Abstract
Synthesis of pyrazolo[1,5-a]pyrimidine ring as a possible bioisosteric replacement of the 5-(1H-pyrrol-1-yl)pyrazole scaffold
Highlights
Heterocyclic compounds with pyrrole and pyrazole structures have aroused increasing interest over time both for their relevance among natural compounds and for their assessed or potential applications in the pharmaceutical field, as demonstrated by some noteworthy contributions in the recent literature.[1,2,3] O N N H NN O O Me NO N N2 X H
Preliminary molecular modeling studies have referred to the unsubstituted N-benzyl-5,7dimethylpyrazolo[1,5-a]pyrimidine-3-carboxamide (Figure 1, X =H)
Conformational analysis identified several conformational minima that show a very similar three-dimensional arrangement with the N4---HN distance between 2.20 and 2.23 Å, and the NH-N4 angle between 133.9 and 139.6 degrees, comparable to that reported in the literature for similar compounds (i.e., 2.06 Å and 134.7 degrees found for the 6-methyl-N[(1R)-1-[4-(trifluoromethyloxy)phenyl]propyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide co-crystallized to the human PDE2A, entry 5xkm of the protein data bank), and in agreement with geometric criteria of the existence of the NH---N hydrogen bond.[11]
Summary
Synthesis of pyrazolo[1,5-a]pyrimidine ring as a possible bioisosteric replacement of the 5-(1H-pyrrol-1-yl)pyrazole scaffold. It is a pleasure to take this opportunity to acknowledge the significant contribution to the chemistry of heterocyclic compounds by Professor Girolamo (Gilmo) Cirrincione and his Palermo group
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
