15948-97-7

Usage

InChI:InChI=1/C11H11ClN4/c12-10-9(13)11(16-7-15-10)14-6-8-4-2-1-3-5-8/h1-5,7H,6,13H2,(H,14,15,16)

Upstream product

• 5413-85-4 5-amino-4,6-dichloropyridimine 
• 100-46-9 benzylamine 
• 54413-44-4 4-(benzylamino)-6-chloro-5-nitropyrimidine 

Downstream Products

• 84762-60-7 Benzyl-(5-oxa-2,4,11-triaza-dibenzo[a,d]cyclohepten-1-yl)-amine 
• 96830-58-9 2-{[(Z)-4-Benzylamino-6-chloro-pyrimidin-5-ylimino]-methyl}-phenol 
• 96830-38-5 Benzyl-(8-chloro-5-oxa-2,4,11-triaza-dibenzo[a,d]cyclohepten-1-yl)-amine 
• 84762-64-1 Benzyl-(8-bromo-5-oxa-2,4,11-triaza-dibenzo[a,d]cyclohepten-1-yl)-amine 
• 83492-10-8 9-benzyl-6-(benzyloxy)-9H-purine 
• 875925-94-3 benzyl-(8-fluoro-5-oxa-2,4,11-triaza-dibenzo[a,d]cyclohepten-1-yl)-amine 
• 1928-76-3 9-benzyl-6-chloro-9H-purine 
• 219735-81-6 N-(6-benzylamino-4-chloropyrimidin-5-yl)-O-ethyl-propionimidate 
• 21324-31-2 3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ol 
• 96830-48-7 Benzyl-(8-chloro-10,11-dihydro-5-oxa-2,4,11-triaza-dibenzo[a,d]cyclohepten-1-yl)-amine 
• 96830-50-1 Benzyl-(10,11-dihydro-5-oxa-2,4,11-triaza-dibenzo[a,d]cyclohepten-1-yl)-amine 

Relevant academic research and scientific papers

Synthesis and preliminary antiproliferative activity of new pteridin-7(8H)-one derivatives

Pteridines are an important class of heterocyclic compounds with diverse biological activities. Here, we report a series of pteridin-7(8H)-one derivatives and their antiproliferative activities toward MKN-45, MGC-803, EC-109, and H1650. Structure-activity relationship studies showed that compound 12 exerted the most potent antiproliferative activity against MKN-45 and MGC-803 with the IC50 values of 4.32 and 7.01 μM, respectively. Besides, compound 12 induced morphological changes and apoptosis of MKN-45 cells, increased expression of Bax, down-regulated expression of Bcl-2 and caused cleavage of caspase-3/9. Additionally, we first reported the construction of the novel bicyclic 8,9-dihydro-7H-purine-8-carboxylate scaffold through the competitive 5-endo cyclization reaction with two C-N bonds and a chiral carbon center established.

1,2,3-Triazole fused with pyridine/pyrimidine as new template for antimicrobial agents: Regioselective synthesis and identification of potent N-heteroarenes

The 1,2,3-triazole ring fused with pyridine/pyrimidine was explored as new template for the identification of potential antimicrobial agents. The regioselective synthesis of these pre-designed N-heteroarenes was achieved via exploring the application of Buchwald's strategy (i.e. C–N bond formation/reduction/diazotization/cyclization sequence) to the N-heteroarene system. Two of them showed promising antibacterial (comparable to streptomycin) and several showed potent antifungal (comparable to mancozeb) activities.

COMPOUNDS FOR TREATING CYSTIC FIBROSIS

The present invention relates to compounds of Formula (I) or pharmaceutically acceptable enantiomers, salts, solvates or prodrugs thereof. The invention further relates to the use of the compounds of Formula (I) for the treatment of cystic fibrosis. The invention also relates to a process for manufacturing compounds of Formula (I).

Synthesis of 6,8,9 poly-substituted purine analogue libraries as pro-apoptotic inducers of human leukemic lymphocytes and DAPK-1 inhibitors

A 18-member library of 6,8,9-poly-substituted purines was prepared from pyrimidines, primary alcohols, and N,N-dimethylamides under basic conditions via a novel one-pot synthetic pathway controlled by amide sizes and the novel analogues were tested against two leukemia cell lines: Jurkat (acute T cell leukemia) and K562 (chronic erythroleukemia) cells. Compounds having a benzoxy group at C6 position of the aromatic ring exhibited antiproliferative activity in Jurkat cells whereas all compounds induced a lower effect on K562 cells. Analysis of cell cycle, Annexin-V staining, and cleavage of initiator caspases assays showed that the active purine analogues induce cell death by apoptosis. Based on these results, a new purine derivative was synthesized, 6-benzyloxy-9-tert-butyl-8-phenyl-9H-purine (6d), which displayed the highest activity of the series against Jurkat cell lines. Finally, 33P-radiolabeled kinase assays using 96 recombinant human kinases known to be involved in apoptotic events were performed. Just one of the kinases tested, DAPK-1, was inhibited 50% or more by the phenotypic hits at 10 μM, suggesting that the inhibition of this target could be responsible for the induction of cell death by apoptosis. In agreement with the phenotypic results, the most active antiproliferative agent, 6d, displayed also the lowest IC50 value against recombinant DAPK1 (2.5 μM), further supporting the potential role of this protein on the observed functional response. DAPK-1 inhibition led by 6d together with its pro-apoptotic properties against the Jurkat line makes it an interesting candidate to further investigate the role of DAPK1 kinase in triggering apoptosis in cancer cells, a role which is attracting recent interest.

Heteroaryl compounds useful as inhibitors of E1 activating enzymes

This invention relates to compounds that inhibit E1 activating enzymes, pharmaceutical compositions comprising the compounds, and methods of using the compounds. The compounds are useful for treating disorders, particularly cell proliferation disorders, including cancers, inflammatory and neurodegenerative disorders; and inflammation associated with infection and cachexia.

Tricyclic azepine derivatives: Pyrimido[4,5-b]-1,4-benzoxazepines as a novel class of epidermal growth factor receptor kinase inhibitors

A novel class of pyrimido[4,5-b]-1,4-benzoxazepines is described as inhibitors of epidermal growth factor receptor (EGFR) tyrosine kinase. Two compounds display potent EGFR inhibitory activity of less than 1 μM in cellular phosphorylation assays (IC50 0.47-0.69 μM) and are highly selective against a small kinase panel. Such compounds demonstrate anti-EGFR activity within a class that is different from any known EGFR inhibitor scaffolds. They also provide a basis for the design of kinase inhibitors with the desired selectivity profile.

Imidazopyridines for the treatment of neurological disorders

Corticotropin releasing factor (CRF) antagonists of formula (I): and their use in treating psychiatric disorders and neurological diseases, anxiety-related disorders, post-traumatic stress disorder, supranuclear palsy and feeding disorders as well as treatment of immunological, cardiovascular or heart-related diseases and colonic hypersensitivity associated with psychopathological disturbance and stress in mammals.

An efficient one-pot synthesis of 6-alkoxy-8,9-dialkylpurines via reaction of 5-amino-4-chloro-6-alkylaminopyrimidines with N,N-dimethylalkaneamides and alkoxide ions

The synthesis of a number of new 6-alkoxy-8,9-(disubstituted)purines has been accomplished by the cyclization of the corresponding intermediate 5-amino-4-chloro-6-(alkylamino)pyrimidines promoted by alkoxides and various N,N-dimethyl amides, where the latter act as solvent-reagents. By this three-component condensation reaction we are able to introduce an alkyl group in the 8 position of the purine ring with the concomitant nucleophilic replacement of the 6-chloro group with an alkoxy moiety.

Imidazopyrimidines and imidazopyridines for the treatment of neurological disorders

Corticotropin releasing factor (CRF) antagonists of formula (I): and their use in treating psychiatric disorders and neurological diseases, anxiety-related disorders, post-traumatic stress disorder, supranuclear palsy and feeding disorders as well as treatment of immunological, cardiovascular or heart-related diseases and colonic hypersensitivity associated with psychopathological disturbance and stress in mammals.