Month: November 2022

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.

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.

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

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.

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.

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

Liu, Yongfu published the artcileDiscovery of 3-Pyridyl Isoindolin-1-one Derivatives as Potent, Selective, and Orally Active Aldosterone Synthase (CYP11B2) Inhibitors, Recommanded Product: 5-Chloroisoindolin-1-one, the main research area is pyridyl isoindolinone derivative preparation oral aldosterone synthase inhibitor.

Aldosterone synthase (CYP11B2) inhibitors have been explored in recent years as an alternative therapeutic option to mineralocorticoid receptor (MR) antagonists to reduce elevated aldosterone levels, which are associated with deleterious effects on various organ systems including the heart, vasculature, kidney, and central nervous system (CNS). A benzamide pyridine hit derived from a focused screen was successfully developed into a series of potent and selective 3-pyridyl isoindolin-1-ones CYP11B2 inhibitors. Our systematic structure-activity relationship study enabled us to identify unique structural features that result in high selectivity against the closely homologous cortisol synthase (CYP11B1). We evaluated advanced lead mols., exemplified by compound 52, in an in vivo cynomolgus monkey acute adrenocorticotropic hormone (ACTH) challenge model and demonstrated a superior 100-fold in vivo selectivity against CYP11B1.

Journal of Medicinal Chemistry published new progress about Aldosterone synthase inhibitors. 74572-29-5 belongs to class indole-building-block, name is 5-Chloroisoindolin-1-one, and the molecular formula is C8H6ClNO, Recommanded Product: 5-Chloroisoindolin-1-one.

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

Kamienski, Bohdan published the artcileA multinuclear NMR study of the tautomeric equilibria of some indolinones, SDS of cas: 1009-27-4, the main research area is NMR indolinone tautomerism.

1H, 13C and 15N NMR data are reported for three indolinones which, in principle, may exhibit tautomeric equilibrium together with the corresponding NMR results for three model compounds It is found that when taken together the 1H, 13C and 15N NMR results provide a greater insight into both fast and slow exchange equilibrium than would either of these techniques considered alone. The results are indicative of the dependence of equilibrium upon the choice of solvent.

Bulletin of the Polish Academy of Sciences, Chemistry published new progress about NMR (nuclear magnetic resonance). 1009-27-4 belongs to class indole-building-block, name is 2-Ethoxy-1H-indole, and the molecular formula is C10H11NO, SDS of cas: 1009-27-4.

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

Dobrowolski, P. published the artcileProton and carbon-13 NMR study of the prototropic equilibriums of 2-indolinone, Application In Synthesis of 1009-27-4, the main research area is NMR indolinone tautomerism.

13C NMR data are reported for 0.5 M CDCl3 solutions of 2-indolinone and six related compounds The question of prototropic equilibrium is discussed involving three possible tautomers, A, B, C. Form A is found to predominate in the dynamic equilibrium established for three of the compounds studied. In the case of a fourth compound slow exchange between forms B and C results in the finding of both of these forms in the approx. ratio 1:1.8. These findings are supported by 1H NMR measurements. Corresponding 1H and 13C NMR measurements on methanol solutions are essentially the same.

Journal of Molecular Structure published new progress about NMR (nuclear magnetic resonance). 1009-27-4 belongs to class indole-building-block, name is 2-Ethoxy-1H-indole, and the molecular formula is C10H11NO, Application In Synthesis of 1009-27-4.

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

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.

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.

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

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.

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.

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

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.

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.

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

Xiong, Dan published the artcileRhodium-Catalyzed Mild C7-Amination of Indolines with Nitrosobenzenes, COA of Formula: C8H8ClN, the main research area is pyrimidinyl indoline nitrosobenzene rhodium catalyst regioselective amination reaction; phenylamino indolinone preparation green chem crystal structure.

A mild and practical Rh(III)-catalyzed C7-H amination of indolines were described, which allows the synthesis of a variety of 7-amino-substituted indolines with good functional group tolerance and high atom economy. Notably, nitrosobenzenes served as nitrogen source in this transformation, and therefore behave environmentally friendly for C-N bond constructions.

ChemistrySelect published new progress about Amination catalysts (regioselective). 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, COA of Formula: C8H8ClN.

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

Yang, Xiao-Hui published the artcileIntermolecular Hydroamination of 1,3-Dienes To Generate Homoallylic Amines, Name: 4-Chloroindoline, the main research area is rhodium catalyzed intermol hydroamination diene Bronsted acid BINAP effect; homoallylic amine preparation anti Markovnikov selectivity.

Authors report a Rh-catalyzed hydroamination of 1,3-dienes to generate homoallylic amines. The work show-cases the first case of anti-Markovnikov selectivity in the intermol. coupling of amines and 1,3-dienes. By tuning the ligand properties and Bronsted acid additive, it was found that a combination of rac-BINAP and mandelic acid is critical for achieving anti-Markovnikov selectivity.

Journal of the American Chemical Society published new progress about Addition reaction (anti-Markovnikov). 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Name: 4-Chloroindoline.

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