[논문]Effect of Substituents on Benzenesulfonyl Motif of 4-Phenyl-1-arylsulfonylimidazolidinones for Their Cytotoxicity

Lee, Hui-Soon; Park, Kyung-Lae; Choi, Sang-Un; Lee, Chong-Ock; Jung, Sang-Hun

doi:10.1007/bf02975244

[국내논문] Effect of Substituents on Benzenesulfonyl Motif of 4-Phenyl-1-arylsulfonylimidazolidinones for Their Cytotoxicity 원문보기

Archives of pharmacal research : a publication of the Pharmaceutical Society of Korea, v.23 no.6, 2000년, pp.579 - 584

Lee, Hui-Soon (College of Pharmacy, Chung-Nam National University) , Park, Kyung-Lae (College of Pharmacy, Chung-Nam National University) , Choi, Sang-Un (Korea Research Institute of Chemical Technology) , Lee, Chong-Ock (Korea Research Institute of Chemical Technology) , Jung, Sang-Hun (College of Pharmacy, Chung-Nam National University)

Abstract ▼ AI-Helper

To explore the effect of substituents' on phenyl motif on sulfonyl function of novel anticancer 4-phenyl-1-benzenesulfonylimidazolidinones (1), electron donating or withdrawing sub-stituents were introduced at 3 or 4-position and the analogs were tested against human lung (A549) and colon (HCT-15) cancer cell lines. Quantitative structure activity relation-ship of the 4-substituted series shows that only STERIMOL L values are well correlated. The increment of substituent's volume enhances the activity against both cell lines. The small substituent at 3-position additionally increases the activity. However naphthyl group in place of phenyl reduces the activity, Therefore the phenyl motif with sterically large substituent at 4-position and small substituent at 3-position may be important for their activity. Integration of these substituents' effects into the structural design led to discover the more potent analog, 4-phenyl-1-(N-acetylindoline-5-sulfonyl) imidazolidinone (1n).

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제안 방법

For the more explicit investigation of this substituents' effect, some analogs of 1 were synthesized and their cytotoxicity were measured against human lung (A549) and colon (HCT-15) cancer cell lines. Further-morez analysis of the stmctural geometry of the series versus their cytotoxicity were performed to search for the best parameter of QSAR. These substituents' effects were then integrated into structural design of 1 to explore the more potent analog.
All commercial chemicals were used as obtained and all solvents were purified by the standard proced나res prior to use (Perrin, 1982). Thin-layer chromatography was performed on E Merck silica gel GF-254 precoated plates and the identification was done with UV light and colorization with spray 10% phosphomolybdic acid followed by heating. Flash column chromatography was performed with E.

대상 데이터

aIC50 values are the mean value of three times measurement. Cell lines used for test are human lung (A549) and colon (HCT-15) cancer cell lines. b Parameter L values are for the substituents on phenyl group of entry number 1 to 7.

이론/모형

44 for 4-hydrogen (1a\ 4-methyl (1b), 4-methoxy (1c), 4-acetamido (1d), 4-chbro (1e), and 4-flu이。(1f) group, respectively. The fitting was done using least square method.

참고문헌 (10)

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원문보기 상세보기
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