Synthesis of 4‐(4‐Methylsulfonylphenyl)‐3‐phenyl‐2(3<i>H</i>)‐thiazole Thione Derivatives as New Potential COX‐2 Inhibitors

Emami, Saeed; Foroumadi, Alireza

doi:10.1002/cjoc.200690150

Cited by 17 publications

(5 citation statements)

References 16 publications

(21 reference statements)

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“…Subsequently, dehydration of 3a – c with diluted hydrochloric acid furnished 2(3 H )‐thiazole thiones 4a – c in a good yield. The 4‐phenyl analogs 5a and b were prepared by the reaction of corresponding α‐bromoacetophenone with triethylammonium N ‐phenyldithiocarbamate 19 in acetone and subsequent dehydration in 80% H 2 SO 4 .…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Evaluation of 2(3H)‐Thiazole Thiones as Tyrosinase Inhibitors

Emami

Hosseinimehr

Shahrbandi

et al. 2012

Archiv der Pharmazie

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A series of 2(3H)-thiazole thiones 3-5 was synthesized and evaluated for tyrosinase inhibition and DPPH radical scavenging activities. Among them, 3-methyl-4-phenyl-2(3H)-thiazole thione (4a) showed good tyrosinase inhibitory activity, even better than that of the well-known tyrosinase inhibitor, namely, kojic acid. From the structure-activity point of view, although it was found that the phenolic hydroxyl group in prototype 3-5 might contribute to the scavenging activity against DPPH radicals, there was no correlation between the potency of tyrosinase inhibition and the presence of the phenolic moiety. The in silico ADME-Tox screening revealed that the drug-likeness and drug-score values of the most potent compound 4a were significantly higher than those of kojic acid.

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Section: Resultsmentioning

confidence: 99%

“…Triethylammonium N ‐phenyldithiocarbamate 19 (270 mg, 1 mmol) suspended in acetone (7 mL) was stirred and cooled in an ice bath. Then, α‐bromoacetophenone 2a and b (1 mmol) was added portion‐wise over a 30 min period.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Evaluation of 2(3H)‐Thiazole Thiones as Tyrosinase Inhibitors

Emami

Hosseinimehr

Shahrbandi

et al. 2012

Archiv der Pharmazie

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“…7 For instance, they display many biological activities such as antimicrobial, 8 antimalarial, 9 anti-inflammatory, 10 anticancer, 11 antiviral, 12 pesticidal, 13 and inhibition of HIV-1, 14 gp41, 15 JSP-1, 16 IKKβ, 17 PRL-3, 18 cholesterol esterase, 19 and potential BACE-1. 20 Furthermore, 3-phenylthiazole-2(3H)-thiones act as COX-2 inhibitors, 21 tyrosinase inhibitors 22 and combretastatin analogs. 23 In this manuscript, we present a new class of atropisomeric compounds belonging to the 3-arylthiazolidine-2-thione family (Scheme 1) that can be easily prepared by reacting an aryl isothiocyanate and 1,4-dithiane-2,5-diol under microwave irradiation.…”

Section: Introductionmentioning

confidence: 99%

Atropisomerism in 3-arylthiazolidine-2-thiones. A combined dynamic NMR and dynamic HPLC study

et al. 2016

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Sterically hindered 3-arylthiazolidine-2-thiones were prepared by a solvent-free reaction with arylisothiocyanates and 1,4-dithiane-2,5-diol. Atropisomerism was observed in two compounds (3 and 4, aryl = 1-naphthyl and 2-methylnaphth-1-yl), whose rotational energy barriers were measured using dynamic NMR and dynamic HPLC. The experimental analyses were supported by DFT calculations. Thermally stable atropisomers were obtained by dehydration of compounds 3 and 4 and the absolute configuration of the atropisomers of compound 6 was determined by theoretical simulation of the ECD and VCD spectra.

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“…Second, the heterocyclic ring of 1a is an imidazole. Thiazoles (an imidazole with an N substituted for an S) are important antiinflammatory and immune-suppressive agents (Emami and Foroumadi, 2006; Nishikaku et al, 1994; Pattan et al, 2009; Siddiqui et al, 2009). In addition, previous studies have suggested that thiazoles may exhibit higher efficacy than imidazoles in rat models of inflammation with edema (Unangst et al, 1994).…”

Section: Introductionmentioning

confidence: 99%

Simple modifications to methimazole that enhance its inhibitory effect on tumor necrosis factor-α-induced vascular cell adhesion molecule-1 expression by human endothelial cells

Alapati

Deosarkar²,

Lanier

et al. 2015

European Journal of Pharmacology

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The expression of vascular cell adhesion molecule-1 (VCAM-1) on the vascular endothelium can be increased by pro-inflammatory cytokines [e.g. tumor necrosis factor – α (TNF-α)]. VCAM-1 contributes to leukocyte adhesion to, and emigration from, the vasculature which is a key aspect of pathological inflammation. As such, a promising therapeutic approach for pathological inflammation is to inhibit the expression of VCAM-1. Methimazole [3-methyl-1, 3 imidazole-2 thione (MMI)] is routinely used for the treatment of Graves’ disease and patients treated with MMI have decreased levels of circulating VCAM-1. In this study we used cultured human umbilical vein endothelial cells (HUVEC) to investigate the effect of MMI structural modifications on TNF-α induced VCAM-1 expression. We found that addition of a phenyl ring at the 4-nitrogen of MMI yields a compound that is significantly more potent than MMI at inhibiting 24 h TNF-α-induced VCAM-1 protein expression. Addition of a para methoxy to the appended phenyl group increases the inhibition while substitution of a thiazole ring for an imidazole ring in the phenyl derivatives yields no clear difference in inhibition. Addition of the phenyl ring to MMI appears to increase toxicity as does substitution of a thiazole ring for an imidazole ring in the phenyl MMI derivatives. Each of the compounds reduced TNF-α-induced VCAM-1 mRNA expression and had a functional inhibitory effect, i.e. each inhibited monocytic cell adhesion to 24 h TNF-α-activated HUVEC under fluid flow conditions. Combined, these studies provide important insights into the design of MMI-related anti-inflammatory compounds.

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Synthesis of 4‐(4‐Methylsulfonylphenyl)‐3‐phenyl‐2(3H)‐thiazole Thione Derivatives as New Potential COX‐2 Inhibitors

Cited by 17 publications

References 16 publications

Synthesis and Evaluation of 2(3H)‐Thiazole Thiones as Tyrosinase Inhibitors

Synthesis and Evaluation of 2(3H)‐Thiazole Thiones as Tyrosinase Inhibitors

Atropisomerism in 3-arylthiazolidine-2-thiones. A combined dynamic NMR and dynamic HPLC study

Simple modifications to methimazole that enhance its inhibitory effect on tumor necrosis factor-α-induced vascular cell adhesion molecule-1 expression by human endothelial cells

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