67718-36-9

Upstream product

• 7501-38-4 2-(2'-nitrophenyl)-3,1-benzoxazin-4-one 
• 28144-70-9 anthranilic acid amide 
• 610-14-0 2-nitrobenzyl chloride 
• 68506-37-6 2-(2-nitrobenzamido)benzoic acid 
• 118-92-3 anthranilic acid 
• 5900-59-4 2-amino-4-chlorobenzamide 
• 612-24-8 o-nitrobenzonitrile 
• 1885-29-6 anthranilic acid nitrile 
• 552-16-9 ortho-nitrobenzoic acid 

Downstream Products

• 36567-87-0 2-(2'-nitrophenyl)-4(3H)-quinazolinone 
• 67718-35-8 N-anthraniloyl-anthranilic acid amide 
• 100088-92-4 6-anilino-quinazolino[4,3-b]quinazolin-8-one 
• 1637443-98-1 N-((2-(4-(N-(4-(2-diethylaminoethoxy))phenyl)amino)-quinazolin-2-yl)phenyl)-3-(4-methylpiperazin-1-yl)propanamide 

Relevant academic research and scientific papers

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

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 μg/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.

Discovery of Small Molecules for Repressing Cap-Independent Translation of Human Vascular Endothelial Growth Factor (hVEGF) as Novel Antitumor Agents

Angiogenesis is important in tumorigenesis and tumor progression. Human vascular endothelial growth factor (hVEGF) is an angiogenic growth factor that plays a crucial role in tumor progression. The G-rich region within the 5′-untranslated regions (5′-UTR) of hVEGF-A mRNA can form 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 translation and significantly impeded tumor cells migration. We also found that compound 1 exhibited tumor-inhibiting activity in MCF-7 xenograft tumors, which might be related to its ability to reduce hVEGF expression. These findings present a new strategy of hVEGF-A translational control in which small molecules interact with G-quadruplex structure in the 5′UTR.

Design, synthesis and biological evaluation of 4-anilinoquinazoline derivatives as new c-myc G-quadruplex ligands

A 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 blot showed that compound 7a could down-regulate transcription and expression of c-myc gene in Hela cells, which was consistent with the behavior of an effective G-quadruplex ligand targeting c-myc oncogene. More importantly, RTCA and colony formation assays indicated that 7a obviously inhibited Hela cells proliferation, without influence on normal primary cultured mouse mesangial cells. Flow cytometric assays suggested that 7a induced Hela cells to arrest in G0/G1 phase both in a time-dependent and dose-dependent manner.

Synthesis and evaluation of 2,4-disubstituted quinazoline derivatives with potent anti- Angiogenesis activities

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.

New quinazoline derivatives for telomeric G-quadruplex DNA: Effects of an added phenyl group on quadruplex binding ability

To improve the selectivity of indoloquinoline or benzofuroquinoline derivatives, we previously reported several quinazoline derivatives [17]. These compounds could mimic a tetracyclic aromatic system through intramolecular hydrogen bond. Studies showed that these quinazoline derivatives were effective and selective telomeric G-quadruplex ligands. With this encouragement, here we synthesized a series of N-(2-(quinazolin-2-yl)phenyl)benzamide (QPB) compounds as modified quinazoline derivatives. In this modification, a phenyl group was introduced to the aromatic core. The evaluation results showed that part of QPB derivatives had stronger binding ability and better selectivity for telomeric G-quadruplex DNA than LZ-11, the most potential compound of reported quinazoline derivatives. Furthermore, telomerase inhibition of QPB derivatives and their cellular effects were studied.

Computer-aided design, synthesis and validation of 2-phenylquinazolinone fragments as CDK9 inhibitors with anti-HIV-1 tat-mediated transcription activity

The activity of the cyclin-dependent kinase 9 (CDK9) is critical for HIV-1 Tat-mediated transcription and represents a promising target for antiviral therapy. Here we present computational studies that, along with preliminary synthetic efforts, allowed us

Cyclisation of 2-(2-aminophenyl)quinazolin-4(3H)-one reexamined: Formation of isomeric angular fused quinazolinoquinazolinones and their spectroscopic identification

Cyclisation of 2-(2-aminophenyl)quinazolin-4(3H)-ones on to N3 and on to N1 leading to 6-alkyl-(8H)-quinazolino[4,3-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.

Microwave-assisted synthesis in aqueous medium of new quinazoline derivatives as anticancer agent precursors

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.

A one-pot synthesis of novel sugar derived 5,6-dihydro-quinazolino[4,3-b]quinazolin-8-ones: an entry towards highly functionalized sugar-heterocyclic hybrids

An efficient and practical one-pot method for the synthesis of novel diversified sugar derived dihydro-quinazolino[4,3-b]quinazolin-8-ones has been reported. Various protected sugar hemiacetals were used to synthesize the hybrid tetracyclic ring system. The one-step reductive transformation of 2-(2-nitrophenyl)-3H-quinazolin-4-one with different sugar hemiacetals furnished the desired tetracyclic product in good yields and with high purity.

Auto-redox reaction: Tin(II) chloride-mediated one-step reductive cyclization leading to the synthesis of novel biheterocyclic 5,6-dihydro-quinazolino[4,3-b]quinazolin-8-ones with three-point diversity

A tin (II) chloride-mediated short, efficient, and practical regioselective synthesis of biheterocyclic 5,6-dihydro-quinazolino[4,3-b]quinazolin-8-ones with three-point diversity is reported. A one-step reductive transformation of 2-(2-nitro-phenyl)-3H-quinazolin-4-one in various alcohols furnished the desired tetracyclic product in good yields with high purity.