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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 39, Number 4
JKCSEZ 39(4)
August 20, 1995 

 
Title
Molecular Orbital Interpretation on Antitumor Activity of trans-Palladium(Ⅱ) Complexes by Geometrical Structure of Ligands (Ⅰ)
Author
Young-Dae Song, Byung-Kak Park*
Keywords
Abstract
이소옥사졸과 그의 유도체를 가진 팔라듐(Ⅱ) 착물[Pd(L)2X2], L=isoxazole(isox), 3,5-dimethylisoxazole(3,5-diMeisox), 3-methyl, 5-phenylisoxazole(3-Me, 5-Phisox), and 4-amino, 3,5-dimethylisoxazole(4-ADI); X=Cl, Br]의 항암활성을 확장분자궤도함수(EHMO)법으로 조사하였다. X 원자의 알짜전하 값은 trans-이성체가 cis-이성체보다 음의 값으로 대체로 크게 나타났고, X=Cl일 때가 X=Br일 때보다 음의 값으로 커서, Cl일 때가 이탈이 용이함을 알 수 있다. Pd(Pd(dx2-y2)-X(px)의 σMO 에너지(Eσ(Pd-N))가 Pd(dx2-y2)-N(px)의 σMO 에너지(Eσ(Pd-N))보다 예외없이 더 높아서 결합이 약함을 알았다. 아울러 같은 착물에서 cis-보다 trans- 착물에서 Eσ(Pd-X)값이 더 높아서 결합이 약함을 알았다. 따라서 X- 이온으로 떨어져 나가는 용이성과 그 구조변화가 항암활성과 관계가 있을 것으로 생각하고 Eσ(Pd-N)-Eσ(Pd-X)값과 저해활성 계수인 logIA의 값을 도시하였던 바 실험치와 상관 계수가 0.96인 좋은 직선성이 성립함을 알았다.

The palladium(Ⅱ) complexes(where, [Pd(L)2X2], L=isoxazole(isox), 3,5-dimethylisoxazole(3,5-diMeisox), 3-methyl, 5-phenylisoxazole(3-Me, 5-Phisox), and 4-amino, 3,5-dimethylisoxazole(4-ADI); X=Cl, Br] with isoxazole and its derivatives are investigated on antitumor activity by EHMO calculation. It is found that the net charge of the two halogen atoms in trans-isomers are greater than those in cis-ones, indicating that ionic character of Pd-X bond in trans-isomers is greater than that of cis-ones, and so dissociation of Cl- ion is easier than that of Br- ion in aqueous solution in body. Furthermore, it is found that the σMO energy of Pd(dx2-y2)-X(px) bond (Eσ(Pd-X)) is higher than that of Pd(dx2-y2)-N(px) bond (Eσ(Pd-N)) without exception, about all the complexes, and also the Eσ(Pd-X) of trans-isomers is higher than that of cis-isomers. From the above facts, the degree of dissociation in Pd-X bond would be related to antitumor activity. In fact, the linear equation of correlation coefficient 0.96 is fairly established between ΔEσ(N-X)(Eσ(Pd-N)-Eσ(Pd-X)) and inhibitory activity coefficient, logIA.

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