Facile Diversity-Oriented Synthesis of Novel Dipeptide Mimetic Compounds Containing Bioactive Molecular Skeletons under Microwave Irradiation

Abstract

The diversity-oriented synthesis of dipeptide mimetic compounds embedded with bioactive molecular skeletons have been successfully established via microwave-assisted reactions between various 4-arylidene-2-phenyloxazol-5(4H)-ones and a broad scope of amines including aliphatic, aromatic, and heteroaromatic ones. This synthetic approach has prominent features of short reaction time, high yields, operational simplicity, as well as widespread applications, leading to a facile and straightforward access to structurally diverse dipeptide analogues with potential bioactivities. Moreover, the preliminary evaluation on the cytotoxic activity of this type of dipeptide derivatives has resulted in the finding of five compounds with stronger cytotoxicity than doxorubicin hydrochloride at the concentration of 10 μg/mL.

Merging Chiral Brønsted Acid/Base Catalysis: An Enantioselective [4 + 2] Cycloaddition of o-Hydroxystyrenes with Azlactones

“…Finally, due to the biological importance of dipeptides, a preliminary derivation of compound 3aa was performed by its aminolysis with propylamine, which efficiently generated chiral dipeptide mimetic compound 11 in a quantitative yield of 99% and a retained enantioselectivity of 99:1 er (eq ). …”

Brønsted Acid Catalyzed Asymmetric Diels–Alder Reactions: Stereoselective Construction of Spiro[tetrahydrocarbazole-3,3′-oxindole] Framework

“…In medicinal chemistry, it is reported that the incorporation of two bioactive moieties into another unique and complex structure may provide good opportunities for obtaining improved or new bioactivities . Besides, structure-based design and diversity-oriented synthesis have proven to be powerful tools to access structurally complex and diverse molecules with potential bioactivity .…”

Catalyst-Free and Green Synthesis of Some Novel Benzamide Derivatives

“…In addition, anti‐retroviral drugs such as HIV‐1 NCp7 inhibitors , anti‐inflammatory, antipyretic, analgesic activities, treatment of atherosclerosis , inhibitors of hepatitis C , and inhibitors for targeted melanoma therapy are remarkable properties of these compounds. Amide group is prepared via different methods such as reaction between primary amine and acyl chloride , nucleophilic attack to isothiocyanate , one‐pot condensation of an aldehyde, acetyl chloride, an enolizable ketone and acetonitrile , condensation of carboxylic acids with amines in the presence of nanosized sulfated titania , and ring‐opening of azlactones with amines . Recently, primary amides were synthesized directly from primary alcohols and ammonia using manganese oxide based octahedral molecular sieve (OMS‐2) as a heterogeneous catalyst .…”