27023-77-4

Basic information

• Product Name: 2,4-diaminoquinazoline-6-carbaldehyde
• Synonyms: 2,4-diaminoquinazoline-6-carbaldehyde;2,4-diamino-6-quinazolinecarboxaldehyde
• CAS NO: 27023-77-4
• Molecular Formula: C₉H₈N₄O
• Molecular Weight: 188.18602
• Mol File: 27023-77-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 536.6°Cat760mmHg
• Flash Point: 278.3°C
• Appearance: /
• Density: 1.49g/cm³
• Vapor Pressure: 1.38E-11mmHg at 25°C
• Refractive Index: 1.831
• PKA: 8.23±0.26(Predicted)
• CAS DataBase Reference: 2,4-diaminoquinazoline-6-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-diaminoquinazoline-6-carbaldehyde(27023-77-4)
• EPA Substance Registry System: 2,4-diaminoquinazoline-6-carbaldehyde(27023-77-4)

Safety Data

• Hazardous Substances Data: 27023-77-4(Hazardous Substances Data)

Usage

General Description

2,4-diaminoquinazoline-6-carbaldehyde is a chemical compound with the molecular formula C9H8N4O. It is an aldehyde derivative of quinazoline, containing two amino groups and an aldehyde functional group. 2,4-diaminoquinazoline-6-carbaldehyde has potential applications in the field of medicinal chemistry, particularly in the development of pharmaceuticals and bioactive compounds. Its structure and reactivity make it a valuable building block for the synthesis of various biologically active molecules. Additionally, its unique properties and potential pharmacological activities make it an important target for future research and development in the field of drug discovery.

InChI:InChI=1/C9H8N4O/c10-8-6-3-5(4-14)1-2-7(6)12-9(11)13-8/h1-4H,(H4,10,11,12,13)

Upstream product

• 13741-90-7 2,4,6-triaminoquinazoline 
• 7154-34-9 2,4-diamino-6-nitroquinazoline 
• 18917-68-5 2,4-diamino-6-quinazoline-6-carbonitrile 

Downstream Products

• 206655-66-5 Benzoic acid 2,4-bis-(2,2-dimethyl-propionylamino)-quinazolin-6-ylmethyl ester 
• 206655-68-7 2,4-Bis-(2,2-dimethyl-propionylamino)-quinazoline-6-carboxylic acid benzyl ester 
• 207562-23-0 2,4-diaminoquinazoline-6-carboxylic acid 

Relevant articles and documents

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.