1912-33-0Relevant articles and documents
Construction of indole and benzofuran systems on the solid phase via palladium-mediated cyclizations
Zhang, Han-Cheng,Maryanoff, Bruce E.
, p. 1804 - 1809 (1997)
Molecular diversity in the area of nonpeptide, small organic molecules has been receiving considerable attention in the chemical community. Herein, we report new solid-phase methodology for the rapid generation of such small-molecule libraries by simultaneous-parallel or combinatorial synthesis. We have adapted a palladium-mediated, intramolecular Heck-type reaction, a mild and versatile method for carbon-carbon bond formation, to the solid phase. This has been applied to the synthesis of diverse indole and benzofuran derivatives, such as 8, 15, and 28, in good to excellent yields.
Reconsidering the Structure of Serlyticin-A
Tsui, Ka Yi,Tombari, Robert J.,Olson, David E.,Tantillo, Dean J.
, p. 3464 - 3468 (2019)
Serlyticin-A is a secondary metabolite first isolated from a culture of Serratia ureilytica grown using squid pen as the sole carbon/nitrogen source. A previous study by Kuo et al. demonstrated that it has antioxidative and antiproliferative properties. However, the proposed chemical structure of serlyticin-A is likely incorrect based on the thermodynamic instability of its three contiguous heteroatom-heteroatom bonds. Here, we use quantum chemical calculations to predict 1H and 13C chemical shifts for serlyticin-A and demonstrate a discrepancy between the calculated and experimental chemical shifts. We then propose several reasonable alternative structures for serlyticin-A. Considering the known antioxidant and antiproliferative activity of hydroxamic acids as well as their stability and prevalence in natural products of bacterial origin, we believe that serlyticin-A is most likely 3-indolylacetohydroxamic acid (4). We provide our rationale for this assignment as well as experimental data for pure 3-indolylacetohydroxamic acid obtained via de novo synthesis. This study highlights the power of computational NMR shift prediction to revise chemical structures for natural products like serlyticin-A.
Reaction of methyl (2E)-3-dimethylamino-2-(1H-indol-3-yl)-propenoate with ureas: Facile entry into the polycyclic meridianin analogues with uracil structural unit
?asar, Zdenko,Bevk, David,Svete, Jurij,Stanovnik, Branko
, p. 7508 - 7519 (2005)
Methyl (2E)-3-dimethylamino-2-(1H-indol-3-yl)-propenoate was prepared simply and efficiently in two steps from 3-indoleacetic acid employing N,N-dimethylformamide dimethylacetal (DMFDMA). Upon treatment of (2E)-3-dimethylamino-2-(1H-indol-3-yl)-propenoate with various (thio)ureas in the presence of an acid 2-(1H-indol-3-yl)-3-(3-substituted(thio)ureido) propenoates were obtained in high yields. A base promoted cyclization of these (thio)ureidopropenoate derivatives afforded 5-(indol-3-yl)-3-substituted- pyrimidine-2,4-diones which represent a new family of meridianine analogues.
QUANTIFICATION OF INDOL-3-YL ACETIC ACID IN PEA AND MAIZE SEEDLINGS BY GAS CHROMATOGRAPHY-MASS SPECTROMETRY
Allen, James R. F.,Rivier, Laurent,Pilet, Paul-Emile
, p. 525 - 530 (1982)
A procedure is described for the identification and quantification of IAA in plant tissues by GC/MS analysis of the N-heptafluorobutyryl ethyl ester of IAA using IAA as an internal standard.The detection limit is ca. 3 pmol IAA/tissue sample.By using this method, IAA levels of 30-90 pmol/g fr. wt were obtained for dark-grown Pisum sativum epicotyls and 71-199 pmol/g fr. wt for dark-grown Zea mays seedlings.When either methanol or ethanol was used as extraction solvent, some esterification of IAA during sample preparation was observed.No evidence for the natural occurence of methyl or ethyl esters of IAA in Pisum sativum seedlings was found.Key Word Index-Pisum sativum; Zea mays; Leguminosae; Gramineae; hormone; indol-2-yl acetic acid; GC/MS; deuterium label.
Discovery of an indole-substituted furanone with tubulin polymerization inhibition activity
Mowery, Patricia,Filkorn, Madison M.,Hurysz, Brianna,Kwansare, Deborah O.,Lafferty, Megan M.,McFadden, Marissa A.,Neerukonda, Namita D.,Patel, Roslyn R.,Pierce, Kelsey,Sockett, Kaitlynn A.,Truax, Nathanyal J.,Webster, Nathan R.,Pelkey, Erin T.
, (2021)
Analogs of diarylpyrrolinone lead compound 1 were prepared and tested for anti-proliferative activity in U-937 cancer cells. Alterations of 1 focused on modifying the two nitrogen atoms: a) the pyrrolinone nitrogen atom was substituted with a propyl group or replaced with an oxygen atom (furanone), and b) the substituents on the indole nitrogen were varied. These changes led to the discovery of a furanone analog 3b with sub-micromolar anti-cancer potency and tubulin polymerization inhibition activity.
Etude spectroscopique (IR, RMN1H, masse) comparee des acides indolyl-1 acetique (AIA-1) indolyl-2 acetique (AIA-2) et indolyl-3 acetique (AIA-3) et de leurs esters methyliques (masse)
Vebrel, Joel,Laude, Bernard,Seguin, Alain,Dubouchet, Jacques
, p. 887 - 894 (1983)
Spectroscopic study (i.r., PMR) of 1-indolyl, 2-indolyl and 3-indolyl acetic acids points out structural differences.Conventional mass spectra of the three acids or their methyl esters are very similar.Use of the MIKE and CID-MIKE techniques on the molecular ion allows an easy discrimination of each methylic ester of the three acids.
Convenient synthesis of long alkyl-chain triazolylglycosides using ionic liquid as dual promoter-solvent: Readily access to non-ionic triazolylglycoside surfactants for evaluation of cytotoxic activity
Ketsomboon, Nutthanicha,Saeeng, Rungnapha,Sirion, Uthaiwan,Srisook, Klaokwan
, (2021/08/26)
A convenient method for the one-pot synthesis of long alkyl-chain triazolylglycosides using ionic liquid as dual promoter and solvent is described via a sequential one-pot two-step glycosidation-CuAAc click reaction. The reaction was carried out using commercially available substrates, including glycosyl bromides, sodium azide and various long alkyl-chain alkynes to achieve the corresponding products in moderate to high yields. Furthermore, this approach was successfully applied for the preparation of non-ionic monocatenary triazolylglycoside surfactants in excellent yields through simple deacetylation. Subsequently, these surfactants were further evaluated for their cytotoxic activity.
Fe-catalyzed Fukuyama-type indole synthesis triggered by hydrogen atom transfer
Huang, Hanmin,Yu, Min,Zhang, Tianze
, p. 10501 - 10505 (2021/08/20)
Fe, Co, and Mn hydride-initiated radical olefin additions have enjoyed great success in modern synthesis, yet the extension of other hydrogen radicalophiles instead of olefins remains largely elusive. Herein, we report an efficient Fe-catalyzed intramolec
