Syntheses, reactivity, and biological applications of coumarins

Frontiers in Chemistry, Год журнала: 2024, Номер 12

Опубликована: Фев. 19, 2024

This comprehensive review, covering 2021-2023, explores the multifaceted chemical and pharmacological potential of coumarins, emphasizing their significance as versatile natural derivatives in medicinal chemistry. The synthesis functionalization coumarins have advanced with innovative strategies. enabled incorporation diverse functional fragments or construction supplementary cyclic architectures, thereby biological physico-chemical properties compounds obtained were enhanced. unique structure coumarine facilitates binding to various targets through hydrophobic interactions pi-stacking, hydrogen bonding, dipole-dipole interactions. Therefore, this important scaffold exhibits promising applications uncountable fields chemistry (e.g., neurodegenerative diseases, cancer, inflammation).

Язык: Английский

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Heterocyclic Compounds as Synthetic Tyrosinase Inhibitors: Recent Advances

International Journal of Molecular Sciences, Год журнала: 2023, Номер 24(10), С. 9097 - 9097

Опубликована: Май 22, 2023

Tyrosinase is a copper-containing enzyme which widely distributed in nature (e.g., bacteria, mammals, fungi) and involved two consecutive steps of melanin biosynthesis. In humans, an excessive production can determine hyperpigmentation disorders as well neurodegenerative processes Parkinson’s disease. The development molecules able to inhibit the high activity remain current topic medicinal chemistry, because inhibitors reported so far present several side effects. Heterocycle-bearing are largely diffuse this sense. Due their importance biologically active compounds, we decided report comprehensive review synthetic tyrosinase possessing heterocyclic moieties within last five years. For reader’s convenience, classified them mushroom (Agaricus bisporus) human tyrosinase.

Язык: Английский

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Synthesis, Anti-Tyrosinase Activity, and Spectroscopic Inhibition Mechanism of Cinnamic Acid–Eugenol Esters

Molecules, Год журнала: 2023, Номер 28(16), С. 5969 - 5969

Опубликована: Авг. 9, 2023

Tyrosinase plays crucial roles in mediating the production of melanin pigment; thus, its inhibitors could be useful preventing melanin-related diseases. To find potential tyrosinase inhibitors, a series cinnamic acid-eugenol esters (c1~c29) was synthesized and their chemical structures were confirmed by 1H NMR, 13C HRMS, FT-IR, respectively. The biological evaluation results showed that all compounds c1~c29 exhibited definite inhibitory activity; especially, compound c27 strongest inhibitor (IC50: 3.07 ± 0.26 μM), being ~4.6-fold stronger than positive control, kojic acid 14.15 0.46 μM). Inhibition kinetic studies validated as reversible mixed-type against tyrosinase. Three-dimensional fluorescence circular dichroism (CD) spectra indicated change conformation secondary structure Fluorescence-quenching quenched static manner with one binding site. Molecular docking also revealed interactions between Therefore, esters, especially c27, used lead to inhibitors.

Язык: Английский

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Rosa × damascena Herrm. essential oil: anti-tyrosinase activity and phytochemical composition

Frontiers in Pharmacology, Год журнала: 2024, Номер 15

Опубликована: Сен. 11, 2024

Tyrosinase is a key enzyme in melanin synthesis, and its natural inhibitors are receiving increasing attention.

Язык: Английский

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Small-Molecule Tyrosinase Inhibitors for Treatment of Hyperpigmentation

Molecules, Год журнала: 2025, Номер 30(4), С. 788 - 788

Опубликована: Фев. 8, 2025

Increasing attention is being focused on skin health currently, especially the excessive deposition of melanin in skin. Tyrosinase, rate-limiting enzyme biosynthesis, a crucial synthesis. However, existing tyrosinase inhibitors pose some degree toxicity to humans. Therefore, development more efficient and low-toxicity urgently needed. This review briefly depicts biosynthesis process crystal structure catalytic mechanism tyrosinase. The latest research progress regarding small-molecule also reviewed. Moreover, structure-function relationships are analyzed summarized. expected provide new scientific insights enable researchers explore safer potent inhibitors.

Язык: Английский

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WELPSA: A Green Catalyst Mediated Microwave Assisted Efficient Synthesis of Novel 5‐Aminopyrazole‐4‐Carbonitrile Derivatives as Anticancer Agents (MCF‐7, A‐549) and In Silico Studies

Archiv der Pharmazie, Год журнала: 2025, Номер 358(4)

Опубликована: Апрель 1, 2025

ABSTRACT Malononitrile, modified hydrazine, and quinoline aldehyde were combined in a one‐pot reaction under microwave irradiation to create the medicinally significant family of heterocyclic scaffolds, quinoline, coumarin, thiazole, pyrazole 4‐carbonitrile derivatives with help green solvent as water. WELPSA (water extract lemon peel‐soaked ash) is used speed up solvent‐free environment, according more environmentally friendly protocols. This methodology offers several advantages like short duration, synthesis, high yield, no need for chromatographic techniques, catalyst recyclability five cycles, so on. Synthesized evaluated anticancer potential against lung (A549) breast cancer cell lines. Among tested compounds, 4i 4j exhibited remarkable activities. Further investigations using Annexin V staining flow cytometry revealed that both compounds effectively induced apoptosis A549 cells. Compound was subjected molecular docking dynamic studies understand basis their activity, which demonstrated strong interaction target protein 1m17, providing insights into its mechanism action. These findings highlight promising candidates drug development.

Язык: Английский

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Evaluation of Tyrosinase Inhibitory Activity of Carbathioamidopyrazoles and Their Potential Application in Cosmetic Products and Melanoma Treatment

International Journal of Molecular Sciences, Год журнала: 2025, Номер 26(8), С. 3882 - 3882

Опубликована: Апрель 19, 2025

Hyperpigmentation can be prevented by regulating melanin synthesis through tyrosinase inhibition. As such, inhibitors like arbutin, kojic acid, and hydroquinone are commonly used for skin lightening. Recent studies suggest that certain pyrazole derivatives with activity may also have anticancer potential influencing melanocyte transformation tumor progression, positioning them as promising candidates both cosmetic therapeutic uses. The aim of this study was to evaluate the inhibitory carbothioamidopyrazole derivatives. Inhibition determined using Dixon method, leveraging in silico molecular docking circular dichroism (CD) spectroscopy analyze fluorescence quenching. Carbothioamidopyrazole at C-3 C-5 positions ring effective alternatives traditional skin-lightening agents. These induce structural changes tyrosinase, thus altering its activity, influence transformation. Their dual action agents makes valuable future research. Two compounds exhibited stronger than acid. Molecular suggests these block preventing substrate access active site. results underscore applications.

Язык: Английский

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Design, synthesis and biological evaluation of novel kojic acid triazole hybrids as tyrosinase inhibitors and antibrowning agents

Scientific Reports, Год журнала: 2025, Номер 15(1)

Опубликована: Апрель 29, 2025

In this study, two series of kojic acid triazole hybrids, namely 6a-6p and 13a-13t, were designed synthesized. Subsequently, their biological activities including anti-tyrosinase, antioxidant, as anti-browning effects investigated. The results showed that most compounds demonstrated excellent inhibitory effect against mushroom tyrosinase compared with standard reference drug (kojic acid, IC50 = 26.090 µM). Of particular note, 13t proved to be the potent inhibitor an value low 1.363 µM. Further kinetic inhibition studies suggested presented such powerful anti-tyrosinase efficacy by functioning a mixed-type (Ki 0.3647 µM, Kis 0.8492 Moreover, from molecular docking fluorescence quenching revealed 13t's on stemmed its ability directly bind active site tyrosinase. Besides, antioxidant activity, effect, cytotoxicity accordingly investigated, all yielding highly satisfactory results. Collectively, these findings position promising candidate, providing valuable framework for development novel, efficient, safe inhibitors endowed capabilities.

Язык: Английский

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In Vitro and In Vivo Biological Evaluation of Indole-thiazolidine-2,4-dione Derivatives as Tyrosinase Inhibitors

Molecules, Год журнала: 2023, Номер 28(22), С. 7470 - 7470

Опубликована: Ноя. 7, 2023

Tyrosinase is an important rate-limiting enzyme in melanin biosynthesis. To find potential tyrosinase inhibitors with anti-melanogenic activity, a series of indole-thiazolidine-2,4-dione derivatives 5a~5z were synthesized by incorporating indole thiazolidine-2,4-dione into one compound and assayed for their biological activities. All compounds displayed inhibitory activities 5w had the highest anti-tyrosinase activity IC50 value 11.2 μM. Inhibition kinetics revealed as mixed-type inhibitor. Fluorescence quenching results indicated that quenched fluorescence static process. CD spectra 3D suggested binding could change conformation microenvironment tyrosinase. Molecular docking also represented between Moreover, inhibit melanogenesis both B16F10 cells zebrafish model. Therefore, serve inhibitor activity.

Язык: Английский

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Inhibition mechanism investigation of quercetagetin as a potential tyrosinase inhibitor

Frontiers in Chemistry, Год журнала: 2024, Номер 12

Опубликована: Июнь 3, 2024

Tyrosinase is one important rate limiting enzyme in melanin synthesis, directly affecting the synthesis. Quercetagetin active ingredient from marigold. Thence, inhibition effects of quercetagetin against tyrosinase were investigated. The results showed could inhibit activity with IC 50 value 0.19 ± 0.01 mM and type was a reversible mixed-type. Results fluorescence quenching quench static process. CD 3D interaction to change conformation activity. Moreover, docking revealed details quercetagetin’s interactions tyrosinase.

Язык: Английский

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