Synthesis, molecular docking studies of coumarinyl-pyrazolinyl substituted thiazoles as non-competitive inhibitors of mushroom tyrosinase

Saeed, Aamer; Mahesar, Parvez Ali; Channar, Pervaiz Ali; Abbas, Qamar; Larik, Fayaz Ali; Hassan, Mubashir; Raza, Hussain; Seo, Sung‐Yum

doi:10.1016/j.bioorg.2017.08.002

Cited by 66 publications

(40 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Various pyrazolinyl thiazoles have pharmacological and biological applications (Abdel-Wahab et al, 2017;Abd-Rabou et al, 2018;Saeed et al, 2017). In addition, heterocycles containing both pyrazole and thiazole moieties have been used as versatile intermediates in organic synthesis of biologically active compounds (Secrieru et al, 2019;Shaabani et al, 2019;Sharma et al, 2020).…”

Section: Structure Descriptionmentioning

confidence: 99%

2-[3-(4-Chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]-5-[(4-fluorophenyl)diazenyl]-4-methylthiazole

et al. 2020

View full text Add to dashboard Cite

The molecule of the title compound, C25H18ClF2N5S, comprises almost co-planar fluorophenyl, methylthiazolyl, pyrazolyl and chlorophenyl rings with the second fluorophenyl ring almost perpendicular to this plane. One fluorophenyl group is disordered over two components of occupancy ratio 0.767 (10):0.233 (10) related by a 24.2 (8)° twist. In the crystal, two molecules related by inversion symmetry are linked by a pair of C—H...F contacts in an R(8)2 2 geometry.

show abstract

Section: Structure Descriptionmentioning

confidence: 99%

2-[3-(4-Chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]-5-[(4-fluorophenyl)diazenyl]-4-methylthiazole

et al. 2020

View full text Add to dashboard Cite

show abstract

“…These result was similar like our findings about DMTA which DMTA caused a moderate inhibition (10.58 % inhibition at 500 mg/L). Another study, 3-(5-(4-(benzyloxy) -3methoxyphenyl) -1-(4-(4-bromophenyl) thiazol-2-yl) -4,5-dihydro-1H-pyrazol-3-yl) -2Hchromen-2-one was shown to be a potential tyrosinase inhibitor [14].…”

Section: Effect Of 2-amino-4-(chloromethyl)thiazole Hydrochloride On mentioning

confidence: 99%

Determination of Glutathione Reductase Activity Changes Exposed to Some 2-Aminothiazole Derivatives

Karadag

Eroğlu

Kırılmış

2019

Cumhuriyet Science Journal

View full text Add to dashboard Cite

In this work, effects of concentrations ranging from 0 to 500 mg/L of some 2-aminothiazole derivatives such as 4,4'-(disulfanediylbis(methylene))bis(thiazol-2-amine) dihyrochloride (DMTA) and 2amino-4-(chloromethyl)thiazole hydrochloride (ACT) on glutathione reductase from baker's yeast (Saccharomyces cerevisiae) (GR) were investigated. With exposure of 25, 50, 100, 250 and 500 mg/L concentrations, % GR activity changes were calculated as-5.29 ;-3.85 ;-2.40 ;-6.73 and-10.58 in DMTA applications, while these changes were calculated as +0.98 ; 0.00 ;-0.49 ;-2.45 and 0.00 in ACT applications, respectively. This work indicated that there was a slight decrease in GR activity with the increase of DMTA concentrations and there was no significant change in GR activity with the increase of ACT concentrations. But according to control activities, no statitistical changes were observed in GR activities with exposure of these 2aminothiazole derivatives (p > 0.05, n=3).

show abstract

“…(It is worth noting that, as no human tyrosinase can be obtained from commercial resources, we here used mushroom tyrosinase as a substitution, like many excellent studies do. (Ashraf et al 2015;Larik et al 2017;Masamoto et al 2003;Saeed et al 2017) Although the entire structure of mushroom tyrosinase is different from human-origin tyrosinase, the catalytic sites of both two kinds of tyrosinase are very similar.) Aliquots (5 μL) of test compounds at various concentrations (10 -11 ~ 10 -4 M, dissolved in methanol and diluted by water) were mixed with 50 μL of L-tyrosine or L-Dopa solution (1.25…”

Section: In Vitro Tyrosinase Inhibition Assaymentioning

confidence: 99%

“…Melanogenesis is a physiological melanin-producing process. The final product of melanogenesis, melanin, which is the pigment produced by epidermis melanocytes, is the main determining factor of pigmentation of human eyes and skin (Hassan et al 2017;Pillaiyar et al 2015;Saeed et al 2017). Under normal physiological states, melanin is primarily responsible for protecting skin against damaging effects of ultraviolet radiation (Abbas et al 2017;Costin & Hearing 2007).…”

Section: Introductionmentioning

confidence: 99%

Peer Review #2 of "Identification by shape-based virtual screening and evaluation of new tyrosinase inhibitors (v0.1)"

2018

View full text Add to dashboard Cite

Targeting tyrosinase is considered to be an effective way to control the production of melanin. Tyrosinase inhibitor is anticipated to provide new therapy to prevent skin pigmentation, melanoma and neurodegenerative diseases. Herein, we report our results in identifying new tyrosinase inhibitors. The shape-based virtual screening was performed to discover new tyrosinase inhibitors. Thirteen potential hits derived from virtual screening were tested by biological determinations. Compound 5186-0429 exhibited the most potent inhibitory activity. It dose-dependently inhibited the activity of tyrosinase, with the IC50 values 6.2 ± 2.0 μM and 10.3 ± 5.4 μM on tyrosine and L-Dopa formation, respectively. The kinetic study and molecular docking of 5186-0429 demonstrated that this compound acted as a competitive inhibitor. We believe the discoveries here could serve as a good starting point for further design of potent tyrosinase inhibitor.

show abstract

Synthesis, molecular docking studies of coumarinyl-pyrazolinyl substituted thiazoles as non-competitive inhibitors of mushroom tyrosinase

Cited by 66 publications

References 25 publications

2-[3-(4-Chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]-5-[(4-fluorophenyl)diazenyl]-4-methylthiazole

2-[3-(4-Chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]-5-[(4-fluorophenyl)diazenyl]-4-methylthiazole

Determination of Glutathione Reductase Activity Changes Exposed to Some 2-Aminothiazole Derivatives

Peer Review #2 of "Identification by shape-based virtual screening and evaluation of new tyrosinase inhibitors (v0.1)"

Contact Info

Product

Resources

About