The synthesis of 2-benzylamino-8-methoxy-4H-chromene-3-carbonitriles 7(a-e) has been realized in four steps, via reductive amination from the 2-amino-8-methoxy-4H-chromene-3-carbonitrile 4 as key intermediate platform with para- and meta-substituted benzaldehydes 5(a-e), in good overall yields. The physicochemical properties of 7(a-e) and also their aldimines 6(a-e) precursors have been determined using the Swiss ADME server platform according to the Lipinski’s descriptors. Biological assays with a panel of six protein kinases such as HsCDK5-p25, HsCDK9/cyclin T, HsPim1, HsHaspin, SscGSK-3a/b and SscCK1d/e showed that aldimines 6(a,b) and 6e are potentially interesting because they showed good percentage of residual activities against HsPim1 and HsHaspin.
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N-benzyl derivatives of 2-amino-8-methoxy-4H-chromene-3-carbonitrile: synthesis via reductive amination, in silico ADME profiling & exploration of their effects against protein kinases.
Published: 01 November 2022 by MDPI in 8th International Electronic Conference on Medicinal Chemistry session Pharmaceutical development
Keywords: 2-amino-4H-chromene; reductive amination; N-benzylation; Lipinski’s descriptors, protein ki-nase, Pim1 inhibitor, Haspin inhibitor