Why are heterocycles so special in medicinal chemistry?

Yang, Xiuyan

doi:10.1111/cbdd.14166

Cited by 3 publications

(1 citation statement)

References 20 publications

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“…Five‐membered heterocyclic rings fused to a phenyl ring play an important role in the field of synthetic chemistry, chemical biology, and drug discovery (Yu & Yang, 2022). Almost most drug molecules in the market contain at least one fused or substituted aliphatic or aromatic heterocycle moiety (Bhutani et al., 2021).…”

Section: Antifungal 123‐triazole Hybridsmentioning

confidence: 99%

Click chemistry beyond metal‐catalyzed cycloaddition as a remarkable tool for green chemical synthesis of antifungal medications

Tahghighi,

Azerang

2024

Chem Biol Drug Des

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Click chemistry is widely used for the efficient synthesis of 1,4‐disubstituted‐1,2,3‐triazole, a well‐known scaffold with widespread biological activity in the pharmaceutical sciences. In recent years, this magic ring has attracted the attention of scientists for its potential in designing and synthesizing new antifungal agents. Despite scientific and medical advances, fungal infections still account for more than 1.5 million deaths globally per year, especially in people with compromised immune function. This increasing trend is definitely related to a raise in the incidence of fungal infections and prevalence of antifungal drug resistance. In this condition, an urgent need for new alternative antifungals is undeniable. By focusing on the main aspects of reaction conditions in click chemistry, this review was conducted to classify antifungal 1,4‐disubstituted‐1,2,3‐triazole hybrids based on their chemical structures and introduce the most effective triazole antifungal derivatives. It was notable that in all reactions studied, Cu(I) catalysts generated in situ by the reduction in Cu(II) salts or used copper(I) salts directly, as well as mixed solvents of t‐BuOH/H2O and DMF/H2O had most application in the synthesis of triazole ring. The most effective antifungal activity was also observed in fluconazole analogs containing 1,2,3‐triazole moiety and benzo‐fused five/six‐membered heterocyclic conjugates with a 1,2,3‐triazole ring, even with better activity than fluconazole. The findings of structure–activity relationship and molecular docking of antifungal derivatives synthesized with copper‐catalyzed azide–alkyne cycloaddition (CuAAC) could offer medicinal chemistry scientists valuable data on designing and synthesizing novel triazole antifungals with more potent biological activities in their future research.

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Section: Antifungal 123‐triazole Hybridsmentioning

confidence: 99%

Click chemistry beyond metal‐catalyzed cycloaddition as a remarkable tool for green chemical synthesis of antifungal medications

Tahghighi,

Azerang

2024

Chem Biol Drug Des

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Highly stereoselective synthesis of α-glycosylated carboxylic acids by phenanthroline catalysis

Alom,

Rani,

Schlegel

et al. 2024

Org. Chem. Front.

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Molybdenum-Mediated One-Pot Synthesis of 2-Hydroxypyrimidines from Isoxazoles

Beaumont

Rochelle

2023

Synthesis

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A one-pot procedure towards substituted 2-hydroxypyrimidines from commercially available isoxazoles is reported. The process involves the cleavage of the isoxazole N-O bond mediated by Mo2(OAc)4, in situ hydrolysis of the resulting β-amino enone to the reactive 1,3-dicarbarbonylated intermediate, followed by hydroxypyrimidine formation in the presence of urea. Moderate to excellent yields are obtained, leading to functionalized hydroxypyrimidines. By using readily available isoxazoles, a wide range of new diverse polysubstituted hydroxypyrimidines may be prepared by this method.

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Why are heterocycles so special in medicinal chemistry?

Cited by 3 publications

References 20 publications

Click chemistry beyond metal‐catalyzed cycloaddition as a remarkable tool for green chemical synthesis of antifungal medications

Click chemistry beyond metal‐catalyzed cycloaddition as a remarkable tool for green chemical synthesis of antifungal medications

Highly stereoselective synthesis of α-glycosylated carboxylic acids by phenanthroline catalysis

Molybdenum-Mediated One-Pot Synthesis of 2-Hydroxypyrimidines from Isoxazoles

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