36075-44-2

Usage

Uses

Used in Pharmaceutical Research:
4-hydrazinoquinazoline is utilized as a pharmaceutical research compound for its potential as an antitumor agent, contributing to the development of novel cancer therapies. Its unique structure allows for interactions with biological targets, making it a promising candidate for further exploration and optimization in drug discovery.
Used in Antitumor Applications:
In the field of oncology, 4-hydrazinoquinazoline is employed as an antitumor agent, where it may exhibit inhibitory effects on the growth and proliferation of cancer cells. Its specific mode of action and target interactions are areas of active research, with the aim of enhancing its therapeutic potential and selectivity for cancer treatment.
Used in Antimicrobial and Antifungal Applications:
4-hydrazinoquinazoline also shows promise in the development of antimicrobial and antifungal agents, given its ability to target and inhibit the growth of various microorganisms. This makes it a valuable compound for the creation of new drugs to combat resistant strains and address the growing need for effective treatments in infectious diseases.
Overall, 4-hydrazinoquinazoline is a compound of significant interest in the pharmaceutical and medicinal chemistry sectors, with its diverse applications and potential for further development in drug discovery and therapeutic innovation.

InChI:InChI=1/C8H8N4/c9-12-8-6-3-1-2-4-7(6)10-5-11-8/h1-5H,9H2,(H,10,11,12)

Upstream product

• 5190-68-1 4-chloroquinazoline 
• 13182-59-7 4-(methylsulfanyl)quinazoline 
• 15018-66-3 4-Aminoquinazoline 
• 491-36-1 4-Hydroxyquinazoline 
• 118-92-3 anthranilic acid 
• 3337-86-8 quinazoline-4(3H)-thione 
• 1885-29-6 anthranilic acid nitrile 

Downstream Products

• 51805-88-0 5-(2'-aminophenyl)-1,3,4-thiadiazole-2-thiol 
• 129177-06-6 4-(2-(2-chlorobenzylidene)hydrazinyl)quinazoline 
• 151657-53-3 N-(2,5-Dichloro-phenyl)-N-[4-(quinazolin-4-yl-hydrazonomethyl)-thiazol-2-yl]-acetamide 
• 129177-08-8 N-[1-(2,4-Dichloro-phenyl)-meth-(E)-ylidene]-N'-quinazolin-4-yl-hydrazine 
• 129177-05-5 N-[1-(4-Bromo-phenyl)-meth-(E)-ylidene]-N'-quinazolin-4-yl-hydrazine 
• 151657-52-2 N-[4-(Quinazolin-4-yl-hydrazonomethyl)-thiazol-2-yl]-N-p-tolyl-acetamide 
• 129177-15-7 3-(2-Chloro-phenyl)-[1,2,4]triazolo[4,3-c]quinazoline 
• 129177-16-8 3-(4-Chloro-phenyl)-[1,2,4]triazolo[4,3-c]quinazoline 
• 129177-14-6 3-(4-Bromo-phenyl)-[1,2,4]triazolo[4,3-c]quinazoline 
• 129177-17-9 3-(2,4-Dichloro-phenyl)-[1,2,4]triazolo[4,3-c]quinazoline 
• 51805-89-1 2-(5-methylsulfanyl-[1,3,4]thiadiazol-2-yl)-aniline 
• 16347-95-8 4-methoxyquinazoline 
• 1394045-57-8 4-methyl-N-(2-(quinazolin-4-yl)hydrazinecarbonothioyl)benzamide 
• 1394045-48-7 2-chloro-N-(2-(quinazolin-4-yl)hydrazinecarbonothioyl)benzamide 

Relevant academic research and scientific papers

Zn(II) complexes of (E)-4-(2-(pyridin-2-ylmethylene)hydrazinyl)quinazoline in combination with non-steroidal anti-inflammatory drug sodium diclofenac: Structure, DNA binding and photo-cleavage studies, antioxidant activity and interaction with albumin

The interaction of the novel quinazoline (E)-4-(2-(pyridin-2-ylmethylene)hydrazinyl)quinazoline (L) with Zn2+ was performed in the absence or presence of the non-steroidal anti-inflammatory drug sodium diclofenac (Nadicl) and resulted in the fo

Metal free [4+1] and [5+1] annulation reactions to prepare heterocycles using DMF and its derivatives as one-carbon source

1,2,4-Triazolo[3,4-a]pyridines and related heterocycles and substituted triazines were commonly discovered scaffolds in a variety of pharmaceutical and agrochemical agents. Herein, we report a highly efficient and practical method using DMF and its derivative for the [4+1] and [5+1] annulation reactions to prepare these heterocycles. This metal free reaction takes advantages of shelf stable DMF as solvent and carbon donor, imidazole chloride as a catalyst, the mild reaction condition tolerates a broad substrate range and substitutes. The prepared 3-unsubstituted 1,2,4-triazolo[3,4-a]pyridine and derivatives allow further introduction of a variety of functional group1 at 3-position.

Synthesis and in vitro cytotoxicity study of novel 4-substituted quinazolines encompassed with thiazolidinone and azetidinone

A series of quinazolines encompassed with thiazolidinone and azetidinone have been synthesized and evaluated for their antioxidant, anticancer and DNA binding studies. All the synthesized compounds were characterized by IR, 1H & 13C NMR and mass spectra. Antioxidant activity was carried out using % free radical scavenging by DPPH assay. Compounds 4b, 5b and 5d have shown better antioxidant activity (60, 67 and 66%, respectively) among the tested compounds. Compounds having % free radical scavenging activity more than 55% were evaluated for anticancer activity by MTT assay towards cell lines A-549 (lung carcinoma) and MDA-231 (human breast cancer). Results revealed that the tested compounds exhibited moderate to low anticancer activity. Further, DNA binding activity was studied by absorption titration method for all the synthesized compounds, and compound 5b showed a good binding constant of 70.05 and % hyperchromicity of 82.93%.

Synthesis and mode of action studies of novel {2-(3-R-1H-1,2,4-triazol-5-yl)phenyl}amines to combat pathogenic fungi

Due to their high specificity and efficacy, triazoles have become versatile antifungals to treat fungal infections in human healthcare and to control phytopathogenic fungi in agriculture. However, azole resistance is an emerging problem affecting human health as well as food security. Here we describe the synthesis of 10 novel {2-(3-R-1H-1,2,4-triazol-5-yl)phenyl}amines. Their structure was ascertained by liquid chromatography–mass spectrometry, 1H and 13C NMR, and elemental analysis data. Applying an in vitro growth assay, these triazoles show moderate to significant antifungal activity against the opportunistic pathogen Aspergillus niger, 12 fungi (Fusarium oxysporum, Fusarium fujikuroi, Colletotrichum higginsianum, Gaeumannomyces graminis, Colletotrichum coccodes, Claviceps purpurea, Alternaria alternata, Mucor indicus, Fusarium graminearum, Verticillium lecanii, Botrytis cinerea, Penicillium digitatum) and three oomycetes (Phytophtora infestans GL-1, P. infestans 4/91; R+ and 4/91; R?) in the concentration range from 1 to 50 μg/ml (0.003–2.1 μM). Frontier molecular orbital energies were determined to predict their genotoxic potential. Molecular docking calculations taking into account six common fungal enzymes point to 14α-demethylase (CYP51) and N-myristoyltransferase as the most probable fungal targets. With respect to effectiveness, structure–activity calculations revealed the strong enhancing impact of adamantyl residues. The shown nonmutagenicity in the Salmonella reverse-mutagenicity assay and no violations of drug-likeness parameters suggest the good bioavailability and attractive ecotoxicological profile of the studied triazoles.

Synthesis, Anticancer, and QSAR Studies of 2-Alkyl(aryl,hetaryl)quinazolin-4(3H)-thione's and [1,2,4]Triazolo[1,5-c]quinazoline-2-thione's Thioderivatives

Considering the frightening high level of mortality from cancer, studies of anticancer agents are vital nowadays. The 24 thioderivatives of 2-alkyl(aryl)-quinazolin-4(3H)-thiones and 20 thioderivatives of [1,2,4]triazolo[1,5-c]quinazoline-2-thiones were synthesized and evaluated for preliminary in?vitro anticancer activity with subsequent in silico QSAR analysis. The substance 18 had the best results inhibiting growth of eight cancer cell lines: CCRF-CEM of leukemia; SF-539, SNB-75, and U251 of CNS cancer; 786, RXF393, and UO-31 of renal cancer; and MDA-MB-231/ATCC of breast cancer (?31.50?–?47.41% of cell growth) with low procancer effect. Calculated QSAR-models for CCRF-CEM of leukemia, T-47D and HS 578T of breast cancer, and mean cell growth demonstrated good rate of anticancer activity prediction (r2?=?0.7?–?0.8, Q2LOO=?0.5?–?0.7).

Synthesis and antitumor activity of novel quinazoline derivatives containing thiosemicarbazide moiety

Series of novel derivatives of quinazoline containing thiosemicarbazide moiety 5 and 9 have been synthesized and tested for their antitumor activities in vitro against a panel of five human cancer cell lines. Bioassay results indicated that most of the prepared compounds exhibited cytotoxicity against various cancer cells. From the structure-activity relationships it was found that unsubstituted quinazoline ring and benzene ring or halogen substituted benzene ring in quinazoline derivatives 5 and 9 would be the most favorable for their antitumor activity.

Inhibitors of apoptosis in lymphocytes: Synthesis and biological evaluation of compounds related to pifithrin-α

The chemoprotection of cells from apoptosis induced by toxins or ionizing radiation could be important for biodefense and in the treatment of acute injuries. We describe a series of small heterocycles, including fused benzothiazoles, benzimidazoles, and related compounds, that abrogate thymocyte apoptosis induced by dexamethasone and γ-irradiation. To optimize the protective activity of the previously reported pifithrin-α (PFT-α, 1), various derivatives and analogues of this and the corresponding ring-closed imidazobenzothiazole (IBT, 39) were synthesized. The aromatic analogues of 39 were more protective than 39, while the aromatic analogues of 1 were not active. Compound 19 containing a pyrrolidinyl substituent on the phenyl ring provided potent antiapoptotic activity (EC50 of 1.31 μM compared to 4.16 μM for 1). Modification of aromatic 39 with a pyrrolidinyl para substituent (compound 60) enhanced the activity, lowering the EC50 to 0.35 μM. Also, 60 provided significant protection against γ-irradiation-induced apoptosis, as expected. Compounds 19 and 60 may be promising for potential clinical development.