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Note | Special issue | Vol 56, No. 1-2, 2002, pp.519-524
Published online, 1st January, 1970
DOI: 10.3987/COM-01-S(K)30
Synthesis of Non-peptidic Tryptamine Derivative (THS-12) which Stimulates TPO Responsive Cell Growth (Synthetic Studies on Indoles and Related Compounds 51)

Hideharu Suzuki, Tomoko Furukawa, Chiaki Yamada, Ichiro Shibuya, Masateru Kurumi, Tetsuo Yokoyama, and Yasuoki Murakami*

*School of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan


A number of synthetic indole compounds were examined for in vitro TPO responsive cell proliferation assay using BaF/mpl cell. Among these compounds 3-(2-aminoacetyl)-1-phenylsulfonylindole hydrochloride (7, THS-12), which was synthesized via α-bromination of 3-acetyl-1-phenylsulfonylindole followed by amination with hexamethylenetetramine, stimulated strongly cell growth. During the synthetic study we found that the Friedel-Crafts reaction of 1-phenylsulfonylindole (1) with chloroacetyl chloride using AlCl3 unexpectedly gave 6-chloroacetyl-1-phenylsulfonylindole as a main product.