Synthesis, evaluation of 6,8-dibromo-2-aryl-2,3-dihydroquinolin-4(1H)-ones in MCF-7 (breast cancer) cell lines and their docking studies

Bheemanapalli, Lakshmi Narayana; Kaur, Amandeep; Arora, Ramandish; Sangeeta, .; Akkinepally, Raghuram Rao; Javali, Narashima Murthy

doi:10.1007/s00044-011-9688-z

Cited by 16 publications

(13 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…amounts through dietary sources and food supplements (more recently termed 'nutraceuticals'). It has been demonstrated that several flavanoid derivatives are potent AIs as well as effective antiproliferative agents against MCF-7 (breast cancer) cell lines (12,13). This substantiates our hypothesis that the flavonoid scaffold could churn out to be a milestone in developing the next generation of safer AIs.…”

supporting

confidence: 85%

Molecular Modeling Evaluation of Non‐Steroidal Aromatase Inhibitors^†

et al. 2012

View full text Add to dashboard Cite

A recent discovery of aromatase crystal structure triggered the efforts to design novel aromatase inhibitors for breast cancer therapy. While correlating docking scores with inhibitory potencies of known ligands, feeble robustness of scoring functions toward prediction was observed. This prompted us to develop new prediction models using stepwise regression analysis based on consensus of different docking and their scoring methods (GOLD, LIGANDFIT, and GLIDE). Quantitative structure-activity relationships were developed between the aromatase inhibitory activity (pIC 50 ) of flavonoid derivatives (n = 39) and docking scores and docking descriptors. QSAR models have been validated internally [using leave-oneout cross-validated r 2 cv (LOO À Q2 )] and externally to ensure the predictive capacity of the models.

show abstract

supporting

confidence: 85%

Molecular Modeling Evaluation of Non‐Steroidal Aromatase Inhibitors^†

et al. 2012

View full text Add to dashboard Cite

show abstract

“…Although 2-aminobenzamide is commercially available and has been used in several transformations before, to our knowledge, direct bromination of this compound has not been explored so far. On the other hand, the analogous 2'-aminoacetophenone has been found to undergo bromination with NaBr-oxone in acetonitrile [18], Br 2 in acetic acid [19], or N-bromosuccinimide (NBS) in CHCl 3 -CCl 4 mixture [20] to afford 2-amino-3,5-dibromoacetophenone in high yield. Based on these literature precedents, we subjected anthranilamide 1 to NBS (2.5 equiv.)…”

Section: Resultsmentioning

confidence: 99%

2-Aryl-6,8-dibromo-2,3-dihydroquinazolin-4(1<i>H</i>)-ones as substrates for the synthesis of 2,6,8-triarylquinazolin-4-ones

Mphahlele

Maluleka²,

Khoza³

2014

Bull. Chem. Soc. Eth.

View full text Add to dashboard Cite

ABSTRACT. Direct bromination of 2-aminobenzamide was achieved using N-bromosuccinimide in chloroform-carbon tetrachloride mixture at room temperature for 3 h to afford 2-amino-3,5-dibromobenzamide in high yield and purity. 2-Amino-3,5-dibromobenzamide was, in turn, condensed with benzaldehyde derivatives in the presence of boric acid to afford novel 2-aryl-6,8-dibromo-2,3-dihydroquinazolin-4(1H)-ones. Suzuki-Miyaura cross-coupling of the latter with arylboronic acids yielded the corresponding 2,6,8-triaryl-2,3-dihydroquinazolin-4(1H)-ones. These triarylquinazolin-4(1H)-ones were dehydrogenated using iodine (2 equiv.) in ethanol under reflux to yield the potentially tautomeric 2,6,8-triarylquinazolin-4(3H)-ones.

show abstract

“…The most active compounds (Fig. 14) form a hydrogen bonding with Ser 478 or Asp 309 amino acids of the active site, which probably account, according the authors, for their better activity compared to other analogs of the series [88]. Fig.…”

Section: Another Docking Model Was Determined For the Interaction Betmentioning

confidence: 92%

“…The same research group of the prior cited work also determined a docking model for 6,8-dibromo-2-aryl-2,3dihydroquinolin-4(1H)-ones, which were evaluated in vitro (for MCF-7 breast cancer cell lines) [88]. The docking stud-ies were determined to recognize the binding motif of the title compounds within the active of aromatase enzyme employing GOLD docking software using the same X-ray crystal structure of human placental microsomal aromatase (PDB ID: 3EQM) [78].…”

Section: Another Docking Model Was Determined For the Interaction Betmentioning

confidence: 99%

SAR, QSAR and Docking of Anticancer Flavonoids and Variants: A Review

Scotti

Mendonça²,

Moreira³

et al. 2013

CTMC

View full text Add to dashboard Cite

Flavonoids are phenolic compounds, secondary metabolites of plants that cause several benefits to our health, including helping the treatment against cancer. These pharmacological properties are associated with the ability of flavonoids in attenuating the generation of reactive oxygen species, acting as chelate compounds or affecting the oxi-redox cycle. In spite of the large number of information in term of SAR and QSAR, no recent review has tabulated and discussed in detail these data. In view of this, we bring here a detailed discussion of the structure-activity relationships (SAR) and quantitative structure-activity relationships (QSAR) models. We have also analyzed the correlation between the chemical structure of flavonoids and analogues to their anticancer activities. A large number of methodologies have been used to identify the characteristics of these compounds with their potential anticancer: multiple linear regression, principal components analysis, comparative molecular field analysis, comparative molecular similarity indices analysis, partial least squares, neural networks, configuration of classification and regression trees, Free-Wilson, docking; using topological, structural and enthalpies' descriptors. We also discussed the use of docking models, together with QSAR models, for the virtual screening of anticancer flavonoids. The importance of docking models to the medicinal chemistry of anticancer flavonoids has increased in the last decade, especially to help in identifying the structural determinants responsible for the activity. We tabulated here the most important examples of virtual screening determined for anticancer flavonoids and we highlighted the structural determinants. The mode of action, the most potent anticancer flavonoids and hints for the structural design of anticancer flavonoids are revised in details and provided here.

show abstract

Synthesis, evaluation of 6,8-dibromo-2-aryl-2,3-dihydroquinolin-4(1H)-ones in MCF-7 (breast cancer) cell lines and their docking studies

Cited by 16 publications

References 22 publications

Molecular Modeling Evaluation of Non‐Steroidal Aromatase Inhibitors^†

Molecular Modeling Evaluation of Non‐Steroidal Aromatase Inhibitors^†

2-Aryl-6,8-dibromo-2,3-dihydroquinazolin-4(1<i>H</i>)-ones as substrates for the synthesis of 2,6,8-triarylquinazolin-4-ones

SAR, QSAR and Docking of Anticancer Flavonoids and Variants: A Review

Contact Info

Product

Resources

About

Synthesis, evaluation of 6,8-dibromo-2-aryl-2,3-dihydroquinolin-4(1H)-ones in MCF-7 (breast cancer) cell lines and their docking studies

Cited by 16 publications

References 22 publications

Molecular Modeling Evaluation of Non‐Steroidal Aromatase Inhibitors†

Molecular Modeling Evaluation of Non‐Steroidal Aromatase Inhibitors†

2-Aryl-6,8-dibromo-2,3-dihydroquinazolin-4(1<i>H</i>)-ones as substrates for the synthesis of 2,6,8-triarylquinazolin-4-ones

SAR, QSAR and Docking of Anticancer Flavonoids and Variants: A Review

Contact Info

Product

Resources

About

Molecular Modeling Evaluation of Non‐Steroidal Aromatase Inhibitors^†

Molecular Modeling Evaluation of Non‐Steroidal Aromatase Inhibitors^†