레티노익 산의 형태와 구조-활성 관계 -레티노벤조익 산-

• 영문명: Conformation of Retinoic Acid and Structure-Activity Relationships -Retinobenzoic Acid -
• 발행기관: 대한약학회
• 저자명: 이종달(Jong Dal Rhee) 이인자(In Ja Rhee)
• 간행물 정보: 『약학회지』제38권 제3호 (1994년), 230~237쪽, 전체 8쪽
• 주제분류: 의약학 > 기타의약학
• 파일형태: PDF
• 발행일자: 1994.06.30

영문 초록

The structure-activity relationships of (E)-chalcone-4-carboxylic acids, flavone-4''-carboxylic acids, two types of aromatic amides, terephthalic monoanilides, and (arylcarboxamido)benzoic acids, which were made by Shudo group, are discussed by conformation analysis(AM1) of retinoic acid and those compounds. Conformer of each compound is superimposed on the conformationally restricted compound, 4-(6,7,8,9-tetrahydro-6,6,9,9-tetramethyl-4H-4-oxonaphto[2,3-b]pyran-2-yl)benzoic acid(Fv8O), possessing the strongest differentiation-inducing activity on human promyelocytic leukemia cells HL-60. The results indicated that the lengths between the carboxylic carbon and the two 6, 9 carbons binding to dimethyl, 1.20nm and 1.09nm, as well as the planarity of molecule are very important factors for the activity, especially 1.20 nm. In the case of the recently synthesized azulenic retinoic acids by Sato, et al. in 1993, the distance probably is also important, resulted from superimposing them on a Ch55 conformer and Fv8O. The distance 1.0nm is also important in Ch55. Several conformers of all-trans retinoic acid (RA) are well superimposed on the almost non-flexible Fv8O, RA, 9-cis RA, and, specifically s-10,12 cis RA. And a simple hexangular model of RA is suggested to draw RA conformers easily without computer drawing model or molecular model.