Oxazolidinones as versatile scaffolds in medicinal chemistry

Abstract

Oxazolidinone is a five-membered heterocyclic ring which find broad biological applications in medicinal chemistry. Among the three possible isomers, 2-oxazolidinone is the most investigated ring in drug discovery. Linezolid was...

Phosphine‐Catalyzed Synthesis and Cytotoxic Evaluation of Michael Adducts of the Sesquiterpene Lactone Arglabin

“…Although 2oxazolidinone has traditionally been known as a pharmacophore with antibacterial effect, [62] recent studies revealed its high anticancer potential. [63][64][65][66][67] Phthalimide 6 b and uracil 6 e derivatives displayed slightly increased antiproliferative activity in M-HeLa cells with IC 50 values of 24.5 (SI = 2.52) and 21.6 μM (SI = 3.31) respectively (Table 3, Figure 5). Compound 6 e was also found to be selective against MCF-7 cells (SI = 2.75, Figure 5), albeit with a higher IC 50 value (26.0 μM) compared to 1 and 2 (Table 3).…”

“…Of special interest is the high selectivity index (SI) for compound 6 c against duodenum adenocarcinoma HuTu 80 versus normal Chang liver cells (SI=5.45, Figure 5). Although 2‐oxazolidinone has traditionally been known as a pharmacophore with antibacterial effect, [62] recent studies revealed its high anticancer potential [63–67] . Phthalimide 6 b and uracil 6 e derivatives displayed slightly increased antiproliferative activity in M‐HeLa cells with IC 50 values of 24.5 (SI=2.52) and 21.6 μM (SI=3.31) respectively (Table 3, Figure 5).…”

A Mechanistic Insight on CuI‐Catalyzed Synthesis of Oxazolidinones through a Four‐Component Reaction

“…The efficiency and selectivity of multicomponent reactions in which three or more substrates are streamlined towards the formation of a single product enable the development of novel synthetic strategies. [1] In particular, the Cu(I)-catalyzed four-component coupling of amines, aldehydes, alkynes and CO 2 is a versatile and attractive method for the synthesis of oxazolidinones, a class of heterocyclic scaffold exhibiting applications in medicinal chemistry (novel antibiotics against microbial resistance, antitubercular activity, antiviral and anti-cancer agents via topoisomerase II inhibition), [2] molecular chemistry (chiral auxiliaries in enantioselective catalysis) [3] and materials science (polymeric biocidal films, flame retardants), [4] due to their unique structural and hydrogen bonding properties.…”

Quantitative evaluation of H-donating abilities of C(sp3)–H bonds of nitrogen-containing heterocycles in hydrogen atom transfer reaction

“…Lactams and other nitrogen-containing heterocyclic compounds such as imidazolidinones, oxazolidinones, and imides are important structural units in a large number of natural products and pharmaceuticals. 1–4 In recent years, the selectivity and reactivity of these nitrogen-containing heterocycles as hydrogen atom donors (H-donor), XH, in hydrogen atom transfer reactions (HAT, X–H + Y → X + Y–H) have attracted significant attention from a large number of researchers, gradually becoming a research hotspot. 5–12 Accordingly, it is necessary to develop methods to evaluate the H-donating ability of these nitrogen-containing heterocyclic compounds as H-donors using their characteristic physical parameters.…”