Design, synthesis, and antimelanogenic effects of (2-substituted phenyl-1,3-dithiolan-4-yl)methanol derivatives

References

• RaperHSThe aerobic oxidasesPhysiol Rev19288245282
   Google Scholar
• MasonHSThe chemistry of melanin: mechanism of the oxidation of dihydroxyphenylalanine by tyrosinaseJ Biol Chem1948172839918920770
   PubMed Web of Science ®Google Scholar
• CookseyCJGarrattPJLandEJEvidence of the indirect formation of the catecholic intermediate substrate responsible for the autoactivation kinetics of tyrosinaseJ Biol Chem199727226226262359334191
   PubMed Web of Science ®Google Scholar
• SchallreuterKUKothariSChavanBSpencerJDRegulation of melanogenesis: controversies and new conceptsExp Dermatol20081739540418177348
   PubMed Web of Science ®Google Scholar
• HalabanRPattonRSChengEAbnormal acidification of melanoma cells induces tyrosinase retention in the early secretory pathwayJ Biol Chem2002277148211482811812790
   PubMed Web of Science ®Google Scholar
• ArtésFCastanerMGilMIEnzymatic browning in minimally processed fruit and vegetablesFood Sci Technol Int19984377389
   Web of Science ®Google Scholar
• RescignoASollaiFPisuBRinaldiASanjustETyrosinase inhibition: general and applied aspectsJ Enzyme Inhib Med Chem20021720721812530473
   PubMed Web of Science ®Google Scholar
• KimYJUyamaHTyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the futureCell Mol Life Sci2005621707172315968468
   PubMed Web of Science ®Google Scholar
• ParvezSKangMChungHSBaeHNaturally occurring tyrosinase inhibitors: mechanism and applications in skin health, cosmetics and agriculture industriesPhytother Res20072180581617605157
   PubMed Web of Science ®Google Scholar
• HanYKParkYJHaYMCharacterization of a novel tyrosinase inhibitor, (2RS,4R)-2-(2,4-dihydroxyphenyl)thiazolidine-4-carboxylic acid (MHY384)Biochim Biophys Acta2012182054254922251576
   PubMed Web of Science ®Google Scholar
• ChungKWJeongHOJangEJCharacterization of a small molecule inhibitor of melanogenesis that inhibits tyrosinase activity and scavenges nitric oxide (NO)Biochim Biophys Acta201318304752476123769841
   PubMed Web of Science ®Google Scholar
• NapolitanoAMicilloRMonfrecolaGMelanin pigmentation control by 1,3-thiazolidines: does NO scavenging play a critical role?Exp Dermatol20162559659727095321
   PubMed Web of Science ®Google Scholar
• MoonKMJeongJWLeeBAntimelanogenic activity of MHY384 via inhibition of NO-induced cGMP signallingExp Dermatol20162565265426799796
   PubMed Web of Science ®Google Scholar
• OhkumaTImaiMNakamuraMOtsujiAinventorsMitsui Chemicals, assigneeAcrylic ester compound and usage thereofEuropean patentEP1193264 A1200243
   Google Scholar
• HyunSKLeeWHJeongDMKimYChoiJSInhibitory effects of kurarinol, kuraridinol, and trifolirhizin from Sophora flavescens on tyrosinase and melanin synthesisBiol Pharm Bull20083115415818175961
   PubMed Web of Science ®Google Scholar
• MoustakasDTLangPTPeggSDevelopment and validation of a modular, extensible docking program: DOCK 5J Comput Aided Mol Des20062060161917149653
   PubMed Web of Science ®Google Scholar
• MorrisGMGoodsellDSHallidayRSAutomated docking using a Lamarckian genetic algorithm and an empirical binding free energy functionJ Comput Chem19981916391662
   Web of Science ®Google Scholar
• ShinDHKimOHJunHSKangMKInhibitory effect of capsaicin on B16-F10 melanoma cell migration via the phosphatidylinositol 3-kinase/Akt/Rac1 signal pathwayExp Mol Med20084048649418985006
   PubMed Web of Science ®Google Scholar
• ChenLGChangWLLeeCJLeeLTShihCMWangCCMelano-genesis inhibition by gallotannins from Chinese galls in B16 mouse melanoma cellsBiol Pharm Bull2009321447145219652388
   PubMed Web of Science ®Google Scholar
• BaeSJHaYMKimJAA novel synthesized tyrosinase inhibitor: (E)-2-((2,4-dihydroxyphenyl)diazenyl)phenyl 4-methylbenzenesulfonate as an azo-resveratrol analogBiosci Biotechnol Biochem201377657223291747
   PubMed Web of Science ®Google Scholar
• MatosMJVarelaCVilarSDesign and discovery of tyrosinase inhibitors based on a coumarin scaffoldRSC Adv201559422794235
   Web of Science ®Google Scholar
• CabanesJChazarraSGarcia-CarmonaFKojic acid, a cosmetic skin whitening agent, is a slow-binding inhibitor of catecholase activity of tyrosinaseJ Pharm Pharmacol1994469829857714722
   PubMed Web of Science ®Google Scholar
• MaedaKFukudaMArbutin: mechanism of its depigmenting action in human melanocyte cultureJ Pharmacol Exp Ther19962767657698632348
   PubMed Web of Science ®Google Scholar
• HaYMParkJYParkYJSynthesis and biological activity of hydroxy substituted phenyl-benzo[d]thiazole analogues for antityrosinase activity in B16 cellsBioorg Med Chem Lett2011212445244921397499
   PubMed Web of Science ®Google Scholar
• ChungKWParkYJChoiYJEvaluation of in vitro and in vivo anti-melanogenic activity of a newly synthesized strong tyrosinase inhibitor (E)-3-(2,4 dihydroxybenzylidene)pyrrolidine-2,5-dione (3-DBP)Biochim Biophys Acta2012182096296922498140
   PubMed Web of Science ®Google Scholar
• BaeSJHaYMParkYJDesign, synthesis, and evaluation of (E)-N-substituted benzylidene-aniline derivatives as tyrosinase inhibitorsEur J Med Chem20125738339023149255
   PubMed Web of Science ®Google Scholar
• KimSHHaYMMoonKMAnti-melanogenic effect of (Z)-5-(2,4-dihydroxybenzylidene) thiazolidine-2,4-dione, a novel tyrosinase inhibitorArch Pharm Res2013361189119723812774
   PubMed Web of Science ®Google Scholar
• ParkJWHaYMMoonKMDe novo tyrosinase inhibitor:4-(6,7-dihydro-5H-indeno[5,6-d]thiazol-2-yl)benzene-1,3-diol (MHY1556)Bioorg Med Chem Lett2013234172417623743286
   PubMed Web of Science ®Google Scholar
• KimSHChoiYJMoonKMThe inhibitory effect of a synthetic compound, (Z)-5-(2,4-dihydroxybenzylidene) thiazolidine-2,4-dione (MHY498), on nitric oxide-induced melanogenesisBioorg Med Chem Lett2013234332433523806552
   PubMed Web of Science ®Google Scholar
• KimHRLeeHJChoiYJBenzylidene-linked thiohydantoin derivatives as inhibitors of tyrosinase and melanogenesis: importance of the β-phenyl-α,β-unsaturated carbonyl functionalityMed Chem Commun2014514101417
   Web of Science ®Google Scholar
• KangKHLeeBSonS(Z)-2-(benzo[d]thiazol-2-ylamino)-5-(substituted benzylidene)thiazol-4(5H)-one derivatives as novel tyrosinase inhibitorsBiol Pharm Bull2015381227123326235587
   PubMed Web of Science ®Google Scholar
• LeeBMoonKMKimSJ(Z)-5-(2,4-dihydroxybenzylidene) thiazolidine-2,4-dione prevents UVB-induced melanogenesis and wrinkle formation through suppressing oxidative stress in HRM-2 hairless miceOxid Med Cell Longev20162016276146327242917
   PubMed Web of Science ®Google Scholar