Pd-catalyzed amination of 6-halo-2-cyclopropyl-3-(pyridyl-3-ylmethyl) quinazolin-4(3H)-one

Synthesis and Biological Evaluation of Pyrroloindolines as Positive Allosteric Modulators of the α1β2γ2 GABAA Receptor

“…From the aryl bromide, Cu-catalyzed methoxylation provided methoxy analogue (+)- 14 . Additionally, Buchwald–Hartwig coupling of aryl bromide (+)- 13 gave morpholine (−)- 15 …”

“…47 Additionally, Buchwald−Hartwig coupling of aryl bromide (+)-13 gave morpholine (−)-15. 48 We also sought to introduce structural variations on the C8a aryl group. Using 1-bromo-4-iodobenzene, Pd-catalyzed C2 arylation of protected tryptamine 4 gave an aryl bromide analogue that was advanced to pyrroloindoline (±)-16 (see Scheme S1 for synthetic details).…”

Quinazolin derivatives as emerging alpha-glucosidase inhibitors

“…We have generated 11,268 unique building blocks from our in-house database, GVKBIO online structure activity relation database (GOSTAR), and primary screening was forwarded using these scaffolds against α-glucosidase active site (pdb id 3WY1). Based on the molecular interaction parameters between protein and molecules, binding profile, and docking experiments, eight quinazoline molecular frames were selected for SAR for the bio-evaluation of α-glucosidase enzyme [4].…”

“…With subject to control this particular disease, one of the best-studied therapeutic target is α-glucosidase and its function inhibition. It is located in the brush border of the small intestine [3][4][5][6][7] and involved in breaking down complex carbohydrates such as starch and glycogen into their monomers, it catalyzes the cleavage of individual glucosyl residues from various glycoconjugates including alpha or beta linked polymers of glucose. The body system which is affected by diabetes mellitus needs external regulators to control the insulin balance in the blood, here the α-glucosidase inhibitors come into action, α-glucosidase inhibitors decrease both postprandial hyperglycemia and hyperinsulinemia, and thereby may improve sensitivity to insulin and release the stress on beta cells [7].…”

Advances in Metal-Catalyzed Cross-Coupling Reactions of Halogenated Quinazolinones and Their Quinazoline Derivatives

“…The Buchwald-Hartwig involves the direct C–N or C–O bond formation between aryl- or heteroaryl halides and amines or alcohols in the presence of stoichiometric amount of a base and palladium as a catalyst. This reaction was previously applied on 6-bromo- and 6-chloro-2-cyclopropyl-3-(pyridyl-3-methyl)quinazolin-4(3 H )-ones 97 using a variety of aryl, heteraryl and alkyl amines as coupling partners in the presence of Pd 2 (dba) 3 –DavePhos catalyst complex and t- BuONa in 1,4-dioxane at 100 °C to afford the corresponding 6-aminated derivatives 98 in moderate to high yields (Scheme 33) [53].…”