Heterocyclic Communications p. 173 - 180 (2010)
Update date:2022-08-03
Topics:
Yamada, Manabu
Asai, Kazuhide
Yamashita, Junko
Suyama, Takuya
Niimi, Taishi
Maddali, Kasthuraiah
Fujie, Michio
Nakamura, Satoki
Kimura, Motohiko
Tanaka, Yasutaka
Toda, Mitsuo
Yamashita, Mitsuji
Novel phosphorus heterocyclic compounds, 3-methyl-1-(3-bromophenyl as well as some 3-substituted phenyl)-2- phospholene 1-oxides (1d as well as 1b, 1c, and 1f), were synthesized from 1-phenyl-2-phospholene 1-oxide 1a via 3-methyl-1-(3-nitrophenyl)-2-phospholene 1-oxide (1b). 1-(4-Bromophenyl)-2- phospholene 1e was prepared by Grignard coupling reaction of 1-chloro-3-methyl-2-phospholene 1-oxide with 4-bromophenylmagnesium bromide. 2,3-Dibromo-3-methyl-1-arylphospholane 1-oxides (2a-2e) were prepared by the addition reaction of bromine to the C=C double bond of 2-phospholenes 1a-1e. The substituent effect of the phenyl group of the 1-aryl-phospho lanes 2 on the observed anti-proliferative effect against U937 leukemia cell lines evaluated by MTT in vitro methods showed that 2,3-dibromo-3-methyl-1-(4-bromophenyl) phospholane (2e) was the most active among 2. These novel dibromophosphorus heterocyclic derivatives exhibit much higher anti-cancer activity than Gleevec (molecular targeting chemotherapeutic agent) against U937 cells.
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Doi:10.1002/cmdc.201200377
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