1047-48-9

Usage

Uses

Used in Pharmaceutical Industry:
6-Benzyl-2-phenyl-5,6,7,8-tetrahydro-3H-pyrido[4,3-d]pyriMidin-4-one is used as a potential therapeutic agent for the treatment of various diseases, including cancer and neurological disorders, due to its unique structure and properties that may offer novel treatment options and mechanisms of action.

Upstream product

• 41276-30-6 C₉H₁₄O₃NC₆H₅ 
• 1670-14-0 benzamidine monohydrochloride 
• 618-39-3 benzamidin 
• 57611-47-9 1-benzyl-4-oxo-piperidine-3-carboxylic acid methyl ester 
• 100-46-9 benzylamine 
• 793-19-1 bis(2-methoxycarbonylethyl)benzylamine 
• 3939-01-3 methyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride 

Downstream Products

• 109229-04-1 2-Phenyl-6-((E)-3-phenyl-allyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-ol 
• 109229-01-8 4-(2-Ethyl-4-hydroxy-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl)-1-(4-fluoro-phenyl)-butan-1-one 
• 109229-00-7 1-(4-Fluoro-phenyl)-4-(4-hydroxy-2-phenyl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl)-butan-1-one 
• 109229-11-0 2-Phenyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-ol; hydrochloride 
• 109229-03-0 6-[4,4-Bis-(4-fluoro-phenyl)-butyl]-2-phenyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-ol 
• 17037-08-0 2-phenyl-3H-pyrido<4,3-d>pyrimidin-4-one 
• 134201-15-3 2-phenyl-5,6,7,8-tetrahydro-3H-pyrido<4,3-d>pyrimidin-4-one 
• 139452-55-4 6-benzyl-2-phenylpyrido<4,3-d>pyrimidin-4-one 
• 849777-03-3 C₂H₄O₂*C₁₃H₁₃N₃O 
• 119377-15-0 2-Phenyl-4-butoxy-6-benzyl-5,6,7,8-tetrahydropyrido<4,3-d>pyrimidin 
• 109229-19-8 4-Hydroxy-2-phenyl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid ethyl ester 
• 849777-41-9 C₁₈H₁₃N₅ 
• 849777-04-4 C₁₃H₈ClN₃ 

Relevant academic research and scientific papers

Transformations of tetrahydrobenzo[b][1,6]naphthyridines and tetrahydropyrido[4,3-b]pyrimidines under the action of dimethyl acetylene dicarboxylate

10-Cyanotetrahydrobenzo[b][1,6]naphthyridines 3, 4 undergo addition of DMAD, followed by a Stevens rearrangement of the intermediate ylide to yield methyl dioates 8 and 9. An alternative transformation sequence starts with migration of the dimethyl butenedioate anion to the carbon of the CN group, followed by the addition of 1 mol of water, to provide succinates 10 and 11. In contrast, tetrahydropyrido[4,3-b]pyrimidines 5-7 undergo a tandem cleavage process, involving one molecule of solvent. The resulting enamines are easily cleaved by strong acids, to give dihydropyrymidinylethylamines, which are scarcely available by other synthetic means.

Structure-based design, synthesis and evaluation in vitro of arylnaphthyridinones, arylpyridopyrimidinones and their tetrahydro derivatives as inhibitors of the tankyrases

Abstract The tankyrases are members of the PARP superfamily; they poly(ADP-ribosyl)ate their target proteins using NAD+ as a source of electrophilic ADP-ribosyl units. The three principal protein substrates of the tankyrases (TRF1, NuMA and axin) are involved in replication of cancer cells; thus inhibitors of the tankyrases may have anticancer activity. Using structure-based drug design and by analogy with known 3-arylisoquinolin-1-one and 2-arylquinazolin-4-one inhibitors, series of arylnaphthyridinones, arylpyridinopyrimidinones and their tetrahydro-derivatives were synthesised and evaluated in vitro. 7-Aryl-1,6-naphthyridin-5-ones, 3-aryl-2,6-naphthyridin-1-ones and 3-aryl-2,7-naphthyridin-1-ones were prepared by acid-catalysed cyclisation of the corresponding arylethynylpyridinenitriles or reaction of bromopyridinecarboxylic acids with β-diketones, followed by treatment with NH3. The 7-aryl-1,6-naphthyridin-5-ones were methylated at 1-N and reduced to 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones. Cu-catalysed reaction of benzamidines with bromopyridinecarboxylic acids furnished 2-arylpyrido[2,3-d]pyrimidin-4-ones. Condensation of benzamidines with methyl 1-benzyl-4-oxopiperidine-3-carboxylate and deprotection gave 2-aryl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ones, aza analogues of the known inhibitor XAV939. Introduction of the ring-N in the arylnaphthyridinones and the arylpyridopyrimidinones caused >1000-fold loss in activity, compared with their carbocyclic isoquinolinone and quinazolinone analogues. However, the 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones showed excellent inhibition of the tankyrases, with some examples having IC50 = 2 nM. One compound (7-(4-bromophenyl)-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-one) showed 70-fold selectivity for inhibition of tankyrase-2 versus tankyrase-1. The mode of binding was explored through crystal structures of inhibitors in complex with tankyrase-2.

Tetrahydropyridine (THP) ring expansion under the action of activated terminal alkynes. The first synthesis and X-ray crystal structure of tetrahydropyrimido[4,5-d]azocines

Tetrahydropyridopyrimidines (THPPm) 1-3 underwent tandem cleavage-cyclization piperidine ring enlargement under the action of terminal activated alkynes to produce tetrahydropyrimido[4,5-d]azocines 4-7 in good preparative yields. The latter compounds are representatives of a new heterocyclic system.

Synthesis of 2,6-disubstituted 4-hydroxy-5,6,7,8-tetrahydropyridopyrimidines

Some 2,6-disubstituted 4-hydroxy-5,6,7,8-tetrahydropyridopyrimidines are synthetized from 1-benzyl-4-piperidon-3-carbonic ester.