Anticancer Efficacy of Antibacterial Quinobenzothiazines (original) (raw)
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International Journal of Molecular Sciences
In this paper, we describe a new method for synthesizing hybrid combinations of 1,2,3-triazoles with a tetracyclic quinobenzothiazinium system. The developed approach allowed for the production of a series of new azaphenothiazine derivatives with the 1,2,3-triazole system in different positions of the benzene ring. In practice, the methodology consists of the reaction of triazole aniline derivatives with thioquinanthrenediinium bis-chloride. The structure of the products was determined by 1H-NMR, 13C-NMR spectroscopy, and HR-MS spectrometry, respectively. Moreover, the spatial structure of the molecule and the arrangement of molecules in the crystal (unit cell) were determined by X-ray crystallography. The anticancer activity profiles of the synthesized compounds were tested in vitro against human cancer cells of the A549, SNB-19, and T47D lines and the normal NHDF cell line. Additional tests of antibacterial activity against methicillin-sensitive and methicillin-resistant staphyloc...
Anticancer evaluation of novel quinazolines carrying a biologically active pyrimidine
2016
A novel series of quinazolines incorporating a biologically active 4, 6-dimethylpyrimidine, 1, 2, 4-triazine, benzo[d][1,3]dioxol, morpholinophenyl, quinoline, sulfonamide and thioureamoieties9-14, 15,16,19, 20 and 2-hydrazinylquinazoline derivative 22were designed and synthesized using methyl 2-isothiocyanato derivative2 as strategic starting material. The structure of the newlysynthesized compounds was confirmed by elemental analyses and spectral data. All the prepared compounds were evaluated for their invitro anticancer activity against breast cancer cell lines. It was found that quinazoline carrying free amino group at 3-position with sulfa-phenazolegroup at 2-position20 and thioureido derivative bearing sulfa-phenazole16 with IC50values (2.64 and 4.60 µg/mL) showed better activity thandoxorubicin as positive control. In addition compounds 14, 12 and 15 are nearly as active as doxorubicin as reference drug, while compounds 9, 13, 11 and 19 exhibited a moderate activity. On the ...
2013
The novel heterocyclization of 5-(2-aminophenyl)-1Н-tetrazole with potassium ethylxanthogenate or carbon disulfide was proposed. The potassium salt of the tetrazolo[1,5-c]quinazoline-5-thione was subsequently modified by alkylation with proper halogen derivatives to (tetrazolo[1,5-c]quinazolin-5-ylthio)alkyls, N,N-dialkylethylamines, 1-aryl-2-ethanones, 1-(alkyl)aryl-2-ethanols, carboxylic acids, and esters. The structures of all newly synthesized compounds were confirmed by FT-IR, UV-vis, LC-MS, 1 H, 13 C NMR, and elemental analysis data. The substances were screened for antibacterial and antifungal activities (100 µg) against Escherichia coli, Staphylococcus aureus, Enterobacter aerogenes, Entrococcus faecalis, Pseudomonas aeruginosa, Klebsiella pneumoniae, and Candida albicans. Preliminary bioluminescence inhibition tests against Photobacterium leiognathi Sh1 showed that substances 5.2-5.4, 6.1, 7.1 with ethanone or carboxylic acid substituents showed toxicity against bacteria cells. The substances chosen by the US National Cancer Institute (NCI) were screened for their ability to inhibit 60 different human tumor cell lines, where 2-(tetrazolo[1,5-c]quinazolin-5-ylthio)-1-(4-tolyl)ethanone (5.2), 3-(tetrazolo[1,5-c]quinazolin-5-ylthio)propanoic and related 3-metyl-butanoic acids (6.2, 6.3), and ethyl tetrazolo[1,5-c]quinazolin-5-ylthio)acetate (7.2) L. M. Antypenko et al.:
Bulletin of environment, pharmacology and life science, 2021
Some novel 4-(substituted aniline)quinazoline were synthesized in good yields and evaluated for their possible antibacterial, anti-fungal and anticancer activities and acute toxicity. The structures of the synthesized compounds were confirmed on the basis of their spectral data and elemental analysis. Their antibacterial activity evaluated by the agar cup method while their anti-fungal activities were evaluated by poison plate method and in-vitro anticancer activity by using HeLa & MCF-7 cell line. Quinazoline derivatives had failed to produce antibacterial activity against the gram negative strains but possess the weak antibacterial activity against the gram positive strains. In other hand, the substitution, 4-bromo and 3-nitro in compound 2(S2), on 4-aniloquinazoline ring had shown the strong antifungal activity (90%) against Fusarium moniliforme, hence it is equipotent with Griseofulvin. These compound suggesting that it could be useful in the treatment of fungal infection.
Quinazoline compounds for antitumor treatment
Experimental Oncology, 2019
Quinazolines are among the most useful heterocyclic compounds due to their diverse chemical reactivity and a wide range of biological activity. Despite a large number of publications devoted to quinazolines and their derivatives, information is presented predominantly regarding the features of the synthesis of these compounds and their structure. The studies of specific pharmacological activity and antitumor activity of these compounds are mainly limited to primary screening using enzyme systems and cell lines. In this mini review information concerning the potential targets for antitumor action of quinazoline compounds is summarized and discussed.
In vivo anti-tumour activity of novel Quinazoline derivatives
European review for medical and pharmacological sciences, 2012
The two scaffold Quinazoline analogues (Compound 21, NSC: 95112/753439 and Compound 12, NSC: D-104834/ 758270) in three different concentrations were evaluated for their anti-tumor activity against Ehrlich ascites carcinoma (EAC) and two different concentration were evaluated for their anti-tumor activity against Dalton's ascites lymphoma (DLA) bearing Swiss albino mice. The in vivo anti-tumor potency of Quinazoline bases was assessed in EAC model by measuring the increase in mean survival time of the drug treated over untreated control mice and treated standard (Gefitinib) mice. Their toxicity was assessed in vivo in normal, standard, and EAC-bearing mice by measuring the drug-induced changes in haematological parameters. The in vivo anti-tumor potency of Quinazoline bases was assessed in DLA model by measuring solid tumor volume, solid tumor weight and % inhibition of the tumor weight of the drug treated over untreated control mice and treated standard (Gefitinib) mice. Among ...
2021
Background: Quinazoline and quinazolinone scaffolds represent an important class of biologically active nitrogen heterocyclic compounds. Many marketed drugs are based on these moieties. A diverse range of molecules with quinazoline/quinazolinone moieties have been reported to exhibit broad spectrum of biological activities Objective: This study is aimed at the synthesis of these quinazolinone derivatives, quinazolin-4(3H)-One, 2-Methyl4(3H)-quinazolinone and 2–Phenyl-4(3H)-quinazolin-4(3H)–one and evaluate them for their antibacterial activities. Method: The consolidation of 2-amino-methyl-4-methoxybenzoate with acetic anhydride produced the cyclic compound 2-methyl-4, 5-disubstituted-1, 3-benzo-oxazine-4-one which also produce a novel 2,3-disubstituted quinazolin-4 ones via the reaction with hydrazine hydrate. The quinazolinone derivatives quinazolin-4(3H)-One, 2Methyl-4(3H)-quinazolinone and 2–Phenyl-4(3H)-quinazolin-4(3H)–one were evaluated pharmacologically for their in vivo ana...
European Journal of Medicinal Chemistry, 2011
A series of novel s-triazine analogs were synthesized and characterized by IR, 1H NMR, 13C NMR, 19F NMR spectroscopy and elemental analysis. Preliminary screening of target compounds against eight bacteria (Staphylococcus aureus, Bacillus cereus, Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae, Salmonella typhi, Proteus vulgaris, Shigella flexneria), four fungi (Aspergillus niger, Aspergillus fumigatus, Aspergillus clavatus, Candida albicans) and Mycobacterium tuberculosis H37Rv indicated that 5d, 5h, 5n, 5p, 5q, 5r, 5s, 5t and 5u were the most active compounds among twenty one studied. Thus, they were further subjected to in vitro biological evaluation against human prostate cancer cell line (DU-145) and the results indicate that two compounds 5n and 5s were markedly active.Twenty one new s-triazine derivatives have been synthesized and evaluated for their efficacy as antimicrobial, antimycobacterial and anticancer agents. The results indicated that some derivatives were potentially active.► A series of novel piperazino(piperidino)-s-triazines have been synthesized. ► Compounds were screened for their in vitro antimicrobial, antimycobacterial and anticancer activities. ► New compounds are characterized adequately by FT-IR, 1H NMR, 13C NMR, 19F NMR spectroscopy and CHN analysis. ► New compounds indicated broad spectrum of potential bioactivities.