New N-(phenoxydecyl)phthalimide derivatives displaying potent inhibition activity towards α-glucosidase

Pascale, Rossana; Carocci, Alessia; Catalano, Alessia; Lentini, Giovanni; Spagnoletta, Anna; Cavalluzzi, Maria Maddalena; Santis, Francesco De; Palma, Annalisa De; Scalera, Vito; Franchini, Carlo

doi:10.1016/j.bmc.2010.06.088

Cited by 44 publications

(27 citation statements)

References 27 publications

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“…The synthetic sequence to (R)-and (S)-MHM (Scheme 1) exploits the one previously reported for the racemate [17]. Homochiral aminopropanols 1 were protected with phthalic anhydride in quantitative yield to give the phthalimido alcohols 2 which were reacted with 4-chloro-2,6dimethylphenol under Mitsunobu conditions [15,24,25]. Nitration of compounds 3 [26] gave nitroderivatives 4.…”

Section: Resultsmentioning

confidence: 98%

Stereospecific Synthesis of m-Hydroxymexiletine Enantiomers

Catalano

Carocci²,

Lentini³

et al. 2013

DML

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m-Hydroxymexiletine (MHM) is a metabolite of mexiletine, a well known class IB anti-arrhythmic drug, which presents almost twice the activity of the parent compound on cardiac voltage-gated sodium channels. Given the different activity of mexiletine enantiomers on sodium currents (being the R-isomer the eutomer), it is conceivable that (R)- and(S)-MHM could differ in pharmacodynamic and pharmacokinetic properties, too. Herein we report the efficient synthesis of MHM enantiomers that could represent useful tools for further investigations on stereospecific requirements of the voltage-gated sodium channel binding site. MHM enantiomers and all the homochiral intermediates were fully characterized. The ee values for (R)- and (S)-MHM were >99%, as assessed by capillary electrophoresis using β-cyclodextrin sulfated sodium salt as a chiral selector.

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Section: Resultsmentioning

confidence: 98%

Stereospecific Synthesis of m-Hydroxymexiletine Enantiomers

Catalano

Carocci²,

Lentini³

et al. 2013

DML

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“…suggesting the molecular formula of C 47 H 77 NO 17 . The IR spectrum exhibited absorptions for a OH (3339 cm À 1 ) and an amide group (1639 cm À 1 ).…”

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“…3). NOESY Correlations HÀC(3)/HÀC(5), HÀC(5)/HÀC(9), HÀC(9)/HÀC (14), HÀC(14)/HÀC (16), and HÀC(14)/HÀC (17) indicated that these Hatoms were all a-oriented. The NOESY correlations HÀC(8)/Me (18), and Me(18)/ Me(19) allowed these to be assigned as b.…”

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confidence: 97%

“…Mammalian a-glucosidase is the key enzyme catalyzing the final step in the digestive process of carbohydrates. Inhibition of a-glucosidase has been demonstrated to be an effective therapeutic target for Type-2 diabetes mellitus [16] [17]. Since the MeOH extract and BuOH fraction used in this study showed inhibitory activities against rat intestinal sucrase and maltase, 1 and 2 were also evaluated for these activities.…”

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confidence: 99%

“…Starting from the anomeric H-atoms, all sugar resonances were assigned by detailed analysis of latter attributable to Me(27) as the starting points. The successive correlations starting from HÀC(1) and terminating at HÀC (17), and those staring from Me(27) ending at HÀC(23) were shown in Fig. 2 (Fig.…”

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Two Novel Steroidal Alkaloid Glycosides from the Seeds of Lycium barbarum

Wang

Sasaki

et al. 2011

Chemistry & Biodiversity

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Physical–chemical studies of new, versatile carbazole derivatives and zinc complexes: Their synthesis, investigation of in vitro inhibitory effects on α‐glucosidase and human erythrocyte carbonic anhydrase I and II isoenzymes

Çol

Emirik

Alım

et al. 2022

Applied Organom Chemis

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In this study, two novel zinc–phthalocyanine complexes (4a and 6a), containing carbazole rings, were investigated. The first phthalocyanine 4a has been synthesized from 4‐(2‐(3‐acetyl‐9H‐carbazol‐9‐yl)ethoxy at the peripheral position. Likewise, the second phthalocyanine 6a has been synthesized from 4‐(2‐(3‐cinnamoyl‐9H‐carbazol‐9‐yl)ethoxy at the same position. The new phthalocyanines (Pcs) and their ligands are soluble in organic solvents, such as dimethylformamide, dimethyl sulfoxide, dichloromethane, ethyl acetate, and methanol/ethanol. The Zn (II) complexes were characterized by Fourier transform infrared spectroscopy, nuclear magnetic resonance (NMR) (except 13C NMR for complexes), elemental analysis, mass spectrometry, and UV–Vis spectroscopy. Also, photophysical and photochemical properties and cyclic voltammogram for the N‐substituted carbazole zinc–Pcs have been reported. The evaluation of carbazole Zn (II) complexes (4a and 6a) and ligands (3, 4, 5, and 6) for in vitro α‐glucosidase inhibitory activities was performed compared to standard drugs acarbose, and kinetic studies were also carried out to determine their inhibition modes. The inhibitory effects of these new Pcs (4a and 6a) and their ligands (3, 4, 5, and 6) on human erythrocytes carbonic anhydrase I (hCA I) and II (hCA II) isoenzymes were investigated. Moreover, in silico studies were also carried out to better investigate the interactions of N‐substituted carbazole containing zinc Pcs with the active sites of hCA I and II isoforms.

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New N-(phenoxydecyl)phthalimide derivatives displaying potent inhibition activity towards α-glucosidase

Cited by 44 publications

References 27 publications

Stereospecific Synthesis of m-Hydroxymexiletine Enantiomers

Stereospecific Synthesis of m-Hydroxymexiletine Enantiomers

Two Novel Steroidal Alkaloid Glycosides from the Seeds of Lycium barbarum

Physical–chemical studies of new, versatile carbazole derivatives and zinc complexes: Their synthesis, investigation of in vitro inhibitory effects on α‐glucosidase and human erythrocyte carbonic anhydrase I and II isoenzymes

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