147149-89-1

Usage

Molecular structure

quinazolin-4-one core with amino group at 2-position, bromine atom at 5-position, and methyl group at 6-position
Exhibits various pharmacological activities

InChI:InChI=1/C9H8BrN3O/c1-4-2-3-5-6(7(4)10)8(14)13-9(11)12-5/h2-3H,1H3,(H3,11,12,13,14)

Upstream product

• 502607-48-9 2-guanidino-5-bromo-3,4-dihydro-6-methylquinazolin-4-one 
• 107-21-1 ethylene glycol 
• 147149-85-7 6-amino-2-bromo-3-methyl-benzoic acid 
• 147149-84-6 4-bromo-5-methyl-1H-indole-2,3-dione 
• 593-85-1 diguanidine carbonate 
• 127489-40-1 5-bromo-6-methyl-1H-benzo<1,3>oxazine-2,4-dione 

Relevant academic research and scientific papers

A large scale process for the preparation of thymitaq

The large scale manufacturing of the anticancer agent 2-amino6-methyl-5- (pyridin-4-ylsulfanyl)-3H-quinazolin-4-one dihydrochloride (thymitaq) from 6-bromo-5-methylanthranilic acid is described. The chemical route consists of two chemical steps: formation of a bromoquinazolinone and a copper-mediated Ullman-like coupling between 4-mercaptopyridine and the bromoquinazolinone. During process development, sodium hydride was replaced with sodium hydroxide and a method for removal of copper, based on 2,4,6-trimercapto-s-triazine, was developed. A number of purification operations were performed to ensure a product of pharmaceutical quality.

Pyridine-4-thiol and amphoteric analogs: Novel protection of aryl bromides in strong alkali

The use of pyridine-4-thiol (PT) to preserve certain aryl bromides in strong alkali is reported (Scheme 1). The presence of this additive or of some of its amphoteric analogs such as 3-hydroxypyridin-4(1H)-ones suppresses the replacement of the Br-substituent by hydroxide and alkoxide ions. A mechanistic interpretation of the effect is proposed.

New straightforward synthesis of 2-amino-6-methyl-5-(pyridin-4-ylsulfanyl)- 3H-quinazolin-4-one

The synthesis of 2-amino-6-methyl-5-(pyridin-4-ylsulfanyl)-3H-quinazolin-4- one (1) was studied via three different synthetic routes starting from 4-bromo-5-methylisatin. The best route was established, which is a straightforward route via 2-guanidino-5-b

ANTIPROLIFERATIVE QUINAZOLINES

Quinazoline compounds which demonstrate antiproliferative activity, such as antitumor activity, processes of preparing these compounds, pharmaceutical compositions containing these compounds, and the use of these compounds. These compounds inhibit the growth and proliferation of the cells of higher organisms and microorganisms,such as bacteria, yeasts and fungi. Preferred quinazoline compounds are capable of inhibiting the enzyme thymidylate synthase. Effects derived from the inhibition of the enzyme thymidylate synthase include those discussed above