- Synthesis and characterization of novel indole-containing half-crowns as new emissive metal probes
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Two new indole derivatives have been synthesized by a one-pot procedure and their potential as fluorescence probes for metal ions was investigated. The sensor capability of 1 and 2 toward cations such as Ag+, Cu2+, Zn2+, C
- Rocha, Angelo,Marques, M. Manuel B.,Lodeiro, Carlos
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- Directed synthesis and immunoactive properties of (2-hydroxyethyl)ammonium salts of 1-R-indol-3-ylsulfanyl(sulfonyl)alkanecarboxylic acids
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A general method for the synthesis of 1-alkyl(allyl)(benzyl)-substituted (indol-3-yl)-sulfanylalkanecarboxylic acids and hexane-1,6-diyl(1,4- phenylenemethylene)bisindol-3-ylsulfanylalkanecarboxylic acids from the corresponding N-substituted indoles and bisindoles, thiourea, iodine, and halogencarboxylic acids was developed. The oxidation of substituted (indol-3-yl)sulfanylalkanecarboxylic acids for the first time afforded their analogs containing the sulfonyl group. New (2-hydroxyethyl)ammonium salts of 1-R-indol-3-ylsulfanyl(sulfonyl)-alkanecarboxylic acids, which are structural analogs of highly active immunomodulators of indacetamin and VILIM, were synthesized. Among the studied (2-hydroxyethyl)ammonium salts of 1-R-indol-3-ylsulfanylacetic and -sulfonylalkanecarboxylic acids, the compounds exhibiting high dose-dependent antiproliferative activity by the ability to affect the spontaneous and mitogen-stimulated splenocyte proliferation of mice in vitro were found.
- Mirskova,Levkovskaya,Kolesnikova,Perminova,Rudyakova,Adamovich
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experimental part
p. 2236 - 2246
(2011/08/05)
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- An expeditious synthesis for γ-carboline analogue 4-aryl-1,3-thiazino[6,5-b]indole derivatives via the trifluoromethanesulfonic acid-promoted isomerization of 3-amidomethylthioindole intermediates to 2-indolyl sulfides
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A highly efficient trifluoromethanesulfonic acid-mediated rearrangement of the benzoylaminomethylthio group of 3-benzoylaminomethylthioindoles (7a-e) to position 2 of the indole ring was developed. Thus, 2-benzoylaminomethylthioindoles (9a-e) were obtained in good yields and were involved as key intermediates in the synthesis of the new γ-carboline analogue ring system: 2,9-dihydro-4-aryl-1,3-thiazino[6,5-b]indole derivatives (11a-e). The target thiazinoindoles (11a-e) were prepared via 2-thiobenzoylaminomethylindoles (10a-e) in modified Bischler-Napieralski reactions.
- Csomós, Péter,Fodor, Lajos,Bernáth, Gábor,Csámpai, Antal,Sohár, Pál
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experimental part
p. 1475 - 1480
(2009/04/11)
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- Regioselective synthesis of 4-aryloxymethylene-2,3,5-trihydrothiopyrano[3, 2-b]indoles by the thio-claisen rearrangement of 3-(4′-aryloxybut- 2′-ynylthio)indoles
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(Chemical Equation Presented) A number of new 4-aryloxymethylene-2,3,5- trihydrothiopyrano[3,2-b]indoles are regioselectively synthesized in 78-84% yield by the thio-Claisen rearrangement of 3-(4′-aryloxybut-2′- ynylthio)indoles. The endocyclic double bon
- Majumdar,Alam,Muhuri
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p. 1395 - 1399
(2008/09/19)
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- Derivatives of 3-Mercaptoindole - Synthesis of a Potent Vasoconstrictor, 3-(2-Imidazolin-2-ylthio)indole (Tinazoline)
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Indoles are oxidatively coupled with various cyclic and acyclic thioureas using iodine to give rise to 3-(2-imidazolin-2-ylthio)indole, 1-30, 32 and 36-40.Similar products 33, 34 and 35 are respectively obtained from benzindole, 1,6,6-trimethyl-4,5,6,7-tetrahydroindole and 7-azaindole, while alkylation of 3-mercaptoindole 44 with chlormethyl imidazoline leads to 31.Among the products so obtained, 3-(2-imidazolin-2-ylthio)indole is a potent vasoconstrictor and the hydrochloride salt forms the active ingredient of VarsylR. 3-Mercaptoindole (44) readily obtained by alkali treatment of S-(3-indolyl)isothiourea (36) is converted into amine derivatives 47 and 52 and to the acids 53-55.Acid-catalysed cyclisation of 55 affords the expected thiopyranone (57), as well as the interesting isomeric ketone (58).A mechanism is proposed for this novel rearrangement. 3-Mercaptoindole (44) is also converted to α-methylaminoacid (64) via the hydantoin (63). 3-Mercaptoindole-2-carboxylic acid (65) obtained from 10 is transformed to a variety of methylated derivatives 66-72.The amino acid 75 arising by the action of ethylenimine on 65 is esterified to 76 and cyclised to the condensed thiazepinone (77).
- Nagarajan, K.,Arya, V. P.,Parthasarathy, T. N.,Shenoy, S. J.,Shah, R. K.,Kulkarni, Y. S.
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p. 672 - 679
(2007/10/02)
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