Synthesis, characterization, and hypoglycemic activity of 3-(arylsulfonyl)spiroimidazolidine-2,4-diones

Iqbal, Zafar; Akhtar, Tashfeen; Hendsbee, Arthur D.; Masuda, Jason D.; Hameed, Shahid

doi:10.1007/s00706-011-0600-9

Cited by 12 publications

(4 citation statements)

References 17 publications

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“…In the present paper, we report the synthesis of a number of N -arylsulfonyl derivatives of benzimidazolones, their coupling with HES, and antidiabetic activity of the resultant conjugates, in line with our previous studies. − The activity of the neat molecules was also determined and is being compared with that of the conjugates.…”

Section: Introductionsupporting

confidence: 72%

Conjugates of Degraded and Oxidized Hydroxyethyl Starch and Sulfonylureas: Synthesis, Characterization, and in Vivo Antidiabetic Activity

et al. 2014

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Orally administered drugs usually face the problem of low water solubility, low permeability, and less retention in bloodstream leading to unsatisfactory pharmacokinetic profile of drugs. Polymer conjugation has attracted increasing interest in the pharmaceutical industry for delivering such low molecular weight (Mw) drugs as well as some complex compounds. In the present work, degraded and oxidized hydroxyethyl starch (HES), a highly biocompatible semisynthetic biopolymer, was used as a drug carrier to overcome the solubility and permeability problems. The HES was coupled with synthesized N-arylsulfonylbenzimidazolones, a class of sulfonylurea derivatives, by creating an amide linkage between the two species. The coupled products were characterized using GPC, FT-IR, (1)H NMR, and (13)C NMR spectroscopy. The experiments established the viability of covalent coupling between the biopolymer and N-arylsulfonylbenzimidazolones. The coupled products were screened for their in vivo antidiabetic potential on male albino rats. The coupling of sulfonylurea derivatives with HES resulted in a marked increase of the hypoglycemic activity of all the compounds. 2,3-Dihydro-3-(4-nitrobenzensulfonyl)-2-oxo-1H-benzimidazole coupled to HES10100 was found most potent with a 67% reduction in blood glucose level of the rats as compared to 41% reduction produced by tolbutamide and 38% by metformin.

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Section: Introductionsupporting

confidence: 72%

Conjugates of Degraded and Oxidized Hydroxyethyl Starch and Sulfonylureas: Synthesis, Characterization, and in Vivo Antidiabetic Activity

et al. 2014

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“…N-Arylsulfonyl derivatives of imidazolidine-2,4-diones, having both a sulfonyl moiety and a urea core, may be the molecules of choice to treat diabetes and associated complications. With this in mind, we have previously reported the synthesis and hypoglycemic activity of a number of N-arylsulfonylureas [26][27][28][29][30]. In continuation of our previous work, we report the synthesis of new N-arylsulfonyl derivatives of imidazolidine-2,4-dione as potent hypoglycemic agents.…”

Section: Introductionmentioning

confidence: 85%

Synthesis and in vivo hypoglycemic activity of new imidazolidine-2,4-dione derivatives

et al. 2014

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A series of new 3-arylsulfonylimidazolidine-2,4-diones (2a-2p) were synthesized by reacting imidazolidine-2,4-diones (1a-1e) with arylsulfonyl chlorides in the presence of triethyl amine. The imidazolidine-2,4-diones (1a-1e) were in turn synthesized from the corresponding ketones through Bucherer-Bergs reaction. All the synthesized compounds were characterized on the basis of their spectral (IR, 1 H and 13 C NMR and MS) and microanalytical data. The hypoglycemic activity of the compounds (2a-2p) was evaluated using alloxanized diabetic rat model. Compound 2a showed an excellent activity with a reduction in the blood glucose level of -286 ± 7 mg/dL after 5 h of drug administration as compared to -270 ± 8 mg/dL for glipizide. The hypoglycemic activity of compound 2b (-268 ± 9 mg/dL) was also comparable to the standard drug. However, only moderate activity was observed for compound 2e.

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“…On the basis of the results, the cytotoxic concentration (CC 50 ), which is the amount of tested substance that is required to reduce the number of viable cells by 50% compared to the control culture, was determined and was calculated by using the Gen 5 software (version 2.01. 14) BioTek. The investigation was carried out in triplicates.…”

Section: Cytotoxicicty Assaymentioning

confidence: 99%

“…Substituted imidazoline are an important class of molecules with a large spectrum of biological properties. Arylsulfonylimidazolinones were reported as analogs possessing broad spectrum of potent activity against various human cancers [9][10][11][12][13] as well as hypoglycemic activity 14,15 ; however, to our best knowledge, they were not tested for antiviral activity. In particular, 1-(1-benzoylindoline-5-sulfonyl)-4-phenylimidazolidinones 11 were found to have cytotoxic activity and it was justified to check if similar compounds will have antiviral activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antiviral activity of 1-(1,3-disubstitutedimidazolidyn-2-ylidene)-3-ethoxycarbonylmethylurea derivatives

Rządkowska

Szacoń

Kaczor

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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Novel 1-(1,3-disubstituted-imidazolidyn-2-ylidene)-3-ethoxycarbonylmethylurea derivatives (3a-3j) were obtained from appropriate 1-aryl-3-arylsulfonyl-1H-imidazolidine-2-imines (1a-1j) and ethyl isocyanatoacetate (2), which were subjected to condensation. Seven compounds were tested for their antiviral activity against HSV-1 and CVB3 viruses. Among the tested compounds, 3c was found to be active against HSV-1, proving that 4-methoxy substituent as R and 4-methyl substituent as R1 are most beneficial for activity against this virus. Furthermore, 3e and 3g were active against CVB3, which demonstrated that both 4-methyl and 4-chloro substitution is tolerated as R1, whereas 4-chloro and 2-methoxy substituents are best as R. It was also shown that the active compounds are characterized by relatively big surface area, small ovality, and greatest HOMO and LUMO energies in comparison to the rest of the compounds.

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Synthesis, characterization, and hypoglycemic activity of 3-(arylsulfonyl)spiroimidazolidine-2,4-diones

Cited by 12 publications

References 17 publications

Conjugates of Degraded and Oxidized Hydroxyethyl Starch and Sulfonylureas: Synthesis, Characterization, and in Vivo Antidiabetic Activity

Conjugates of Degraded and Oxidized Hydroxyethyl Starch and Sulfonylureas: Synthesis, Characterization, and in Vivo Antidiabetic Activity

Synthesis and in vivo hypoglycemic activity of new imidazolidine-2,4-dione derivatives

Synthesis and antiviral activity of 1-(1,3-disubstitutedimidazolidyn-2-ylidene)-3-ethoxycarbonylmethylurea derivatives

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