Synthesis, Tautomeric Structure and Antimicrobial Activity of 3-Arylhydrazono-4-phenyl-[1,2,4]-triazepino[2,3-a]quinazoline-2,7(1H)-diones (original) (raw)
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Research on Chemical Intermediates, 2019
A series of novel substituted hydrazone-bearing (unsymmetrical azines, RR 1 C=N-N=CR 2 R 3) tricyclic quinazoline derivatives are reported. All novel compounds were characterized by 1 H, 13 C nuclear magnetic resonance (NMR), and Fourier-transform infrared (FT-IR) analyses. An important intermediate (E/Z)-hydrazono-1,2,3,9tetrahydropyrrolo[2,1-b]quinazoline (8) was synthesized from tricyclic quinazoline-4-thione 7 using 80 % of hydrazine hydrate. In addition, the antimicrobial activity of all synthesized novel compounds against three types of pathogenic microorganism was tested, revealing that some compounds showed satisfactory good activity and could serve as lead compounds for further drug discovery and development.
The title compounds have been prepared by incorporating the anthranilic acid with substituted benzoylchloride which lead to the formation of oxazin-4-ones followed by subjecting it in the presence of pyridine, hydrazine hydrochloride, sodium cyano oxide lead to the formation of 1-(4-oxo-2-arylquinazolin-3(4H)-yl) semicarbazide. Various aromatic carbonyl compound with 1-(4-oxo-2-arylquinazolin-3(4H)-yl) semicarbazide in the presence of glacial acetic acid and ethanol gives (S1-S10) quinazoline derivatives. Structures of newly synthesized compound have been established on the basis of their IR and NMR spectral data. All the synthesized compounds have been screened for their antimicrobial activity.
Synthesis and Antimicrobial Activity of Some Novel Hydrazinyl Quinazoline Amine Derivatives
2-chloro-4-aminoquinazolines 3a-b were synthesized by intramolecular cyclization of substituted formamide 2a-b in presence of phosphorus oxychloride in one pot. These were further condensed with 5-aryl/alkyl-2-hydrazino-1,3,4thiadiazoles 8a-e. synthesized by condensation of hydrazine hydrate with 2-chloro-5-aryl/alkyl-1,3,4-thiadiazoles 7a-e which in turn were obtained by copper mediated diazotization of 2-amino-5-aryl/alkyl-1,3,4-thiadiazoles 6a-e in acetic acid to give various 2-[2-(1,3,4-thiadiazol-2-yl)hydrazinyl] quinazolin-4-amines 9a-l. The structures of the compounds have been confirmed by elemental analysis and spectral analysis. Newly synthesized compounds were screened for their antimicrobial activities.
Synthesis and Characterization of New Quinazolines as Potential Antimicrobial Agents
ChemInform, 2007
Ethyl 4-[2-(2-chlorophenyl)-4-oxo-3-hydroquinazolin-3yl]benzoate 1 which reacts with hydrazine hydrate in presence of methanol resulted into N-amino{4-[2-(2-chlorophenyl)-4-oxo(3hydroquinazolin-3-yl)phenyl}carboxamide 2. Compound 2 on treatment with aryl isothiocyanates in presence of acetone is converted into aryl-N-{[({4-[2-(2-chlorophenyl)-4-oxo(3-hydroquinazolin-3-yl)]phenyl}carbonylamino)amino]thioxo methyl}amides 3. Compound 3, in presence of sulphuric acid has yielded aryl-N-(5-{4-[2-(2-chlorophenyl)-4-oxo(3-hydroquinazolin-3-yl)]-phenyl}(1,3,4,thiadiazol-2-yl))amides 4a-l. Newly synthesized compounds 4a-l have been screened for their antibacterial and antifungal activities on Eschericia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Staphylococcus pyogenes, C. albicans, A. niger and A. clavatus.
Synthesis, Characterization and Anti-Microbial Evaluation of a Series of Quinazoline Analogs
Journal of Advanced Scientific Research
A series of substituted 6-bromo-3-(3-chloro-2-oxo-4-arylazetidin-1-yl)-2-methylquinazolin-4(3H)-one has been synthesized and evaluated for their biological activity. The title compounds (G1-G10) were prepared by the reaction of 5- bromo anthranilic acid with acetic anhydride to form 6-bromo-2-methyl-4H-benzo[1,3]oxazin-4-one which upon treatment with hydrazine hydrate in the presence of anhydrous pyridine form 3-amino-6-bromo-2-methylquinazolin- 4(3H)-one. The resulting intermediate underwent Schiff reaction with different aromatic aldehyde followed by reflux with chloroacetyl chloride and triethylamine. Ten different quinazoline derivatives (G1-G10) were synthesized. Structural assignments of these compounds have been made by elemental analysis, FTIR, 1HNMR 8 Mass spectral data and the purity of the compounds was determined by TLC. The anti-microbial activity of the newly isolated heterocyclic compounds was evaluated against Gram-positive, Gram-negative bacteria and fungi. Most of ...
Scientia Pharmaceutica, 2004
A series of quinoxaline derivatives has been synthesized by reacting 3hydrazinoquinoxalines 1a,b with many bifunctional reagents. Reaction of 1a,b with chloroacetyl chloride and ethyl chloroacetate afforded 1-chloromethyl [I .2.4]tnazoIo[4.3-alquinoxalines 2a,b and dihydro[l,2,4]triazino[4,3-alquinoxalin-2-ones 3a,b respectively. Condensation of 1a,b with ethyl acetoacetate and acetylacetone yielded 2-quinoxalinylhydrazonobutanoates 4a,b and 2quinoxalinylhydrazono-2-pentanones 5a,b respectively. Cyclization of 5a,b gave 3,5-dimethylpyrazolylquinoxalines 6a,b. Moreover, reaction of compounds 2a,b with N-phenyl piperazine derivatives afforded 4-(4-Arylpiperazin-1-yl)-1-[(4arylpiperazin-1-yl) methyl)]triazoloquinoxalines 7a+. The prepared compounds were screened for In vitro antibacterial and antifungal activities. None of the tested compounds showed significant activity towards Pseudomonas aeruginosa. However, remarkable activities were noticed for compounds 5a and Sb against Eschenchia coli. Staphylococcus aureus and Candida albicans. Compounds 6a and 6b lacked any antimicrobial activities against the tested microorganisms.
Archiv der Pharmazie, 1990
A short series of arylhydrazones of 4‐[(2‐methylimidazo[1,2‐a]pyridine‐3‐yl)azo]benzoic acid hydrazide was synthesized and tested for antimicrobial activity. All of the compounds show antimicrobial activity against Escherichia coli. A few members were also active against Klebsiella pneumoniae, Staphylococcus aureus and Pseudomonas aeruginosa. The interplanar angle (θ) between the aryl ring and the adjacent azomethine group of some representative compounds was measured by electronic absorption spectroscopy. No structure‐activity‐relationship between interplanar angle or lipophily and activity was found.
Maher A El-Hashash, Sameh A Rizk, Fakhry A El-Bassiouny Khalid M Darwish, 2012
The reactions of 2-ethoxy-4-hydrazinoquinazoline 2 with diethyl oxalate and ethyl chloroacetate gave 6-ethoxy-2H-[1,2,4] triazino [4,3-c] quinazoline-3,4-dione 3 and 6-ethoxy-2,3-dihydro-4H-[1,2,4] triazino [4, 3-c] quinazolin-4-one 4 respectively. A series of 5-ethoxy-2-X-[1, 2, 4] triazolo [1, 5-c] quinazolines 5a-d was also produced by reacting 2 with the acid chlorides namely: benzoyl, crotonyl, cinnamyl and 2-furoyl chlorides via Dimroth rearrangement. Also, 2 reacted with ethyl chloroformate giving 6. Condensation of 2 with acetone gave Schiff base 7, and with monosaccharides gave the sugar hydrazones 8a-e which was thereafter acetylated giving the corresponding 9a-e. Cyclization of 8a-e by iron(III) chloride gave triazoloquinazolines 10a-e acyclic C-nucleosides which, by acetylation, afforded 11a-e. All productswere confirmed by elemental, IR, MS, and 1H-NMR analysis. Products 8-11 were chosen for biological screening test against gram (+ ive) and gram (- ive)
Aims: This aims of this study was to synthesis new quinoxaline-based heterocycles and study its antibacterial properties. Objective: This study was designed to synthesis some 3-methyl-6-nitroquinoxaline-2-one with hydrazine moiety, characterize the synthesized compounds, and study their antibacterial properties on some bacterial strains. Materials and Methods: Six 3-methylquinoxaline-2-hydrazone derivatives were synthesized by reacting 2-hydrazinyl-3-methyl-6-nitroquinoxaline with various substituted acetophenones. The hydrazones were screened for their potential antibacterial properties. Results: All the test compounds were found to possessed promising antibacterial properties against a panel of bacterial strains screened for this study. The MIC values exhibited by these compounds ranged between 0.0313 and 0.250 mg/mL. The lowest MBC of the compounds against the test organism was 0.0625 mg/mL while the highest MBC was 0.250 mg/mL. Discussion and Conclusion: The study concluded that all the compounds exhibited appreciable bactericidal effects against all the bacterial strains, which is an indication that such synthetic Original Research Article