Document Detail


Oligomerization of indole derivatives with incorporation of thiols.
MedLine Citation:
PMID:  18794789     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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]-1Hindole-5-carboxylic acid. Parallel formation of dimers, such as 2,3-dihydro-1H,1'H-2,3'-biindole-5,5'-dicarboxylic acid and trimers, such as 3,3'-[2-(2-amino-5-carboxyphenyl) ethane-1,1-diyl]bis(1H-indole-5-carboxylic acid) of the indole derivatives was also observed. Reaction of a mixture of indole and indole-5-carboxylic acid with 2-phenylethanethiol proceeded in a regioselective way, affording 3-[2-(2-aminophenyl)-1-(phenethylthio)ethyl]-1H-indole-5-carboxylic acid. An additional product of this reaction was 3-[2-(2-aminophenyl)-1-(phenethylthio)ethyl]-2,3-dihydro-1H,1'H-2,3'-biindole-5'-carboxylic acid, which upon standing in DMSO-d6 solution gave 3-[2-(2-aminophenyl)-1-(phenethylthio)ethyl]-1H,1'H-2,3'-biindole-5'-carboxylic acid. Structures of all compounds were elucidated by NMR, and a mechanism for their formation was suggested.
Authors:
Felikss Mutulis; Adolf Gogoll; Ilze Mutule; Sviatlana Yahorava; Aleh Yahorau; Edvards Liepinsh; Jarl E S Wikberg
Related Documents :
9394029 - Glucuronidation of opioids, carboxylic acid-containing drugs, and hydroxylated xenobiot...
12044169 - An isotope-edited ft-ir study of a symporter, the lactose permease.
21785579 - The discovery of the fat-regulating phosphatidic acid phosphatase gene.
24861999 - Economical production of poly(ε-l-lysine) and poly(l-diaminopropionic acid) using cane ...
23640369 - Remarkably durable high temperature polymer electrolyte fuel cell based on poly(vinylph...
24420099 - Isolation and identification of soluble polysaccharides in epidermal tissue of allium c...
12435269 - A non-modular type b feruloyl esterase from neurospora crassa exhibits concentration-de...
14985189 - Characterization of phenolic compounds in some indian mango cultivars.
8146659 - Mutational isolation of a sieve for editing in a transfer rna synthetase.
Publication Detail:
Type:  Journal Article     Date:  2008-08-26
Journal Detail:
Title:  Molecules (Basel, Switzerland)     Volume:  13     ISSN:  1420-3049     ISO Abbreviation:  Molecules     Publication Date:  2008  
Date Detail:
Created Date:  2008-09-16     Completed Date:  2008-12-08     Revised Date:  2009-10-27    
Medline Journal Info:
Nlm Unique ID:  100964009     Medline TA:  Molecules     Country:  Switzerland    
Other Details:
Languages:  eng     Pagination:  1846-63     Citation Subset:  IM    
Affiliation:
Department of Pharmaceutical Biosciences, Division of Pharmaceutical Pharmacology, Uppsala Biomedical center, Uppsala University, S-751 24, Uppsala, Sweden. fmutulis@osi.lv
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
Dimerization
Indoles / chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
Sulfhydryl Compounds / chemistry*
Chemical
Reg. No./Substance:
0/Indoles; 0/Sulfhydryl Compounds; 120-72-9/indole

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


Previous Document:  Synthesis of a novel D-glucose-conjugated 15-crown-5 ether with a spiro ketal structure.
Next Document:  Evaluation of the chemical composition of Brazilian commercial Cymbopogon citratus (D.C.) stapf samp...