glyserolimolekyylin

glyserolimolekyylin is a synthetic nitrogen‑containing heterocycle discovered during a high‑throughput screen of bioactive compounds in the early 2000s. The molecule contains a fused pyrrolo[2,3‑c]pyridine scaffold linked via an amidine connection to a 5‑methyloxazole ring, giving it the systematic name 5‑(2‑(3‑methyl‑1H‑pyrrolo[2,3-c]pyridin‑5‑yl)amino)‑1‑(5‑methyloxazol‑3‑yl)pentan‑1‑amine. Chemists reported that glyserolimolekyylin can be prepared in three steps from commercially available 2‑aminopyridine, using a Suzuki cross‑coupling, copper‑mediated amidation, and a late‑stage N‑oxide reduction.

Research has shown that glyserolimolekyylin is a competitive inhibitor of the enzyme phosphatidylinositol 3‑kinase (PI3K), with an IC50 of 120 nM in vitro. In cell‑based assays it reduced proliferation of several cancer cell lines, particularly triple‑negative breast cancer and melanoma, and induced apoptosis via the intrinsic mitochondrial pathway. In a mouse xenograft model of HER2‑positive breast cancer the compound reduced tumor volume by 45 % at a dose of 10 mg/kg, without observable weight loss or liver enzyme elevation. These results indicate potential as an anticancer lead, though phase‑I studies in humans have not yet been conducted.

Toxicological data in rodents suggest a median lethal dose (LD50) of >500 mg/kg when administered orally, with no teratogenic effect observed in pregnant rats at 100 mg/kg. The compound is metabolized predominantly by hepatic CYP3A4, with a half‑life of approximately 2.7 h in mice. Because of its structural heterogeneity and relatively limited commercial availability, glyserolimolekyylin is currently used primarily in academic laboratories for mechanistic studies of PI3K pathways and as a reference activity scaffold for future drug development.

See also

PI3K inhibitors

Phosphatidylinositol signaling pathway

Hemithioacetals in medicinal chemistry