Category: 93247-78-0

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

Zhang, Xiaoxiang; Yu, Wenhua; Nie, Yiyu; Zhang, Yingying; Gu, Xiaoting; Wei, Wanxing; Zhang, Zhuan; Liang, Taoyuan published the artcile< Copper-iodine co-catalyzed C-H aminoalkenylation of indoles via temperature-controlled selectivity switch: facile synthesis of 2-azolyl-3-alkenylindoles>, Electric Literature of 93247-78-0, the main research area is azolyl alkenylindole preparation green chem regioselective chemoselective; indole azole phenol aminoalkenylation copper iodine.

An efficient copper-iodine co-catalyzed 2,3-difunctionalization of indoles with azoles and phenols via temperature-controlled selectivity switch has been developed for the green synthesis of 2-azolyl-3-alkenylindoles. The strategy involves the simultaneous establishment of C-C and C-N bonds in one single operation and provides straightforward access to a wide range of functionalized indoles with high regio-selectivity and good functional group compatibility. The utility of the new protocol was demonstrated by the concise synthesis of the analog of a potent anticancer agent. This work paves the way for further innovative direct difunctionalization of carbon-carbon double bonds.

Organic Chemistry Frontiers published new progress about Alkenylation. 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Electric Literature 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

Pedrazzani, Riccardo; Pinosa, Emanuele; Bertuzzi, Giulio; Monari, Magda; Lauzon, Samuel; Ollevier, Thierry; Bandini, Marco published the artcile< Convenient synthesis of tricyclic N(1)-C(2)-fused oxazino-indolones via [Au(I)] catalyzed hydrocarboxylation of allenes>, Electric Literature of 93247-78-0, the main research area is oxazinoindolone preparation; allenyl indole carboxylic acid hydrocarboxylation gold catalyst.

A new [Au(I)] catalyzed intramol. hydrocarboxylation of allenes was presented as a valuable synthetic route to oxazino[4,3-a]indolones I [R = H, Me, c-hexyl; R1 = H, 8-Me, 8-F, etc.]. The use of 3,5-(CF3)2-C6H3-ImPyAuSbF6 as the optimal catalyst (5 mol%) was necessary to guarantee (i) wide tolerance of functional groups, (ii) mild reaction conditions (r.t., 16 h), and (iii) high yields (up to 90%). Preliminary attempts toward an enantioselective version (81 : 19 er) were also documented by means of a new family of chiral C1-sym. ImPyAuCl complexes.

Chemical Communications (Cambridge, United Kingdom) published new progress about Carboxylation. 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Electric Literature 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

Pu, Xingwen; Zhang, Mangang; Lan, Jingbo; Chen, Shuyou; Liu, Zheng; Liang, Wenbo; Yang, Yudong; Zhang, Min; You, Jingsong published the artcile< Tandem Rh(III)-Catalyzed C-H Heteroarylation of Indolyl Ketones and Cu(II)-Promoted Intramolecular Cyclization: One-Pot Access to Blue-Emitting Phenanthrone-Type Polyheterocycles>, Synthetic Route of 93247-78-0, the main research area is indolyl ketone rhodium copper catalyst tandem heteroarylation cyclization; phenanthrone type polyheterocycle one pot preparation blue emission.

Disclosed herein is a highly efficient one-pot synthetic strategy to phenanthrone-type polyheterocycles via tandem rhodium(III)-catalyzed ortho-C-H heteroarylation of indolyl ketones and copper(II)-promoted intramol. cyclization. This protocol enables a library of blue-emitting fluorophores with high quantum yields and narrow full widths at half-maximum to be rapidly built from readily available substrates, among of which 6,6,7,9,12-pentamethyl-6,12-dihydro-5H-benzofuro[2,3-a]carbazol-5-one exhibits pure blue emission with Commission Internationale de I’Eclairage coordinates of (0.15, 0.09) and a high quantum yield of 85% in CH2Cl2 solution

Organic Letters published new progress about C-H bond activation. 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Synthetic Route 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

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

Cadelis, Melissa M.; Pike, Elliot I. W.; Kang, Weirong; Wu, Zimei; Bourguet-Kondracki, Marie-Lise; Blanchet, Marine; Vidal, Nicolas; Brunel, Jean Michel; Copp, Brent R. published the artcile< Exploration of the antibiotic potentiating activity of indolglyoxylpolyamines>, Quality Control of 93247-78-0, the main research area is bis indolyloxoacetamidopropyl butane diaminium trifluoroacetate preparation; antibacterial antifungal activity cytotoxicity SAR; Antimicrobial; Indole; Indolglyoxylamide; Polyamine; Potentiation.

A series of substituted di-indolglyoxylamido-spermine analogs I [R1 = 7-Me, 5-F, 5,6-di-Br, etc.] were prepared and evaluated for intrinsic antimicrobial properties and the ability to enhance antibiotic action. As a compound class, intrinsic activity was typically observed towards Gram-pos. bacteria and the fungus Cryptococcus neoformans, with notable exceptions being the compounds I [R1 = 5-Br, 5-Cl] analogs which also exhibited modest activity (MIC 34-50 μM) towards the Gram-neg. bacteria Escherichia coli and Klebsiella pneumoniae. Several analogs enhanced the activity of doxycycline towards the Gram-neg. bacteria Pseudomonas aeruginosa, E. coli, K. pneumoniae and Acinetobacter baumannii. Of particular note was the identification of five antibiotic enhancing analogs I [R1 = 5-Br, 7-F, 7-Me] which also exhibited low to no cytotoxicity and red blood cell haemolytic properties. The mechanisms of action of the I [R1 = 5-Br, 7-F] analogs were attributed to the ability to disrupt the integrity and depolarize, bacterial membranes.

European Journal of Medicinal Chemistry published new progress about Amines Role: ADV (Adverse Effect, Including Toxicity), PAC (Pharmacological Activity), RCT (Reactant), SPN (Synthetic Preparation), THU (Therapeutic Use), BIOL (Biological Study), RACT (Reactant or Reagent), PREP (Preparation), USES (Uses). 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Quality Control 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

Kim, Yong-Guy; Lee, Jin-Hyung; Park, Sunyoung; Lee, Jintae published the artcile< The anticancer agent 3,3'-diindolylmethane inhibits multispecies biofilm formation by acne-causing bacteria and Candida albicans>, Recommanded Product: Methyl 1H-indole-7-carboxylate, the main research area is diindolylmethane anticancer Candida albicans acne causing bacteria agent biofilm; 3,3′-diindolylmethane; Cutibacterium acnes; antibiofilm; indole-3-carbinol; multispecies biofilms.

The Gram-pos. anaerobic bacterium Cutibacterium acnes is a major inhabitant of human skin and has been implicated in acne vulgaris formation and in the formation of multispecies biofilms with other skin-inhabiting organisms like Staphylococcus aureus and Candida albicans. Indoles are widespread in nature (even in human skin) and function as important signaling mols. in diverse prokaryotes and eukaryotes. In the present study, we investigated the antibacterial and antibiofilm activities of 20 indoles against C. acnes. Of the indoles tested, indole-3-carbinol at 0.1 mM significantly inhibited biofilm formation by C. acnes without affecting planktonic cell growth, and the anticancer drug 3,3′-diindolylmethane (DIM) at 0.1 mM (32μg/mL) also significantly inhibited planktonic cell growth and biofilm formation by C. acnes, whereas the other indoles and indole itself were less effective. Also, DIM at 0.1 mM successfully inhibited multispecies biofilm formation by C. acnes, S. aureus, and C. albicans. Transcriptional analyses showed that DIM inhibited the expressions of several biofilm-related genes in C. acnes, and at 0.05 mM, DIM inhibited hyphal formation and cell aggregation by C. albicans. These results suggest that DIM and other indoles inhibit biofilm formation by C. acnes and have potential use for treating C. acnes associated diseases.

Microbiology Spectrum published new progress about Acne vulgaris. 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Recommanded Product: Methyl 1H-indole-7-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

Zhang, Xiaoxiang; Zhang, Yingying; Gu, Xiaoting; Zhang, Zhuan; Wei, Wanxing; Liang, Taoyuan published the artcile< Synthesis of 3-halogenated 2,3'-biindoles by a copper-mediated 2,3-difunctionalization of indoles>, Formula: C10H9NO2, the main research area is halo biindole green regioselective preparation; indole difunctionalization catalyst copper.

A copper-mediated 2,3-difunctionalization of indoles to afford 3-halogenated 2,3′-biindoles I [R1 = 5-Me, 4-Cl, 5-Cl, etc.; R2 = Me, Et, Ph, etc.; X = Cl, Br] was described herein. The protocol uses readily available feedstocks and a naturally abundant copper catalyst system, which allowed the regioselective formation of C-C and C-X (X = Cl and Br) bonds in one single operation. Here the copper metal salt served not only as a catalyst but also as a reactant to provide the source of halogen. This operationally simple procedure avoided the utilization of environmentally unfriendly reagents and displays good functional group compatibility. Noteworthily, the introduction of halogen into mols. would offered great potential for further chem. transformations.

Organic & Biomolecular Chemistry published new progress about C-C bond formation. 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Formula: C10H9NO2.

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

Xu, Chong-Hui; Xiong, Zhi-Qiang; Li, Yang; Zhu, Yan-Ping; Li, Jin-Heng published the artcile< Copper-catalyzed oxidative phosphonoheteroarylation of alkenes with phosphonates and N-heteroarenes via P-H/C-H functionalization>, Formula: C10H9NO2, the main research area is heteroaryl alkylphosphonate preparation; alkene phosphonate heteroarene oxidative intermol phosphonoheteroarylation copper catalyst.

A copper-catalyzed oxidative intermol. phosphonoheteroarylation of alkenes R1C(R1)=CHR2 (R1 = 4-methoxyphenyl, 6-bromo-2H-1,3-benzodioxol-5-yl, 3-methylthiophen-2-yl, etc.; R2 = H, Me, Ph, 4-methylphenyl, 4-chlorophenyl; R3 = H, Me) with phosphonates ((R4)2)P(O)H [R4 = OMe, OEt, Oi-Pr, Ph, (2-methylpropyl)oxidanyl] and nucleophilic N-heteroarenes I (R5 = 5-OMe, 4-CHO, 7-COOMe ; R6 = H, Bn, Me, Ph; R7 = H, Me, COOMe) and 1-phenyl-1H-pyrrole involving P-H/C-H functionalization for the synthesis of highly valuable β-(N-heteroaryl)-alkylphosphonates II and III is disclosed. This method allows the incorporation of two functional groups, a phosphonate and a N-heteroarene, into the alkene in a single reaction step through oxidative formation of the P-centered radicals, addition across the C=C bond, single electron oxidation and C-H functionalization cascades.

Organic Chemistry Frontiers published new progress about Aryl alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Formula: C10H9NO2.

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

Qin, Jing-Hao; Luo, Mu-Jia; An, De-Lie; Li, Jin-Heng published the artcile< Electrochemical 1,2-Diarylation of Alkenes Enabled by Direct Dual C-H Functionalizations of Electron-Rich Aromatic Hydrocarbons>, Reference of 93247-78-0, the main research area is alkene arene cobalt electrochem diarylation dehydrogenative cycloaddition annulation cascade; aryl alkene preparation; dihydroindolo carbazole preparation; alkenes; dehydrogenative [2+2+2] cycloaddition; diarylation; electrochemistry; polyarenes.

A cobalt-promoted electrochem. 1,2-diarylation of alkenes with electron-rich aromatic hydrocarbons via direct dual C-H functionalizations is described, which employs a radical relay strategy to produce polyaryl-functionalized alkanes. Simply by using graphite rod cathode instead of platinum plate cathode, chemoselectivity of this radical relay strategy is shifted to the dehydrogenative [2+2+2] cycloaddition via 1,2-diarylation, annulation, and dehydrogenation cascades leading to complex 11,12-dihydroindolo[2,3-a]carbazoles. Mechanistical studies indicate that a key step for the radical relay processes is transformations of the aromatic hydrocarbons to the aryl sp2-hybridized carbon-centered radicals via deprotonation of the corresponding aryl radical cation intermediates with bases.

Angewandte Chemie, International Edition published new progress about [2+2+2] Cycloaddition reaction. 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