Category: 877-03-2

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Amino derivatives of indole as potent inhibitors of isoprenylcysteine carboxyl methyltransferase

The enzyme isoprenylcysteine carboxyl methyltransferase (Icmt) plays an important role in the post-translational modification of proteins that are involved in the regulation of cell growth. The indole acetamide cysmethynil is by far the most potent and widely investigated Icmt inhibitor, but it has modest antiproliferative activity and may have pharmacokinetic limitations due to its lipophilic character. We report here that cysmethynil can be structurally modified to give analogues that are as potent in inhibiting Icmt but with significantly greater antiproliferative activity. Key modifications were the replacement of the acetamide side chain by tertiary amino groups, the n-octyl side chain by isoprenyl and the 5-m-tolyl ring by fluorine. Moreover, these analogues have lower lipophilicities that could lead to improved pharmacokinetic profiles.

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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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Iodine-catalyzed C3-formylation of indoles using hexamethylenetetramine and air

An efficient iodine-catalyzed chemoselective 3-formylation of free (N?H) and N-substituted indoles was achieved by using hexamethylenetetramine (HMTA) in the presence of activated carbon under air atmosphere. This new method could provide 3-formylindoles in moderate to excellent yields with fairly short reaction times. Moreover, this catalytic formylation of indoles procedure can be applied to gram-scale synthesis.

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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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Novel, recyclable, and thermally stable task-specific ionic liquid (TBA acetate) medium/catalyst for the synthesis of indolylidinecyclic-1,3- and -1,4-diketones

A simple and efficient synthesis of indolylidinethiazolidnediones (3) and indolylidinecyclic-1,3-diketones (5) has been developed by reaction of indole-3-aldehyde (1) with thiazolidinedione (2) or cyclic-1,3-diketones (4) using tetra butyl ammonium acetate (TBAA) melt as novel, cost-effective, and recyclable ionic liquid under solvent-free green conditions at 100 C for 15-20 min without additional use of catalyst. [Supplementary materials are available for this article. Go to the publisher’s online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

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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

A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, Recommanded Product: 877-03-2, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 877-03-2, Name is 5-Bromo-1H-indole-3-carbaldehyde, molecular formula is C9H6BrNO. In a Patent, authors is £¬once mentioned of 877-03-2

ORGANIC COMPOUNDS

The invention relates to novel amino alcohols of the general formula (I) where X, R1, R2, R3, R4, R5 and R6 are each as defined in detail in the description, to a process for their preparation and to the use of these compounds as medicines, in particular as renin inhibitors.

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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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Total synthesis and biological activity of marine alkaloid eudistomins Y1-Y7 and their analogues

Eudistomin Y class compounds are a series of beta-carbolines which was originally isolated from a marine turnicate or ascidian near the South Korea Sea. These compounds contain bromo-substituted groups, which is one of the typical characters of marine natural products. We report herein the chemical synthesis and biological evaluation of seven new beta-carboline-based metabolites, Eudistomins Y1-Y7, and their hydroxyl-methylated phenyl derivatives. Using bromo-substituted tryptamines and bromo-substituted phenylglyoxals as the key intermediates, Eudistomins Y 1-Y7 and their derivatives were synthesized via the acid-catalyzed Pictet-Spengler reaction and fully characterized by 1H- and 13C-NMR and mass spectroscopy. Biological studies revealed that all of the compounds showed moderate growth inhibitory activity against breast carcinoma cell line MDA-231 with IC50 of 15-63 muM and the inhibitory activities of hydroxyl-methylated phenyl products were higher than that of the corresponding natural products Eudistomins Y 1-Y7.

Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. Recommanded Product: 5-Bromo-1H-indole-3-carbaldehyde, If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 877-03-2, in my other articles.

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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Unusual Formation of Cyclopenta[ b]indoles from 3-Indolylmethanols and Alkynes

Acid-promoted synthesis of cyclopenta[b]indole frameworks from 3-indolylmethanols and alkynes has been reported. The overall transformation represents a formal [3 + 2] annulation via rearrangement. This protocol showed good generality for the carbinol substrates as well as alkynes and allowed the generation of structurally diverse cyclopenta[b]indoles. Terminal alkynes, dialkyl-substituted internal alkynes, and alkynes with electron-deficient substituents were found to be not suitable for this transformation. Similarly, N-Ts and N-Boc groups were compatible with reaction conditions, whereas N-Ac and N-Tf failed to undergo this reaction. Isolation of vinyl chloride intermediate suggested the involvement of a vinylic carbocation intermediate. A mechanism has been proposed involving a ring-opening-ring-closing cascade followed by a 1,3-indole migration process via a spirocyclobutene intermediate.

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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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.877-03-2,5-Bromo-1H-indole-3-carbaldehyde,as a common compound, the synthetic route is as follows.

877-03-2, 5-bromoindole-3-carbaldehyde 2 (10 mmol) was dissolved in acetonitrile and to this powdered NaOH (5 mmol) was added and stirred for 10 min. Methyl iodide (10 mmol) was added dropwise to the reaction mixture. After 3h of stirring at room temperature, the solvent was completely evaporated. It was extracted with ethyl acetate (3×20 ml) and dried over Na2SO4. The combined organic layer was concentrated in vacuo to give a light yellow color solid purified by recrystallization with diethyl ether. Pale yellow solid; Yield: 96%; mp 122-124 C; IR (KBr) numax 3103, 2923, 2813, 1700, 1654. 1533, 1467, 1369, 1083, 799, 726; 1H NMR (DMSO-d6, 300 MHz) delta 9.88 (s, 1H), 8.33 (s, 1H), 8.23 (d, J = 1.70 Hz, 1H), 7.60 (d, J = 8.68 Hz, 1H), 7.48 (dd, J = 2.08, 8.87 Hz, 1H), 3.89 (s, 3H); TOF-HRMS (m/z) for C10H8BrNO, calculated 237.9862, observed 237.9855 [M+1] +

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Reference£º
Article; Prajapti, Santosh Kumar; Nagarsenkar, Atulya; Guggilapu, Sravanthi Devi; Gupta, Keshav Kumar; Allakonda, Lingesh; Jeengar, Manish Kumar; Naidu; Babu, Bathini Nagendra; Bioorganic and Medicinal Chemistry Letters; vol. 26; 13; (2016); p. 3024 – 3028;,
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