1016-47-3Relevant articles and documents
Indolic metabolites from the new marine bacterium Roseivirga echinicomitans KMM 6058T
Oleinikova,Ivchuk,Denisenko,Chaikina,Menzorova,Nedashkovskaya,Kuznetsova
, p. 713 - 717 (2006)
N-Acetyl-(1) and N,N-diacetyl-(2) tryptamines were isolated from the butanol extract of culture medium of the new marine bacterium Roseivirga echinicomitans KMM 6058T. The structures of the compounds were proved using mass spectrometry, UV, PMR, and 13C NMR spectroscopy and by comparing these data with mass and NMR spectra of synthetic samples of 1 and 2. Compound 2 was isolated from a natural source and synthesized for the first time. The cytotoxic activity of the compounds was studied using Erlich carcinoma tumor cells, murine erythrocytes, and sperm and egg cells of the sea urchin Strongylocentrotus intermedius.
Synthesis of chiral 3-substituted hexahydropyrroloindoline via intermolecular cyclopropanation
Song, Hao,Yang, Jun,Chen, Wei,Qin, Yong
, p. 6011 - 6014 (2006)
(Chemical Equation Presented) A new and efficient synthetic route to chiral 3-substituted hexahydropyrroloindoline 18 possessing absolute configurations in accordance with indole alkaloids has been developed from readily available L-tryptophan. The key step relies on the one-pot cascade reaction of oxazolidinone 17 with diazoester, which proceeds through intermolecular cyclopropanation, ring opening, and cyclization.
CARBON TRANSFER REACTIONS OF Δ2-OXAZOLINIUM AND THIAZOLINIUM CATIONS
Singh, Harjit,Sarin, Rakesh
, p. 1449 - 1460 (1986)
Δ2-Oxazolinium and thiazolinium cations with or without an appendage at any of the heteroatoms transfer their C(2) units at the carboxylic acid oxidation level to binucleophiles and provide the corresponding heterocycles, thus mimicking carbon transfer reactions exhibited by THF models, N-methyl N'-tosyl/acetyl imidazolinium cations.However, these azolinium cations react with phenethylamine and tryptamine to furnish their N-acyl derivatives.
One-pot synthesis of tricyclo-1,4-benzoxazines via visible-light photoredox catalysis in continuous flow
Wu, Guolin,Lv, Tingting,Mo, Wenhui,Yang, Xiping,Gao, Yu,Chen, Haijun
, p. 1395 - 1398 (2017)
A facile one-pot synthesis of tricyclo-1,4-benzoxazines has been developed via metal-free intramolecular cyclization of indole derivates. These reactions were efficiently achieved at ambient temperature by using visible-light photoredox catalysis in conti
Application of Imine Reductases (IREDs) in Micro-Aqueous Reaction Systems
Maugeri, Zaira,Rother, D?rte
, p. 2745 - 2750 (2016)
Here we present the applicability of different imine reductases (IREDs) in micro-aqueous reaction systems. Subjects of the study were the IREDs from Streptomyces aurantiacus (SaIR), Streptomyces sp. GF3587 (RGF3587IR), Streptomyces kanamyceticus (SkIR), Streptomyces ipomoeae 91-03 (SiIR), Streptomyces sp. GF3546 (SGF3546IR), and Paenibacillus elgii B69 (PeIR). The IREDs were overexpressed in Escherichia coli (E. coli) cells and used directly after lyophilization. Several organic solvents and buffer amounts were screened for the reduction of the two substrates β-carboline harmane and 1-methyl-3,4-dihydroisoquinoline to the corresponding amines. Cyclopentyl methyl ether (CPME) proved to be the best solvent choice for the envisaged reduction. In addition, CPME is currently referred to as an environmentally benign solvent. Optimized reaction conditions were applied to 20 mM of the hardly water soluble substrates, leading to good conversions (up to 96%) and excellent enantiomeric excesses (>99%) in the best cases. The use of micro-aqueous reaction systems opens the way to further applications of IREDs with hardly water soluble substrates. (Figure presented.).
Iridium-catalyzed direct synthesis of tryptamine derivatives from indoles: Exploiting N-protected β-amino alcohols as alkylating agents
Bartolucci, Silvia,Mari, Michele,Bedini, Annalida,Piersanti, Giovanni,Spadoni, Gilberto
, p. 3217 - 3222 (2015)
The selective C3-alkylation of indoles with N-protected ethanolamines involving the "borrowing hydrogen" strategy is described. This method provides convenient and sustainable access to several tryptamine derivatives.
Biocatalytic N-Acylation of Amines in Water Using an Acyltransferase from Mycobacterium smegmatis
Contente, Martina Letizia,Pinto, Andrea,Molinari, Francesco,Paradisi, Francesca
, p. 4814 - 4819 (2018)
A straightforward one-step biocatalyzed synthesis of different N-acyl amides in water was accomplished using the versatile and chemoselective acyltransferase from Mycobacterium smegmatis (MsAcT). Acetylation of primary arylalkyl amines was achieved with a range of acetyl donors in biphasic systems within 1 hour and at room temperature. Vinyl acetate was the best donor which could be employed in the N-acetylation of a large range of primary amines in excellent yields (85–99%) after just 20 minutes. Other acyl donors (including formyl-, propionyl-, and butyryl-donors) were also efficiently employed in the biocatalytic N-acylation. Finally, the biocatalyst was tested in transamidation reactions using acetamide as acetyl donor in aqueous medium, reaching yields of 60–70%. This work expands the toolbox of preparative methods for the formation of N-acyl amides, describing a biocatalytic approach easy to accomplish under mild conditions in water. (Figure presented.).
Insecticidal activity of indole derivatives against Plutella xylostella and selectivity to four non-target organisms
Costa, ?ngela C. F.,Cavalcanti, Sócrates C. H.,Santana, Alisson S.,Lima, Ana P. S.,Brito, Thaysnara B.,Oliveira, Rafael R. B.,Macêdo, Nathália A.,Cristaldo, Paulo F.,Araújo, Ana Paula A.,Bacci, Leandro
, p. 973 - 982 (2019)
The diamondback moth Plutella xylostella (Linnaeus, 1758) (Lepidoptera: Plutellidae) is a destructive pest of brassica crops of economic importance that have resistance to a range of insecticides. Indole derivates can exert diverse biological activities, and different effects may be obtained from small differences in their molecular structures. Indole is the parent substance of a large number of synthetic and natural compounds, such as plant and animal hormones. In the present study, we evaluate the insecticidal activity of 20 new synthesized indole derivatives against P. xylostella, and the selectivity of these derivatives against non-target hymenopteran beneficial arthropods: the pollinator Apis mellifera (Linnaeus, 1758) (Hymenoptera: Apidae), and the predators Polybia scutellaris (White, 1841), Polybia sericea (Olivier, 1791) and Polybia rejecta (Fabricius, 1798) (Hymenoptera: Vespidae). Bioassays were performed in the laboratory to determine the lethal and sublethal effects of the compounds on P. xylostella and to examine their selectivity to non-target organisms by topical application and foliar contact. The treatments consisted of two synthesized derivatives (most and least toxic), the positive control (deltamethrin) and the negative control (solvent). The synthesized compound 4e [1-(1H-indol-3-yl)hexan-1-one] showed high toxicity (via topical application and ingestion) and decreased the leaf consumption by P. xylostella, displaying a higher efficiency than the pyrethroid deltamethrin, widely used to control this pest. In addition, the synthesized indole derivatives were selective to the pollinator A. mellifera and the predators P. scutellaris, P. sericea and P. rejecta, none of which were affected by deltamethrin. Our results highlight the promising potential of the synthesized indole derivatives for the generation of new chemical compounds for P. xylostella management.
Molecular evolution of multiple arylalkylamine N-acetyltransferase (AANAT) in fish
Zilberman-Peled, Bina,Bransburg-Zabary, Sharron,Klein, David C.,Gothilf, Yoav
, p. 906 - 921 (2011)
Arylalkylamine N-acetyltransferase (AANAT) catalyzes the transfer of an acetyl group from acetyl coenzyme A (AcCoA) to arylalkylamines, including indolethylamines and phenylethylamines. Multiple aanats are present in teleost fish as a result of whole genome and gene duplications. Fish aanat1a and aanat2 paralogs display different patterns of tissue expression and encode proteins with different substrate preference: AANAT1a is expressed in the retina, and acetylates both indolethylamines and phenylethylamines; while AANAT2 is expressed in the pineal gland, and preferentially acetylates indolethylamines. The two enzymes are therefore thought to serve different roles. Here, the molecular changes that led to their specialization were studied by investigating the structure-function relationships of AANATs in the gilthead seabream (sb, Sperus aurata). Acetylation activity of reciprocal mutated enzymes pointed to specific residues that contribute to substrate specificity of the enzymes. Inhibition tests followed by complementary analyses of the predicted three-dimensional models of the enzymes, suggested that both phenylethylamines and indolethylamines bind to the catalytic pocket of both enzymes. These results suggest that substrate selectivity of AANAT1a and AANAT2 is determined by the positioning of the substrate within the catalytic pocket, and its accessibility to catalysis. This illustrates the evolutionary process by which enzymes encoded by duplicated genes acquire different activities and play different biological roles.
The formal total synthesis of (±)-strychnine via a cobalt-mediated [2 + 2 + 2]cycloaddition
Eichberg, Michael J.,Dorta, Rosa L.,Lamottke, Kai,Vollhardt, K. Peter C.
, p. 2479 - 2481 (2000)
(equation presented) A short, highly convergent total synthesis of racemic isostrychnine, and thus strychnine, has been completed. The route involves 14 steps in the longest linear sequence and is highlighted by a cobalt-mediated [2 + 2 + 2]cycloaddition of an alkynylindole nucleus to acetylene.
