154-07-4Relevant articles and documents
1,3,4,9-TETRAHYDRO-2H-PYRIDO[3,4-B]INDOLE DERIVATIVE COMPOUNDS AND USES THEREOF
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, (2020/03/05)
The present invention relates to 1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole derivative compounds and uses thereof. In particular, compounds of the invention have antibacterial activity and/or are capable of re-sensitizing methicillin-resistant Staphylococcus aureus to a P-lactam antibiotic or a combination of a P-lactam antibiotic and a P-lactamase inhibitor. The present invention also relates to a method for producing and using said compounds.
Cyclic Tautomers of Tryptophans and Tryptamines. VI. Preparation of Na-Alkyl-, 5-Chloro-, and 5-Nitrotryptophan Derivatives
Taniguchi, Mikio,Gonsho, Akinori,Nakagawa, Masako,Hino, Tohru
, p. 1856 - 1865 (2007/10/02)
Selective Na-alkylation , 5-chlorination, 5-bromination, and 5-nitration of tryptophan derivatives were achieved.The alkylation of the cyclic tautomer 2 of Nb-methoxycarbonyl-DL-tryptophan methyl ester (1) with alkyl halides in acetone-K2CO3 gave the Na-alkyl derivatives (3a and 4) in excellent yields.The chlorination of the cyclic tautomer 3b with NCS-AcOH gave the 5-chloro derivative (5b) in 89percent yield, and this was readily converted to the 5-chlorotryptophan derivatives (7a, 7b, 9).The similar chlorination of 12 gave the 5-chloro derivatives (13a, 15a) and the 3a-chloropyrroloindole derivative (17).On the other hand the bromination of 12 with NBS-AcOH gave the 5-bromo derivative (13b) in good yield, and this was readily converted to 15d and further to 15c.The nitration of 3b and 12 with fuming nitric acid also gave the 5-nitro derivatives (5c, 7c, 13c, 15e) in excellent yields.Keywords --- tryptophan derivatives; cyclic tautomer of Nb-acyltryptophans; chlorination; bromination; nitration; N-alkylation; 5-substituted tryptophan derivatives; N-chlorosuccinimide; N-bromosuccinimide
