Synthetic access to poly-substituted 11H-pyrido[3,2-a]carbazoles, A dna-intercalating ellipticine related structure, and their antiproliferative activity

Article abstract of DOI:10.3987/COM-14-12994

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.

Full text of DOI:10.3987/COM-14-12994

Supporting Information
for
Synthetic Access to Poly-Substituted 11H-Pyrido[3,2-a]carbazoles, a
DNA-Intercalating Ellipticine Related Structure, and Their Antiproliferative
Activity
Ming-Yu Wu,1,5 Elkhabiry Shaban,1 Marta Świtalska,3 Ning Wang,1
Miho Shimoda,1 Yusuke Mizutani,4 Zhen-Wu Mei,1 Hiroyuki
Kawafuchi,2 Junzo Nokami,4 Joanna Wietrzyk,3* Xiao-Qi Yu,5 and
Tsutomu Inokuchi1*
1Division of Chemistry and Biotechnology, Graduate School of Natural Science
and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama
700-8530, Japan, 2Toyama National College of Technology, Hongo-machi,
Toyama, 939-8630, Japan, 3Institute of Immunology and Experimental Therapy,
Polish Academy of Science, 12, R. Weigl Street, 53-114 Wroclaw, Poland,
4Department of Applied Chemistry, Faculty of Engineering, Okayama University
of Science, Ridai-cho, Kita-ku, Okayama, 700-0005, Japan, 5Key Laboratory of
Green Chemistry & Technology, Ministry of Education, College of Chemistry,
Sichuan University, Chengdu 610064, P. R. China
E-mail*: inokuchi@cc.okayama-u.ac.jp
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