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Relevant academic research and scientific papers

Synthesis of (Z)-3-[amino(phenyl)methylidene]-1,3-dihydro-2Hindol-2-ones using an Eschenmoser coupling reaction

A highly modular method for the synthesis of (Z)-3-[amino(phenyl/methyl)methylidene]-1,3-dihydro-2H-indol-2-ones starting from easily available 3-bromooxindoles or (2-oxoindolin-3-yl)triflate and thioacetamides or thiobenzamides is described. A series of 49 compounds, several of which have previously been shown to possess significant tyrosin kinase inhibiting activity, was prepared in yields varying mostly from 70 to 97% and always surpassing those obtained by other published methods. The method includes an Eschenmoser coupling reaction, which is very feasible (even without using a thiophile except tertiary amides) and scalable. The (Z)configuration of all products was confirmed by NMR techniques.

1-Substituted pyrazolo[1,5-c]quinazolines as novel Gly/NMDA receptor antagonists: Synthesis, biological evaluation, and molecular modeling study

A new set of 5,6-dihydro-pyrazolo[1,5-c]quinazoline-2-carboxylates (2-18), bearing different substituents (COOEt, Cl, Br, CH3, and COOH) at position-1, were synthesized in order to investigate the influence of various groups at this specific position on Gly/NMDA receptor affinity and/or selectivity. All the herein reported compounds were evaluated for their binding at the Gly/NMDA, AMPA, and KA receptors. Some selected compounds were also tested for their functional antagonistic activity at both the AMPA and NMDA receptor-ion channels. The results obtained in this study have highlighted that a C-1 lipophilic substituent on the pyrazolo[1,5-c]quinazoline-2-carboxylate core shifts selectivity toward the Gly/NMDA receptor, while a C-1 anionic carboxylate residue is able to increase affinity toward this receptor subtype. In particular, the 2-carboxylic acids 15 and 16, bearing a chlorine atom at position-1, are not only potent (Ki = 0.18 and 0.16 μM, respectively), but also highly Gly/NMDA versus AMPA selective (selectivity ratio > 500). Furthermore, the 1,2-dicarboxylic acids 13 and 14 are endowed with the highest Gly/NMDA receptor binding activity (Ki = 0.09 and 0.059 μM, respectively), among the pyrazoloquinazoline series of derivatives. A molecular modeling study has been carried out to better understand receptor affinity and selectivity of these new pyrazoloquinazoline derivatives.

Pyrazolo[1,5-c]quinazoline derivatives and related compounds

Compounds are provided having the structure STR1 wherein R1 is hydrogen, alkyl of 1 to 3 carbons, 1-(hydroxyimino)alkyl, alkanoylamino, amino, or STR2 wherein alkyl in the above groups contains 1 to 4 carbons; R2 is 1-(hydroxyimino)alkyl, alkanoylamino, amino, STR3 hydrogen, lower alkyl or phenyl (optionally substituted by R4) wherein alkyl in the above groups contains 1 to 4 carbons; R3 is hydrogen, lower alkyl, benzyl or phenyl (optionally substituted with R4), dialkylaminoalkyl, hydroxyalkyl, STR4 (wherein R6 is hydrogen or alkyl, and R7 is alkyl); with the proviso that R1 or R2 is 1-(hydroxyimino)alkyl, alkanoylamino or amino, when R3 is hydrogen, lower alkyl, benzyl or phenyl; and R4 and R5 are the same or different and represent hydrogen, lower alkyl, lower alkoxy, alkanoyloxy, benzyloxy, hydroxy, halogen (Cl, Br and F), nitro and trifluoromethyl. The above compounds are useful as anti-allergy agents and antiinflammatory agents.