M.W=200-250 | - Page 12 of 14 - Indole Building Blocks

Boger, Dale L.’s team published research in Bioorganic & Medicinal Chemistry in 1995-06-30 | CAS: 136818-66-1

Bioorganic & Medicinal Chemistry published new progress about Biochemical alkylation. 136818-66-1 belongs to class indole-building-block, name is Methyl 6-nitro-1H-indole-2-carboxylate, and the molecular formula is C10H8N2O4, Category: indole-building-block.

Boger, Dale L. published the artcileCC-1065 CBI analogs: an example of enhancement of DNA alkylation efficiency through introduction of stabilizing electrostatic interactions, Category: indole-building-block, the main research area is CC1065 CBI analog preparation DNA alkylation.

The three trimethylammonium salts I (R1 and R2 and R3 = H or NMe3+) proved to be 100 times more efficient at alkylating DNA than I (R1 and R2 and R3 = H) and exhibited DNA alkylation efficiencies identical to that of (+)-CC-1065. In addition, the agents I (R1 and R2 = H and R3 = NMe3+) and I (R1 and R3 = H and R2 = NMe3+) exhibited DNA alkylation selectivities identical to that of I (R1 and R2 and R3 = H). This may be attributed to spatially well-defined stabilizing electrostatic interactions between the pos. charged trimethylammonium salt lying on the peripheral face of the agents and the bracketing, neg. charged phosphates located in the DNA backbone that enhance the DNA noncovalent binding affinity without affecting DNA binding or alkylation selectivity. The agent I (R2 and R3 = H and R1 = NMe3+) exhibited an altered and more discriminating AT-rich adenine N3 alkylation selectivity than the other agents that may be attributed to the groove placement of the large trimethylammonium salt.

Referemce:
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

Jiang, Zhigan’s team published research in Bioorganic & Medicinal Chemistry Letters in 2014-09-01 | CAS: 13523-93-8

Bioorganic & Medicinal Chemistry Letters published new progress about Aspergillus fumigatus. 13523-93-8 belongs to class indole-building-block, name is 4-(Benzyloxy)-1-methyl-1H-indole, and the molecular formula is C16H15NO, Recommanded Product: 4-(Benzyloxy)-1-methyl-1H-indole.

Jiang, Zhigan published the artcileScaffold hopping of sampangine: discovery of potent antifungal lead compound against Aspergillus fumigatus and Cryptococcus neoformans, Recommanded Product: 4-(Benzyloxy)-1-methyl-1H-indole, the main research area is antifungal sampangine derivative; Antifungal activity; Sampangine; Scaffold hopping.

Discovery of novel antifungal agents against Aspergillus fumigatus and Cryptococcus neoformans remains a significant challenge in current antifungal therapy. Here, the antifungal natural product sampangine (I) was used as the lead compound for novel antifungal drug discovery. D-ring scaffold hopping derivatives were designed and synthesized to improve antifungal activity and water solubility Among them, the thiophene derivative S2 showed broad-spectrum antifungal activity, particularly for Aspergillus fumigatus and Cryptococcus neoformans. Moreover, compound S2 also revealed better water solubility than sampangine, which represents a promising antifungal lead compound for further structural optimization.

Williams, John D.’s team published research in Bioorganic & Medicinal Chemistry in 2013-12-15 | CAS: 104291-81-8

Bioorganic & Medicinal Chemistry published new progress about Antibacterial agents. 104291-81-8 belongs to class indole-building-block, name is Ethyl 6-cyano-1H-indole-2-carboxylate, and the molecular formula is C12H10N2O2, Recommanded Product: Ethyl 6-cyano-1H-indole-2-carboxylate.

Williams, John D. published the artcilePotent and broad-spectrum antibacterial activity of indole-based bisamidine antibiotics: Synthesis and SAR of novel analogs of MBX 1066 and MBX 1090, Recommanded Product: Ethyl 6-cyano-1H-indole-2-carboxylate, the main research area is indole bisamidine preparation antibacterial antibiotic; Amidine; Antibacterial; Antibiotic; Broad-spectrum; Cadogan–Sundberg reaction; Imidazoline; Indole; McMurry reductive homocoupling reaction; Reissert indole synthesis; Tetrahydropyrimidine.

The prevalence of drug-resistant bacteria in the clinic has propelled a concerted effort to find new classes of antibiotics that will circumvent current modes of resistance. The authors have previously described a set of bisamidine antibiotics that contains a core composed of two indoles and a central linker. The first compounds of the series, MBX 1066 and MBX 1090, have potent antibacterial properties against a wide range of Gram-pos. and Gram-neg. bacteria. The authors have conducted a systematic exploration of the amidine functionalities, the central linker, and substituents at the indole 3-position to determine the factors involved in potent antibacterial activity. Some of the newly synthesized compounds have even more potent and broad-spectrum activity than MBX 1066 and MBX 1090.

Qi, Liang-Wen’s team published research in Nature Chemistry in 2018-01-31 | CAS: 69622-40-8

Nature Chemistry published new progress about Arylation catalysts, stereoselective. 69622-40-8 belongs to class indole-building-block, name is 2-(tert-Butyl)-5-chloro-1H-indole, and the molecular formula is C12H14ClN, Recommanded Product: 2-(tert-Butyl)-5-chloro-1H-indole.

Qi, Liang-Wen published the artcileOrganocatalytic asymmetric arylation of indoles enabled by azo groups, Recommanded Product: 2-(tert-Butyl)-5-chloro-1H-indole, the main research area is organocatalytic asym arylation indole azo directing activating group; nucleophilic aromatic substitution asym organocatalytic; pyrroloindole preparation asym arylation azo directing activating group; arylindole preparation asym arylation azo directing activating group.

Arylation is a fundamental reaction that can be mostly fulfilled by electrophilic aromatic substitution and transition-metal-catalyzed aryl functionalization. Although the azo group has been used as a directing group for many transformations via transition-metal-catalyzed aryl carbon-hydrogen (C-H) bond activation, there remain significant unmet challenges in organocatalytic arylation. Here, we show that the azo group can effectively act as both a directing and activating group for organocatalytic asym. arylation of indoles via formal nucleophilic aromatic substitution of azobenzene derivatives Thus, a wide range of axially chiral arylindoles, e.g., I and II, have been achieved in good yields with excellent enantioselectivities by utilizing chiral phosphoric acid as catalyst. Furthermore, highly enantioenriched pyrroloindoles, e.g., III, bearing two contiguous quaternary chiral centers, have also been obtained via a cascade enantioselective formal nucleophilic aromatic substitution-cyclization process. This strategy should be useful in other related research fields and will open new avenues for organocatalytic asym. aryl functionalization.

Zhang, Weijie’s team published research in ACS Catalysis in 2018-09-07 | CAS: 13523-93-8

ACS Catalysis published new progress about Cyanation catalysts, thiocyanation. 13523-93-8 belongs to class indole-building-block, name is 4-(Benzyloxy)-1-methyl-1H-indole, and the molecular formula is C16H15NO, Name: 4-(Benzyloxy)-1-methyl-1H-indole.

Zhang, Weijie published the artcileVisible Light-Driven C-3 Functionalization of Indoles over Conjugated Microporous Polymers, Name: 4-(Benzyloxy)-1-methyl-1H-indole, the main research area is visible light conjugated microporous polymer formylation thiocyanation catalyst; green indole.

Metal-free and heterogeneous organic photocatalysts provide an environmentally friendly alternative to traditional metal-based catalysts. This paper reports a series of carbazole-based conjugated microporous polymers (CMPs) with tunable redox potentials and explores their photocatalytic performance with regard to C-3 formylation and thiocyanation of indoles. Conjugated polymers were synthesized through FeCl3 mediated Friedel-Crafts reactions, and their redox potentials were well regulated by simply altering the nature of the core (i.e., 1,4-dibenzyl, 1,3,5-tribenzyl, or 1,3,5-triazin-2,4,6-triyl). The resulting CMPs exhibited high surface areas, visible light absorptions and tunable semiconductor-range band gaps. With the highest oxidative capability, CMP-CSU6 derived from 1,3,5-tri(9H-carbazol-9-yl)benzene showed the highest efficiency for C-3 formylation and thiocyanation of indoles at room temperature Notably, the as-made catalysts can be easily recovered with good retention of photocatalytic activity and reused at least five times, suggesting good recyclability. These results are significant for constructing high-performance porous polymer catalysts with tunable photoredox potentials targeting an efficient material design for catalysis.

Patil, Nitin T.’s team published research in Tetrahedron Letters in 2009-11-25 | CAS: 13523-93-8

Tetrahedron Letters published new progress about Alkoxylation catalysts, reductive. 13523-93-8 belongs to class indole-building-block, name is 4-(Benzyloxy)-1-methyl-1H-indole, and the molecular formula is C16H15NO, Related Products of indole-building-block.

Patil, Nitin T. published the artcileThorpe-Ingold effect in copper(II)-catalyzed formal hydroalkoxylation-hydroarylation reaction of alkynols with indoles, Related Products of indole-building-block, the main research area is alkynol indole hydroalkoxylation hydroarylation copper; substituted indole preparation; copper hydroalkoxylation hydroarylation catalyst.

The use of Cu(OTf)2 as a catalyst for tandem hydroalkoxylation-hydroarylation reaction of alkynes tethered with hydroxyl group is reported. The reaction proceeded with catalytic amount of the copper(II) triflate and produces C-3-substituted indoles in good to high yields. The method was shown to be applicable to a broad range of indoles, containing electron-withdrawing and electron-donating substituents, and alkynol substrates bearing sterically demanding substituents in the tether. Interestingly, it was found that Thorpe-Ingold effect is operating for this cyclization reaction. Easy availability and low cost of Cu(OTf)2 make this method attractive and amenable for large-scale synthesis compared to known literature methods.

Lazo, John S.’s team published research in Bioorganic & Medicinal Chemistry in 2006-08-15 | CAS: 104291-81-8

Bioorganic & Medicinal Chemistry published new progress about Enzyme functional sites, active. 104291-81-8 belongs to class indole-building-block, name is Ethyl 6-cyano-1H-indole-2-carboxylate, and the molecular formula is C12H10N2O2, Recommanded Product: Ethyl 6-cyano-1H-indole-2-carboxylate.

Lazo, John S. published the artcileNovel benzofuran inhibitors of human mitogen-activated protein kinase phosphatase-1, Recommanded Product: Ethyl 6-cyano-1H-indole-2-carboxylate, the main research area is benzofuran preparation mitogen activated protein kinase phosphatase inhibition SAR.

Protein tyrosine phosphatases have a central role in the maintenance of normal cellular functionality. For example, PTP1B has been implicated in insulin-resistance, obesity, and neoplasia. Mitogen-activated protein kinase phosphatase-1 (MKP-1 or DUSP1) dephosphorylates and inactivates mitogen-activated protein kinase (MAPK) substrates, such as p38, JNK, and Erk, and has been implicated in neoplasia. The lack of readily available selective small mol. inhibitors of MKP family members has severely limited interrogation of their biol. role. Inspired by a previously identified inhibitor, NSC 357756 (I) of MKP-3, we synthesized seven NSC 357756 congeners, which were evaluated for in vitro inhibition against several protein phosphatases. Remarkably, none displayed potent inhibition against MKP-3, including the desamino NSC 357756 analog NU-154. Interestingly, NU-154 inhibited human PTP1B in vitro with an IC50 value of 24 ± 1 μM and showed little inhibition against Cdc25B, MKP-1, and VHR phosphatases. NU-126 [2-((E)-2-(5-cyanobenzofuran-2-yl)vinyl)-1H-indole-6-carbonitrile] inhibited MKP-1 and VHR in vitro but was less active against human MKP-3, Cdc25B, and PTP1B. The inhibition of MKP-1 by NU-126 was independent of redox processes. The benzofuran substructure represents a new potential scaffold for further analog development and provides encouragement that more selective and potent inhibitors of MKP family members may be achievable.

Polychronopoulos, Panagiotis’s team published research in Journal of Medicinal Chemistry in 2004-02-12 | CAS: 1677-47-0

Journal of Medicinal Chemistry published new progress about AM1 (molecular orbital method). 1677-47-0 belongs to class indole-building-block, name is 4,5-Dichloroisatin, and the molecular formula is C8H3Cl2NO2, Application In Synthesis of 1677-47-0.

Polychronopoulos, Panagiotis published the artcileStructural Basis for the Synthesis of Indirubins as Potent and Selective Inhibitors of Glycogen Synthase Kinase-3 and Cyclin-Dependent Kinases, Application In Synthesis of 1677-47-0, the main research area is indirubin derivative preparation; glycogen synthase kinase inhibitor indirubin derivative; cyclin dependent kinase inhibitor indirubin derivative; mol modeling AM1 Monte Carlo indirubin derivative.

Pharmacol. inhibitors of glycogen synthase kinase-3 (GSK-3) and cyclin-dependent kinases have promising potential for applications against several neurodegenerative diseases such as Alzheimer’s disease. Indirubins, a family of bis-indoles isolated from various natural sources, are potent inhibitors of several kinases, including GSK-3. Using the co-crystal structures of various indirubins with GSK-3β, CDK2 and CDK5/p25, we have modeled the binding of indirubins within the ATP-binding pocket of these kinases. This modeling approach provided some insight into the mol. basis of indirubins’ action and selectivity and allowed us to forecast some improvements of this family of bis-indoles as kinase inhibitors. Predicted mols., including 6-substituted and 5,6-disubstituted indirubins, were synthesized and evaluated as CDK and GSK-3 inhibitors. Control, kinase-inactive indirubins were obtained by introduction of a Me substitution on N1.

Damgaard, Maria’s team published research in ACS Chemical Neuroscience in 2015-09-16 | CAS: 1677-47-0

ACS Chemical Neuroscience published new progress about Central nervous system agents. 1677-47-0 belongs to class indole-building-block, name is 4,5-Dichloroisatin, and the molecular formula is C8H3Cl2NO2, COA of Formula: C8H3Cl2NO2.

Damgaard, Maria published the artcileIdentification of the First Highly Subtype-Selective Inhibitor of Human GABA Transporter GAT3, COA of Formula: C8H3Cl2NO2, the main research area is isatin derivative screening structure preparation GABA transporter GAT3 inhibitor; GABA uptake; hGAT3 selective; inhibitor; isatin; kinetics; noncompetitive.

Screening a library of small-mol. compounds using a cell line expressing human GABA transporter 3 (hGAT3) in a [3H]GABA uptake assay identified isatin derivatives as a new class of hGAT3 inhibitors. A subsequent structure-activity relationship (SAR) study led to the identification of hGAT3-selective inhibitors (i.e., compounds 20 and 34) that were superior to the reference hGAT3 inhibitor, (S)-SNAP-5114, in terms of potency (low micromolar IC50 values) and selectivity (>30-fold selective for hGAT3 over hGAT1/hGAT2/hBGT1). Further pharmacol. characterization of compound 20 (5-(thiophen-2-yl)indoline-2,3-dione) revealed a noncompetitive mode of inhibition at hGAT3. This suggests that this compound class, which has no structural resemblance to GABA, has a binding site different from the substrate, GABA. This was supported by a mol. modeling study that suggested a unique binding site that matched the observed selectivity, inhibition kinetics, and SAR of the compound series. These compounds are the most potent GAT3 inhibitors reported to date that provide selectivity for GAT3 over other GABA transporter subtypes.

Duan, Yingqian’s team published research in Organic Chemistry Frontiers in 2016 | CAS: 13523-93-8

Organic Chemistry Frontiers published new progress about Fluoroalkylation (heteroaryl). 13523-93-8 belongs to class indole-building-block, name is 4-(Benzyloxy)-1-methyl-1H-indole, and the molecular formula is C16H15NO, Recommanded Product: 4-(Benzyloxy)-1-methyl-1H-indole.

Duan, Yingqian published the artcileVisible-light-induced three-component 1,2-difluoroalkylarylation of styrenes with α-carbonyl difluoroalkyl bromides and indoles, Recommanded Product: 4-(Benzyloxy)-1-methyl-1H-indole, the main research area is indole difluoro preparation regioselective; styrene indole carbonyl difluoroalkyl bromide difluoroalkylarylation multicomponent photoredox catalyst.

A novel visible light photoredox catalysis three-component 1,2-difluoroalkylarylation of alkenes RCH=CH2 (R = 4-methoxyphenyl, 2-methoxyphenyl, 4-methylphenyl) and 1,2-dihydronaphthalene was disclosed, and two new C-C bonds were generated in a single step through regioselective incorporation of a CF2 group and a variety of indoles I (R1 = H, 5-MeO, 4-OBn, 6-F, etc.; R2 = Me, Bn) to C=C bonds. The well-designed photoredox system achieved the synthesis of a series of difluoro-containing indole derivatives, e.g., II with mild conditions and a broad substrate scope.