A convenient synthesis of lubeluzole and its enantiomer: Evaluation as chemosensitizing agents on human ovarian adenocarcinoma and lung carcinoma cells

Cavalluzzi, Maria Maddalena; Viale, Maurizio; Bruno, Claudio; Carocci, Alessia; Catalano, Alessia; Carrieri, Antonio; Franchini, Carlo; Lentini, Giovanni

doi:10.1016/j.bmcl.2013.06.077

Cited by 13 publications

(8 citation statements)

References 19 publications

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“…Moreover, the activity of test compounds must be compared with one or two well-known reference standards sharing the same biological property. When synergistic behaviour is investigated, the isobole analysis should also be performed [192]. On these analysis basis, a number of studies on CLs isolated from plants in recent years approximate the above ideal drug leads picture.…”

Section: General Summary and Conclusionmentioning

confidence: 99%

The Chemistry and Pharmacology of Citrus Limonoids

et al. 2016

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Citrus limonoids (CLs) are a group of highly oxygenated terpenoid secondary metabolites found mostly in the seeds, fruits and peel tissues of citrus fruits such as lemons, limes, oranges, pumellos, grapefruits, bergamots, and mandarins. Represented by limonin, the aglycones and glycosides of CLs have shown to display numerous pharmacological activities including anticancer, antimicrobial, antioxidant, antidiabetic and insecticidal among others. In this review, the chemistry and pharmacology of CLs are systematically scrutinised through the use of medicinal chemistry tools and structure-activity relationship approach. Synthetic derivatives and other structurally-related limonoids from other sources are include in the analysis. With the focus on literature in the past decade, the chemical classification of CLs, their physico-chemical properties as drugs, their biosynthesis and enzymatic modifications, possible ways of enhancing their biological activities through structural modifications, their ligand efficiency metrics and systematic graphical radar plot analysis to assess their developability as drugs are among those discussed in detail.

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Section: General Summary and Conclusionmentioning

confidence: 99%

The Chemistry and Pharmacology of Citrus Limonoids

et al. 2016

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“…Mexiletine (1a) and its analogues (1b,c) were prepared in two steps according to the synthetic route depicted in Scheme 1, carried out in both traditional conditions and microwave-assisted synthesis. In the first step, 2,6-dimethylphenol underwent Williamson reaction [21] with the suitable halo ketone (2aec) to obtain aryloxyalkyl ketones (3aec) which were converted into the corresponding amines 1aec by reductive amination under both traditional and microwave conditions [22]. The corresponding hydrochloride salts (1aec·HCl) were obtained by treating 1aec with gaseous HCl.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis, antiarrhythmic activity, and toxicological evaluation of mexiletine analogues

Roselli

Carocci

Budriesi

et al. 2016

European Journal of Medicinal Chemistry

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Four mexiletine analogues have been tested for their antiarrhythmic, inotropic, and chronotropic effects on isolated guinea pig heart tissues and to assess calcium antagonist activity, in comparison with the parent compound mexiletine. All analogues showed from moderate to high antiarrhythmic activity. In particular, three of them (1b,c,e) were more active and potent than the reference drug, while exhibiting only modest or no negative inotropic and chronotropic effects and vasorelaxant activity, thus showing high selectivity of action. All compounds showed no cytotoxicity and 1b,c,d did not impair motor coordination. All in, these new analogues exhibit an interesting cardiovascular profile and deserve further investigation.

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“…1). It is reported that S-and R-enantiomers of a chiral drug usually have different biological activities, one could be selected as a drug with a therapeutic action while the other to be avoided due to toxic or side effects [16,17] . As a LTD4 (leukotriene D4) receptor antagonist, montelukast sodium has a superior in vitro and in vivo compared with its S-enantiomer [7] .…”

Section: [[[(1r)-1-[3-[(e)-2-(7-chloroquinolin-2-yl)-ethenyl]phenyl]-mentioning

confidence: 99%

Simultaneous Determination of Montelukast Sodium S-Enantiomer and A5 Enantiomers in Montelukast Sodium Bulk Drug by Normal-Phase Chiral HPLC

Wang¹

2017

ijps

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Wang, et al.: Simultaneous Determination of Montelukast Enantiomers by Normal-Phase Chiral HPLCA sensitive and validated high performance liquid chromatographic method was developed for determination of montelukast sodium S-enantiomer, A5 and A5 R-enantiomer in montelukast sodium bulk drug. Chromatographic analysis was performed on a Daicel Chiralpak ® AD-H column at 30°, the flow rate was set 0.9 ml/min, eluent was n-hexane:isopropanol:ethanol:trifluoroacetic acid:diethylamine (65:15:20:0.1:0.1, v/v/v/v/v), determination wavelength was 280 nm and the injection volume was 10 μl. The high performance liquid chromatography was validated for system suitability, precision, limit of detection and limit of quantitation, linearity, accuracy and robustness. The results indicated that the system suitability test met the requirement with resolution more than 2.0 between montelukast sodium enantiomers and greater than 6.0 between A5 enantiomers. The values of relative standard deviation were not more than 4.0% for precision test, the limit of detection from 0.11 to 0.24 μg/ml, and the limit of quantitation from 0.22 to 0.61 μg/ml, respectively. The linearity correlation coefficients (r) were greater than 0.99 for three analytes. The recovery values were ranged from 89.35 to 108.78%. The proposed method was adequate for the determination of montelukast sodium S-enantiomer, A5 and A5 R-enantiomer in montelukast sodium bulk drug.

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A convenient synthesis of lubeluzole and its enantiomer: Evaluation as chemosensitizing agents on human ovarian adenocarcinoma and lung carcinoma cells

Cited by 13 publications

References 19 publications

The Chemistry and Pharmacology of Citrus Limonoids

The Chemistry and Pharmacology of Citrus Limonoids

Synthesis, antiarrhythmic activity, and toxicological evaluation of mexiletine analogues

Simultaneous Determination of Montelukast Sodium S-Enantiomer and A5 Enantiomers in Montelukast Sodium Bulk Drug by Normal-Phase Chiral HPLC

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