Steroidal pyrimidines: Synthesis, characterization, molecular docking studies with DNA and in vitro cytotoxicity

Shamsuzzaman, _; Dar, Ayaz Mahmood; Yaseen, Zahid; Alam, Khursheed; Hussain, Altaf; Gatoo, Manzoor Ahmad

doi:10.1016/j.molstruc.2013.04.033

Cited by 25 publications

(9 citation statements)

References 46 publications

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“…Furthermore, non-methyl ketones such as 3-pentanone ( 4m ), cyclohexanone ( 4n ), cycloheptanone ( 4o ), and 2-methylcyclohexanone ( 4p ) were also tolerable for this conversion and gave favorable yields of the desired pyrimidines ( 5am–p ). The initial success led us to further investigate the synthesis of steroidal pyrimidines which possess broad biological activities . In this regard, we selected pregnenolone ( 4q ) as a representative of methyl ketones and androsterone ( 4r ) as a non-methyl ketone, where the 3-hydroxy group of both compounds was unprotected.…”

Section: Resultsmentioning

confidence: 99%

Construction of a Pyrimidine Framework through [3 + 2 + 1] Annulation of Amidines, Ketones, and N,N-Dimethylaminoethanol as One Carbon Donor

Qin

2021

J. Org. Chem.

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An efficient, facile, and eco-friendly synthesis of pyrimidine derivatives has been developed. It involves a [3 + 2 + 1] three-component annulation of amidines, ketones, and one carbon source. N,N-Dimethylaminoethanol is oxidized through C(sp3)–H activation to provide the carbon donor. One C–C and two C–N bonds are formed during the oxidative annulation process. The reaction shows good tolerance to many important functional groups in air, making this methodology a highly versatile alternative, and significant improvement to the existing methods for structuring a pyrimidine framework, especially 4-aliphatic pyrimidines.

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Section: Resultsmentioning

confidence: 99%

Construction of a Pyrimidine Framework through [3 + 2 + 1] Annulation of Amidines, Ketones, and N,N-Dimethylaminoethanol as One Carbon Donor

Qin

2021

J. Org. Chem.

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“…Molecular docking is a useful tool for obtaining information about the structural features of ligand–receptor complexes and the binding affinity of a ligand with its receptor . Docking studies were therefore performed in an attempt to ascertain the type and amount of interaction between a double‐stranded DNA dodecamer [d(CGCGAATTCGCG) 2 , PDB ID http://www.rcsb.org/pdb/search/structidSearch.do?structureId=1BNA] and naproxen.…”

Section: Resultsmentioning

confidence: 99%

Naproxen intercalates with DNA and causes photocleavage through ROS generation

Husain

Yaseen

Rehman

et al. 2013

FEBS J

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Naproxen is an important non-steroidal anti-inflammatory drug with many pharmacological and biological properties. In this study, we have attempted to ascertain the mode of action and the mechanism of binding of naproxen to DNA. We have also demonstrated that, upon irradiation with white light, naproxen generates reactive oxygen species, causing DNA cleavage. Generation of reactive oxygen species from photo-irradiated naproxen as determined spectrophotometrically was found to lead to nicking of plasmid DNA as analyzed by agarose gel electrophoresis. Without photo-irradiation, naproxen binds to DNA and forms drug-DNA complexes as revealed by spectroscopic techniques. Several experiments such as determination of the effect of urea, iodide-induced quenching and a competitive binding assay with ethidium bromide showed that naproxen binds to DNA primarily in an intercalative manner. These observations were further supported by CD analysis, viscosity measurements and molecular docking. Using DNA as a template, fluorescence resonance energy transfer between naproxen and ethidium bromide was also observed, further strengthening the evidence for intercalative binding of naproxen with DNA.

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“…Some of the derivatives of 4-(4-(6-phenyl-pyrimidin-4-yl)-phenoxymethyl]-chromen-2-ones were tested for DNA cleavage activity by agarose gel electrophoresis method [ 45 ]. Shamsuzzaman et al synthesized some steroidal pyrimidines for interaction with DNA and indicated higher binding affinity of compounds towards DNA [ 46 ]. In view of the above findings, the compounds synthesized in this study were evaluated for their DNA cleavage activity.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, anti-angiogenic and DNA cleavage studies of novel N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)piperidine-4-carboxamide derivatives

Vinaya

Chandrashekara²,

Rekha³

et al. 2017

Chemistry Central Journal

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A series of novel N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)piperidine-4-carboxamide derivatives 10(a–f), 12(a–c) and 14(a–c) were synthesized and characterized by FTIR, 1H-NMR, mass spectral and elemental analysis. The efficacy of these derivatives to inhibit in vivo angiogenesis was evaluated using chick chorioallantoic membrane (CAM) model and their DNA cleavage abilities were evaluated after incubating with calf thymus DNA followed by gel electrophoresis. These novel piperidine analogues efficiently blocked the formation of blood vessels in vivo in CAM model and exhibited differential migration and band intensities in DNA binding/cleavage assays. Among the tested compounds 10a, 10b, 10c, 12b, 14b and 14c showed significant anti-angiogenic and DNA cleavage activities compared to their respective controls and the other derivatives used in this study. These observations suggest that the presence of electron donating and withdrawing groups at positions 2, 3 and 4 of the phenyl ring of the side chain may determine their potency and as anticancer agents by exerting both anti-angiogenic and cytotoxic effects.

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Steroidal pyrimidines: Synthesis, characterization, molecular docking studies with DNA and in vitro cytotoxicity

Cited by 25 publications

References 46 publications

Construction of a Pyrimidine Framework through [3 + 2 + 1] Annulation of Amidines, Ketones, and N,N-Dimethylaminoethanol as One Carbon Donor

Construction of a Pyrimidine Framework through [3 + 2 + 1] Annulation of Amidines, Ketones, and N,N-Dimethylaminoethanol as One Carbon Donor

Naproxen intercalates with DNA and causes photocleavage through ROS generation

Synthesis, anti-angiogenic and DNA cleavage studies of novel N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)piperidine-4-carboxamide derivatives

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