155184-79-5

Upstream product

• 302-17-0 chloral hydrate 
• 7745-89-3 3-chloro-4-methylaniline hydrochloride 
• 75-87-6 chloral 
• 95-74-9 3-chloro-p-toluidine 

Downstream Products

• 450407-83-7 2-(N-tert-butyloxycarbonyl)amino-5-methyl-6-chlorobenzoic acid 
• 450407-84-8 methyl 2-(N-tert-butyloxycarbonyl)amino-5-methyl-6-chlorobenzoate 
• 342411-56-7 methyl 2-amino-5-methyl-6-chlorobenzoate 
• 155184-81-9 2-amino-5-methyl-4-chlorobenzoic acid 
• 155184-82-0 2-amino-5-methyl-6-chlorobenzoic acid 
• 53003-18-2 4-chloro-5-methyl-1H-indole-2,3-dione 
• 96187-75-6 6-chloro-5-methylisatin 

Relevant academic research and scientific papers

Synthesis and in vitro antitumor activity of thiophene analogues of 5-chloro-5,8-dideazafolic acid and 2-methyl-2-desamino-5-chloro-5,8-dideazafolic acid

N-[5-[N-(2-Amino-5-chloro-3,4-dihydro-4-oxoquinazolin-6-yl)methylamino]-2- thenoyl]-L-glutamic acid (6) and N-[5-[N-(5-chloro-3,4-dihydro-2-methyl-4-oxoquinazolin-6-yl)methylamino]-2- thenoyl]-L-glutamic acid (7), the first reported thiophene analogues of 5-chloro-5,8-dideazafolic acid, were synthesized and tested as inhibitors of tumor cell growth in culture. 4-Chloro-5-methylisatin (10) was converted stepwise to methyl 2-amino-5-methyl-6-chlorobenzoate (22) and 2-amino-5-chloro-3,4-dihydro-6-methyl-4-oxoquinazoline (19). Pivaloylation of the 2-amino group, followed by NBS bromination, condensation with di-tert-butyl N-(5-amino-2-thenoyl)-L-glutamate (28), and stepwise cleavage of the protecting groups with ammonia and TFA yielded 6. Treatment of 9 with acetic anhydride afforded 2,6-dimethyl-5-chlorobenz[1,3-d]oxazin-4-one (31), which on reaction with ammonia, NaOH was converted to 2,6-dimethyl-5-chloro-3,4-dihydroquinazolin-4-one (33). Bromination of 33, followed by condensation with 28 and ester cleavage with TFA, yielded 7. The IC50 of 6 and 7 against CCRF-CEM human leukemic lymphoblasts was 1.8±0.1 and 2.1±0.8 μM, respectively.

Synthesis of substituted tryptanthrin via aryl halides and amines as antitumor and anti-MRSA agents

The natural alkaloid, tryptanthrin (indolo[2,1-b]quinazoline-6,12-dione), and its analogues are found to exhibit potent antitumor and anti-MRSA activities. An efficient and convenient method has been developed for the synthesis of tryptanthrin D-ring derivatives through the reaction of substituted tryptanthrins and secondary amines in moderate to good yields. Some of the new compounds exhibited antitumor activities against the human tumor cell lines A549, HCT116 and MDA-MB-231, with mean IC50 values at low micromolar levels. In addition, some of the compounds showed excellent anti-MRSA activities and were more effective than vancomycin, with MIC values of 0.31–1.25 μg/mL for Mu50,RN4220, and Newman strains.