• 한국응용약물학회:학술대회논문집
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• 한국응용약물학회 1994년도 춘계학술대회 and 제3회 신약개발 연구발표회
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• pp.224-224
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• 1994

N-arylsulfonylimidazolenes를 항암효과가 우수한 화합물로 설정하여 이들 유도체를 합성하고 이들의 세포독성을 측정한바 있다. 그 이유는 2번 위치의 alkoxy기에 의하여 alkylating agent로서 작용할 수 있다는 개념과 생체 반응 후 생성될 것으로 예상되는 N-arylsulfonylimidazolidinone이 sulofenur와 유사한 작용을 갖을 것으로 기대 되었기 때문이다. 이에따라 N-arylsulfonylimidazolidinone 유도체의 항암효과의 측정이 관심의 대상이 됨에 따라 이들 유도체를 합성하고 이들의 세포독성을 관찰함으로써N-arylsulfonylimidazolidinone 유도체들의 구조 활성 상관관계를 관찰하고자 하였다. 합성은 출발물질을 N-arylsulfonyl-2-alkoxyimidazoline에서 시작 몇단계를 거쳐 목적하는 화합물을 합성 하였다.

• Bulletin of the Korean Chemical Society
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• 제34권7호
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• pp.2011-2015
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• 2013

To improve the water solubility of arylsulfonylimidazolidinone (JSH-2282), a potent anti-cancer agent, two urea derivatives, sodium (S)-2-(3-(4-(5-((S)-2-oxo-4-phenylimidazolidin-1-ylsulfonyl)indoline-1-carbonyl)-phenyl)ureido)succinate (2a) and sodium (S)-2-(3-(4-(5-((S)-2-oxo-4-phenylimidazolidin-1-ylsulfonyl)indoline-1-carbonyl)phenyl)ureido)pentanedioate (2b), were synthesized and studied for solubility and anti-cancer activity.

• 대한약학회:학술대회논문집
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• 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2
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• pp.357.1-357.1
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• 2002

Three-dimensional quantitative activity relationship (3D-QSAR) study for a series of arylsulfonylimidazolidinone derivatives with antitumor activity was conducted using comparative molecular field analysis (CoMFA) and comparative molecular similarity indices anaysis (CoMSIA). The in vitro cytotoxicity against human lung carcinoma (A549) exhibited a strong correlation with steric and electrostatic factors of the molecules. (omitted)

• Bulletin of the Korean Chemical Society
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• 제32권spc8호
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• pp.3009-3016
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• 2011

To investigate the possible isosteric replacement of imidazolidinone moiety in 4-phenyl-N-arylsulfonylimidazolidinone for broad and potent anticancer agents, a series of 4-phenyl-l(N)-arylsulfonylimidazolidinones 6a-k, imidazolidinethione analogs 7a-i, and imidazolidine oxime analogs 8a-c were prepared and evaluated for their in vitro anticancer activity against four human cancer cell lines (human lung A549, human colon COLO205, human leukemia K562, human ovary SK-OV-3). Among all the derivatives of N-arylsulfonylimidazolidinone 6a-k, compounds 6f and 6g showed the best inhibition comparable to doxorubicin against all cancer cell lines. Increasing the carbon chain on alkyl moieties of carbamates as shown in 6c-g did not alter the activity. The imidazolidinethione analogs 7a-i and imidazolidin-2-one oxime derivatives 8a-c did not possess any good activity. Therefore, imidazolidinone moiety is the best pharmacophore among the 4-phenyl-Narylsulfonylimidazolidinone derivatives.

• Bulletin of the Korean Chemical Society
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• 제35권10호
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• pp.2922-2928
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• 2014

To investigate the possible isosteric replacement of imidazolidinone moiety in 4-phenyl-1-arylsulfonylimidazolidinones (2) for broad and potent anti-cancer agents, a series of 5-phenyl-1H-pyrazol-3-yl 1-(acyl)indoline-5-sulfonates (4) and 1-(1-(acyl)indolin-5-ylsulfonyl)-5-phenylpyrazolidin-3-ones (5) were prepared and evaluated for their cytotoxicity against six human cancer cell lines. Although the pyrazoles 4 or pyrazolidinones 5 showed relatively good activity, still they showed lesser activity in comparison to imidazolidinones 2. These activity decreases could be interpreted with the effect of change of the hydrogen bonding characteristics and the substitution pattern on structural variations of five membered rings from imidazolidinones 2 to pyrazoles 4 and pyrazolidinones 5, respectively. Therefore, it can be concluded that 4-phenyl-1-arylsulfonylimidazolidinone is a basic pharmacophore of imidazolidinones 2.

• Archives of Pharmacal Research
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• 제24권6호
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• pp.499-502
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• 2001

To evaluate the role of imidazolidinone moiety of potential anticancer 4-phenyl-1-arylsulfonylimidazolidinones 1 for their cytotoxicity conformationally similar 4-phenyl-2-arylsulfonylaminooxazolines 2 were synthesized and compared their cytotoxicities with those of the corresponding 1. Compounds 2 showed much reduced activity compared to N-arylsulfonylimidazolidinones 1. This result might indicate that the imidazolidinone ring of 1 have the other roles for the activity as an essential structural motif in addition to conformational contribution .

• Archives of Pharmacal Research
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• 제23권6호
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• pp.579-584
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• 2000

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).