E,E-2-Benzylidene-6-(nitrobenzylidene)cyclohexanones: syntheses, cytotoxicity and an examination of some of their electronic, steric, and hydrophobic properties.
Three series of structurally isomeric 2-benzylidene-6-(nitrobenzylidene) cyclohexanones 1-3 were prepared and evaluated against human Molt/C8 and CEM T-lymphocytes as well as murine L1210 cells. The IC(50) values of the majority of compounds are less than 10microM and in some assays, the figures for 1d and 1e are submicromolar. Correlations were discerned between cytotoxic potencies and the atomic charges on one of the olefinic carbon atoms, the torsion angles between an aryl ring, and the adjacent unsaturated group as well as logP values. Three representative compounds were examined for their effect on respiration in rat liver mitochondria.
Das
Umashankar
U
College of Pharmacy and Nutrition, University of Saskatchewan, 110 Science Place, Saskatoon, Sask., Canada S7N 5C9.
Doroudi
Alireza
A
Das
Swagatika
S
Bandy
Brian
B
Balzarini
Jan
J
De Clercq
Erik
E
Dimmock
Jonathan R
JR
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D001597:Benzylidene Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D045744:Cell Line, Tumor; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D020128:Inhibitory Concentration 50; D007939:Leukemia L1210; D051379:Mice; D008930:Mitochondria, Liver / Q000187:drug effects / Q000378:metabolism; D010101:Oxygen Consumption / Q000187:drug effects; D011407:Propane / Q000031:analogs & derivatives / Q000633:toxicity; D051381:Rats; D013237:Stereoisomerism
C526289:2,6-bis(benzylidene)cyclohexanone; C520655:3-(3,4,5-trimethoxyphenyl)-1-oxo-2-propene; D000970:Antineoplastic Agents; D001597:Benzylidene Compounds; D003512:Cyclohexanones; D011407:Propane