119567-96-3Relevant academic research and scientific papers
Retinobenzoic Acids. Structure-Activity Relationships of Chalcone-4-carboxylic Acids and Flavone-4'-carboxylic Acids
Kagechika, Hiroyuki,Kawachi, Emiko,Hashimoto, Yuichi,Shudo, Koichi
, p. 834 - 840 (2007/10/02)
The structure-activity relationships of (E)-chalcone-4-carboxylic acids, which are retinoidal benzoic acids represented by R-Ph-X-Ph-COOH (4, X=-COCH=CH-), are discussed on the basis of differentiation-inducing activity on human promyelocytic leukemia cells HL-60.The activity was increased by the substitution of a bulky alkyl group(s) (R), and among such compounds, (E)-4-benzoic acid (Ch55) and (E)-4-benzoic acid (Ch80) are several times more active than retinoic acid.Though the stable conformer of chalcone derivatives is linear (s-cis form), the conformationally restricted analogue 4-(6,7,8,9-tetrahydro-6,6,9,9-tetramethyl-4H-4-oxonaphthopyran-2-yl)benzoic acid (Fv80) is more active than Ch80.While the effect of introduction of an oxygen atom varied, 4-benzoic acid (Re80), regarded as a derivative of Ch80 with two additional hydroxyl groups, has very strong activity.
