51768-01-5

Usage

Chemical Properties

Gray solid

Synthesis Reference(s)

Journal of Medicinal Chemistry, 44, p. 2391, 2001 DOI: 10.1021/jm010856uJournal of the American Chemical Society, 80, p. 2832, 1958 DOI: 10.1021/ja01544a060

InChI:InChI=1/C7H3ClN4/c8-6-4(2-9)1-5(3-10)7(11)12-6/h1H,(H2,11,12)

Upstream product

• 32019-26-4 H-TCNP 
• 51767-89-6 4-chloro-7-methyl-5,7-diaza-1,3,5-octatriene-1,1,3-tricarbonitrile 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 109-77-3 malononitrile 
• 13572-75-3 1,1,3,3-tetracyanopropene pyridine salt 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 172208-08-1 2-chloro-3,5-dicyanopyridine 
• 1415570-65-8 C₂₃H₂₈N₆ 
• 1415570-64-7 C₂₂H₂₆N₆ 
• 1415570-62-5 C₂₁H₂₄N₆ 
• 1415570-61-4 C₁₉H₂₀N₆ 
• 1335032-40-0 7-(2-(1-benzylpiperidin-4-yl)ethyl)-2-(methyl(prop-2-yn-1-yl)amino)-1,8-naphthyridine-3-carbonitrile 
• 63196-29-2 2,6-diamino-3,5-dicyanopyridine 
• 74786-61-1 2-hydroxy-6-aminopyridine-3,5-dicarbonitrile 
• 1313212-53-1 6-amino-3-imino-2-phenyl-2,3-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile 

Relevant academic research and scientific papers

Synthesis of 2,4-Diamino-6-(thioarylmethyl)pyrido[2,3-d]pyrimidines as dihydrofolate reductase inhibitors

Six 2,4-diaminopyrido[2,3-d]pyrimidines with a 6-merhylthio bridge to an aryl group were synthesize and biologically evaluate as inhibitors of Pneumocystis carinii (pc) and Toxoplasma gondii (tg) dihydrofolate reductase (DHFR). The syntheses of analogues

Discovery of Novel Pyrido-pyridazinone Derivatives as FER Tyrosine Kinase Inhibitors with Antitumor Activity

To obtain a new anticancer drug, we focused on FER tyrosine kinase. Starting with high-throughput screening with our in-house chemical library, compound 1, which has a pyridine moiety, was found. Referring to their X-ray crystal structure with FES proto-oncogene tyrosine kinase, as a surrogate of FER followed by chemical modification including scaffold hopping of the pyridine template, we discovered pyrido-pyridazinone derivatives with potent FER kinase inhibitory activity. Here, we disclose the structure-activity relationship on the scaffold and representative compound 21 (DS21360717), which showed in vivo antitumor efficacy in a subcutaneous tumor model.

Medicine comprising dicyanopyridine derivative

Compounds having a high conductance-type of calcium-activated K channel opening effect and a smooth muscle relaxant effect for bladder based on the K-channel opening effect, which can be used in treating pollakiuria and urinary incontinence, are provided.

MEDICINE COMPRISING DICYANOPYRIDINE DERIVATIVE

Compounds having a high conductance-type of calcium-activated K channel opening effect and a smooth muscle relaxant effect for bladder based on the K-channel opening effect, which can be used in treating pollakiuria and urinary incontinence, are provided. 3,5-Dicyanopyridine derivatives or their salts.

Design, synthesis, computational prediction, and biological evaluation of ester soft drugs as inhibitors of dihydrofolate reductase from pneumocystis carinii

A series of lipophilic soft drugs structurally related to the nonclassical dihydrofolate reductase (DHFR) inhibitors trimetrexate and piritrexim have been designed, synthesized, and evaluated in DHFR assays, with special emphasis on the inhibition of P. c

One pot synthesis of 2,6-dichloro-3,5-dicyanopyridine from aliphatic precursors

Malononitrile is condensed with triethyl orthoformate in the presence of pyridine; the mixture is acidified with HCl gas and after addition of further pyridine, HCl diazotised to form 2,6-dichloro-3,5-dicyanopyridine in a convenient, high yield process.

5-methyl-5-deaza analogues of methotrexate and N10 -ethylaminopterin

It is disclosed that 5-methyl-5-deazamethotrexate and 5-methyl-5-deaza-10-ethylaminopterin are more than 10 times as potent as 5-deazamethotrexate in the L1210 cell growth inhibition test.

Syntheses and Antifolate Activity of 5-Methyl-5-deaza Analogues of Aminopterin, Methotrexate, Folic Acid, and N10-Methylfolic Acid

Evidence indicating that modifications at the 5- and 10-positions of classical folic acid antimetabolites lead to compounds with favorable differential membrane transport in tumor vs. normal proliferative tissue prompted an investigation of 5-alkyl-5-deaz

REACTION OF DIMETHYLFORMAMIDE AND DIMETHYLACETAMIDE DIETHYL ACETALS WITH MALONONITRILE

In the reaction of N,N-dimethylacetamide diethyl acetal with malononitrile the dimethylammonium salt (or the N, N, N', N'-tetramethylacetamidinium salt with an excess of the acetal) of 2-methyl-1,1,3,3-propenetetracarbonitrile was obtained in addition to α-cyano-β-dimethylaminocrotononitrile.Its structure was proved by 1H and 13C NMR spectroscopy and mass spectrometry and also by its conversion into 2-chloro-4-methyl-3,5-dicyano-6-aminopyridine.The reaction of dimethylformamide diethyl acetal with malononitrile takes place similarly.

Syntheses with Nitriles. 62. 3,5-Dicyanopyridine Derivatives by Vilsmeier Formylation of Malononitrile and Tetracyanopropenides (2)

Reaction of malononitrile with dimethylformamide and phosphorus oxychloride gave (dimethylaminomethylene)malononitrile (1), 4-chloro-7-methyl-5,7-diaza-1,3,5-octatriene-1,1,3-tricarbonitrile (3a) and the pyridine 2.Compounds 3a and 3b as well as the triaza-derivative 3c may also be obtained by treatment of tetracyanopropenides 4a-c with dimethylformamide and phosphorus oxychloride.Ring closures were achieved by heating 3 under alkaline or acidic conditions.Substitution of chlorine in 3a with aromatic amines provided 1-aryl-1,2-dihydro-2-imino-3,5-pyridinedicarbonitriles 7.Hydrolysis of 7 gave the 2-oxo-derivatives 8.