activity at a dose of 300 mg/kg. Antidepressant activities were investigated by forced swimming test. Two compounds, namely 5‐(hexyloxy)tetrazolo[1,5‐a]quinazoline and 5‐(4‐methoxyphenoxy)tetrazolo[1,5‐a]quinazoline, showed significant antidepressant activity, which decreased the immobility time by 62.2 and 51.7% at 100 mg/kg dose level.

  通过 2,4-二氯喹唑啉与各种酚或脂肪醇，然后与叠氮化钠反应，合成了几种 5-烷氧基-四唑并[1,5-a]喹唑啉衍生物。这些化合物的结构已通过IR、MS、1H-NMR和元素分析确证。使用最大电休克 (MES) 测试评估抗惊厥活性。大多数合成的化合物在 300 mg/kg 的剂量下显示出微弱的抗惊厥活性。通过强迫游泳试验研究抗抑郁活性。两种化合物，即5-(己氧基)四唑并[1,5-a]喹唑啉和5-(4-甲氧基苯氧基)四唑并[1,5-a]喹唑啉，显示出显着的抗抑郁活性，将不动时间减少了62.2和51.7 % 在 100 mg/kg 剂量水平。
• Access to antimycobacterial and anticancer potential of some fused quinazolines
  作者：Amit B. Patel、Kishor H. Chikhalia、Premlata Kumari

  DOI：10.1007/s11164-014-1542-8

  日期：2015.7

  Two series of some various N-phenyl/benzothiazolyl acetamide-fused quinazoline derivatives were synthesized and tested for their antimycobacterial activity against M. tuberculosis H37Rv. Moreover, the synthesized analogs were also screened against human PC3 cells in order to explore their anticancer activity. The in vitro antimycobacterial screening revealed that, among the synthesized analogs, N-benzothiazolyl acetamide derivatives showed remarkable antimycobacterial activity. However, the best anticancer results were observed amongst the N-phenyl acetamide-substituted quinazoline derivatives. The newly synthesized compounds were characterized through IR, 1H NMR, 13C NMR, MS, and elemental analysis.

  合成了两系列不同的N-苯基/苯噻唑乙酰胺融合喹唑啉衍生物，并测试了它们对结核分枝杆菌H37Rv的抗分枝杆菌活性。此外，还对合成的类似物进行了对人PC3细胞的检测，以探讨其抗癌活性。体外抗分枝杆菌筛选结果显示，在合成的类似物中，N-苯噻唑乙酰胺衍生物表现出显著的抗分枝杆菌活性。然而，在N-苯基乙酰胺取代的喹唑啉衍生物中观察到了最佳的抗癌结果。新合成的化合物通过红外光谱、1H NMR、13C NMR、质谱和元素分析进行了表征。
• Synthesis and biological evaluation of novel quinazoline derivatives obtained by Suzuki C–C coupling
  作者：Amit B. Patel、Kishor H. Chikhalia、Premlata Kumari

  DOI：10.1007/s00044-013-0839-2

  日期：2014.5

  In the present investigation, two series of novel urea/thiourea-based quinazoline analogs (7a-g/8a-g) have been synthesized by introducing C-C Suzuki coupling between quinazoline and phenyl ring followed by condensation of various N-phenyl isocyanates/isothiocyanates. The synthesized analogs were investigated for their antimicrobial activity against two Gram-positive bacteria, three Gram-negative bacteria, and two fungal species. They were also tested for the antimycobacterial activity against Mycobacterium tuberculosis H37Rv. The biological screening data revealed that majority of the compounds have demonstrated noticeable activity (MIC; 6.25-50 mu g/mL) against most of the microorganisms. All the synthesized analogs were well characterized through IR, H-1 NMR, C-13 NMR, and elemental analyses.
• Patel, Amit B.; Kumari, Premlata; Chikhalia, Kishor H., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 2, p. 260 - 271
  作者：Patel, Amit B.、Kumari, Premlata、Chikhalia, Kishor H.

  DOI：——

  日期：——
• Hybrid diarylbenzopyrimidine non-nucleoside reverse transcriptase inhibitors as promising new leads for improved anti-HIV-1 chemotherapy
  作者：Zhao-Sen Zeng、Qiu-Qin He、Yong-Hong Liang、Xiao-Qing Feng、Fen-Er Chen、Erik De Clercq、Jan Balzarini、Christophe Pannecouque

  DOI：10.1016/j.bmc.2010.05.081

  日期：2010.7

  Molecular hybridization of the known anti-HIV-1 template DPC083 and etravirine based on docking model overlay has been generated a novel series of diarylbenzopyrimidine analogues (DABPs) (5a-z). These new hybrids were assessed for their activity against HIV in MT-4 cell cultures. Most of these compounds showed good activity against wild-type HIV-1 and mutant viruses. In particular, compound 5r showed the most potent activity against wild-type HIV-1 with an EC50 value of 1.8 nM, and with a selectivity index up to 111,954. It also proved more active against mutant L100I, K103N, Y188L, and K103N + Y181C RT HIV-1 strains than efavirenz. (C) 2010 Elsevier Ltd. All rights reserved.