<P><B>Abstract</B></P> <P>This work describes a solid-phase synthetic method for building a compound library of <I>N</I>-alkyl-4-alkylamino-1-aryl-1<I>H</I>-pyrazolo[3,4-<I>d</I>]pyrim...
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https://www.riss.kr/link?id=A107506783
2017
-
SCI,SCIE,SCOPUS
학술저널
5959-5973(15쪽)
0
상세조회0
다운로드다국어 초록 (Multilingual Abstract)
<P><B>Abstract</B></P> <P>This work describes a solid-phase synthetic method for building a compound library of <I>N</I>-alkyl-4-alkylamino-1-aryl-1<I>H</I>-pyrazolo[3,4-<I>d</I>]pyrim...
<P><B>Abstract</B></P> <P>This work describes a solid-phase synthetic method for building a compound library of <I>N</I>-alkyl-4-alkylamino-1-aryl-1<I>H</I>-pyrazolo[3,4-<I>d</I>]pyrimidine-6-carboxamide derivatives, that are based on the biologically active 1-aryl-1<I>H</I>-pyrazolo[3,4-<I>d</I>]pyrimidine scaffold. In the first step of this synthetic sequence, condensation reactions of ethyl 5-amino-1-aryl-1<I>H</I>-pyrazole-4-carboxylates with methyl cyanoformate resulted in the formation of esters that underwent hydrolysis to give 1-aryl-4,5-dihydro-1<I>H</I>-pyrazolo[3,4-<I>d</I>]pyrimidin-4-one-6-carboxylic acids. The coupling reaction of these carboxylic acids with primary alkylamine-loaded acid-sensitive methoxybenzaldehyde (AMEBA) resins was followed by amination reactions mediated by benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP). Subsequent cleavage from the solid support resulted in the formation of the target <I>N</I>-alkyl-4-alkylamino-1-aryl-1<I>H</I>-pyrazolo[3,4-<I>d</I>]pyrimidine-6-carboxamide derivatives. The reaction conditions for solid-phase transformations were optimized using a solution-phase model study with 2,4-dimethoxybenzyl-protected isobutylamine as a reactant in place of the AMEBA resin-loaded isobutylamine. The progress of the solid-phase reactions was monitored by on-bead ATR-FTIR spectroscopy. Diversification experiments were performed by using 1-aryl-4,5-dihydro-1<I>H</I>-pyrazolo[3,4-<I>d</I>]pyrimidin-4-one-6-carboxylic acids and a variety of primary and secondary amine building blocks to build the target compound library.</P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>