On March 7, 2019, Goergler, Annick; Norcross, Roger; Dey, Fabian; Kusznir, Eric Andre published a patent.COA of Formula: C8H8ClN The title of the patent was Dihydrobenzimidazolones as anticancer agents and their preparation. And the patent contained the following:
The invention provides compounds of formula I which bind to the ubiquitously expressed E3 ligase protein cereblon (CRBN) and alter the substrate specificity of the CRBN E3 ubiquitin ligase complex, resulting in breakdown of intrinsic downstream proteins. Compounds of formula I are thus useful for the treatment of various cancers. Compounds of formula I wherein X1 and X2 are independently H, and C1-6 alkyl; W1, W2 and W3 are independently CH and N, provided that if one of W1 – W3 is N, then the other two are CH; Z is absent, (CH2)1-3, (CH2)0-2O(CH2)0-2, etc.; A is (un)substituted aryl, (un)substituted heteroaryl, (un)substituted heterocyclyl, etc.; and pharmaceutically acceptable salts thereof, are claimed. Example compound II was prepared by amination of 4-fluoro-N-methyl-3-nitrobenzamide with 5-amino-1H-benzo[d]imidazol-2(3H)-one; the resulting N-methyl-3-nitro-4-((2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)amino)benzamide underwent hydrogenation to give compound II. The invention compounds were evaluated for their CRBN binding affinity. From the assay, it was determined that compound II exhibited Kd value of 0.587 μM. The experimental process involved the reaction of 6-Chloro-2,3-dihydro-1H-indole(cas: 52537-00-5).COA of Formula: C8H8ClN
The Article related to dihydrobenzimidazolone preparation anticancer crbn protein degradation, Heterocyclic Compounds (More Than One Hetero Atom): Imidazoles and other aspects.COA of Formula: C8H8ClN
Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles