Molecules 2010, 15(11), 7971-7984; doi:10.3390/molecules15117971
Article

Structural Necessity of Indole C5-O-Substitution of seco-Duocarmycin Analogs for Their Cytotoxic Activity

Taeyoung Choi and Eunsook Ma* email
College of Pharmacy, Catholic University of Daegu, Hayang, 712-702, Korea
* Author to whom correspondence should be addressed.
Received: 28 September 2010; in revised form: 24 October 2010 / Accepted: 28 October 2010 / Published: 8 November 2010
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Abstract: A series of racemic indole C5-O-substituted seco-cyclopropylindole (seco-CI) compounds 1-5 were prepared by coupling in the presence of EDCI of 1-(tert-butyloxycarbonyl)-3-(chloromethyl)indoline (seg-A) with 5-hydroxy-, 5-O-methylsulfonyl, 5-O-aminosulfonyl, 5-O-(N,N-dimethylaminosulfonyl)- and 5-O-benzyl-1H-indole-2-carboxylic acid as seg-B. Compounds 1-5 were tested for cytotoxic activity against four human cancer cell lines (COLO 205, SK-MEL-2, A549, and JEG-3) using a MTT assay. Compounds 2 and 3 with small sized sulfonyl substituents like 5-O-methylsulfonyl and 5-O-aminosulfonyl exhibit a similar level of activity as doxorubicin against all cell lines tested.
Keywords: duocarmycin; Indole C5-O-substituted seco-CI; cytotoxicity; DNA minor groove alkylation

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Cite This Article

MDPI and ACS Style

Choi, T.; Ma, E. Structural Necessity of Indole C5-O-Substitution of seco-Duocarmycin Analogs for Their Cytotoxic Activity. Molecules 2010, 15, 7971-7984.

AMA Style

Choi T, Ma E. Structural Necessity of Indole C5-O-Substitution of seco-Duocarmycin Analogs for Their Cytotoxic Activity. Molecules. 2010; 15(11):7971-7984.

Chicago/Turabian Style

Choi, Taeyoung; Ma, Eunsook. 2010. "Structural Necessity of Indole C5-O-Substitution of seco-Duocarmycin Analogs for Their Cytotoxic Activity." Molecules 15, no. 11: 7971-7984.

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