Reactiohs with α -thiocarbamoylcinnamonitriles: Synthesis of pyrazolo [1,5-a] pyrimidines

Hussain, S. M.; El‐Reedy, A. M.; Elsharabasy, Salwa A.

doi:10.1016/s0040-4020(01)85113-9

Cited by 27 publications

(7 citation statements)

References 10 publications

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“…Previous literature, explains the reactivity of the endocyclic NH of the substituted 2‐aminopyrazoles.Accordingly,we thought of obtaining the product structure as 3 ( a–k ) ( Scheme ) which is the other isomeric structure of 4 ( a–k ). The synthetic sequence of reactions leading to the unexpected compound 4 ( a–k ) was assumed to proceed via initial Michael addition of the endocyclic ‐NH of 5 ‐ amino‐4‐cyano‐3‐cyanomethylpyrazole ( 1) to the double bond of benzylidenemalononitrile to yield the intermediate (II) followed by intramolecular cyclization and aromatization by loss hydrogen molecule to afford 4 ( a–k) .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Polyfunctionalized Fused Pyrazolo‐Pyridines: Characterization, Anticancer Activity, Protein Binding and Molecular Docking Studies

Naik

Shastri

et al. 2019

ChemistrySelect

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The reaction of a multi-substituted pyrazole 1 with aryl or heteroaryl aldehydes and active methylene compounds afford unexpected pyrazolo[1,5-a]pyridine derivatives 4(a-k). Mechanism for this unexpected reaction involving reactivity of the active methylene moiety with a neighboring endocyclic NH group is proposed and structure has been established by the NMR and single crystal X-ray diffraction studies. Moreover, all the newly synthesized compounds were tested for their anticancer activity against sixty human cell lines at NCI. Among all the compounds, three scaffolds 4d, 4 h and 4k showed enhancement in anticancer activity in comparison with remaining synthesized compounds. Interestingly compound 4k was found to highly active even at a five dose concentration. The IC 50 values were determined against two cell lines MCF-7 and HepG2, the results obtained have shown promising effects against cancer cell lines. Further, the molecular docking studies revealed that substituted pyrazolo[1,5-a]pyridine derivatives are good candidates in the medicinal field.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Polyfunctionalized Fused Pyrazolo‐Pyridines: Characterization, Anticancer Activity, Protein Binding and Molecular Docking Studies

Naik

Shastri

et al. 2019

ChemistrySelect

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“…Following previously described experimental procedures, 8,21,22 we successfully synthesized compound 9, which has a methoxy group at R 2 . Its anti-inflammatory activity was then evaluated following experimental procedures also described in the literature.…”

Section: Resultsmentioning

confidence: 99%

Quantitative structure-activity relationships (QSAR) of 4-amino-2,6-diarylpyrimidine-5-carbonitriles with anti-inflammatory activity

Silva¹,

Ramos²,

Neto³

et al. 2008

J. Braz. Chem. Soc.

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As atividades antiinflamatórias de oito compostos 4-amino-2,6-diarilpirimidina-5-carbonitrilas foram sujeitas a uma análise QSAR baseada nos resultados de cálculos de estrutura eletrônica B3LYP/6-31G(d,p) e AM1. Análise de Componentes Principais e regressões baseados nesses dados indicam que compostos potencialmente mais ativos teriam menores valores de momentos de dipolo e de coeficientes de partição e também seriam afetados pelos valores de cargas dos átomos de carbono através dos quais os dois anéis aromáticos estão ligados ao anel pirimidínico. Duas novas moléculas foram previstas serem, ao menos, tão ativas como aquelas com as maiores atividades usadas no estágio de construção do modelo. Uma delas, tendo o grupo metoxila conectado a um dos anéis aromáticos, foi prevista ter um valor de atividade antiinflamatória de 52,3%. Essa molécula foi sintetizada e sua atividade experimental foi determinada em 52,8%, em concordância com a previsão teórica AM1. Esse valor é 5% maior que o maior valor usado para a modelagem.The experimental anti-inflammatory activities of eight 4-amino-2,6-diarylpyrimidine-5-carbonitriles were subjected to a QSAR analysis based on results from B3LYP/6-31G(d,p) and AM1 electronic structure calculations. Principal component analyses and regressions based on these data indicate that potentially more active compounds should have low dipole moment and partition coefficient values and also be affected by the values of the charges of the carbon atoms through which the two aromatic rings are bonded to the pyrimidinic ring. Two new molecules were predicted to be at least as active as those with the highest activities used in the model building stage. One of them, having a methoxy group attached to one of the aromatic rings, was predicted to have an anti-inflammatory activity value of 52.3%. This molecule was synthesized and its experimental activity was found to be 52.8%, in agreement with the AM1 theoretical prediction. This value is 5% higher than the largest value used for modeling.

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“…It is difficult to rationalize for this signal if the reaction product was 4a since it will appear at a lower field (Ca δ ~ 8.8ppm) (19). This may be formulated as the 7-aminopyrido[2,3-d]pyrimidine 4a or its 5-amino isomer 7a (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

A CONVENIENT ONE POT SYNTHESIS OF PYRIDO[2,3-d]- PYRIMIDINES AND PYRIMIDO[2,3-c]PYRIMIDINES (N5-DEAZAPETRINS)

Mekheimer¹,

El‐Nabi²,

Abd-Elhameed³

et al. 2000

Heterocyclic Communications

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Reactiohs with α -thiocarbamoylcinnamonitriles: Synthesis of pyrazolo [1,5-a] pyrimidines

Cited by 27 publications

References 10 publications

Synthesis of Polyfunctionalized Fused Pyrazolo‐Pyridines: Characterization, Anticancer Activity, Protein Binding and Molecular Docking Studies

Synthesis of Polyfunctionalized Fused Pyrazolo‐Pyridines: Characterization, Anticancer Activity, Protein Binding and Molecular Docking Studies

Quantitative structure-activity relationships (QSAR) of 4-amino-2,6-diarylpyrimidine-5-carbonitriles with anti-inflammatory activity

A CONVENIENT ONE POT SYNTHESIS OF PYRIDO[2,3-d]- PYRIMIDINES AND PYRIMIDO[2,3-c]PYRIMIDINES (N5-DEAZAPETRINS)

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