Design, synthesis, and preliminary biological evaluation of 2,3-dihydro-3-hydroxymethyl-1,4-benzoxazine derivatives.
We synthesized a series of novel small molecules, 2,3-dihydro-3-hydroxymethyl-1,4-benzoxazine derivatives, by tandem reduction-oxirane opening of 2-nitroaroxymethyloxiranes in moderate or excellent yields. We investigated the effects of all of the compounds on HUVEC apoptosis and A549 cell growth. The results showed that 6,8-dichloro-2,3-dihydro-3-hydroxymethyl-1,4-benzoxazine was the most effective small molecule in promoting HUVEC apoptosis and inhibiting A549 cell proliferation, but 6-amino-2,3-dihydro-3-hydroxymethyl-1,4-benzoxazine could remarkably inhibit HUVEC apoptosis and might induce the formation of microvessel.
Jiao
Pei-Fu
PF
Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, China.
Zhao
Bao-Xiang
BX
Wang
Wei-Wei
WW
He
Qiu-Xia
QX
Wan
Mao-Sheng
MS
Shin
Dong-Soo
DS
Miao
Jun-Ying
JY
D017209:Apoptosis / Q000187:drug effects; D048588:Benzoxazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D048430:Cell Shape; D002478:Cells, Cultured; D015195:Drug Design; D042783:Endothelial Cells / Q000166:cytology / Q000187:drug effects; D006801:Humans; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D014470:Umbilical Cord / Q000166:cytology / Q000187:drug effects
D048588:Benzoxazines