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1.
Chemistry ; 25(16): 4062-4066, 2019 Mar 15.
Artigo em Inglês | MEDLINE | ID: mdl-30620121

RESUMO

Air and visible light have been used in facile direct C-H oxidation of cyclic tertiary amines at ambient conditions, employing organic dyes as photocatalysts and LED. Tolerance of this new environmentally compatible protocol to various side-chain derivatizations of tryptoline and tetrahydroisoquinoline substrates was demonstrated. The developed method provides a straightforward and sustainable route towards δ-lactams, which feature strong antiviral properties (EC50 down to 4.6±1.8 µm) against human cytomegalovirus (HCMV). The clear advantages, which are easily available and inexpensive reagents, organic dyes, visible light, air/O2 and atom efficiency, make this system highly appealing for synthesis of versatile Strychnocarpine alkaloid derivatives with antiviral activity.


Assuntos
Alcaloides/farmacologia , Aminas/química , Antivirais/farmacologia , Citomegalovirus/efeitos dos fármacos , Strychnos/química , Carbolinas/química , Radicais Livres/química , Luz , Estrutura Molecular , Oxirredução , Oxigênio/química , Processos Fotoquímicos , Tetra-Hidroisoquinolinas/química
2.
Nat Commun ; 8: 15071, 2017 05 02.
Artigo em Inglês | MEDLINE | ID: mdl-28462939

RESUMO

Most of the known approved drugs comprise functionalized heterocyclic compounds as subunits. Among them, non-fluorescent quinazolines with four different substitution patterns are found in a variety of clinically used pharmaceuticals, while 4,5,7,8-substituted quinazolines and those displaying their own specific fluorescence, favourable for cellular uptake visualization, have not been described so far. Here we report the development of a one-pot synthetic strategy to access these 4,5,7,8-substituted quinazolines, which are fluorescent and feature strong antiviral properties (EC50 down to 0.6±0.1 µM) against human cytomegalovirus (HCMV). Merging multistep domino processes in one-pot under fully metal-free conditions leads to sustainable, maximum efficient and high-yielding organic synthesis. Furthermore, generation of artesunic acid-quinazoline hybrids and their application against HCMV (EC50 down to 0.1±0.0 µM) is demonstrated. Fluorescence of new antiviral hybrids and quinazolines has potential applications in molecular imaging in drug development and mechanistic studies, avoiding requirement of linkage to external fluorescent markers.

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