Refinement of the pharmacophore of 3,4-dihydroquinazoline-2(1H)-thiones for their anti-melanogenesis activity

Pillaiyar, Thanigaimalai; Sharma, Vinay K.; Lee, Ki-Cheul; Yun, Cheong-Yong; Kim, Youngsoo; Jung, Sang‐Hun

doi:10.1016/j.bmcl.2010.06.123

Cited by 35 publications

(15 citation statements)

References 26 publications

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“…Quinazolinones and their derivatives occur frequently in natural and synthetic pharmaceutical products. Such compounds act as inhibitors of inducible and neuronal nitric oxide synthases (Camacho et al, 2016), possess anti-melanogenesis activity (Thanigaimalai et al, 2010), inhibit aldosterone synthase (CYP11B) and act as antagonists of platelet activating factor (Walser et al, 1991; Grombein et al, 2015). In recent years, many studies have been directed toward the design of 3,4-dihydroquinazolin-2( 1H )-ones for the modulation of cardiotonic contractility (Campbell et al, 1988), inhibition of methionyl-tRNA synthetase (Buckner et al, 2015) and inhibition of HIV-1 Tat-TAR (Zeiger et al, 2014) together with the design of highly selective naked-eye sensors (Mei et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

A Simple Metal-Free Cyclization for the Synthesis of 4-Methylene-3-Substituted Quinazolinone and Quinazolinthione Derivatives: Experiment and Theory

et al. 2019

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A new series of 3-substituted 4-methylene-quinazolinthiones and 4-methylene-quinazolinones were synthesized in moderate to excellent yield through a simple reaction of 2-aminoacetophenones with isocyanates or isothiocyanates. The reaction shows good tolerance of many important functional groups in the presence of air and water under metal-free conditions. Only water is produced as a coproduct, rendering this “green” methodology a highly versatile and eco-friendly alternative to the existing methods for the construction of the quinazolinone/quinazolinthione framework. We have interpreted the reaction mechanism by use of quantum chemical calculations on the basis of state-of-the-art computational methods SMD-B3LYP-D3(BJ)/BS1//B3LYP/BS1.

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Section: Introductionmentioning

confidence: 99%

A Simple Metal-Free Cyclization for the Synthesis of 4-Methylene-3-Substituted Quinazolinone and Quinazolinthione Derivatives: Experiment and Theory

et al. 2019

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“…As can be seen from the Figure b, ellagic acid could effectively inhibit tyrosinase activity. Compared with arbutin (Thanigaimalai et al, ) ( IC 50 = 180 µM), amoxicillin (Chen et al, ) ( IC 50 = 900 µM), and hesperetin (Si et al, ) ( IC 50 = 11.25 ± 1.73 mM), the value of semi‐inhibitory rate of ellagic acid was 0.2 ± 0.05 mM. These results of activity assay showed that ellagic acid was an effective tyrosinase inhibitor.…”

Section: Resultsmentioning

confidence: 91%

Antityrosinase mechanism of ellagic acid in vitro and its effect on mouse melanoma cells

Huang

Chai

et al. 2019

J Food Biochem

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The activities of ellagic acid in inhibiting mushroom tyrosinase and cell proliferation were evaluated in this research. The results of enzyme kinetics indicated that ellagic acid could effectively inhibit tyrosinase activity. The value of the semi‐inhibitory rate (IC50) was 0.2 ± 0.05 mM. Ellagic acid inhibited tyrosinase activity in a reversible manner and was a mixed tyrosinase inhibitor. Furthermore, ellagic acid had a good inhibitory effect on the proliferation of mouse melanoma B16 cells and could induce apoptosis. The results acquired from fluorescence spectroscopy revealed that the interaction of ellagic acid with tyrosinase depended on hydrogen bond and electrostatic force. In addition, computational docking showed that ellagic acid interacted with amino acid residues of tyrosinase (Asn19 and Lys372) by hydrogen bond and produced electrostatic interaction with amino residue Lys18. Practical applications In the present research, the antityrosinase mechanism of ellagic acid and its effect on mouse melanoma cells were investigated. This study suggested that ellagic acid had a strong inhibitory activity against tyrosinase and cell proliferation,which laid an experimental foundation for the development of new drugs and whitening products. The combined multispectral methods used in this research can be applied to the screening of other antityrosinase inhibitors, further promoting the development and utilization of tyrosinase inhibitors.

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“…Benzothiazines and 3,4-dihydroquinazoline-2-thiones are an important class of heterocyclest hat are prevalent in ag reat number of natural products and biologically activem olecules. [33][34][35][36] In this context, the Xu and Shen group developed catalyst-controlled solvent-free chemoselective syntheses of 2amino-3,1-benzothiazines 15 and 3,4-dihydroquinazoline-2-thiones 16 by using ortho-aminocinnamates 13 and isothiocyanates 14 (Scheme 11). They tested aw ide range of Lewis acids, including Yb(OTf) 3 ,S m(OTf) 3 3 ], and LiN(SiMe 3 ) 2 ,t oa ttemptt oa ttain exclusive chemoselectivity.…”

Section: Acid-catalyzed Thia-michaela Ddition Reactionsmentioning

confidence: 99%

Thia‐Michael Addition: An Emerging Strategy in Organic Synthesis

2018

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The thia-Michael addition reactionh as been demonstrated to be ah ighly powerful tool in organic synthesis. Indeed, the influential natureo ft his reactionh as been wellestablished in the fields of medicinal chemistry,c atalysis, drug discovery,a nd materials science. The emergence of numerous synthetic strategies that take advantage of thia-Michael addition reactions of electron-deficienta lkenes has unleashed countless opportunities for the design and synthesis of diverse biologically relevant organosulfurc ompounds. However,d espite myriad potential synthetic applications, there has not been anye xclusive reviewso ft he thia-Michael addition reaction. Therefore, this Focus Review plots the journeyo ft he thia-Michael addition reaction in organic synthesis, and is categorized according to catalyzed and catalyst-free thia-Michael addition reactions. Figure 1. Summary of the applicationsoft hia-Michael adducts.[a] Dr.Scheme1.Catalyzed pathways for the thia-Michael addition reaction.EW-G = electron-withdrawing group.Scheme2.Acetic-acid-catalyzed thia-Michael additionr eaction proposed by Allen et al. [24] AsianJ.O rg.Scheme3.Indium-bromide-catalyzed thia-Michael addition reaction.Scheme4.Thia-Michael addition reaction followed by a1 ,2-addition of TMSCN in one pot. TMSCN = trimethylsilyl cyanide.Scheme5.Bi III -catalyzedt hia-Michael additionreactiono fa,b-unsaturated carbonyl compounds. Tf = trifluoromethanesulfonyl.Scheme6.Bismuth-triflate-catalyzed synthesis of bis-thioether compounds. Bn = benzyl.Scheme7.Iron-/copper-catalyzed thia-Michael additionr eaction.Scheme8.VO(OTf) 2 -mediated synthesis of b-mercapto ketones. Np = naphthyl.Scheme9.Substrate scope for the synthesis of 3-sulfanyl-substituted 1-(arylamino)-pyrrolidine-2,5-diones.Scheme10. Regio-and enantioselective addition at the d position of conjugated systems.Scheme11. Mechanistic modelf or the enantioselective d addition of at hiol to an a,b,g,d-unsaturated dienone,catalyzed by achiral Fe III Àsalenc omplex.Scheme12. Chemoselectivesynthesis of 2-amino-3,1-benzothiazines (15) and 3,4-dihydroquinazoline-2-thiones (16)byu sing ortho-aminocinnamate (13)a nd isothiocyanates 14.Scheme13. Reactionmechanism for the chemoselective synthesis of 2amino-3,1-benzothiazines (15)and 3,4-dihydroquinazoline-2-thiones (16).Scheme14. ZrCl 4 -assisted three-component reactionf or the synthesiso fbaryl-b-mercapto ketones.Scheme15. LiF-nanocube-mediated thia-Michael addition reaction.Scheme57. Ni II -catalyzed enantioselective synthesiso f2-aryl-3-nitrothiochroman-4-ols.Scheme58. Te ntative reaction mechanism for the Ni II -catalyzed asymmetric synthesis of 2-aryl-3-nitrothiochroman-4-ols.Scheme59. Pepsin-catalyzed synthesis of functionalized chiral dihydrothiophenes.Scheme69. Mechanistic aspects of the stereoselectives ynthesis of tetrahydrothioxanthenones.Scheme70. Enantioselectivesynthesis of methyl 2-((R)-2-nitro-1-(aryl/heteroaryl)ethylthio)acetatesa nd thiomorpholin-3-ones.Scheme71. Water-accelerated thia-Michael additionr eaction proposedb y Chakraborti and co-work...

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Refinement of the pharmacophore of 3,4-dihydroquinazoline-2(1H)-thiones for their anti-melanogenesis activity

Cited by 35 publications

References 26 publications

A Simple Metal-Free Cyclization for the Synthesis of 4-Methylene-3-Substituted Quinazolinone and Quinazolinthione Derivatives: Experiment and Theory

A Simple Metal-Free Cyclization for the Synthesis of 4-Methylene-3-Substituted Quinazolinone and Quinazolinthione Derivatives: Experiment and Theory

Antityrosinase mechanism of ellagic acid in vitro and its effect on mouse melanoma cells

Thia‐Michael Addition: An Emerging Strategy in Organic Synthesis

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