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제120회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Synthesis and Cytotoxic Evaluation of N-Aroylureas Under Rh(III)-Catalyst via C-H Activation

2017년 8월 31일 15시 52분 19초
ORGN.P-439 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
10월 20일 (금요일) 13:00~14:30
Organic Chemistry
저자 및
Sukhun Lee, IN SU KIM1,*
University of Pharmacy, Sungkyunkwan University, Korea
1College of Pharmacy / Department of Pharmacy, Sungkyunkwan University, Korea

The rhodium(III)-catalyzed C-H amidation and subsequent C-N bond formation reaction of indolines with aryl and alkyl isocyanates at room temperature are reported. These transformations allow the generation of N-aroylurea functionality at the C7-position of indolines, which is known as a crucial scaffold found in biologically active molecules. In addition, the synthesis of pyrroloindolidione derivatives is also described through sequential C6-amidation reaction and intramolecular cyclization of C7-amidated indolines. All synthesized products were evaluated for in vitro cytotoxic effect against human prostate adenocarcinoma cells (DU145), human breast cancer cells (MCF-7), and triple negative human breast cancer cells (MDAMB-231), respectively. Notably, compounds 4d and 4e with linear alkyl side chains were found to be highly cytotoxic, which is comparable to that of anticancer doxorubicin and cisplatin as positive controls. we herein present the unexpected formation of N-aroylureas derived from indolines and aryl/alkyl isocyanates via the Rh(III)-catalyzed direct amidation reaction of indolines at the C7-position followed by subsequent C−N bond formation. In addition, all synthesized products have been evaluated for cytotoxic activity against various cancer cell lines such as human prostate adenocarcinoma cell lines (DU145), human breast cancer cell lines (MCF-7) and triple negative human breast cancer cell lines (MDA-MB-231), and were found to display promising cytotoxic effect competitive with well-known anticancer doxorubicin and cisplatin.