2-(4-chlorophenyl)-6-iodo-4H-3,1-benzoxazin-4-one | 244032-42-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 2-(4-chlorophenyl)-6-iodo-4H-3,1-benzoxazin-4-one
• 英文别名: 2-(4-chlorophenyl)-6-iodo-3,1-benzoxazin-4-one
• CAS: 244032-42-6
• 化学式: C₁₄H₇ClINO₂
• 分子量: 383.573
• InChiKey: ZFRLRYDFLXLVBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-6-iodo-4H-3,1-benzoxazin-4-one 在 formamide 作用下， 生成 2-(4-chlorophenyl)-6-iodo-3H-quinazolin-4-one
  参考文献：
  名称：

  一些新型喹唑啉衍生物的合成，镇痛和抗炎作用

  摘要：

  制备了两个系列的一些新的2,4,6-三取代喹唑啉衍生物，并对其镇痛，抗炎活性和急性毒性进行了筛选。四种化合物比参考药物消炎痛更有效的镇痛药，十三种化合物表现出显着的抗炎活性。七种化合物具有抑制疼痛和炎症的综合能力。化合物经急性毒性测试后，给药后24小时无毒性症状或死亡率，这表明它们具有良好的安全性。

  DOI：

  10.1016/j.ejmech.2010.07.067
• 作为产物：
  描述：

  2-[(4-chlorobenzoyl)amino]-5-iodobenzoic acid 在 乙酸酐 作用下， 生成 2-(4-chlorophenyl)-6-iodo-4H-3,1-benzoxazin-4-one
  参考文献：
  名称：

  一些新型喹唑啉衍生物的合成，镇痛和抗炎作用

  摘要：

  制备了两个系列的一些新的2,4,6-三取代喹唑啉衍生物，并对其镇痛，抗炎活性和急性毒性进行了筛选。四种化合物比参考药物消炎痛更有效的镇痛药，十三种化合物表现出显着的抗炎活性。七种化合物具有抑制疼痛和炎症的综合能力。化合物经急性毒性测试后，给药后24小时无毒性症状或死亡率，这表明它们具有良好的安全性。

  DOI：

  10.1016/j.ejmech.2010.07.067

文献信息

• Rao, A. Raghu Ram; Bahekar, Rajesh H., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 4, p. 434 - 439
  作者：Rao, A. Raghu Ram、Bahekar, Rajesh H.

  DOI：——

  日期：——
• 10.1002/ardp.202400389
  作者：Alsulaimany, Marwa、El-Hddad, Sanadelaslam S. A.、Akrim, Zuhir S. M.、Aljohani, Ahmed K. B.、Almohaywi, Basmah、Alatawi, Omar M.、Almadani, Sara A.、Alharbi, Hussam Y.、Aljohani, Majed S.、Miski, Samar F.、Alghamdi, Read、El-Adl, Khaled

  DOI：10.1002/ardp.202400389

  日期：——

  AbstractNovel inhibitors of epidermal growth factor receptor (EGFR)T790M/vascular endothelial growth factor receptor‐2 (VEGFR‐2) were synthesized based on the iodoquinazoline scaffold linked to different heteroaromatic, aromatic, and/or aliphatic moieties. The novel derivatives were in vitro examined for anticancer activities against A549, HCT116, michigan cancer foundation‐7 (MCF‐7), and HepG2 cells. Molecular modeling was applied to discover their orientation of binding with both VEGFR‐2 and EGFR active sites. Compounds 8d, 8c, 6d, and 6c indicated the highest cytotoxicity with IC50 = 6.00, 6.90, 6.12 and 6.24 µM, 7.05, 7.35, 6.80, and 6.80 µM, 5.75, 7.50, 6.90, and 6.95 µM, and 6.55, 7.88, 7.44, and 7.10 µM against the A549, HepG2, HCT116, and MCF‐7 cell lines, correspondingly. The cytotoxicity against normal VERO (normal african green monkey kidney cells) of the extremely active eight compounds 6a–d and 8a–d was evaluated. Our compounds exhibited low toxicity concerning normal VERO cells with IC50 = 45.66–51.83 μM. Furthermore, inhibition assays for both the EGFRT790M and VEGFR‐2 enzymes were done for all compounds. Remarkable inhibition of EGFRT790M activity was achieved with compounds 6d, 8d, 6c, and 8c at IC50 = 0.35, 0.42, 0.48, and 0.50 µM correspondingly. Moreover, remarkable inhibition of VEGFR‐2 activity was achieved with compounds 8d, 8c, 6d, and 6c at IC50 = 0.92, 0.95, 1.00, and 1.20 µM correspondingly. As planned, derivatives 6d, 8d, 6c, and 8c presented exceptional inhibition of both EGFRT790M/VEGFR‐2 activities. Finally, in silico absorption, distribution, metabolism, excretion and toxicity (ADMET) studies were made for the highly active four compounds 6c, 6d, 8c, and 8d in comparison with erlotinib and sorafenib as reference standards.
• Synthesis, analgesic and anti-inflammatory evaluation of some novel quinazoline derivatives
  作者：Ahmed M. Alafeefy、Adnan A. Kadi、Omar A. Al-Deeb、Kamal E.H. El-Tahir、Nabila A. Al-jaber

  DOI：10.1016/j.ejmech.2010.07.067

  日期：2010.11

  Two series of some new 2,4,6-trisubstituted-quinazoline derivatives were prepared and screened for their analgesic, anti-inflammatory activity and acute toxicity. Four compounds were more potent analgesic agents than the reference drug Indomethacin and thirteen compounds showed significant anti-inflammatory activity. Seven compounds showed combined ability to inhibit both pain and inflammation. Compounds

  制备了两个系列的一些新的2,4,6-三取代喹唑啉衍生物，并对其镇痛，抗炎活性和急性毒性进行了筛选。四种化合物比参考药物消炎痛更有效的镇痛药，十三种化合物表现出显着的抗炎活性。七种化合物具有抑制疼痛和炎症的综合能力。化合物经急性毒性测试后，给药后24小时无毒性症状或死亡率，这表明它们具有良好的安全性。