53745-23-6

Usage

Uses

Used in Pharmaceutical Industry:
2,6-DIAMINO-4-HYDROXYQUINAZOLINE serves as a crucial pharmaceutical intermediate, playing a pivotal role in the synthesis of diverse pharmaceutical compounds. Its unique structure, featuring a quinazoline ring with amino and hydroxy functional groups, allows for the creation of a wide array of therapeutic agents.
Used in Research and Development:
In the field of research and development, 2,6-DIAMINO-4-HYDROXYQUINAZOLINE is utilized for its potential in organic synthesis and medicinal chemistry. It aids scientists in understanding and developing new chemical pathways and therapeutic agents, contributing to the advancement of medical treatments and drug discovery.
Used in Industrial Applications:
While further research is necessary to fully comprehend its potential, 2,6-DIAMINO-4-HYDROXYQUINAZOLINE may also find applications in various industrial sectors. Its unique chemical properties could be harnessed for uses that are yet to be discovered, highlighting the importance of ongoing research in this area.

Upstream product

• 87597-83-9 2-amino-4-hydroxy-6-nitroquinazoline 
• 4693-02-1 6-nitroisatoic anhydride 
• 87597-83-9 2-amino-6-nitro-3H-quinazolin-4-one 
• 7154-34-9 2,4-diamino-6-nitroquinazoline 

Downstream Products

• 56239-21-5 5,8-dideazaisofolic acid 
• 87597-88-4 D-5,8-dideazaisofolic acid 
• 87539-56-8 9-formyl-5,8-dideazaisofolic acid 
• 87614-69-5 9-methyl-5,8-dideazaisofolic acid 
• 87597-85-1 (R)-2-{4-[(2-Amino-4-hydroxy-quinazolin-6-ylamino)-methyl]-benzoylamino}-pentanedioic acid di-tert-butyl ester 
• 87597-85-1 di-tert-butyl 5,8-dideazaisofolate 

Relevant academic research and scientific papers

The synthesis of novel nonclassical reversed bridge quinazoline antifolates as inhibitors of thymidylate synthase [1a,b]

2-Amino-6-methyl-5-(pyridin-4-ylsulfanyl)-3H-quinazolin-4-one (3, AG337) a lipophilic thymidylate synthase inhibitor, is currently in clinical trials as an antitumor agent. On the basis of the crystal structure of 3 and the classical inhibitor 10-propargyl-5,8-dideazafolic acid (1, PDDF) with thymidylate synthase, we designed and synthesized a series of nonclassical 2-amino-6-substituted-3H-quinazolin-4-ones 4-13, with a variety of electron withdrawing groups in the side chain (with the exception of compound 4). Molecular modeling indicates that these reversed bridge (N9-C10) 6-substituted analogues orient their side chain C10-substituent such that it lies between that of 1 and 3. These compounds were obtained by reductive amination of 6-aminoquinazoline 16 and the appropriate aryl aldehyde 17 or aryl ketone 18. For analogues 11-13, the yield depended on the substitutents on the aryl ketone 18 (comparison of 11 and 13). With the exception of analogue 13, all the compounds in the series were poor inhibitors of thymidylate synthase from Lactobacillus casei, Pneumocystis carinii and human sources.

Discovery of N-(6-Fluoro-1-oxo-1,2-dihydroisoquinolin-7-yl)-5-[(3R)-3-hydroxypyrrolidin-1-yl]thiophene-2-sulfonamide (LSN 3213128), a Potent and Selective Nonclassical Antifolate Aminoimidazole-4-carboxamide Ribonucleotide Formyltransferase (AICARFT) Inhibitor Effective at Tumor Suppression in a Cancer Xenograft Model

A hallmark of cancer is unbridled proliferation that can result in increased demand for de novo synthesis of purine and pyrimidine bases required for DNA and RNA biosynthesis. These synthetic pathways are frequently upregulated in cancer and involve various folate-dependent enzymes. Antifolates have a proven record as clinically used oncolytic agents. Our recent research efforts have produced LSN 3213128 (compound 28a), a novel, selective, nonclassical, orally bioavailable antifolate with potent and specific inhibitory activity for aminoimidazole-4-carboxamide ribonucleotide formyltransferase (AICARFT), an enzyme in the purine biosynthetic pathway. Inhibition of AICARFT with compound 28a results in dramatic elevation of 5-aminoimidazole 4-carboxamide ribonucleotide (ZMP) and growth inhibition in NCI-H460 and MDA-MB-231met2 cancer cell lines. Treatment with this inhibitor in a murine based xenograft model of triple negative breast cancer (TNBC) resulted in tumor growth inhibition.

Improved Synthesis and Antitumor Evaluation of 5,8-Dideazaisofolic Acid and Closely Related Analogues

A new synthetic route to 5,8-dideazaisofolic acid (IAHQ) is described which precludes the possibility of contamination due to its 4-amino counterpart 5,8-dideazaisoaminopterin.Substitution of D-glutamic acid in this synthetic scheme gave D-IAHQ.The 9-form