N-(2-carbamoylphenyl)-2-nitrobenzamide | 67718-36-9

• 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: N-(2-carbamoylphenyl)-2-nitrobenzamide
• 英文别名: N-[2-(aminocarbonyl)phenyl]-2-nitrobenzamide；2-[(2-Nitrobenzoyl)amino]benzamide
• CAS: 67718-36-9
• 化学式: C₁₄H₁₁N₃O₄
• mdl: MFCD01163386
• 分子量: 285.259
• InChiKey: QAIPVRZSDNCLFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-carbamoylphenyl)-2-nitrobenzamide 在 tin(II) chloride dihdyrate 、 乙醇 、 溶剂黄146 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 21.0h， 生成 8H-quinazolino[4,3-b]quinazolin-8-one
  参考文献：
  名称：

  Luotonin A and Its Derivatives as Novel Antiviral and Antiphytopathogenic Fungus Agents

  摘要：

  Plant diseases caused by viruses and fungi have posed a serious threat to global agricultural production. The discovery of new leads based on natural products is an important way to innovate pesticides. In this work, natural product luotonin A was found to have good antiviral activity against tobacco mosaic virus (TMV) for the first time. A series of luotonin A derivatives were designed, synthesized, and evaluated for their antiviral activities and fungicidal activities systematically. Most compounds displayed better antiviral activities against TMV than commercial ribavirin. Compounds 9k, 12b, and 12d displayed about similar inhibitory effects as ningnanmycin (inhibitory rates of 55, 57, and 59% at 500 mu g/mL for inactivation, curative, and protection activities in vivo, respectively), the best antiviral agent at present, and emerged as novel antiviral leads for further research. We selected 9k for further antiviral mechanism research via transmission electron microscopy and molecular docking, which revealed that compound 9k can interact with TMV coat protein through the hydrogen bond, leading to its polymerization, thus preventing virus assembly. Further fungicidal activity tests showed that these compounds also showed broad-spectrum fungicidal activities against 14 kinds of phytopathogenic fungi. Especially, compound 14 with a 100% antifungal effect against Botrytis cinereal emerged as a lead for further research. This work provides a reference for the development of agricultural active ingredients based on Chinese medicine plants.

  DOI：

  10.1021/acs.jafc.0c04278
• 作为产物：
  描述：

  2-硝基苯甲腈 在 乙醇 、 镍 、 一水合肼 作用下， 反应 2.0h， 生成 N-(2-carbamoylphenyl)-2-nitrobenzamide
  参考文献：
  名称：

  480.环am。第九部分 三环喹唑啉

  摘要：

  DOI：

  10.1039/jr9590002396

文献信息

• Microwave-assisted synthesis in aqueous medium of new quinazoline derivatives as anticancer agent precursors
  作者：Y. Kabri、A. Gellis、P. Vanelle

  DOI：10.1039/b816723k

  日期：——

  Fast and eco-friendly microwave-irradiated reactions permitting the “green synthesis” of new 2-substituted quinazoline derivatives in aqueous medium via S-alkylation or SRN1 reaction from 2-chloromethyl-3-methylquinazolin-4(3H)-one derivatives with different benzenesulfinic acids and nitronate anions, are reported herein.

  快速，环保的微波辐射反应可实现新的2-取代基的“绿色合成” 喹唑啉通过水介质中的衍生物S-烷基化或来自的S RN 1反应2-氯甲基-3-甲基喹唑啉-4（3 H）-one 具有不同苯磺酸的衍生物和 亚硝酸盐 阴离子，在本文报道。
• Design, synthesis and biological evaluation of 4-anilinoquinazoline derivatives as new c-myc G-quadruplex ligands
  作者：Yin Jiang、Ai-Chun Chen、Guo-Tao Kuang、Shi-Ke Wang、Tian-Miao Ou、Jia-Heng Tan、Ding Li、Zhi-Shu Huang

  DOI：10.1016/j.ejmech.2016.06.040

  日期：2016.10

  series of 4-anilinoquinazoline derivatives were designed and synthesized as novel c-myc promoter G-quadruplex binding ligands. Subsequent biophysical and biochemical evaluation demonstrated that the introduction of aniline group at 4-position of quinazoline ring and two side chains with terminal amino group improved their binding affinity and stabilizing ability to G-quadruplex DNA. RT-PCR assay and Western

  设计并合成了一系列4-苯胺基喹唑啉衍生物，作为新型c-myc启动子G-四链体结合配体。随后的生物物理和生化评估表明，在喹唑啉环的4位上引入苯胺基和两个带有末端氨基的侧链可提高它们对G-四链体DNA的结合亲和力和稳定能力。RT-PCR和Western blot结果表明，化合物7a可以下调Hela细胞中c-myc基因的转录和表达，这与靶向c-myc癌基因的有效G-四链体配体的行为一致。更重要的是，RTCA和菌落形成试验表明7a明显抑制Hela细胞增殖，而不影响正常的原代培养的小鼠肾小球系膜细胞。流式细胞仪检测表明7a诱导Hela细胞以时间依赖性和剂量依赖性方式停滞在G0 / G1期。
• Synthesis and Evaluation of 2,4-Disubstituted Quinazoline Derivatives with Potent Anti-Angiogenesis Activities
  作者：Guangjin Yu、Zeng Li、Liang Tang、Qiru Xiong

  DOI：10.3390/molecules19078916

  日期：——

  A series of 2,4-disubstituted quinazoline derivatives were designed and synthesized. The biological results showed that most of quinazoline derivatives exhibited potent antiproliferative activities against a panel of three tumor cell lines and a good inhibitory effect against the adhesion and migration of human umbilical vein endothelial cells (HUVECs). Among these compounds, 11d was the most potent agent, that also exhibited the highest anti-angiogenesis activities in the chick embryo chorioallantoic membrane (CAM) assay.

  一系列2,4-二取代喹嗪衍生物被设计和合成。生物结果显示，大多数喹嗪衍生物表现出对三种肿瘤细胞系的强抗增殖活性，并对人脐静脉内皮细胞（HUVECs）的粘附和迁移具有良好的抑制效果。在这些化合物中，11d是最有效的药物，在小鸡胚胎绒毛膜-尿囊膜（CAM）测定中也表现出最高的抗血管生成活性。
• Discovery of Small Molecules for Repressing Cap-Independent Translation of Human Vascular Endothelial Growth Factor (h<i>VEGF</i>) as Novel Antitumor Agents
  作者：Shi-Ke Wang、Yue Wu、Xiao-Qin Wang、Guo-Tao Kuang、Qi Zhang、Shu-Ling Lin、Hui-Yun Liu、Jia-Heng Tan、Zhi-Shu Huang、Tian-Miao Ou

  DOI：10.1021/acs.jmedchem.6b01444

  日期：2017.7.13

  a “switchable” RNA G-quadruplex structure that is essential for a cap-independent translation initiation. We screened our small-molecule library for binders of this G-tract. One novel quinazoline derivative, compound 1, showed a significant specific interaction with the G-tract and destabilized the G-quadruplex structure. The results of cellular experiments revealed that compound 1 down-regulated hVEGF-A

  血管生成在肿瘤发生和肿瘤进展中很重要。人血管内皮生长因子（hVEGF）是一种血管生成生长因子，在肿瘤的进展中起着至关重要的作用。h VEGF -A mRNA的5'非翻译区（5'-UTR）内的富含G的区域可以形成“可切换的” RNA G-四链体结构，这对于不依赖于帽的翻译起始而言是必不可少的。我们在小分子文库中筛选了该G-tract的粘合剂。一种新的喹唑啉衍生物化合物1显示出与G链的显着特异性相互作用，并使G四联体结构不稳定。细胞实验结果表明，化合物1下调了h VEGF-A翻译并显着阻碍肿瘤细胞迁移。我们还发现化合物1在MCF-7异种移植肿瘤中表现出肿瘤抑制活性，这可能与其降低h VEGF表达的能力有关。这些发现提出了h VEGF -A翻译控制的新策略，其中小分子与5'UTR中的G-四链体结构相互作用。
• Cyclisation of 2-(2-aminophenyl)quinazolin-4(3H)-one reexamined: formation of isomeric angular fused quinazolinoquinazolinones and their spectroscopic identification
  作者：Somepalli Venkateswarlu、Meka Satyanarayana、Gandrothu Narasimha Murthy、Vidavalur Siddaiah

  DOI：10.1016/j.tetlet.2012.03.055

  日期：2012.5

  3-b]quinazolin-8-one and 6-alkyl-(13H)-quinazolino[3,4-a]quinazolin-13-one, respectively was described for the first time. The differences in the IR and carbon NMR data of these isomeric fused quinazolinoquinazolinones afford a useful method for distinguishing between the two series.

  2-（2-氨基苯基）喹唑啉-4（3 H）-one在N 3上和在N 1上的环化导致6-烷基-（8 H）-quinazolino [4,3- b ] quinazolin-8-首次描述了一个和一个6-烷基-（13 H）-喹唑啉代[3,4- a ]喹唑啉-13-。这些异构体稠合的喹唑啉基喹唑啉酮的IR和碳NMR数据差异为区分这两个系列提供了一种有用的方法。