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Paper | Regular issue | Vol 89, No. 6, 2014, pp.1427-1440
Published online, 25th April, 2014
DOI: 10.3987/COM-14-12994
Synthetic Access to Poly-Substituted 11H-Pyrido[3,2-a]carbazoles, a DNA-Intercalating Ellipticine Related Structure, and Their Antiproliferative Activity

Ming-Yu Wu, Elkhabiry Shaban, Marta Świtalska, Ning Wang, Miho Shimoda, Yusuke Mizutani, Megumi Yoshida, Zhen-Wu Mei, Hiroyuki Kawafuchi, Junzo Nokami, Joanna Wietrzyk,* Xiao-Qi Yu, and Tsutomu Inokuchi*

*Division of Chemsitry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Okayama 700-8530, Japan

Abstract

The facile procedure for the synthesis of the 11H-pyrido[3,2-a]carbazole structure involving the Fischer indole cyclization on tetrahydroquinolinones, available from enaminones and methyl 2-formyl-3-oxopropanoate, followed by the aromatization of the resulting 5,6-dihydro derivatives is described. This method allows for the introduction of substituents at C2, C6, and C8 to the scaffold by choice of the starting materials. In the biological testing, introduction of the phenyl group at C6 is significantly effective to improve the antiproliferative activity.