Tag: M.W=150-200

Yang, Song published the artcileRhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanes, Safety of 4-Chloroindoline, the main research area is indolinyl tetrahydropyridinol preparation regioselective enantioselective; indoline keto vinylidenecyclopropane hydroamination rhodium catalyst; indolyl tetrahydropyridinol preparation regioselective enantioselective; indole keto vinylidenecyclopropane hydroindolation rhodium catalyst; amino tetrahydropyridinol preparation regioselective enantioselective; secondary amine keto vinylidenecyclopropane hydroamination rhodium catalyst.

A highly regio- and enantioselective hydroamination and hydroindolation of keto-vinylidenecyclopropanes via cationic Rh(I) catalysis was reported in this context. The combination of indolines, various secondary amines and indoles with keto-vinylidenecyclopropanes afforded the corresponding hydrofunctionalization products, e.g., I, II and III resp. in good to excellent yields with outstanding ee values under mild conditions. A new TMM-Rh model complex was proposed, providing an atom economical Rh-π-allyl precursor at the same time. Moreover, the resulting products could easily be transformed into more complex polyheterocycles upon further synthetic manipulation.

Chemical Science published new progress about Bromides Role: RCT (Reactant), RACT (Reactant or Reagent) (α-keto). 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Safety of 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

Yang, Yunhui published the artcileRe-Catalyzed Annulations of Weakly Coordinating N-Carbamoyl Indoles/Indolines with Alkynes via C-H/C-N Bond Cleavage, Computed Properties of 41910-64-9, the main research area is pyrroloindolone preparation; alkyne carbamoyl indole annulation rhenium catalyst; pyrroloquinolinone preparation; carbamoyl indolines alkyne annulation rhenium catalyst; C−H activation; annulations; indoles; indolines; rhenium catalysis.

A rhenium-catalyzed [3+2] annulations of N-carbamoyl indoles with alkynes via C-H/C-N bond cleavage, provided rapid access to fused-ring pyrroloindolone derivs I [R1 = H, 6-F, 7-Br, etc.; R2 = R3 = Ph, 4-MeC6H4, 1-naphthyl, etc.]. For the first time, the weakly coordinating O-directing group was successfully employed in rhenium-catalyzed C-H activation reactions, enabled by the unique catalytic ratio of Re2(CO)10, Me2Zn and ZnCl2. Mechanistic studies revealed that aminozinc species played an important role in the reaction. Based on the mechanistic understanding, a more powerful catalytic ratio of Re2(CO)10, [MeZnNPh2]2 and Zn(OTf)2 was devised and applied successfully in the [4+2] annulations of indolines and alkynes affording pyrroloquinolinone derivs II.

Chemistry – A European Journal published new progress about C-H bond activation. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Computed Properties 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

Zhang, Wen-Qian published the artcileDearomative Arylcyanation of Indoles via C-CN Bond Activation Enabled by Ni/Lewis Acid Cooperative Catalysis, Product Details of C11H11NO2, the main research area is isoindoloindole carbonitrile preparation stereoselective nickel Lewis acid cooperative catalysis; indolecarbonyl benzonitrile intramol dearomative arylcyanation.

A nickel/Lewis acid cooperatively catalyzed intramol. dearomative arylcyanation of indoles is presented. The reaction proceeds through a C-CN bond activation, dearomatization, and benzylic cyanation sequence, affording 3-cyano fused indolinyl heterocycles in good to excellent yields and excellent diastereoselectivity. The asym. version of the reaction can be established in moderate enantioselectivity by using a chiral ligand.

Organic Letters published new progress about Benzoyl chlorides Role: RCT (Reactant), RACT (Reactant or Reagent). 57663-18-0 belongs to class indole-building-block, name is Methyl 2-methyl-1H-indole-5-carboxylate, and the molecular formula is C11H11NO2, Product Details of C11H11NO2.

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

Varlet, Thomas published the artcileEnantioselective and Diastereodivergent Synthesis of Spiroindolenines via Chiral Phosphoric Acid-Catalyzed Cycloaddition, Recommanded Product: 2-Ethoxy-1H-indole, the main research area is spiroindolenine preparation diastereoselective enantioselective; indolylmethanol dienecarbamate cycloaddition chiral phosphoric acid catalyst.

A diastereodivergent and enantioselective synthesis of chiral spirocyclohexyl-indolenines with four contiguous stereogenic centers is achieved by a chiral phosphoric acid-catalyzed cycloaddition of 2-susbtituted 3-indolylmethanols with 1,3-dienecarbamates. Modular access to two different diastereoisomers with high enantioselectivities was obtained by careful choice of reaction conditions. Their functional group manipulation provides an efficient access to enantioenriched spirocyclohexyl-indolines and -oxindoles. The origins of this stereocontrol have been identified using DFT calculations, which reveal an unexpected mechanism compared to previous work dealing with enecarbamates.

Journal of the American Chemical Society published new progress about [4+2] Cycloaddition reaction. 1009-27-4 belongs to class indole-building-block, name is 2-Ethoxy-1H-indole, and the molecular formula is C10H11NO, Recommanded Product: 2-Ethoxy-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

Shultz, Michael D. published the artcileOptimization of the in vitro cardiac safety of hydroxamate-based Histone deacetylase inhibitors, Quality Control of 5654-92-2, the main research area is hydroxamate derivative preparation SAR HDAC inhibotor anticancer.

Histone deacetylase (HDAC) inhibitors have shown promise in treating various forms of cancer. However, many HDAC inhibitors from diverse structural classes have been associated with QT prolongation in humans. Inhibition of the human ether a-go-go related gene (hERG) channel has been associated with QT prolongation and fatal arrhythmias. To determine if the observed cardiac effects of HDAC inhibitors in humans is due to hERG blockade, a highly potent HDAC inhibitor devoid of hERG activity was required. Starting with dacinostat (LAQ824), a highly potent HDAC inhibitor, we explored the SAR to determine the pharmacophores required for HDAC and hERG inhibition. We disclose here the results of these efforts where a high degree of pharmacophore homol. between these two targets was discovered. This similarity prevented traditional strategies for mitigating hERG binding/modulation from being successful and novel approaches for reducing hERG inhibition were required. Using a hERG homol. model, two compounds, I and II, were discovered to be highly efficacious with weak affinity for the hERG and other ion channels.

Journal of Medicinal Chemistry published new progress about Aldehydes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 5654-92-2 belongs to class indole-building-block, name is N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, and the molecular formula is C10H13N3, Quality Control of 5654-92-2.

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

Seal, Jonathan T.; Atkinson, Stephen J.; Aylott, Helen; Bamborough, Paul; Chung, Chun-wa; Copley, Royston C. B.; Gordon, Laurie; Grandi, Paola; Gray, James R. J.; Harrison, Lee A.; Hayhow, Thomas G.; Lindon, Matthew; Messenger, Cassie; Michon, Anne-Marie; Mitchell, Darren; Preston, Alex; Prinjha, Rab K.; Rioja, Inmaculada; Taylor, Simon; Wall, Ian D.; Watson, Robert J.; Woolven, James M.; Demont, Emmanuel H. published the artcile< The Optimization of a Novel, Weak Bromo and Extra Terminal Domain (BET) Bromodomain Fragment Ligand to a Potent and Selective Second Bromodomain (BD2) Inhibitor>, Reference of 93247-78-0, the main research area is second bromodomain inhibitor.

The profound efficacy, yet associated toxicity of pan-BET inhibitors is well documented. The possibility of an ameliorated safety profile driven by significantly selective (>100-fold) inhibition of a subset of the eight bromodomains is enticing, but challenging given the close homol. Herein, we describe the X-ray crystal structure-directed optimization of a novel weak fragment ligand with a pan-second bromodomain (BD2) bias, to potent and highly BD2 selective inhibitors. A template hopping approach, enabled by our parallel research into an orthogonal template (15, GSK046, I), was the basis for the high selectivity observed This culminated in two tool mols., 20 (GSK620) and 56 (GSK549), which showed an anti-inflammatory phenotype in human whole blood, confirming their cellular target engagement. Excellent broad selectivity, developability, and in vivo oral pharmacokinetics characterize these tools, which we hope will be of broad utility to the field of epigenetics research.

Journal of Medicinal Chemistry published new progress about Anti-inflammatory agents. 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Reference of 93247-78-0.

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

Zhou, Zijun; Li, Yanjun; Gong, Lei; Meggers, Eric published the artcile< Enantioselective 2-Alkylation of 3-Substituted Indoles with Dual Chiral Lewis Acid/Hydrogen-Bond-Mediated Catalyst>, Application In Synthesis of 4771-48-6, the main research area is enantioselective alkylation indole unsaturated acylimidazole chiral cyclometalated iridium complex; bifunctional chiral Lewis acid hydrogen bond mediated alkylation catalyst; pyrroloindole preparation.

A chiral-at-metal bis-cyclometalated iridium complex combines electrophile activation via metal coordination with nucleophile activation through hydrogen bond formation [e.g., indole I + acylimidazole II → III (89% conversion, 98% ee (S)) in presence of Δ-Ir complex IV.BARF]. This new bifunctional chiral Lewis acid/hydrogen-bond-mediated catalyst permits the challenging enantioselective 2-alkylation of 3-substituted indoles with α,β-unsaturated 2-acylimidazoles in up to 99% yield and with up to 98% enantiomeric excess at a catalyst loading of 2 mol %. As an application, the straightforward synthesis of a chiral pyrrolo[1,2-a]indole is demonstrated.

Organic Letters published new progress about Alkylation catalysts, stereoselective. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Application In Synthesis of 4771-48-6.

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

Huang, Yong; Song, Liangliang; Gong, Lei; Meggers, Eric published the artcile< Asymmetric Synthesis of Hydrocarbazoles Catalyzed by an Octahedral Chiral-at-Rhodium Lewis Acid>, Application In Synthesis of 4771-48-6, the main research area is hydrocarbazole enantioselective synthesis regioselective synthesis; vinylindole carboxylic ester substituted unsaturated acyl imidazole; Diels Alder reaction chiral Rh complex catalyst; Diels-Alder; asymmetric catalysis; chiral-at-metal; hydrocarbazoles; rhodium.

A bis-cyclometalated chiral-at-metal rhodium complex catalyzes the Diels-Alder reaction between N-Boc-protected 3-vinylindoles (Boc=tert-butyloxycarbonyl) and β-carboxylic ester-substituted α,β-unsaturated 2-acyl imidazoles with good-to-excellent regioselectivity (up to 99:1) and excellent diastereoselectivity (>50:1 d.r.) as well as enantioselectivity (92-99 % ee), e. g., I, under optimized conditions. The rhodium catalyst serves as a chiral Lewis acid to activate the 2-acyl imidazole dienophile by two-point binding and overrules the preferred regioselectivity of the uncatalyzed reaction.

Chemistry – An Asian Journal published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Application In Synthesis of 4771-48-6.

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

Kleinmans, Roman; Pinkert, Tobias; Dutta, Subhabrata; Paulisch, Tiffany O.; Keum, Hyeyun; Daniliuc, Constantin G.; Glorius, Frank published the artcile< Intermolecular [2π+2σ]-photocycloaddition enabled by triplet energy transfer>, COA of Formula: C9H6FNO2, the main research area is bicyclohexane preparation thioxanthone catalyst diastereoselective regioselective; coumarin flavone indole bicyclobutane intermol photocycloaddition.

For more than one century, photochem. [2+2]-cycloadditions have been used by synthetic chemists to make cyclobutanes, four-membered carbon-based rings. In this reaction, typically two olefin subunits (two π-electrons per olefin) cyclize to form two new C-C σ-bonds. Although the development of photochem. [2+2]-cycloadditions has made enormous progress within the last century, research has been focused on such [2π+2π]-systems, in which two π-bonds are converted into two new σ-bonds. Here an intermol. [2+2]-photocycloaddition that uses bicyclo[1.1.0]butanes as 2σ-electron reactants was reported. This strain-release-driven [2π+2σ]-photocycloaddition reaction was realized by visible-light-mediated triplet energy transfer catalysis. A simple, modular and diastereoselective synthesis of bicyclo[2.1.1]hexanes from heterocyclic olefin coupling partners, namely coumarins, flavones and indoles, is disclosed. Given the increasing importance of bicyclo[2.1.1]hexanes as bioisosteres-groups that convey similar biol. properties to those they replace-in pharmaceutical research and considering their limited access, there remains a need for new synthetic methodologies. Applying this strategy enabled to extend the intermol. [2+2]-photocycloadditions to σ-bonds and provides previously inaccessible structural motifs.

Nature (London, United Kingdom) published new progress about [2+2] Cycloaddition reaction, stereoselective (regioselective, photochem.). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, COA of Formula: C9H6FNO2.

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

Fang, Fang; Zheng, Haolin; Mao, Guojiang; Chen, Shanping; Deng, Guo-Jun published the artcile< Metal- and Solvent-Free Synthesis of Tetrahydrobenzo[c]carbazolones through NaI-Catalyzed Formal [4+2] Annulation>, Application In Synthesis of 93247-78-0, the main research area is indolyl cyclohexanone unsaturated compound sodium iodide catalyst regioselective cycloaddition; tetrahydrobenzocarbazolone preparation.

A novel strategy for the preparation of functional carbazoles through NaI-catalyzed formal [4+2] annulation of 2-(indol-3-yl)cyclohexanones and alkynes/alkenes was developed. The present approach started from easily available raw materials and provided a variety of tetrahydrobenzo[c]carbazolones in satisfactory yields under metal- and solvent-free conditions. The products could be further transformed into structurally valuable carbazole-based conjugated derivatives

Journal of Organic Chemistry published new progress about [4+2] Cycloaddition reaction (regioselective). 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Application In Synthesis of 93247-78-0.

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