The natural-based optimization of kojic acid conjugated to different thio-quinazolinones as potential anti-melanogenesis agents with tyrosinase inhibitory activity

Sepehri, Nima; Iraji, Aida; Yavari, Ali; Asgari, Mohammad; Zamani, Saman; Hosseini, Samanesadat; Bahadorikhalili, Saeed; Pirhadi, Somayeh; Larijani, Bagher; Khoshneviszadeh, Mahsima; Hamedifar, Halleh; Mahdavi, Mohammad; Khoshneviszadeh, Mehdi

doi:10.1016/j.bmc.2021.116044

Cited by 45 publications

(48 citation statements)

References 21 publications

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“…2 . Intermediates 3a-n were synthesized by the method reported in our previous study 44 . Briefly, isatoic anhydride ( 1 ) was reacted with different amine ( 2a-n ) in ethanol under reflux conditions for 3 h to obtain compound 3a-n .…”

Section: Resultsmentioning

confidence: 99%

Design and synthesis of novel nitrothiazolacetamide conjugated to different thioquinazolinone derivatives as anti-urease agents

Sohrabi

Montazer

Farid

et al. 2022

Sci Rep

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The present article describes the design, synthesis, in vitro urease inhibition, and in silico molecular docking studies of a novel series of nitrothiazolacetamide conjugated to different thioquinazolinones. Fourteen nitrothiazolacetamide bearing thioquinazolinones derivatives (8a-n) were synthesized through the reaction of isatoic anhydride with different amine, followed by reaction with carbon disulfide and KOH in ethanol. The intermediates were then converted into final products by treating them with 2-chloro-N-(5-nitrothiazol-2-yl)acetamide in DMF. All derivatives were then characterized through different spectroscopic techniques (1H, 13C-NMR, MS, and FTIR). In vitro screening of these molecules against urease demonstrated the potent urease inhibitory potential of derivatives with IC50 values ranging between 2.22 ± 0.09 and 8.43 ± 0.61 μM when compared with the standard thiourea (IC50 = 22.50 ± 0.44 μM). Compound 8h as the most potent derivative exhibited an uncompetitive inhibition pattern against urease in the kinetic study. The high anti-ureolytic activity of 8h was confirmed against two urease-positive microorganisms. According to molecular docking study, 8h exhibited several hydrophobic interactions with Lys10, Leu11, Met44, Ala47, Ala85, Phe87, and Pro88 residues plus two hydrogen bound interactions with Thr86. According to the in silico assessment, the ADME-Toxicity and drug-likeness profile of synthesized compounds were in the acceptable range.

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Section: Resultsmentioning

confidence: 99%

Design and synthesis of novel nitrothiazolacetamide conjugated to different thioquinazolinone derivatives as anti-urease agents

Sohrabi

Montazer

Farid

et al. 2022

Sci Rep

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“…These activities are commonly associated with quinazoline derivatives [15,21,22]. In addition, synthetic quinazoline derivatives are known to have antioxidant and anti-melanogenesis effects [23,24]. Therefore, we hypothesized that deoxyvasicinone, which is a quinazoline derivative, might have anti-melanogenic effects.…”

Section: Discussionmentioning

confidence: 99%

Deoxyvasicinone with Anti-Melanogenic Activity from Marine-Derived Streptomyces sp. CNQ-617

et al. 2022

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The tricyclic quinazoline alkaloid deoxyvasicinone (DOV, 1) was isolated from a marine-derived Streptomyces sp. CNQ-617, and its anti-melanogenic effects were investigated. Deoxyvasicinone was shown to decrease the melanin content of B16F10 and MNT-1 cells that have been stimulated by α-melanocyte-stimulating hormone (α-MSH). In addition, microscopic images of the cells showed that deoxyvasicinone attenuated melanocyte activation. Although, deoxyvasicinone did not directly inhibit tyrosinase (TYR) enzymatic activity, real-time PCR showed that it inhibited the mRNA expression of TYR, tyrosinase-related protein 1 (TRP-1), and tyrosinase-related protein 2 (TRP-2). In the artificial 3D pigmented skin model MelanodermTM, deoxyvasicinone brightened the skin significantly, as confirmed by histological examination. In conclusion, this study demonstrated that the marine microbial natural product deoxyvascinone has an anti-melanogenic effect through downregulation of melanogenic enzymes.

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“…One of the most accessible methods of functionalization of kojic acid is its transformation into bromo-or chlorokojic acid 11, with further replacement of the halogen atom by various nucleophiles such as thioureas [28][29][30][31][32][33], alkyl mercaptans [29,30,34], thiophenols [21,35], sodium arylsulfinates [36], alkali metal thiocyanates [36][37][38][39], S-glycosylisothiuronium salts [40], various mercaptoazoles [22,25,28,29,41], 2-mercaptopyrimidines [24,42], 2-mercaptoquinazolines [43,44], mono-and dithiophosphates [45,46]. Many of the compounds obtained in this way are of interest for agrochemistry as growth regulators and herbicides comparable in efficiency to Fluazifop-P [29], or as insecticides [45,46].…”

Section: Doi: 101134/s107036322109005xmentioning

confidence: 99%

Synthesis and Some Properties of New 5-Hydroxy-2-[(hetarylthio)methyl]-4H-pyran-4-ones

et al. 2021

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The natural-based optimization of kojic acid conjugated to different thio-quinazolinones as potential anti-melanogenesis agents with tyrosinase inhibitory activity

Cited by 45 publications

References 21 publications

Design and synthesis of novel nitrothiazolacetamide conjugated to different thioquinazolinone derivatives as anti-urease agents

Design and synthesis of novel nitrothiazolacetamide conjugated to different thioquinazolinone derivatives as anti-urease agents

Deoxyvasicinone with Anti-Melanogenic Activity from Marine-Derived Streptomyces sp. CNQ-617

Synthesis and Some Properties of New 5-Hydroxy-2-[(hetarylthio)methyl]-4H-pyran-4-ones

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