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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

 and *
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 duocarmycin; Indole C5-O-substituted seco-CI; cytotoxicity; DNA minor groove alkylation
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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