Day: November 16, 2022

Lopez-Valdez, German published the artcileConvenient access to isoindolinones via carbamoyl radical cyclization: Synthesis of cichorine and 4-hydroxyisoindolin-1-one natural products, Recommanded Product: 4-Hydroxy-2,3-dihydroisoindol-1-one, the main research area is isoindolinone preparation oxidative radical cyclization; cichorine synthesis oxidative radical cyclization; hydroxyisoindolinone synthesis oxidative radical cyclization; zinnimidine formal synthesis oxidative radical cyclization.

An efficient and convenient access to 2-tert-butylisoindolin-1-ones via an oxidative radical cyclization process from stable carbamoylxanthates, derived from secondary tert-butylamines, is described. The proposed mechanism for this transformation involves, the generation of a carbamoyl radical, its cyclization to the aromatic system, and the dilauroyl peroxide (DLP) mediated rearomatization to generate the isoindolinone ring system. Addnl., the syntheses of cichorine and 4-hydroxyisoindolin-1-one natural products were carried out to underscore the synthetic potential of this xanthate-based carbamoyl radical-oxidative cyclization.

Tetrahedron published new progress about Radical oxidative cyclization. 366453-21-6 belongs to class indole-building-block, name is 4-Hydroxy-2,3-dihydroisoindol-1-one, and the molecular formula is C8H7NO2, Recommanded Product: 4-Hydroxy-2,3-dihydroisoindol-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

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.

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.

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

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.

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.

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

Zhao, Fei published the artcileMonoamine Oxidase (MAO-N) Biocatalyzed Synthesis of Indoles from Indolines Prepared via Photocatalytic Cyclization/Arylative Dearomatization, Application In Synthesis of 41910-64-9, the main research area is monoamine oxidase indole indoline photocatalytic cyclization dearomatization.

The biocatalytic aromatization of indolines into indole derivatives exploiting monoamine oxidase (MAO-N) enzymes is presented. Indoline substrates were prepared via photocatalytic cyclization of arylaniline precursors or via arylative dearomatization of unsubstituted indoles and in turn chemoselectively aromatized by the MAO-N D11 whole cell biocatalyst. Computational docking studies of the indoline substrates in the MAO-N D11 catalytic site allowed for the rationalization of the biocatalytic mechanism and exptl. results of the biotransformation. This methodol. represents an efficient example of biocatalytic synthesis of indole derivatives and offers a facile approach to access these aromatic heterocycles under mild reaction conditions.

ACS Catalysis published new progress about Biotransformation (whole-cell). 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Application In Synthesis of 41910-64-9.

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

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