Synthesis, characterization, hypoglycemic and aldose reductase inhibition activity of arylsulfonylspiro[fluorene-9,5′-imidazolidine]-2′,4′-diones

Iqbal, Zafar; Hameed, Shahid; Ali, Sahibzada Muhammad; Tehseen, Yildiz; Shahid, Mohammad; Iqbal, Jamshed

doi:10.1016/j.ejmech.2015.05.011

Cited by 40 publications

(12 citation statements)

References 26 publications

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“…Activity was not really affected when the 2-naphthyl group replaced the para substituted phenyl ring; however, 2-anthraquinyl group was found to be detrimental to the activity. The large size of the 2anthraquinyl group might be responsible for this negative effect [92].…”

Section: Anti-diabetic Activitymentioning

confidence: 99%

Pharmaceutical and medicinal significance of sulfur (SVI)-Containing motifs for drug discovery: A critical review

Zhao

Rakesh

Ravidar

et al. 2019

European Journal of Medicinal Chemistry

409

183

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a b s t r a c tSulfur (S VI ) based moieties, especially, the sulfonyl or sulfonamide based analogues have showed a variety of pharmacological properties, and its derivatives propose a high degree of structural diversity that has established useful for the finding of new therapeutic agents. The developments of new less toxic, low cost and highly active sulfonamides containing analogues are hot research topics in medicinal chemistry. Currently, more than 150 FDA approved Sulfur (S VI )-based drugs are available in the market, and they are widely used to treat various types of diseases with therapeutic power. This comprehensive review highlights the recent developments of sulfonyl or sulfonamides based compounds in huge range of therapeutic applications such as antimicrobial, anti-inflammatory, antiviral, anticonvulsant, antitubercular, antidiabetic, antileishmanial, carbonic anhydrase, antimalarial, anticancer and other medicinal agents. We believe that, this review article is useful to inspire new ideas for structural design and developments of less toxic and powerful Sulfur (S VI ) based drugs against the numerous death-causing diseases.

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Section: Anti-diabetic Activitymentioning

confidence: 99%

Pharmaceutical and medicinal significance of sulfur (SVI)-Containing motifs for drug discovery: A critical review

Zhao

Rakesh

Ravidar

et al. 2019

European Journal of Medicinal Chemistry

409

183

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“…Inhibition Following the procedure previously described, [28] the activity of aldose reductase (ALR2) was determine by observing the change in the absorbance at 340 nm. Sorbinil [29] and valproic acid [30] were used as positive control for ALR2 and ALR1, respectively The reaction mixture contained 100 mM potassium phosphate buffer (pH 6.2), 20 µL of the inhibitor, 0.1 mM NADPH and enzyme preparation in a total volume of 300 µL. The resulting mixture was incubated for 10 min at 37 º C. The reaction was initiated by the addition of 90 µL of 10 mM sodium DL-glyceraldehyde as a substrate.…”

Section: In-vitro Assay Of Aldose and Aldehyde Reductasementioning

confidence: 99%

Benzopyrazines: Synthesis, Characterization and Evaluation as Aldose Reductase Inhibitors

Bhatti¹,

Zaheer²,

Tehseen³

et al. 2019

SJC

Self Cite

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Role of aldose reductase (ALR2) in diabetic complications such as retinopathy, nephropathy, neuropathy, and cataract etc. is well-evident. ALR2 in the first step of polyol pathway reduces glucose to sorbitol whose elevated level leads to diabetic cataract, characterize by clouding of the lens in the eye that affects vision. Inhibition of ALR2 enzyme with small molecules as inhibitor is a rapid approach for diabetic management. In the present study the synthetic route to synthesize desired benzopyrazines and a library of sixteen (16) methyl benzopyrazines were screened against aldose reductase. From the bioactivity results, the 3'-hydroxyphenyl benzopyrazine 6l was found most active (IC 50 = 1.34 ± 0.07 µM) while 3'bromophenyl analogue 6i showed comparable activity for ALR2 (IC 50 = 3.48 ± 0.66 µM) as compared to standard sorbinil (IC 50 = 3.14 ± 0.02 µM). Both compounds (6l and 6i) showed excellent selectivity for ALR2 over aldehyde reductase (ALR1) which has important role in detoxification of toxic aldehydes. The structure of two regio-isomers were fully characterize by 1 H and 13 C NMR two dimensional NMR techniques including COSY, NOESY, HSQC, and HMBC. Regio-isomers separation was proved to be difficult in different solvent systems. Only an isomer of 3'-bromo benzopyrazine 6i' was isolated that help to assign the structure of regioisomers from NMR data. All the benzopyrazines were fully characterized by using different spectral techniques including 1 H, 13 C NMR, IR spectroscopy, and mass spectrometry.

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“…But the literature reveals that derivatives of fluorenone have exhibited interesting biological activities. Arylsulfonylspiro[fluorene-9,5΄-imidazolidine]-2΄,4΄-diones are found to be effective as aldose reductase inhibitors [15]. Azabenzo[a]fluorene-5,6-diones have comparable cytotoxicities against cancer cell lines in vitro, with that of standard drug doxorubicin [16].…”

Section: Introductionmentioning

confidence: 99%

“…Arylsulfonylspiro[fluorene-9,5΄-imidazolidine]-2΄,4΄-diones are found to be effective as aldose reductase inhibitors [15]. Azabenzo[a]fluorene-5,6-diones have comparable cytotoxicities against cancer cell lines in vitro, with that of standard drug doxorubicin [16]. Our previous publication [17] have successfully established the anticancer efficacy of copper complex of fluorenone based ligand; which exhibited better anticancer activity against human breast carcinoma (MCF-7) cell line when compared to that of standard drug paclitaxel.…”

Section: Introductionmentioning

confidence: 99%

Anticancer activity studies of novel metal complexes of ligands derived from polycyclic aromatic compound via greener route

Kumbar

Patil

Toragalmath³

et al. 2020

Journal of Organometallic Chemistry

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Synthesis, characterization, hypoglycemic and aldose reductase inhibition activity of arylsulfonylspiro[fluorene-9,5′-imidazolidine]-2′,4′-diones

Cited by 40 publications

References 26 publications

Pharmaceutical and medicinal significance of sulfur (SVI)-Containing motifs for drug discovery: A critical review

Pharmaceutical and medicinal significance of sulfur (SVI)-Containing motifs for drug discovery: A critical review

Benzopyrazines: Synthesis, Characterization and Evaluation as Aldose Reductase Inhibitors

Anticancer activity studies of novel metal complexes of ligands derived from polycyclic aromatic compound via greener route

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