An Efficient Synthetic Approach Towards Benzo[b]pyrano[2,3-e][1,4]diazepines, and Their Cytotoxic Activity

Azab, Islam H. El; Elkanzi, Nadia A. A.

doi:10.3390/molecules25092051

Cited by 7 publications

(4 citation statements)

References 27 publications

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“…As an extension of our approach to the intended N -heterocycles [ 41 , 42 , 43 , 44 , 45 , 46 , 47 ], we studied the utilization of 2-(1,5-dimethyl-1 H -pyrazol-3-yl)-5-acetyl-4-methyl-thiazole ( 2 ) to construct a potentially bioactive pyran and/or pyridine hybrids. Thus, coupling of the pyrazolecarbothiamide 1 with 3-chloropentane-2,4-dione in refluxing ethanol afforded the acetyl compound 2 in a 75% yield.…”

Section: Resultsmentioning

confidence: 99%

“…Based on the aforementioned applications of nitrogen-containing heterocycles, as well as the need for the construction of new bioactive N -heterocycles [ 41 , 42 , 43 , 44 , 45 , 46 , 47 ], herein, we report an efficient and facile approach for building up novel nitrogen-containing heterocycles with promising anti-proliferative effects, starting with 2-amino-6-(2-(1,5-dimethyl-1 H -pyrazol-3-yl)-4-methylthiazol-5-yl)-4-(thiophen-2-yl)nicotinonitrile ( 4 ).…”

Section: Introductionmentioning

confidence: 99%

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Facile One-Pot Multicomponent Synthesis of Pyrazolo-Thiazole Substituted Pyridines with Potential Anti-Proliferative Activity: Synthesis, In Vitro and In Silico Studies

2021

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Pyrazolothiazole-substituted pyridine conjugates are an important class of heterocyclic compounds with an extensive variety of potential applications in the medicinal and pharmacological arenas. Therefore, herein, we describe an efficient and facile approach for the synthesis of novel pyrazolo-thiazolo-pyridine conjugate 4, via multicomponent condensation. The latter compound was utilized as a base for the synthesis of two series of 15 novel pyrazolothiazole-based pyridine conjugates (5–16). The newly synthesized compounds were fully characterized using several spectroscopic methods (IR, NMR and MS) and elemental analyses. The anti-proliferative impact of the new synthesized compounds 5–13 and 16 was in vitro appraised towards three human cancer cell lines: human cervix (HeLa), human lung (NCI-H460) and human prostate (PC-3). Our outcomes regarding the anti-proliferative activities disclosed that all the tested compounds exhibited cytotoxic potential towards all the tested cell lines with IC50 = 17.50–61.05 µM, especially the naphthyridine derivative 7, which exhibited the most cytotoxic potential towards the tested cell lines (IC50 = 14.62–17.50 µM) compared with the etoposide (IC50 = 13.34–17.15 µM). Moreover, an in silico docking simulation study was performed on the newly prepared compounds within topoisomerase II (3QX3), to suggest the binding mode of these compounds as anticancer candidates. The in silico docking results indicate that compound 7 was a promising lead anticancer compound which possesses high binding affinity toward topoisomerase II (3QX3) protein.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Facile One-Pot Multicomponent Synthesis of Pyrazolo-Thiazole Substituted Pyridines with Potential Anti-Proliferative Activity: Synthesis, In Vitro and In Silico Studies

2021

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“…In 2020, a synthetic approach for the preparation of benzo[ b ]pyrano[2,3‐ e ][1,4]diazepine 73 and its derivatives was presented by Azab and Elkanzi (Scheme 30). [51] The reaction was initiated by cyclocondensation of benzodiazepine 73 with ester 74 to form benzo[ b ]pyrano[2,3‐ e ][1,4]diazepine 75 under basic conditions. In the next stage, the researchers performed further functionalization reactions.…”

Section: Cycloaddition/annulation Reactions On Tri‐cyclic Seven‐membe...mentioning

confidence: 99%

Recent Progress in Transformations of Azepine/Oxazepine/Thiazepine Derivatives

Doraghi,

Ameli,

Karimian

et al. 2024

ChemistrySelect

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Dibenzoazepine, dibenzoxazepine and dibenzothiazepine scaffolds are an important class of N‐heterocycles that possess multiple biological activities. Due to the widespread application of these motifs in drug discovery, the synthesis of tri‐cyclic seven‐membered imines/amines has gained huge attention of chemists. In the present review, we have highlighted recent advances in functionalization and cyclization reactions of these valuable organic compounds over the last six years.

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“…Based on these applications of triazole motifs and as extension of our efforts in the synthesis and modulation of azoles as a new anticancer agent [ 21 , 22 , 23 , 24 , 25 , 26 , 27 ], we report herein the annulation of novel pharmacophore architectures via the integration of small chemical moieties, pyrazole and 1,2,3-triazole, of significant pharmacophoric impact, with aim of developing their therapeutic impacts.…”

Section: Introductionmentioning

confidence: 99%

New 1,2,3-Triazole-Containing Hybrids as Antitumor Candidates: Design, Click Reaction Synthesis, DFT Calculations, and Molecular Docking Study

et al. 2021

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In an effort to improve and achieve biologically active anticancer agents, a novel series of 1,2,3-triazole-containing hybrids were designed and efficiently synthesized via the Cu-catalyzed azide-alkyne cycloaddition (CuAAC) reaction of substituted-arylazides with alkyne-functionalized pyrazole-[1,2,4]-triazole hybrids. The structure geometry of these new clicked 1,2,3-triazoles was explored by density functional theory (DFT) using the B3LYP/6-311++G(d,p) level; also, the potential activity of the compounds for light absorption was simulated by time-dependent DFT calculations (TD-DFT). The antitumor impacts of the newly synthesized compounds were in vitro estimated to be towards the human liver cancer cell line (HepG-2), the human colon cancer cell line (HCT-116), and human breast adenocarcinoma (MCF-7). Among the tested compounds, conjugate 7 was the most potent cytotoxic candidate towards HepG-2, HCT-116, and MCF-7, with IC50 = 12.22, 14.16, and 14.64 µM, respectively, in comparison to that exhibited by the standard drug doxorubicin (IC50 = 11.21, 12.46, and 13.45 µM). Finally, a molecular docking study was conducted within the epidermal growth factor receptor (EGFR) active site to suggest possible binding modes. Hence, it could conceivably be hypothesized that analogies 7, 6, and 5 could be considered as decent lead candidate compounds for anticancer agents.

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An Efficient Synthetic Approach Towards Benzo[b]pyrano[2,3-e][1,4]diazepines, and Their Cytotoxic Activity

Cited by 7 publications

References 27 publications

Facile One-Pot Multicomponent Synthesis of Pyrazolo-Thiazole Substituted Pyridines with Potential Anti-Proliferative Activity: Synthesis, In Vitro and In Silico Studies

Facile One-Pot Multicomponent Synthesis of Pyrazolo-Thiazole Substituted Pyridines with Potential Anti-Proliferative Activity: Synthesis, In Vitro and In Silico Studies

Recent Progress in Transformations of Azepine/Oxazepine/Thiazepine Derivatives

New 1,2,3-Triazole-Containing Hybrids as Antitumor Candidates: Design, Click Reaction Synthesis, DFT Calculations, and Molecular Docking Study

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