101449-10-9Relevant academic research and scientific papers
Aza-retinoids as novel retinoid X receptor-specific agonists
Farmer, Luc J.,Marron, Kristen S.,Canan Koch, Stacie S.,Hwang,Kallel, E. Adam,Zhi, Lin,Nadzan, Alex M.,Robertson, Dave W.,Bennani, Youssef L.
, p. 2352 - 2356 (2007/10/03)
A new structurally simple series of potent lipophilic aza-retinoids RXR agonists has been developed. SAR studies for the N-alkyl-azadienoic acids described here demonstrate that the RXR activity profile is sensitive to the N-alkyl chain length. Further, we have expanded the work to include azadienoic acids, which exhibited many accessible conformations leading to a better understanding of the SAR around the series.
Retinobenzoic Acids. 1. Structure-Activity Relationships of Aromatic Amides with Retinoidal Activity
Kagechika, Hiroyuki,Kawachi, Emiko,Hashimoto, Yuichi,Himi, Toshiyuki,Shudo, Koichi
, p. 2182 - 2192 (2007/10/02)
Two types of aromatic amides, terephthalic monoanilides and (arylcarboxamido)benzoic acids, have been shown to possess potent retinoidal activities and can be classified as retinoids.The structure-activity relationships of these amides are discussed on the basis of differentiation-inducing activity on human promyelocytic leukemia cells HL-60.In generic formula 4 (X = NHCO or CONH), the necessary factors to elicit the retinoidal activities are a medium-sized alkyl group (isopropyl, tert-butyl, etc.) at the meta position and a carboxyl group at the para position of the other benzene ring.The bonding of the amide structure can be reversed, this moiety apparently having the role of locating the two benzene rings at suitable positions with respect to each other.Substitution at the ring position ortho to the amide group or N-methylation of the amido group caused loss of activity, presumably owing to the resultant change of conformation.It is clear that the mutual orientation of the benzylic methyl group(s) and the carboxyl group and their distance apart are essential factors determining the retinoidal activity.Among the synthesized compounds, 4-benzoic acid (Am80) and 4-benzoic acid (Am580) were several times more active than retinoic acid in the assay.They are structurally related to retinoic acid, as is clear from the biological activity of the hybrid compounds (M2 and R2).
