Category: 399-76-8

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

Xu, Hai-Feng; Pan, You-Lu; Li, Gang-Jian; Hu, Xu-Yang; Chen, Jian-Zhong published the artcile< Copper(II)-Catalyzed Direct C-H (Hetero)arylation at the C3 Position of Indoles Assisted by a Removable N,N-Bidentate Auxiliary Moiety>, Recommanded Product: 5-Fluoroindole-2-carboxylic acid, the main research area is arylated indole regioselective preparation; indole arylboronic ester arylation copper catalyst.

The regioselective arylation of inert C3-H bonds in indoles reacting with arylboronates via effective copper-mediated catalysis with the aid of a facile and removable 2-pyridinylisopropyl (PIP) group without ligand participation was reported. This newly established method features high compatibility with diverse functional groups between coupling partners, including both indole substrates and arylboron reagents, consequentially leading to operational simplicity and providing access to generate the desired arylated products I [R = H, 4-Me, 5-MeO, 6-Br, etc.; R1 = Me, Bn; Ar = Ph, 2-thienyl, 3-pyridyl, etc.] in good to excellent yields of up to 97%. Synthetically, the PIP-derived amide moiety could subsequently be readily removed under mild reaction conditions to produce useful indolecarboxylic acids for further transformation.

Journal of Organic Chemistry published new progress about Amides, secondary Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Recommanded Product: 5-Fluoroindole-2-carboxylic acid.

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, Yuqi; Xu, Jie; Yue, Kairui; Huang, Chao; Qin, Mengting; Chi, Dongyu; Yu, Qixin; Zhu, Yue; Hou, Xiaohan; Xu, Tongqiang; Li, Min; Chou, C. James; Li, Xiaoyang published the artcile< Potent Hydrazide-Based HDAC Inhibitors with a Superior Pharmacokinetic Profile for Efficient Treatment of Acute Myeloid Leukemia In Vivo>, HPLC of Formula: 399-76-8, the main research area is hydrazide HDAC inhibitor pharmacokinetic myeloid leukemia.

As “”Michael acceptors”” may induce promiscuous responses in mammalian cells by reacting with various proteins, we modified the cinnamamide of our previous hydrazide-based HDAC inhibitors (HDACIs) to deactivate the Michael reaction. Representative compound 11h is 2-5 times more potent than lead compound 17 in both HDAC inhibitory activity (IC50 = 0.43-3.01 nM) and cell-based antitumor assay (IC50 = 19.23-61.04 nM). The breakthrough in the pharmacokinetic profile of 11h (oral bioavailability: 112%) makes it a lead-in-class oral active agent, validated in the in vivo anti-AML study (4 mg/kg p.o., TGI = 78.9%). Accumulated AcHH3 and AcHH4 levels in tumor tissue directly correlate with the in vivo efficacy, as panobinostat with lower AcHH3 and AcHH4 levels than 11h displays limited activity. To the best of our knowledge, this work contributes the first report of in vivo antitumor activity of hydrazide-based HDACIs. The outstanding pharmacokinetic/pharmacodynamic and antitumor activity of 11h could potentially extend the clin. application of current HDACIs.

Journal of Medicinal Chemistry published new progress about Acetylated histone H3 Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, HPLC of Formula: 399-76-8.

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

Makra, Zsofia; Benyei, Attila; Puskas, Laszlo G.; Kanizsai, Ivan published the artcile< One-Pot Access towards 4,5-Disubstituted 2-Amino-1H-imidazoles Starting from Mannich Substrates and their Transformation Utilities>, SDS of cas: 399-76-8, the main research area is Mannich substrate one pot oxidative annulation ring cleavage sequence; amino imidazole preparation.

An efficient protocol for the preparation of 4,5-functionalized 2-amino-1H-imidazoles, e.g., I, as fragment-like structures was developed in isolated yields up to 95%. The demonstrated one-pot manner includes an intramol. oxidative annulation and ring cleavage sequence starting from Mannich precursors. The suggested one-pot sequential synthetic methodol. is easy to apply in automatic and robotic chem. laboratories for which a rapidly increasing demand is foreseen because of the ongoing revolution in the field of continuous manufacturing of pharmaceutical drug substances and products. Further transformation utilities such as Groebke-Blackburn-Bienayme 3CR and the formation of marine alkaloid analogs were also represented.

European Journal of Organic Chemistry published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, SDS of cas: 399-76-8.

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

Butkevich, Alexey N.; Bossi, Mariano L.; Lukinavicius, Grazvydas; Hell, Stefan W. published the artcile< Triarylmethane Fluorophores Resistant to Oxidative Photobluing>, Recommanded Product: 5-Fluoroindole-2-carboxylic acid, the main research area is triarylmethane fluorophore oxidative photobluing STED nanoscopy.

Spectral stability of small-mol. fluorescent probes is required for correct interpretation and reproducibility of multicolor fluorescence imaging data, in particular under high (de)excitation light intensities of super-resolution imaging or in single-mol. applications. The authors propose a synthetic approach to a series of spectrally stable rhodamine fluorophores based on sequential Ru- and Cu-catalyzed transformations, evaluate their stability against photobleaching and photoconversion in the context of other fluorophores using chemometric anal., and demonstrate chem. reactivity of fluorophore photoproducts. The substitution patterns providing the photoconversion-resistant triarylmethane fluorophores have been identified, and the applicability of nonbluing labels in live-cell STED nanoscopy is demonstrated.

Journal of the American Chemical Society published new progress about Fluorescence. 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Recommanded Product: 5-Fluoroindole-2-carboxylic acid.

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

Kong, Lingkai; Tian, Wenyue; Liu, Zhiyan; Xu, Ting; Wen, Haoyue; Chen, Zihan; Gao, Jin; Bai, Li-Ping published the artcile< TfOH-Catalyzed Cascade C-H/N-H Chemo-/Regioselective Annulation of Indole-2-carboxamides with Benzoquinones for the Construction of Anticancer Tetracyclic Indolo[2,3-c]quinolinones>, Reference of 399-76-8, the main research area is indoloquinolinone preparation antitumor human; indole carboxamide benzoquinone cyclization trifluoromethanesulfonic acid.

An efficient TfOH-catalyzed cascade C-H/N-H annulation of indole-2-carboxamides with benzoquinones has been developed for the synthesis of tetracyclic indolo[2,3-c]quinolinones. This reaction exhibits excellent chemo-/regioselectivity, achieving functionalization of the C-3 of indole and N-H of the amide moiety to form the new C-C and C-N bonds. Various expected products were synthesized from readily available starting materials in good to high yields with a wide substrate scope and good functional group tolerance. Among all synthetic products, I showed the most potent cytotoxicity toward the 4T1 cancer cell line with an IC50 value of 0.62 +/- 0.05μM. In vivo study demonstrated that I remarkably suppressed 4T1 xenograft tumor growth without body weight loss.

Journal of Organic Chemistry published new progress about Antitumor agents. 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Reference of 399-76-8.

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, Xiao-Yu; Chen, Xia; Liu, Hai-Long published the artcile< KI catalyzed C-H functionalization of acetone for the synthesis of 2-oxopropyl hetero-aromatic carboxylates>, Category: indole-building-block, the main research area is heteroaryl carboxylic acid acetone potassium iodide catalyst bond activation; oxopropyl heteroarylcarboxylate preparation.

KI catalyzed C-H functionalization of acetone with hetero-aromatic carboxylic acids was developed. With potassium iodide as catalyst and sodium chlorite as oxidant, cascade reaction including α-H electrophilic substitution of acetone and nucleophilic substitution of iodoacetone occurred smoothly. 2-Oxopropyl hetero-aromatic carboxylates were obtained with the good to excellent yields.

Synthetic Communications published new progress about Aromatic carboxylic acids Role: RCT (Reactant), RACT (Reactant or Reagent) (hetero). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Category: 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

Ding, Lu; Gao, Run-Duo; You, Shu-Li published the artcile< Palladium(0)-Catalyzed Intermolecular Asymmetric Cascade Dearomatization Reaction of Indoles with Propargyl Carbonate>, Safety of 5-Fluoroindole-2-carboxylic acid, the main research area is alkylindolyl methyl malonate preparation propargyl carbonate palladium tandem dearomatization; alkyl methylene dihydrocarbazole dicarboxylate chemoselective regioselective enantioselective preparation; allylic compounds; asymmetric catalysis; cascade reactions; dearomatization; palladium.

An intermol. asym. cascade dearomatization reaction of indole derivatives with propargyl carbonate was developed. The challenges associated with both the chemoselectivity between the carbon and nitrogen nucleophile and the enantioselective control during the formation of an all-carbon quaternary stereogenic center were well addressed by a Pd catalytic system derived from the Feringa ligand. A series of enantioenriched multiply substituted fused indolenines were provided in good yields (71-86%) with excellent enantioselectivity (91-96% ee) and chemoselectivity (3/4>19:1 in most cases).

Chemistry – A European Journal published new progress about Acid chlorides Role: RCT (Reactant), RACT (Reactant or Reagent). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Safety of 5-Fluoroindole-2-carboxylic acid.

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

Palomba, Martina; Pompei, Sara; Roscini, Luca; Bagnoli, Luana published the artcile< Synthesis and biological evaluation of new indole and pyrrole carboxamides based on amino acids>, Category: indole-building-block, the main research area is indolecarboxamide preparation antifungal; pyrrolecarboxamide preparation antifungal.

A series of indole-carboxamides I [R = H, 5-MeO, 5-F, 7-NO2, 5,6-di-MeO; R1 = i-Pr, CH(Me)Et, Bn, etc.; R2 = Me, Et] and II was synthesized through coupling reactions. Several substitutions on the aromatic ring and on the amino acids were well tolerated, and corresponding indole-carboxamides I and II were obtained with good yields. The same procedure could be also extended to pyrrole-carboxamides III. The compounds I [R = 5-MeO, 5,6-di-MeO, 7-NO2; R1 = i-Pr; R2 = Et] and III [R1 = i-Pr, R2 = Et] were screened for their antimicrobial activity against ten different yeast strains and only compounds I [R = 7-NO2, R1 = i-Pr, R2 = Et] and III [R1 = i-Pr, R2 = Et] showed an antifungal activity. Further explorations were required to clarify a potential applicability in biol. fields.

ARKIVOC (Gainesville, FL, United States) published new progress about Amides Role: PAC (Pharmacological Activity), SPN (Synthetic Preparation), THU (Therapeutic Use), BIOL (Biological Study), PREP (Preparation), USES (Uses). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Category: 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

Kilic-Kurt, Zuehal; Acar, Cemre; Ergul, Mustafa; Bakar-Ates, Filiz; Altuntas, Tunca G. published the artcile< Novel indole hydrazide derivatives: Synthesis and their antiproliferative activities through inducing apoptosis and DNA damage>, Recommanded Product: 5-Fluoroindole-2-carboxylic acid, the main research area is anticancer activity apoptosis cell cycle DNA damage Bax Bcl2; DNA damage; anticancer activity; apoptosis; cell cycle; synthesis.

A series of novel indole hydrazide derivatives was synthesized and evaluated for their anticancer activities. Compound 12(I) exhibited the highest antiproliferative activity against the MCF-7 cell line, with an IC50 value of 3.01μM. Treatment of MCF-7 cells with compound 12 led to cell cycle arrest at the G0/G1 phase and also displayed a significant annexin V binding pattern, indicating that compound 12 is effective in apoptotic cell death. The Western blot anal. showed that compound 12 increased the expression of proapoptotic Bax and decreased the levels of the antiapoptotic Bcl-2 protein. It was also observed that MCF-7 cells treated with compound 12 showed reduced levels of procaspase-3 and -9 proteins. Moreover, compound 12 treatment induced a significant DNA damage in MCF-7 cells by increasing H2AX and ATM phosphorylation.

Archiv der Pharmazie (Weinheim, Germany) published new progress about Annexin V Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Recommanded Product: 5-Fluoroindole-2-carboxylic acid.

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