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Synthesis of Novel 8‐ cyclo ‐1,5,3, 7‐Diazadiphosphocine Derivatives Via [4 + 2] Cycloaddition
Author(s) -
Bae Song Mi,
Chen Yu,
Jeong Il Soo,
Cho Jong Hyun,
Song Ju Hyun,
Jung Dai Il
Publication year - 2021
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.12154
Subject(s) - paraformaldehyde , dimethyl acetylenedicarboxylate , cycloaddition , chemistry , amine gas treating , medicinal chemistry , mannich reaction , methylamine , combinatorial chemistry , organic chemistry , catalysis
As part of our research program into pharmacologically valuable compounds and chelating agents for transition metal ions, novel 8‐ cyclo ‐1,5,3,7‐diazadiphosphocines ( 5 – 16 ) were successfully synthesized in good yields via [4 + 2] cycloaddition reaction between 8‐ cyclo ‐1,5,3,7‐diazadiphosphocines ( 4a ‐ c ) with dienophiles (dimethyl acetylenedicarboxylate [DMAD], diethyl acetylenedicarboxylate [DEAD], diethyl diazene‐1,2‐dicarboxylate [DEDAD], and diisopropyl diazene‐1,2‐dicarboxylate [DIPDAD]). The core precursor scaffolds ( 4a ‐ c ) were prepared via a one‐pot reaction between heteroaromatic amine analogs ( 1a ‐ c ), paraformaldehyde and hypophosphorous acid in the presence of 6 M HCl. The biological activity of all synthesized 8‐ cyclo ‐1,5,3,7‐diazadiphosphocines ( 4a ‐ c , and 5 – 16 ) was evaluated against several cancer cell lines.