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성낙도 ( Nack-do Sung ),정훈성 ( Hoon-sung Jung ),김상진 ( Sang-jin Kim ) 대한화장품학회 2004 대한화장품학회지 Vol.30 No.4
일련의 Alkyl-3,4-dihydroxybenzoate (A)와 N-Alkyl-3,4-dihydroxybenzamide (B) 유도체들의 치환기(R<sub>1</sub> 및 R<sub>2</sub>) 변화에 따른 멜라닌생성 저해활성 관계들을 HQSAR 방법으로 분석하였다. 멜라닌생성 저해활성에 관하여 유도된 HQSAR 모델은 매우 양호한 예측성(cross-validated r<sup>2</sup><sub>cv.</sub>, q<sup>2</sup>=0.674)과 적합성(non-cross-validated, r<sup>2</sup><sub>ncv</sub>=0.936)을 나타내었다. 멜라닌생성 저해활성과 가수분해 반응성은 공히, (A)가 (B)보다 컸으며(A>B), R<sub>1</sub>-치환기가 R<sub>2</sub>-치환기보다 저해활성에 의존적인 경향을 나타내었다(R<sub>1</sub>>R<sub>2</sub>). 또한, 경계분자궤도(FMO) 이론에 따라 가수분해 반응은 (A), (B)의 LUMO와 물분자의 HOMO 사이에 강한 상호작용으로 orbital-control 반응인 친핵성 첨가-제거반응(Ad<sub>N-E</sub>)이 주로 일어나는 것을 알 수 있었다. Holographic quantitative structure activity relationships (HQSAR) between the melanogenesis inhibitory activities of alkyl-3,4-dihydroxybenzoate (A) and N-Alkyl-3,4-dihydroxybenzamide (B) derivatives were analyzed and discussed. The statistical results of HQSAR model for the activities showed the best predictability of the activities based on the cross-validated r<sup>2</sup><sub>cv</sub>(q<sup>2</sup>=0.674), non-cross-validated, conventional coefficient (r<sup>2</sup><sub>ncv</sub>=0.936). The melanogenesis inhibitory activities and hydrolytic reactivity of (A) were slightly higher than that of (B) (A>B) and the activities depends upon the R<sub>1</sub>-substituents (R<sub>1</sub>>R<sub>2</sub>). It has been found using frontier molecular orbital (FMO) theory that the hydrolysis reactions of (A) and (B) proceeded to an orbital-controlled reactions, while the nucleophillc addition-elimination reactions (Ad<sub>N-E</sub>) between LUMO energy of (A) and (B) and HOMO energy of water molecule are occurred.
성낙도 ( Nack-do Sung ),정훈성 ( Hoon-sung Jung ),김상진 ( Sang-jin Kim ) 대한화장품학회 2005 대한화장품학회지 Vol.31 No.1
일련의 alkyl-3,4-dihydroxybenzoate (A)와 N-alkyl-3,4-dihydroxybenzamide (B) 유도체들의 치환기(R1 및 R2) 변화에 따른 피부 감작성과의 관계를 HQSTR 방법으로 분석하였다. 유도된 피부 감작성에 관한 HQSTR 모델은 매우 양호한 예측성(cross-validated r<sup>2</sup><sub>cv.</sub>, q<sup>2</sup>=0.744)과 적합성(non-cross-validated, r<sup>2</sup><sub>ncv.</sub>=0.978)을 나타내었다. 이들 두 화합물은 멜라닌 생성 저해 활성이 클수록 피부 감작성이 낮은 반비례적인 경향을 보였으며 R1-치환기 사슬 중 C1 ~ C3 원자 부분은 피부 감작성에 기여하지 않는 경향을 나타내었다. 따라서 ester (A)는 amide (B)보다 피부 감작성이 낮으나(A< B) 멜라닌 생성 저해 활성이 큰(A >B) 특징을 나타내므로 미백제의 활성 성분으로서 매우 이상적인 화합물임을 알았다. Holographic quantitative structure-toxicity relationships (HQSTR) of alkyl-3,4-dihydroxybenzoate (A) and N-alkyl-3,4-dihydroxybenzamide (B) derivatives were analyzed and discussed. The HQSTR model X for the skin sensitivity showed the best predictability based on the cross-validated r<sup>2</sup><sub>cv.</sub> (q<sup>2</sup>=0.744), non cross-validated, and conventional coefficient (r<sup>2</sup><sub>ncv.</sub>=0.978). The relationships between melanogenesis inhibitory activities and skin sensitization of compounds have a tendency to a reciprocal proportion. Therefore, the more higher melanogenesis inhibitory activities of compounds were, the more lower skin sensitization of compounds became. The side chain, C1 ~ C3 part of R1-substituents in (A) and (B) did not exhibit any contribution to skin sensitization. Particularly, it is reveals that the skin sensitization of ester (A) were slightly lower (A < B) than that of amide (B) and melanogenesis Inhibitory activities of (A) were slightly higher (A > B) than that of (B). It is founded that the alkyl-3,4-dihydroxybenzoate derivatives (A) were an ideal compound as an ingredient of whitening agents.