823-45-0Relevant articles and documents
Application of pfitzinger reaction in synthesis of hetero ring annelated quinoline carboxylic acid derivatives
Yadav, Taruna,Yadav, Neelam K.,Yadav, Manju,Singh, Bhawani,Kishore
, p. 1177 - 1180 (2016)
The diazotized 8-aminoquinoline (4) was reacted with 2-(hydroxymethylidine)cyclohexanone and N-benzyl 3-(hydroxymethylidine)-piperidine-4-one (5, 6) (generated from the reaction of cyclohexanone and N-benzyl-4-piperidone with ethyl formate in the presence of NaOEt) under the conditions of Japp-Klingemann reaction, followed by Fisher-indolization of the resulting hydrazones in acid, formed the quinolinooxocarbazole (7) and N-benzyl quinolinooxoazacarbazole (8), respectively. Pfitzinger reaction of compounds 7 and 8 with isatin in alkali afforded the corresponding quinoline carboxylic acid derivatives 10 and 11, respectively. In accord to generally accepted mechanism of Pfitzinger reaction, we suggest that the reaction of compounds 7 and 8 with isatin in alkali proceeds with the formation of isatoic acid which undergoes instantaneous cyclocondensation with carbonyl species 7 and 8 to generate compounds 10 and 11, respectively.
Design and synthesis of spirocyclic ligands of glucocorticoid receptors
Badarau, Eduard,Robert, Frédéric,Massip, Stéphane,Jakob, Florian,Lucas, Simon,Frormann, Sven,Ghosez, Léon
, p. 5119 - 5128 (2018/03/07)
Spirocyclic indazoles were designed as potential ligands for the glucocorticoid receptors (GRs). A short and efficient synthetic sequence was developed allowing the preparation of pure diastereomeric spirocyclic analogs of fluorocortivazol. Our studies also revealed a new application of Burgess reagent leading to a ring expansion. The structures and conformations of several key intermediates and products were confirmed by single crystal X-ray diffraction analysis. Conformational assignments were also supported by DFT calculations. As a proof of concept we tested the affinity of diastereomeric compounds 13b and 14b for the GRs. Rewardingly, it was found that 14b showed a promising IC50 of 27 nM.
GLUCOSYLCERAMIDE SYNTHASE INHIBITORS FOR THE TREATMENT OF DISEASES
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Paragraph 000608, (2015/04/15)
Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).
