Category: 23077-43-2

Hu, Yuanyuan; Ruan, Wenchen; Gao, Anhui; Zhou, Yubo; Gao, Lixin; Xu, Meng; Gao, Jianrong; Ye, Qing; Li, Jia; Pang, Tao published the artcile< Synthesis and biological evaluation of novel 4,5-bisindolyl-1,2,4-triazol-3-ones as glycogen synthase kinase-3β inhibitors and neuroprotective agents>, Name: 5-Fluoro-1H-indole-3-carboxylic acid, the main research area is bisindolyltriazolone preparation glycogen synthase kinase inhibitor SAR neuroprotective agent.

A series of novel 4,5-bisindolyl-1,2,4-triazol-3-ones, compounds I [R1 = H, 6-F, 5-Cl, 6-Br, etc.; R2 = H, Me] were designed, prepared and evaluated for their glycogen synthase kinase (GSK)-3β inhibitory activities. Compounds exhibited favorable inhibitory potency towards GSK-3β kinase at the mol. level and in cells indicated by significantly reducing GSK-3β substrate Tau phosphorylation at Ser396 in primary neurons showing the inhibition of cellular GSK-3β. In an in vitro model of neuronal injury, compounds I [R1 = 5-F, 5-Cl, 5-Br; R2 = Me] prevented glutamate-induced neuronal death which was closely associated with cerebral ischemic stroke. Preliminary structure-activity relationship was examined and showed that different substituents on the indole ring had significant influences on the GSK-3β inhibitory potency. These findings may provide new insights into the development of novel GSK-3β inhibitors as neuroprotective agents.

Pharmazie published new progress about Blood-brain barrier. 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Name: 5-Fluoro-1H-indole-3-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

Kalir, Asher; Balderman, D. published the artcile< Improved synthesis of some fluoroindoles>, Product Details of C9H6FNO2, the main research area is fluoroindoles; indoles fluoro.

2,5-F2-C6-H3NO2 (109 g.) was treated with 155 g. NCCH2CO2Et and 31.6 g. Na in 1000 ml. EtOH for 2 hrs. to give 26% 4-fluoroanthro-xanonitrile, m. 70-1°. 2,4-(O2N)FC6H3Me (155 g.) was refluxed 14 hrs. with 196 g. N-bromosuccinimide in 600 ml. CCl4 and 2 g. benzoyl peroxide and treated directly with pyridine to give 198 g. I (X = 4-F), m. 201-2°, and 37 g. 2,4-(O2N)FC6H3-CHBr2, m. 63-4°. I (X = 5-F and 6-F), m. 189-90°, and 202-4°, resp., were similarly obtained in 64 and 71% yield. I (X = 4-F) was treated with 150 g. p-ONC6H4NMe2.HCl in 1 l. EtOH and 720 ml. 2.5N NaOH at <5° for 1 hr., and then treated with 1.5 l. 6N H2SO4 to give 86 g. 2-O2N X C6H3CHO (II) (where X = 4-F), m. 32-3°, via III (X = 4-F), m. 165-6°. The following compounds were similarly prepared (X, % yield II, m.p. II, % yield III, and m.p. III given): 5-F, 86, 94-5°, 92, 155-6°; 6-F, 95, 62-3°, 96, 151-2°. II (X = 6-F) was treated with MeNO2 to give 76% 2,4-F(O2N)C6H3CH:CHNO2, m. 84°, which was catalytically reduced to 34-63% 4-fluoroindole, m. 29-30°, accompanied by IV, m. 200° (decomposition). The method of K. and S. Szara (1963) was used to prepare V (R, % yield, and m.p. given): CHO, 73, 190-1°; CH:CMeNO2, 81, 191-2°; CH2CHMeNH2, 64, 103-5° (HCl salt m. 240-1°, picrate m. 222-3°). 6-Fluoro-3-(2-nitrovinyl)indole, m. 190-2°, and 6-fluorotryptamine m. 83-4°, were similarly prepared in 68 and 51% yield, resp. V (R = CHO) (3.5 g.) was treated with 6 g. KMnO4 in 120 ml. Me2CO at <40° to give 47% V (R = CO2H), m. 273° (decomposition). 5-Fluoro-3-indolecarboxylic acid, m. 234-6° (decomposition), and 6-fluoro-3-indolecarboxylic acid, m. 242-4° (decomposition), were similarly prepared in 54 and 48% yield, resp. V (R = CH2CHMeNH2) was less active than the 5-fluoro derivative, but more active than the 6-fluoro derivative in the activity cage test on mice. Israel Journal of Chemistry published new progress about 23077-43-2. 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Product Details of 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

Boldron, Christophe; Besse, Angelina; Bordes, Marie-Francoise; Tissandie, Stephanie; Yvon, Xavier; Gau, Benjamin; Badorc, Alain; Rousseaux, Tristan; Barre, Guillaume; Meneyrol, Jerome; Zech, Gernot; Nazare, Marc; Fossey, Valerie; Pflieger, Anne-Marie; Bonnet-Lignon, Sandrine; Millet, Laurence; Briot, Christophe; Dol, Frederique; Herault, Jean-Pascal; Savi, Pierre; Lassalle, Gilbert; Delesque, Nathalie; Herbert, Jean-Marc; Bono, Francoise published the artcile< N-[6-(4-Butanoyl-5-methyl-1H-pyrazol-1-yl)pyridazin-3-yl]-5-chloro-1-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-1H-indole-3-carboxamide (SAR216471), a Novel Intravenous and Oral, Reversible, and Directly Acting P2Y12 Antagonist>, Safety of 5-Fluoro-1H-indole-3-carboxylic acid, the main research area is indolecarboxamide preparation purinoceptor antagonist anticoagulant antithrombotic thrombosis blood coagulation.

In the search of a potential backup for clopidogrel, the authors have initiated a HTS campaign designed to identify novel reversible P2Y12 antagonists. Starting from a hit with low micromolar binding activity, the authors report here the main steps of the optimization process leading to the identification of the preclin. candidate SAR216471, I. It is a potent, highly selective, and reversible P2Y12 receptor antagonist and by far the most potent inhibitor of ADP-induced platelet aggregation among the P2Y12 antagonists described in the literature. I displays potent in vivo antiplatelet and antithrombotic activities and has the potential to differentiate from other antiplatelet agents.

Journal of Medicinal Chemistry published new progress about Anticoagulants. 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Safety of 5-Fluoro-1H-indole-3-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

Henderson, Scott H.; West, Ryan A.; Ward, Simon E.; Honey, Mark A. published the artcile< Metal-free selective mono-halodecarboxylation of heteroarenes under mild conditions>, Application In Synthesis of 23077-43-2, the main research area is haloheteroarene preparation; heteroarene carboxylic acid mono halodecarboxylation; halodecarboxylation; mild conditions; selective halogenation.

A mild and efficient protocol was developed for the synthesis of haloheteroarenes such as I [R = H, 5-F, 5-NO2, etc.; R1 = Cl, Br; X = C, N] via mono-halodecarboxylation of heteroarene carboxylic acids by treatment with N-bromosuccinimide or N-chlorosuccinimide. This method was metal-free and displayed significant advantages over traditional halodecarboxylation procedures that require expensive and toxic metal catalysts, basic conditions, time-consuming intermediate isolation and elevated reaction temperatures

Royal Society Open Science published new progress about Decarboxylation (halo). 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Application In Synthesis of 23077-43-2.

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

Yoo, Woo-Jin; Capdevila, Montse Guiteras; Du, Xiangwei; Kobayashi, Shu published the artcile< Base-Mediated Carboxylation of Unprotected Indole Derivatives with Carbon Dioxide>, Computed Properties of 23077-43-2, the main research area is indole carboxylic acid preparation; base carboxylation unprotected indole carbon dioxide.

A simple and straightforward method for the preparation of indole-3-carboxylic acids was discovered through the direct carboxylation of indoles with atm. pressure of carbon dioxide (CO2) under basic conditions. The key for the reaction was found to be the use of a large excess of LiOtBu as a base to suppress the undesired decarboxylation side reaction.

Organic Letters published new progress about Carboxylation. 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Computed Properties of 23077-43-2.

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

Yoo, Woo-Jin; Nguyen, Thanh V. Q.; Capdevila, Montse Guiteras; Kobayashi, Shu published the artcile< Lithium tert-butoxide-mediated carboxylation reactions of unprotected indoles and pyrroles with carbon dioxide>, SDS of cas: 23077-43-2, the main research area is indole carbon dioxide lithium butoxide Friedel Crafts type carboxylation; indolecarboxylic acid preparation; pyrrole carbon dioxide lithium butoxide Friedel Crafts type carboxylation; pyrrolecarboxylic acid preparation.

Unprotected indoles and pyrroles were found to underwent base-mediated carboxylation reactions under ambient pressure of carbon dioxide. It was found that this transition metal-free carboxylation reaction proceeded smoothly with the use of a large excess of LiOtBu.

Heterocycles published new progress about Aromatic carboxylic acids Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, SDS of cas: 23077-43-2.

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

Swain, C. J.; Baker, R.; Kneen, C.; Moseley, J.; Saunders, J.; Seward, E. M.; Stevenson, G.; Beer, M.; Stanton, J.; Watling, K. published the artcile< Novel 5-HT3 antagonists. Indole oxadiazoles>, Computed Properties of 23077-43-2, the main research area is hydroxytryptaminergic structure activity indolyloxadiazole oxadiazole; receptor model 5HT3 hydroxytryptamine; antagonist hydroxytryptamine receptor indolyloxadiazole preparation; receptor antagonist hydroxytryptamine oxadiazole preparation.

The synthesis and biochem. evaluation of a series of oxadiazole and indolyloxadiazole 5-HT3 (hydroxytryptamine) antagonists are described. The key pharmacophoric elements have been defined as a basic nitrogen, a linking group capable of H-bonding interactions, and an aromatic moiety. The steric limitations of the aromatic binding site have been determined by substitution about the indole ring. Variation of the heterocyclic linking group has shown that while 2 H-bonding interactions are possible, only 1 is essential for high affinity. The environment of the basic nitrogen has been investigated and shown to be optimal when constrained within an azabicyclic system. These results have been incorporated into a proposed binding model for the 5-HT3 antagonist binding site, in which the optimum distance between the aromatic binding site and the basic amine is 8.4-8.9 Å and the steric limitations are defined by van der Waals difference mapping.

Journal of Medicinal Chemistry published new progress about 5-HT receptors Role: RCT (Reactant), RACT (Reactant or Reagent). 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Computed Properties of 23077-43-2.

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

Becker, Daniel P.; Flynn, Daniel L.; Moormann, Alan E.; Nosal, Roger; Villamil, Clara I.; Loeffler, Richard; Gullikson, Gary W.; Moummi, Chafiq; Yang, Dai-C. published the artcile< Pyrrolizidine esters and amides as 5-HT4 receptor agonists and antagonists>, Name: 5-Fluoro-1H-indole-3-carboxylic acid, the main research area is pyrrolizidine arylamide preparation 5HT4 antagonist; arylester pyrrolizidine preparation 5HT4 agonist.

A series of pyrrolizidine esters, amides, and ureas was prepared and tested for 5-HT4 and 5-HT3 receptor binding, 5-HT4 receptor agonism in the rat tunica muscularis mucosae assay (TMM), and for 5-HT3 receptor-mediated functional antagonism in the Bezold-Jarisch reflex assay. Several pyrrolizidine derivatives were identified with high affinity for the 5-HT4 receptor, including benzamide I (SC-53116), a potent and selective 5-HT4 partial agonist that exhibits efficacy in promoting antral contractions and activity in promoting gastric emptying in canine models. Also discovered were 5-HT4 receptor antagonists, including imidazopyridine amide II (SC-53606), which was a potent and selective 5-HT4 receptor antagonist with a pA2 value of 8.13 in the rat TMM assay. N-Me indole ester III was identified as a potent 5-HT4 antagonist with a pA2 value of 8.93. High selectivity was observed for these pyrrolizidine derivatives vs. other monoamine receptors, including 5-HT1, 5-HT2, D1, D2, α1, α2, and β receptors.

Journal of Medicinal Chemistry published new progress about 5-HT receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Name: 5-Fluoro-1H-indole-3-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

Caspar, Yvan; Jeanty, Matthieu; Blu, Jerome; Burchak, Olga; Le Pihive, Emmanuelle; Maigre, Laure; Schneider, Dominique; Jolivalt, Claude; Paris, Jean-Marc; Hequet, Arnaud; Minassian, Frederic; Denis, Jean-Noel; Maurin, Max published the artcile< Novel synthetic bis-indolic derivatives with antistaphylococcal activity, including against MRSA and VISA strains>, Quality Control of 23077-43-2, the main research area is bis indole derivative preparation antibacterial structure activity Staphylococcus; antibiotics; bis-indoles; drug development; drug susceptibility testing; efflux pumps; staphylococci.

Objectives: The authors report the synthesis, antibacterial activity and toxicity of 24 bis-indolic derivatives obtained during the development of new ways of synthesis of marine bis-indole alkaloids from the spongotine, topsentin and hamacanthin classes. Methods: Innovative ways of synthesis and further structural optimizations led to bis-indoles presenting either the 1-(1H-indol-3′-yl)-1,2-diaminoethane unit or the 1-(1H-indol-3-yl)ethanamine unit. MIC determination was performed for reference and clin. strains of Staphylococcus aureus and CoNS species. MBC, time-kill kinetics, solubility, hydrophobicity index, plasma protein-binding and cytotoxicity assays were performed for lead compounds Inhibition of the S. aureus NorA efflux pump was also tested for bis-indoles with no antistaphylococcal activity. Results: Lead compounds were active against both S. aureus and CoNS species, with MICs between 1 and 4 mg/L. Importantly, the same MICs were found for MRSA and vancomycin-intermediate S. aureus strains. Early concentration-dependent bactericidal activity was observed for lead derivatives Compounds with no intrinsic antibacterial activity could inhibit the S. aureus NorA efflux pump, which is involved in resistance to fluoroquinolones. At 0.5 mg/L, the most effective compound led to an 8-fold reduction of the ciprofloxacin MIC for the SA-1199B S. aureus strain, which overexpresses NorA. However, the bis-indole compounds displayed a high hydrophobicity index and high plasma protein binding, which significantly reduced antibacterial activity. Conclusions: The authors have synthesized and characterized novel bis-indole derivatives as promising candidates for the development of new antistaphylococcal treatments, with preserved activity against MDR S. aureus strains.

Journal of Antimicrobial Chemotherapy published new progress about Antibacterial agent resistance. 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Quality Control of 23077-43-2.

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

Luo, Yang-Hui; Sun, Bai-Wang published the artcile< An investigation into the substituent effect of halogen atoms on the crystal structures of indole-3-carboxylic acid (ICA)>, Application of C9H6FNO2, the main research area is halogen atom crystal structure indolecarboxylic acid ICA.

A study into the substituent effect of halogen atoms (F, Cl, Br) on the crystal structure of indole-3-carboxylic acid (ICA) was prepared The study was done through the aspect of crystal structure, intermol. interactions and π···π stacking motifs with the assistance of IR spectra, elemental analyses, NMR spectra, DSC, thermogravimetric analyses (TGA) and hot stage microscopy (HSM) measurements. The different kinds of halogen atoms and the different substituted positions have a significant effect on the crystal structures, mol. π···π stacking motifs and the kinds of intermol. interactions. The authors further correlated the m.ps. of the ICAs with the H-H, O-H and X-H (X = F, Cl, Br) interactions, and found a pos. correlation between them.

CrystEngComm published new progress about Correlation analysis. 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Application of 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