Synthesis, X-ray powder diffraction and DFT calculations of vasorelaxant active 3-(arylmethylidene)pyrrolidine-2,5-diones

Shalaby, ElSayed M.; Girgis, Adel S.; Farag, Hanaa; Mabied, Ahmed F.; Fitch, Andrew N.

doi:10.1039/c6ra24302a

Cited by 9 publications

(12 citation statements)

References 56 publications

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“…Density functional theory (DFT, ground state, in-vacuo) was undertaken for molecular structure optimization for compound AO-5 applying hybrid functional B3LYP (Becke's three-parameter hybrid functional) with 6-311G+(2d,p) basis set, utilizing the Gaussian 03 package (Tables 2 and 3, Fig. 2) [33].…”

Section: Methodsmentioning

confidence: 99%

Protective effects of Aporosa octandra bark extract against D-galactose induced cognitive impairment and oxidative stress in mice

Panda

Girgis

Prakash

et al. 2018

Heliyon

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Aporosa octandra (Buch.-Ham. ex D.Don) Vickery is a native species of India. Different parts of the plant are used for the medicinal purpose by the tribal peoples of south-eastern part of India. However, the biological properties of A. octandra have not been studied well. The extracts obtained from the bark of A. octandra were evaluated to determine their protective effect on cognitive impairment and oxidative stress in mice induced by D-galactose using the standard protocol. Different dosages of extract AOE-4 (100, 200, and 300 mg/kg, p.o.) were administered to mice, which were previously treated for six weeks with D-galactose (100 mg/kg s.c.). The D-galactose-induced mice showed significantly impaired cognitive behavior, i.e., oxidative defense, compared to the sham group. Six weeks of treatment with A. octandra extract AOE-4 (100, 200 and 300 mg/kg, p.o.) considerably improved the cognitive behavior and oxidative impairment of mice compared to the control alone (D-galactose). For the phytochemical investigation, the bark of A. octandra was successively extracted with dichloromethane and methanol. The chemical constituents of A. octandra were isolated by multiple column chromatography and characterized by different spectral analyses. (R)-Coclaurine (AO-5), an alkaloid, was isolated along with two other compounds from the AOE-4 extract; three more compounds were also isolated from the AOE-1 extract of the bark of A. octandra. All the compounds were isolated for the first time from the bark of A. octandra, and their structures were established by detailed spectral studies. The structure of compound AO-5 was also investigated and confirmed by X-ray diffraction and DFT studies. This study highlights the protective effect of A. octandra bark extract against D-galactose-induced biochemically dysfunction in mice. (R)-Coclaurine (AO-5) was isolated as one of the major components of A. octandra bark from AOE-4 extract; this compound could be further evaluated for the development of new potential drug candidates.

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Section: Methodsmentioning

confidence: 99%

Protective effects of Aporosa octandra bark extract against D-galactose induced cognitive impairment and oxidative stress in mice

Panda

Girgis

Prakash

et al. 2018

Heliyon

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“…The standard pre-contracted (norepinephrine hydrochloride) rat aorta technique was utilized for determination the vasodilation properties of the synthesized compounds 10c, 13a-i and compared with Doxazosin (a 1 -AR antagonist). 38 From the exhibited data (Table 1, ESI Fig. S33 and S34 †) it can be concluded that, many of the synthesized quinazolines are vasorelaxant active agents with efficacy comparable to that of Doxazosin.…”

Section: Vasodilation Studiesmentioning

confidence: 96%

Facile synthetic approach towards vasorelaxant active 4-hydroxyquinazoline-4-carboxamides

et al. 2019

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“…vasorelaxant, 12 anti-HIV 13 ), some of which could indeed be attributed to these compounds' Michael acceptor behavior. Moreover, the ability of these compounds to react with thiols via the conjugate addition was exploited in a recent study on bioconjugation.…”

Section: Paper Synthesismentioning

confidence: 99%

“…Indeed, the scaffold comprises a Michael acceptor moiety and the two easily and independently variable periphery groups, one of which (arylidene) could potentially assume two distinct geometrical configurations. Unsurprisingly, compounds such as 1 have been explored in connection with various biological activities (e.g., anticancer, 11 vasorelaxant, 12 anti-HIV 13 ), some of which could indeed be attributed to these compounds' Michael acceptor behavior. Moreover, the ability of these compounds to react with thiols via the conjugate addition was exploited in a recent study on bioconjugation.…”

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confidence: 99%

(E)-3-Arylidene-4-diazopyrrolidine-2,5-diones: Preparation and Use in RhII-Catalyzed X–H Insertion Reactions towards Novel, Medicinally Important Michael Acceptors

et al. 2020

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The use of readily available 1-aryl-3-arylidenepyrrolidine-2,5-diones in high yielding direct diazo-transfer reactions and subsequent involvement of the resulting diazo compounds in RhII-catalyzed O–H, S–H, and N–H insertion reactions delivered 4-substituted 1-aryl-3-arylidenepyrrolidine-2,5-diones of defined regiochemistry and geometrical configuration. These products are intended to be studied as Michael acceptors capable of inhibiting thioredoxin reductase, a promising cancer target.

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Synthesis, X-ray powder diffraction and DFT calculations of vasorelaxant active 3-(arylmethylidene)pyrrolidine-2,5-diones

Abstract: Two 3-(arylmethylidene)pyrrolidine-2,5-diones, 12a and 12b, were synthesized and characterized by powder X-ray diffraction utilizing a high-resolution synchrotron X-ray powder technique as well as DFT calculations.

Cited by 9 publications

References 56 publications

Protective effects of Aporosa octandra bark extract against D-galactose induced cognitive impairment and oxidative stress in mice

Protective effects of Aporosa octandra bark extract against D-galactose induced cognitive impairment and oxidative stress in mice

Facile synthetic approach towards vasorelaxant active 4-hydroxyquinazoline-4-carboxamides

(E)-3-Arylidene-4-diazopyrrolidine-2,5-diones: Preparation and Use in RhII-Catalyzed X–H Insertion Reactions towards Novel, Medicinally Important Michael Acceptors

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