18917-68-5

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Diaminoquinazoline-6-carbonitrile is used as a chemical intermediate for the synthesis of various pharmaceutical compounds due to its potential in the development of anticancer and antiviral drugs.
Used in Anticancer Drug Development:
2,4-Diaminoquinazoline-6-carbonitrile is used as a lead compound in anticancer drug development for its ability to inhibit the growth of cancer cells, as demonstrated in preclinical studies.
Used in Antiviral Drug Development:
2,4-Diaminoquinazoline-6-carbonitrile is used as a potential antiviral agent for its capacity to inhibit the replication of certain viruses, making it a candidate for the development of antiviral medications.

Upstream product

• 151-50-8 potassium cyanide 
• 13741-90-7 2,4,6-triaminoquinazoline 
• 7154-34-9 2,4-diamino-6-nitroquinazoline 

Downstream Products

• 52128-06-0 6-[(4-Chloro-phenylamino)-methyl]-quinazoline-2,4-diamine; compound with acetic acid 
• 1955-63-1 4-[(2,4-diamino-quinazolin-6-ylmethyl)-amino]-benzoic acid 
• 52128-04-8 6-[(3-Chloro-phenylamino)-methyl]-quinazoline-2,4-diamine; compound with acetic acid 
• 87174-61-6 6-[(2-Chloro-phenylamino)-methyl]-quinazoline-2,4-diamine; compound with acetic acid 
• 52128-08-2 6-[(3,5-Dichloro-phenylamino)-methyl]-quinazoline-2,4-diamine; compound with acetic acid 
• 52128-16-2 6-<<(3,4-dichlorophenyl)amino>methyl>-2,4-quinazolinediamine acetate 
• 52128-20-8 6-<<<4-chloro-3-(trifluoromethyl)phenyl>-amino>methyl>-2,4-quinazolinediamine acetate 
• 52128-10-6 6-[(3,4,5-Trimethoxy-phenylamino)-methyl]-quinazoline-2,4-diamine; compound with acetic acid 
• 52128-18-4 6-[(3-Bromo-phenylamino)-methyl]-quinazoline-2,4-diamine; compound with acetic acid 
• 52128-12-8 6-[(6-Chloro-naphthalen-2-ylamino)-methyl]-quinazoline-2,4-diamine; compound with acetic acid 
• 93502-97-7 (S)-2-{4-[(2,4-Diamino-quinazolin-6-ylmethyl)-amino]-benzoylamino}-pentanedioic acid di-tert-butyl ester 
• 27023-77-4 2,4-diamino-quinazoline-6-carboxaldehyde 
• 27133-39-7 6-anilinomethyl-quinazoline-2,4-diamine 
• 207562-23-0 2,4-diaminoquinazoline-6-carboxylic acid 

Relevant academic research and scientific papers

Process for synthesizing antifolates

A process for synthesizing antifolate compounds is disclosed. The process includes cyclization of a readily available starting reagent, followed by one or more coupling steps to produce compounds that mimic folic acid. The compounds synthesized have commercial use as drugs in oncology, inflammatory disease, and other medical fields.

Synthesis of 2,4-diaminopyrido[2,3-d]pyrimidines and 2,4-diamino-quinazolines with bulky dibenz[b,f]azepine and dibenzo[a,d]-cycloheptene substituents at the 6-position as inhibitors of dihydrofolate reductases from Pneumocystis carinii, Toxoplasma gondii, and Mycobacterium avium

The synthesis of four previously undescribed 2,4-diaminopyrido[2,3-d]pyrimidines (3,4) and 2,4-diaminoquinazolines (5,6) with a bulky tricyclic aromatic group at the 6-position is described. Condensation of dibenz[b,f]azepine with 2,4-diamino-6-bromomethylpyrido[2,3-d]pyrimidine (8) and 2,4-diamino-6-bromomethylquinazoline (17) in the presence of sodium hydride afforded N-[(2,4-diaminopyrido[2,3-d]-pyrimidin-6-yl)methyl]dibenz[b,f]azepine (3) and N-[(2,4-diaminoquinazolin-6-yl)methyl]dibenz[b,f]-azepine (4), respectively. Condensation of 5-chlorodibenzo[a,d]cycloheptene (19) and 5-chloro-10,11-dihydrodibenzo[a,d]cycloheptene (20) with 2,4,6-triaminoquinazoline (13) afforded 5-[(2,4-diamino-quinazolin-6-yl)amino]-5H-dibenzo[a,d]cycloheptene (5) and the corresponding 10,11-dihydro derivative (6), respectively. The bromides 8 and 17, as hydrobromic acid salts, were obtained from the corresponding nitriles according to a standard three-step sequence consisting of treatment with Raney nickel in formic acid followed by reduction with sodium borohydride and bromination with dry hydrogen bromide in glacial acetic acid. Compounds 3-6 were evaluated in vitro for the ability to inhibit dihydrofolate reductase from Pneumocystis carinii, Toxoplasma gondii, Mycobacterium avium, and rat liven Compounds 3 and 4 were potent inhibitors of all four enzymes, with IC50 values in the 0.03-0.1 μM range, whereas 5 was less potent. However the selectivity of all four compounds for the parasite enzymes relative to the rat enzyme was 100-fold selectivity for the T. gondii and M. avium enzyme and 21-fold selectivity for the P. carinii enzyme.

Synthesis and enzymatic hydrolysis of esters, constituting simple models of soft drugs

One way to minimise systemic side effects of drugs is to design molecules, soft drugs, in such a way that they are metabolically inactivated rapidly after having acted on their pharmacological target. Hydrolases (esterases, peptidases, lipases, glycosidas