Discovery of potent antiproliferative agents from selected oxygen heterocycles as EGFR tyrosine kinase inhibitors from the U.S. National Cancer Institute database by in silico screening and bioactivity evaluation

Q4 · MEDICINE

Article

Author: Ruchirawat, Somsak ; Seetaha, Supaporn ; Saruengkhanphasit, Rungroj ; Niwetmarin, Worawat ; Choowongkomon, Kiattawee ; Jiwacharoenchai, Nattanan ; Eurtivong, Chatchakorn

A similarity search was conducted on the U.S. Enhanced National Cancer Institute Database Browser 2.2 to find structures related to 1,5-dihydroxy-9H-xanthen-9-one, a previously established EGFR-TK inhibitor. Compounds were virtually screened and selected for bioactivity testing revealed 5 candidates, mostly displayed stronger antiproliferative activities than erlotinib with IC₅₀ values between 0.95 and 17.71 μM against overexpressed EGFR-TK cancer cell lines: A431 and HeLa. NSC107228 displayed the strongest antiproliferative effects with IC₅₀ values of 2.84 and 0.95 μM against A431 and HeLa cancer cell lines, respectively. Three compounds, NSC81111, NSC381467 and NSC114126 inhibited EGFR-TK with IC₅₀ values between 0.15 and 30.18 nM. NSC81111 was the best inhibitor with IC₅₀ = 0.15 nM. Molecular docking analysis of the 3 compounds predicted hydrogen bonding and hydrophobic interactions with key residues were important for the bioactivities observed. Furthermore, calculations of the physicochemical properties suggest the compounds are drug-like and are potentially active orally.

02 Oct 2020·Organic LettersQ1 · CHEMISTRY

Regiodivergent Hydration–Cyclization of Diynones under Gold Catalysis

Q1 · CHEMISTRY

Article

Author: Sanz, Roberto ; Suárez-Pantiga, Samuel ; Muñoz, Miguel A. ; Solas, Marta

Skipped diynones, efficiently prepared from biomass-derived ethyl lactate, undergo a tandem hydration-oxacyclization reaction under gold(I) catalysis. Reaction conditions have been developed for a switchable process that allows selective access to 4-pyrones or 3(2H)-furanones from the same starting diynones. Further application of this methodology in the total synthesis of polyporapyranone B was demonstrated.

01 Jan 2017·Monatshefte für Chemie - Chemical MonthlyQ4 · CHEMISTRY

Synthesis of γ-pyrones via decarboxylative condensation of β-ketoacids

Q4 · CHEMISTRY

Article

Author: Maier, Thomas ; Rodrigues, Catarina A B ; Maulide, Nuno ; Merad, Jérémy

ABSTRACTThis manuscript describes the convergent synthesis of aryl- and alkyl-disubstituted γ-pyrones from β-ketoacids. The reaction proceeds in the presence of trifluoromethanesulfonic anhydride via an unprecedented decarboxylative auto-condensation of the starting material. Herein, the scope and limitations of this transformation are reported.GRAPHICAL ABSTRACT

100 Deals associated with NSC-81111

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Indication	Highest Phase	Country/Location	Organization	Date
Neoplasms	Discovery	Thailand	Kasetsart University	04 Jan 2022

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