POTENTIAL PHOTOAFFINITY LABELS FOR TUBULIN - SYNTHESIS AND EVALUATIONOF DIAZOCYCLOHEXADIENONE AND AZIDE ANALOGS OF COLCHICINE, COMBRETASTATIN, AND 3,4,5-TRIMETHOXYBIPHENYL
Jd. Olszewski et al., POTENTIAL PHOTOAFFINITY LABELS FOR TUBULIN - SYNTHESIS AND EVALUATIONOF DIAZOCYCLOHEXADIENONE AND AZIDE ANALOGS OF COLCHICINE, COMBRETASTATIN, AND 3,4,5-TRIMETHOXYBIPHENYL, Journal of organic chemistry, 59(15), 1994, pp. 4285-4296
Analogs of tubulin assembly inhibitors such as colchicine, combretasta
tin, and 3,4,5-trimethoxybiphenyl which incorporate a 6-diazo-2,4-cycl
ohexadienone (o-quinone diazide) ring have been synthesized and charac
terized. The compounds synthesized include 2',3',4'-trimethoxyphenyl)c
yclohexa-2,4-dien-1-one and its 3-methyl and 3-ethyl analogs (1a-c), 3
-(2,3,4-trimethoxyphenyl)-2,4-cyclohexadien-1-one and its 4-methyl and
4-ethyl derivatives (2a-c), ethoxyphenyl)ethenyl]-6-diazocyclohexa-2,
4-dienone (3), oxyphenyl)ethenyl]-6-diazocyclohexa-2,4-dien-1-one (4),
the corresponding dihydro derivatives (5, 6) and two isomeric diazocy
clohexadienones derived from N-acetylcolchinol (7, 8). Compounds in wh
ich the cyclohexadienone oxygen is approximately isostructural with ca
rbonyl or hydroxy functions of the parent compounds exhibit good activ
ity in the tubulin assembly inhibition assay. 2'-Alkyl-4'azido-3,4,5-t
rimethoxy-1,1'-biphenyls also show good activity as tubulin assembly i
nhibitors.