Retinobenzoic acids. 5. Retinoidal activities of compounds having a trimethylsilyl or trimethylgermyl group(s) in human promyelocytic leukemia cells HL-60.
The retinoidal activities of trimethylsilyl or trimethylgermyl-containing retinobenzoic acids are discussed on the basis of differentiation-inducing activity on human promyelocytic leukemia cells HL-60. Compounds with a trimethylsilyl or trimethylgermyl group at the meta position of the generic formula 2 have more potent activities than the corresponding retinobenzoic acids with a m-tert-butyl group. Compounds having two m-trimethylsilyl or -trimethylgermyl groups also have strong activities, and (E)-4-[3-[3,5-bis(trimethylsilyl)phenyl]-3-oxo-1-propenyl]benzoic acid (22, Ch55S) and (E)-4-[3-[3,5-bis(trimethylgermyl)phenyl]-3-oxo-1- propenyl]benzoic acid (35, Ch55G) are more active than retinoic acid by 1 order of magnitude. However, in the para-substituted chalcone derivatives, the replacement of a tert-butyl group (49, Ch40) with a trimethylsilyl (27, Ch40S) or a trimethylgermyl (30, Ch40G) group caused the disappearance of the activity.
Yamakawa
T
T
Faculty of Pharmaceutical Sciences, University of Tokyo, Japan.
Kagechika
H
H
Kawachi
E
E
Hashimoto
Y
Y
Shudo
K
K
D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D001565:Benzoates / Q000138:chemical synthesis* / Q000627:therapeutic use; D002454:Cell Differentiation / Q000187:drug effects; D055598:Chemical Phenomena; D002621:Chemistry; D006801:Humans; D015463:Leukemia, Prolymphocytic / Q000188:drug therapy; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000627:therapeutic use; D012825:Silicon; D013329:Structure-Activity Relationship; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis* / Q000627:therapeutic use; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000970:Antineoplastic Agents; D001565:Benzoates; D009942:Organometallic Compounds; D014297:Trimethylsilyl Compounds; C063794:4-(3-(3,5-bis(trimethylsilyl)phenyl)-3-oxo-1-propenyl)benzoic acid; C063795:Ch 55G; D012825:Silicon