1332493-26-1Relevant articles and documents
Pyrimidinone nicotinamide mimetics as selective tankyrase and Wnt pathway inhibitors suitable for in vivo pharmacology
Johannes, Jeffrey W.,Almeida, Lynsie,Barlaam, Bernard,Boriack-Sjodin, P. Ann,Casella, Robert,Croft, Rosemary A.,Dishington, Allan P.,Gingipalli, Lakshmaiah,Gu, Chungang,Hawkins, Janet L.,Holmes, Jane L.,Howard, Tina,Huang, Jian,Ioannidis, Stephanos,Kazmirski, Steven,Lamb, Michelle L.,McGuire, Thomas M.,Moore, Jane E.,Ogg, Derek,Patel, Anil,Pike, Kurt G.,Pontz, Timothy,Robb, Graeme R.,Su, Nancy,Wang, Haiyun,Wu, Xiaoyun,Zhang, Hai-Jun,Zhang, Yue,Zheng, Xiaolan,Wang, Tao
, p. 254 - 259 (2015)
The canonical Wnt pathway plays an important role in embryonic development, adult tissue homeostasis, and cancer. Germline mutations of several Wnt pathway components, such as Axin, APC, and ?-catenin, can lead to oncogenesis. Inhibition of the poly(ADP-r
Acid-Catalyzed Synthesis of Isatoic Anhydride-8-Secondary Amides Enables IASA Transformations for Medicinal Chemistry
Gondi, Sudershan R.,Shaik, Althaf,Westover, Kenneth D.
, p. 125 - 136 (2022/01/12)
Quinazolin-dione-N-3-alklyl derivatives are the core scaffolds for several categories of bioactive small molecules, but current synthetic methods are costly, involve environmental hazards, and are not uniformly scalable. Here, we report an inexpensive, flexible, and scalable method for the one-pot synthesis of substituted quinazolin-dione-N-3-alkyls (isomers of isatoic-8-secondary amides (IASAs)) from isatin that take advantage of in situ capture of imidic acid under acidic conditions. We further show that this method can be used for the synthesis of a wide variety of derivatives with medicinal uses.
Synthesis of Novel Hydroxymethyl-Substituted Fused Heterocycles
Holmes, Jane L.,Almeida, Lynsie,Barlaam, Bernard,Croft, Rosemary A.,Dishington, Allan P.,Gingipalli, Laksmaiah,Hassall, Lorraine A.,Hawkins, Janet L.,Ioannidis, Stephanos,Johannes, Jeffrey W.,McGuire, Thomas M.,Moore, Jane E.,Patel, Anil,Pike, Kurt G.,Pontz, Timothy,Wu, Xiaoyun,Wang, Tao,Zhang, Hai-Jun,Zheng, Xiaolan
supporting information, p. 1226 - 1234 (2016/05/19)
Examples of hydroxymethylated analogues of heteroaryl cores such as quinazolin-4-ones, isoquinolin-1(2H)-ones, pyrido[3,4-d]pyrimidin-4(3H)-ones, chromen-4-ones and pyrrolo[2,1-f][1,2,4]triazin-4(3H)-ones are sparse or non-existent in the scientific literature. We have demonstrated that such compounds are accessible by using standard procedures from readily available raw materials.
N3-Alkylation during formation of quinazolin-4-ones from condensation of anthranilamides and orthoamides
Nathubhai, Amit,Patterson, Richard,Woodman, Timothy J.,Sharp, Harriet E. C.,Chui, Miranda T. Y.,Chung, Hugo H. K.,Lau, Stephanie W. S.,Zheng, Jun,Lloyd, Matthew D.,Thompson, Andrew S.,Threadgill, Michael D.
experimental part, p. 6089 - 6099 (2011/10/08)
Dimethylformamide dimethylacetal (DMFDMA) is widely used as a source of electrophilic one-carbon units at the formate oxidation level; however, electrophilic methylation with this reagent is previously unreported. Reaction of anthranilamide with DMFDMA at 150 °C for short periods gives mainly quinazolin-4-one. However, prolonged reaction with dimethylformamide di(primary-alkyl)acetals leads to subsequent alkylation at N3. 3-Substituted anthranilamides give 8-substituted 3-alkylquinazolin-4-ones. Condensation of anthranilamides with dimethylacetamide dimethylacetal provides 2,3-dimethylquinazolin-4-ones. In these reactions, the source of the N 3-alkyl group is the O-alkyl group of the orthoamides. By contrast, reaction with the more sterically crowded dimethylformamide di(isopropyl)acetal diverts the alkylation to the oxygen, giving 4-isopropoxyquinazolines, along with N3-methylquinazolin-4-ones where the methyl is derived from N-Me of the orthoamides. Reaction of anthranilamide with the highly sterically demanding dimethylformamide di(t-butyl)acetal gives largely quinazolin-4-one, whereas dimethylformamide di(neopentyl)acetal forms a mixture of quinazolin-4-one and N3-methylquinazolin-4-one. The observations are rationalised in terms of formation of intermediate cationic electrophiles (alkoxymethylidene-N,N-dimethylammonium) by thermal elimination of the corresponding alkoxide from the orthoamides. These are the first observations of orthoamides as direct alkylating agents.
