A new method has been designed to prepare the known benzoxazinone derivative 2-(N-phthaloylmethyl)-4H-3,1-benzoxazin-4-one (4). The acyl chloride derivative N-phthaloylglycine reacts with anthranilic acid in chloroform, in the presence of triethylamine, to give an intermediate that is then reacted with cyanuric chloride, used as a cyclization agent, to produce the benzoxazinone derivative.

The benzoxazinone and dihydroquinoxalinone fragments were employed as novel acetyl lysine mimics in the development of CREBBP bromodomain ligands. While the benzoxazinone series showed low affinity for the CREBBP bromodomain, expansion of the dihydroquinoxalinone series resulted in the first potent inhibitors of a bromodomain outside the BET family. Structural and computational studies reveal t...

The crystal structures of porcine pancreatic elastase complexed to two similar benzoxazinone inhibitors are reported to 2.09 A and 1.76 A resolution, and refined to conventional R factors of 0.153 and 0.172.

Molecules that serve as versatile branch points for the synthesis of pharmaceutically or biologically active products, besides being of interest in their own right, are especially valuable targets for asymmetric catalysis. The 1,4-benzoxazinone and 1,4-benzoxazine systems are intriguing because they are present in clinically significant pharmaceuticals and other biologically active molecules. O...

Herpes simplex virus infections have been described in the medical literature for centuries, yet the the drugs available nowadays for therapy are largely ineffective and low oral bioavailability plays an important role on the inefficacy of the treatments. Additionally, the details of the inhibition of Herpes Virus type 1 are still not fully understood. Studies have shown that several viruses en...

Mycobacterium tuberculosis (Mtb) maintains its intrabacterial pH (pHIB) near neutrality in the acidic environment of phagosomes within activated macrophages. A previously reported genetic screen revealed that Mtb loses this ability when the mycobacterial acid resistance protease (marP) gene is disrupted. In the present study, a high throughput screen (HTS) of compounds against the protease doma...

Akira Oikawa, Kenkichi Ebisui, Masayuki Sue, Atsushi Ishihara and Hajime Iwamura Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Kyoto 606-8502, Japan, and CREST, Japan Science and Technology Corporation (JST) Z. Naturforsch. 54c, 181-185 (1999); received November 19, 1998/January 11, 1999 Benzoxazinones, Zea mays, Gramineae, ß-Glucosidase Occurrence and pro...

Quinazolinones are interesting molecules with a wide range of biological activities. We prepared a number of quinazolinone derivatives by the condensation of 5-bromo- or 5-nitro-substituted anthranilic acids with chloro-acyl chlorides. Anthranilic acid derivatives were treated with either 3-chloro-propionyl chloride or 4-chloro-butyryl chloride to yield the corresponding N-acyl-anthranilic acid...