title: 3D-QSAR study of adamantyl N-benzylbenzamides as melanogenesis inhibitors.
abstract: Three-dimensional quantitative structure-activity relationship (3D-QSAR) modeling, comparative molecular field analysis (CoMFA), and comparative molecular similarity indices analysis (CoMSIA) of polyhydroxylated N-benzylbenzamide derivatives containing an adamantyl moiety were performed to understand the mechanism of action and structure-activity relationship of these compounds. Contour map analysis indicated that steric contributions of the adamantyl moiety and electrostatic contributions of the hydroxyl group at the 3-position are important in the activity. Activities of the training set and test sets predicted by CoMFA fit well with actual activities, demonstrating that CoMFA, along with the best calculated q(2) value, has the best predictive ability.
authors.affiliation: Materials Science, Medical Beauty Research Division, AmorePacific Corporation R&D Center, 314-1 Bora-Dong, Kiheung-Gu, Yongin-si, Kyounggi-do 446-729, South Korea.
authors.forename: Yong Deog
authors.initials: YD
authors.lastname: Hong
authors.affiliation: Materials Science, Medical Beauty Research Division, AmorePacific Corporation R&D Center, 314-1 Bora-Dong, Kiheung-Gu, Yongin-si, Kyounggi-do 446-729, South Korea.
authors.forename: Heung Soo
authors.initials: HS
authors.lastname: Baek
authors.affiliation: T&J Tech Inc., Kasan-Dong, Keumchun-Gu, Seoul 153-770, South Korea.
authors.forename: Haelim
authors.initials: H
authors.lastname: Cho
authors.affiliation: Kyung Hee University Skin Biotechnology Center, Suwon 443-759, South Korea.
authors.forename: Soo Mi
authors.initials: SM
authors.lastname: Ahn
authors.affiliation: Materials Science, Medical Beauty Research Division, AmorePacific Corporation R&D Center, 314-1 Bora-Dong, Kiheung-Gu, Yongin-si, Kyounggi-do 446-729, South Korea.
authors.forename: Ho Sik
authors.initials: HS
authors.lastname: Rho
authors.affiliation: Materials Science, Medical Beauty Research Division, AmorePacific Corporation R&D Center, 314-1 Bora-Dong, Kiheung-Gu, Yongin-si, Kyounggi-do 446-729, South Korea.
authors.forename: Young-Ho
authors.initials: YH
authors.lastname: Park
authors.affiliation: Materials Science, Medical Beauty Research Division, AmorePacific Corporation R&D Center, 314-1 Bora-Dong, Kiheung-Gu, Yongin-si, Kyounggi-do 446-729, South Korea.
authors.forename: Yung Hyup
authors.initials: YH
authors.lastname: Joo
authors.affiliation: Materials Science, Medical Beauty Research Division, AmorePacific Corporation R&D Center, 314-1 Bora-Dong, Kiheung-Gu, Yongin-si, Kyounggi-do 446-729, South Korea. Electronic address: hydhong@amorepacific.com.
authors.forename: Song Seok
authors.initials: SS
authors.lastname: Shin
mesh_terms: D000818:Animals; D001549:Benzamides / Q000737:chemistry* / Q000494:pharmacology; D045744:Cell Line, Tumor; D002478:Cells, Cultured; D008543:Melanins / Q000037:antagonists & inhibitors* / Q000378:metabolism; D008544:Melanocytes / Q000187:drug effects / Q000502:physiology; D051379:Mice; D017433:Protein Structure, Secondary; D021281:Quantitative Structure-Activity Relationship
chemical_list: D001549:Benzamides; D008543:Melanins
keywords: 3D-QSAR; CoMFA; CoMSIA; Melanogenesis; N-Benzylbenzamide