oligomerization of indole derivatives with incorporation of thiols低聚吲哚衍生物的硫醇的合并.pdfVIP

Molecules 2008, 13, 1846-1863; DOI: 10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /molecules Article Oligomerization of Indole Derivatives with Incorporation of Thiols Felikss Mutulis 1, 2 *, Adolf Gogoll 3, Ilze Mutule 1, 2, Sviatlana Yahorava 1, Aleh Yahorau 1, 2 1 Edvards Liepinsh and Jarl E.S. Wikberg 1 Department of Pharmaceutical Biosciences, Division of Pharmaceutical Pharmacology, Uppsala Biomedical center, Uppsala University, S-751 24, Uppsala, Sweden; E-mails: Sviatlana.Yahorava@farmbio.uu.se; Aleh.Yahorau@farmbio.uu.se; Jarl.Wikberg@farmbio.uu.se 2 Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006, Riga, Latvia; E-mail: ilzem@osi.lv; edv@osi.lv 3 Department of Biochemistry and Organic Chemistry, Box 576, Uppsala University, S-751 23, Uppsala, Sweden; E-mail: Adolf.Gogoll@biorg.uu.se * Author to whom correspondence should be addressed. E-mail: fmutulis@osi.lv. Received: 10 June 2008; in revised form: 18 August 2008 / Accepted: 19 August 2008 / Published: 26 August 2008 Abstract: Two molecules of indole derivative, e.g. indole-5-carboxylic acid, reacted with one molecule of thiol, e.g. 1,2-ethanedithiol, in the presence of trifluoroacetic acid to yield adducts such as 3-[2-(2-amino-5-carboxyphenyl)-1-(2-mercaptoethylthio)ethyl]-1H- indole-5-carboxylic acid. Parallel formation of dimers, such as 2,3-dihydro-1H,1H-2,3- biindole-5,5-dicarboxylic acid and trimers, such as 3,3-[2-(2-amino-5-carboxy- phen