Molecular docking simulation and anticancer assessment on human breast carcinoma cell line using novel bis(1,4-dihydropyrano[2,3- c ]pyrazole-5-carbonitrile) and bis(1,4-dihydropyrazolo[4′,3′:5,6]pyrano[2,3- b ]pyridine-6-carbonitrile) derivatives

Salama, Soad K.; Mohamed, Magda F.; Darweesh, Ahmed F.; Elwahy, Ahmed H. M.; Abdelhamid, Ismail A.

doi:10.1016/j.bioorg.2017.01.009

Cited by 70 publications

(20 citation statements)

References 34 publications

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“…4 Department of Pharmaceutics, Faculty of Pharmacy, Umm Al-Qura University, Makkah, Saudi Arabia. 5 Department of Pharmaceutics and Industrial Pharmacy, Faculty of Pharmacy, Minia University, Minia, Egypt. 6 Department of Medical Microbiology & Immunology, Faculty of Medicine Assiut University, Assiut 71516, Egypt.…”

Section: Supplementary Informationmentioning

confidence: 99%

“…The fabulous ability of heterocyclic moiety to serve as both biomimetic and active pharmacophores has mainly contributed to their distinctive value as traditional key elements of various drugs. Due to their broad pharmacological profile, the nitrogen and sulfur-containing heterocycles demonstrate an imperative class in the biological research and drug industry areas [3][4][5][6][7][8]. Amongst them, the thiazole ring is a core structural moiety found in a wide range of biologically and medicinally active molecules.…”

Section: Introductionmentioning

confidence: 99%

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Bioactive fluorenes. Part III: 2,7-dichloro-9H-fluorene-based thiazolidinone and azetidinone analogues as anticancer and antimicrobial against multidrug resistant strains agents

et al. 2020

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Background: Thiazoles, thiazolidinones and azetidinones are highly ranked amongst natural and synthetic heterocyclic derivatives due to their great pharmaceutical potential. Results: New thiazolidinone and azetidinone class of bioactive agents based on 4-(2,7-dichloro-9H-fluoren-4-yl) thiazole moiety have been successfully synthesized. 4-(2,7-dichloro-9H-fluoren-4-yl)thiazol-2-amine was synthesized and allowed to react with various aryl/heteroaryl aldehydes to afford the corresponding Schiff base intermediates. The target thiazolidinone and azetidinone analogues have derived from Schiff bases by their reactions with thioglycolic acid and chloroacetyl chloride, respectively. The newly synthesized compounds were then evaluated for their antimicrobial activity against some multidrug resistant strains and examined for cytotoxic activity against normal lung fibroblast (WI-38), human lung carcinoma (A549), and human breast carcinoma (MDA-MB-231) cell lines to develop a novel class of fluorene-based bioactive agents. The mode of action and the binding interaction of the synthesized compound with the active sites of dihydrofolate reductase enzyme were well identified by fluorescence-activated cell sorting (FACS) analysis and molecular docking study. Conclusion: Some of the synthesized compounds showed remarkable activity against A-549 and MDA-MB-231 when compared to Taxol, which was used as a reference drug. 2,7-dichloro-9H-fluorene-based azetidinones are more efficient as antimicrobial and anticancer agents compared to dichloro-9H-fluorene-based thiazolidinones derivatives.

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Section: Supplementary Informationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Bioactive fluorenes. Part III: 2,7-dichloro-9H-fluorene-based thiazolidinone and azetidinone analogues as anticancer and antimicrobial against multidrug resistant strains agents

et al. 2020

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“…To date, several pyrazolone derivatives have been shown to possess promising antiproliferative activity in human cancer cell lines [56][57][58][59][60][61]. Metamizole is pyrazolone derivative with pronounced analgesic, antipyretic, spasmolytic properties and favourable gastro-intestinal safety profile [62,63].…”

Section: Dapi Stainingmentioning

confidence: 99%

Metamizole (dipyrone) – cytotoxic and antiproliferative effects on HeLa, HT-29 and MCF-7 cancer cell lines

Nikolova

Marinov

Georgieva

et al. 2018

Biotechnology & Biotechnological Equipment

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“…Heterocyclic ring systems possessing a pyrazole ring fused to an oxygen-containing six-membered heterocycle are present in a wide variety of biologically active compounds. For example, the 1,4- and 2,4-dihydropyrano[2,3- c ]pyrazole ring systems [1] often represent the main structural motifs of anticancer [2–4], anti-inflammatory [5], and antidiabetic agents [6]. The numerous known methods for the preparation of these compounds are generally based on multicomponent reactions of an aromatic aldehyde, a β-keto ester, a hydrazine and malononitrile [7].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2H-furo[2,3-c]pyrazole ring systems through silver(I) ion-mediated ring-closure reaction

Milišiūnaitė¹,

Paulavičiūtė²,

Arbačiauskienė³

et al. 2019

Beilstein J. Org. Chem.

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Fused pyrazole ring systems are common structural motifs of numerous pharmaceutically important compounds. Nevertheless, access to derivatives of the aromatic 2H-furo[2,3-c]pyrazole ring system is still quite limited, and their chemistry and functional properties remain largely underexplored. The current study investigates routes to construct this system from easily accessible starting materials using metal-catalyzed reactions. A simple and efficient procedure to access the 2H-furo[2,3-c]pyrazole ring system was developed by employing the silver(I) ion-mediated ring-closure reaction of 4-alkynyl-3-hydroxy-1-phenyl-1H-pyrazoles as a key step. The required intermediate hydroxyalkynyl substrates for this reaction were prepared by a Pd-catalyzed coupling of 4-iodo-1-phenyl-1H-pyrazol-3-ol with ethyne derivatives. The structures of the obtained target compounds were unequivocally confirmed by detailed 1H, 13C and 15N NMR spectroscopic experiments, HRMS and a single-crystal X-ray diffraction analyses. This silver(I)-mediated 5-endo-dig cyclization of readily available 4-alkynyl-3-hydroxy-1H-pyrazoles can be used as an efficient method to access many novel 2,5-disubstituted 2H-furo[2,3-c]pyrazoles.

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Molecular docking simulation and anticancer assessment on human breast carcinoma cell line using novel bis(1,4-dihydropyrano[2,3- c ]pyrazole-5-carbonitrile) and bis(1,4-dihydropyrazolo[4′,3′:5,6]pyrano[2,3- b ]pyridine-6-carbonitrile) derivatives

Cited by 70 publications

References 34 publications

Bioactive fluorenes. Part III: 2,7-dichloro-9H-fluorene-based thiazolidinone and azetidinone analogues as anticancer and antimicrobial against multidrug resistant strains agents

Bioactive fluorenes. Part III: 2,7-dichloro-9H-fluorene-based thiazolidinone and azetidinone analogues as anticancer and antimicrobial against multidrug resistant strains agents

Metamizole (dipyrone) – cytotoxic and antiproliferative effects on HeLa, HT-29 and MCF-7 cancer cell lines

Synthesis of 2H-furo[2,3-c]pyrazole ring systems through silver(I) ion-mediated ring-closure reaction

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