Simple exploration of Ethyl 1H-indole-3-carboxylate

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The stereochemistries of the 2 + 2 cycloaddition products obtained from the photochemical addition reaction between N-benzoylindole or N-carboethoxyindole and the alkenes cyclopentene, cyclohexene, cycloheptene, cis- and trans-2-butene, and cis- and trans-4-octene are examined.The structures of the products are shown to be consistent with a photo-cycloaddition mechanism involving the intermediacy of triplet 1,4-biradical species.The quantum yields of adduct formation between N-benzoylindole and both cis- and trans-octene were measured as a function of alkene concentration.The results suggest that cis-octene reacts with the indole derivative’s triplet excited state with a rate constant of (1.7 +/- 0.3) * 107 M-1 s-1.The results are also consistent with the immediate products of this reaction being 1,4-biradicals, 98percent of which revert to the ground state indole derivative and alkene, and only 2percent of which proceed to cycloadduct.In marked contrast, the same treatment suggests that trans-octene reacts with the triplet excited state of N-benzoylindole with a rate constant estimated to be in the range of 1 * 106 and 6 * 105 M-1 s-1, and it appears that the 1,4-biradicals formed revert much less efficiency to the starting materials; it is estimated that between 67 and 100percent of the 1,4-biradicals proceed to cycloadducts.In the reaction with cis-octene biradical reversion leads to the formation of trans-octene (“Schenk isomerization”); the quantum yield of this process is determined to be 0.074 +/- 0.004, which may imply that approximately 75percent of the biradicals collapse to cis-alkene and 25percent collapse to the trans-isomer. Key words: indole, photocycloaddition, 1,4-biradicals.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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Synthetic Route of 776-41-0, Because a catalyst decreases the height of the energy barrier, its presence increases the reaction rates of both the forward and the reverse reactions by the same amount.776-41-0, Name is Ethyl 1H-indole-3-carboxylate, molecular formula is C11H11NO2. In a article£¬once mentioned of 776-41-0

A method for catalytic synthesis of indole compounds (by machine translation)

The invention discloses a process for catalytic synthesis of indole compounds, comprising the following steps : (1) the adjoining nitrostyrolene or its derivatives, frequency that alcohol esterjoint boric acid, alkali and lower saturated monohydric alcohol reaction stirring under a nitrogen atmosphere ; (2) the step (1) cooling to room temperature, the reaction product of, adding ethyl acetate to be fully mixed, filtered, washed with ethyl acetate ; (3) steps turns on lathe does (2) the organic phase of the material of the lower saturated monohydric alcohol, a silica gel column, then by the petroleum ether and ethyl acetate for the elution agent leaching the above-mentioned silica gel column, the product to be purified, i.e. the indole compound. Process for catalytic synthesis of this invention under the neutral condition, by utilizing cheap joint boric acidfrequency that ester as the raw material, by friendly lower saturated monohydric alcohol used as a solvent, by a simple operation to obtain the indole compound, cheap raw material cost, high efficiency, good safety, has a wide range of expansibility, and good industrial application prospects. (by machine translation)

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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Design and synthesis of novel 2-amino-5-hydroxyindole derivatives that inhibit human 5-lipoxygenase

Compounds that inhibit 5-lipoxygenase (5-LO), the key enzyme in the biosynthesis of leukotrienes (LTs), possess potential for the treatment of inflammatory and allergic diseases as well as of atherosclerosis and cancer. Here we present the design and the synthesis of a series of novel 2-amino-5-hydroxyindoles that potently inhibit isolated human recombinant 5-LO as well as 5-LO in polymorphonuclear leukocytes, exemplified by ethyl 2-[(3-chlorophenyl)amino]-5-hydroxy-1H-indole-3-carboxylate (3n, IC50 value ? 300 nM). Introduction of an aryl/arylethylamino group or 4-arylpiperazin-1-yl residues into position 2 of the 5-hydroxyindoles was essential for biological activity. Whereas the 4-arylpiperazin-1-yl derivatives were more potent in cell-free assays as compared to intact cell test systems, aryl/arylethylamino derivatives inhibited 5-LO activity in intact cells and cell-free assays almost equally well. On the basis of their 5-LO inhibitory properties, these novel 2-amino-5-hydroxyindoles represent potential candidates for the pharmacological intervention with LT-associated diseases.

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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Chemistry is an experimental science, 776-41-0, and the best way to enjoy it and learn about it is performing experiments.Introducing a new discovery about 776-41-0, Name is Ethyl 1H-indole-3-carboxylate

Design and synthesis of novel 2-amino-5-hydroxyindole derivatives that inhibit human 5-lipoxygenase

Compounds that inhibit 5-lipoxygenase (5-LO), the key enzyme in the biosynthesis of leukotrienes (LTs), possess potential for the treatment of inflammatory and allergic diseases as well as of atherosclerosis and cancer. Here we present the design and the synthesis of a series of novel 2-amino-5-hydroxyindoles that potently inhibit isolated human recombinant 5-LO as well as 5-LO in polymorphonuclear leukocytes, exemplified by ethyl 2-[(3-chlorophenyl)amino]-5-hydroxy-1H-indole-3-carboxylate (3n, IC50 value ? 300 nM). Introduction of an aryl/arylethylamino group or 4-arylpiperazin-1-yl residues into position 2 of the 5-hydroxyindoles was essential for biological activity. Whereas the 4-arylpiperazin-1-yl derivatives were more potent in cell-free assays as compared to intact cell test systems, aryl/arylethylamino derivatives inhibited 5-LO activity in intact cells and cell-free assays almost equally well. On the basis of their 5-LO inhibitory properties, these novel 2-amino-5-hydroxyindoles represent potential candidates for the pharmacological intervention with LT-associated diseases.

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles