A Practical Regioselective Synthesis of Alkylthio- or Arylthioindoles without the Use of Smelly Compounds Such as Thiols

A convenient method for the synthesis of 3-methylthioindoles has been established which does not use smelly compounds such as thiol derivatives. The method, which introduces an alkyl- or arylthio-group into the C3-position of the indole skeleton, was extended to the direct introduction of a methylth...

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Published inChemical & pharmaceutical bulletin Vol. 61; no. 3; pp. 292 - 303
Main Authors Hamashima, Toshihiko, Mori, Yoshiaki, Sawada, Kazunori, Kasahara, Yuko, Murayama, Daisuke, Kamei, Yuto, Okuno, Hiroaki, Yokoyama, Yuusaku, Suzuki, Hideharu
Format Journal Article
LanguageEnglish
Published TOKYO The Pharmaceutical Society of Japan 01.03.2013
Pharmaceutical Soc Japan
Japan Science and Technology Agency
Subjects
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
Dimerization
electrophilic aromatic substitution
indole
Indoles - chemistry
Life Sciences & Biomedicine
Methicillin-Resistant Staphylococcus aureus - drug effects
Pharmacology & Pharmacy
Physical Sciences
Science & Technology
Sulfhydryl Compounds - chemistry
sulfoxide
thioether
trifluoroacetic anhydride
ECHINOSULFONE
POTENT
indole
SULFONIUM SALTS
thioether
trifiuoroacetic anhydride
ALGA LAURENCIA-BRONGNIARTII
SULFUR-CONTAINING POLYBROMOINDOLES
INHIBITORS
electrophilic aromatic substitution
CATALYZED SULFENYLATION
sulfoxide
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Summary:A convenient method for the synthesis of 3-methylthioindoles has been established which does not use smelly compounds such as thiol derivatives. The method, which introduces an alkyl- or arylthio-group into the C3-position of the indole skeleton, was extended to the direct introduction of a methylthio or bromo group at the C2-position using 3-methylthioindoles. No dimerization occurred, and the reaction mechanism was confirmed. The products have the partial structure of potent anti-methicillin-resistant Staphylococcus aureus (anti-MRSA) bromomethylthioindoles (MC 5-8) isolated from marine algae. Furthermore, this reaction could be applied to the synthesis of 3,3-diindolyl thioether which is a core structure of Echinosulfone A.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.c12-00882