M.W=150-200 | - Page 10 of 152 - Indole Building Blocks

Huang, Y.’s team published research in Bioorganic & Medicinal Chemistry Letters in 2001-06-04 | CAS: 5654-92-2

Bioorganic & Medicinal Chemistry Letters published new progress about Dopamine D4 receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study) (antagonists). 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, Computed Properties of 5654-92-2.

Huang, Y. published the artcileSynthesis of potent and selective dopamine D4 antagonists as candidate radioligands, Computed Properties of 5654-92-2, the main research area is pyridinylpyrrolyl arylpiperazine preparation dopamine serotonin antagonist; substitution azagramine arylpiperazine.

A series of dopamine D4 antagonists, pyridinylpyrrolyl arylpiperazines I (R = F, MeO, R1 = H; R = H, R1 = F, MeO, MeS, CF3, CH:CH2, Et, Pr, Ph), was synthesized and evaluated as potential candidates for development as positron emission tomog. (PET) radioligands. Thus, azagramine II was reacted with the corresponding arylpiperazine in xylene under reflux to give I in 45 to 82% yield. All new compounds display high affinity and selectivity for the D4 receptors and compounds I (R = H, R1 = MeO; R = MeO, R1 = H; R = H, R1 = MeS) were identified as candidates for radioligand development. The activity against serotonin receptors was also examined

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

Nakamura, Hidemitsu’s team published research in Molecular Plant in 2019-01-07 | CAS: 41910-64-9

Molecular Plant published new progress about Germination. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Safety of 4-Chloroindoline.

Nakamura, Hidemitsu published the artcileTriazole Ureas Covalently Bind to Strigolactone Receptor and Antagonize Strigolactone Responses, Safety of 4-Chloroindoline, the main research area is Oryza tillering triazole urea strigolactone signaling; covalent antagonist; crystal structure; strigolactone; triazole urea.

Strigolactones, a class of plant hormones with multiple functions, mediate plant-plant and plant-microorganism communications in the rhizosphere. In this study, we developed potent strigolactone antagonists, which covalently bind to the strigolactone receptor D14, by preparing an array of triazole urea compounds Using yeast two-hybrid and rice-tillering assays, we identified a triazole urea compound KK094 as a potent inhibitor of strigolactone receptors. Liquid chromatog.-tandem mass spectrometry anal. and X-ray crystallog. revealed that KK094 was hydrolyzed by D14, and that a reaction product of this degradation covalently binds to the Ser residue of the catalytic triad of D14. Furthermore, we identified two triazole urea compounds KK052 and KK073, whose effects on D14-D53/D14-SLR1 complex formation were opposite due to the absence (KK052) or presence (KK073) of a trifluoromethyl group on their Ph ring. These results demonstrate that triazole urea compounds are potentially powerful tools for agricultural application and may be useful for the elucidation of the complicated mechanism underlying strigolactone perception.

Lamotte, Yann’s team published research in Bioorganic & Medicinal Chemistry Letters in 2010-02-15 | CAS: 57663-18-0

Bioorganic & Medicinal Chemistry Letters published new progress about Hematocrit. 57663-18-0 belongs to class indole-building-block, name is Methyl 2-methyl-1H-indole-5-carboxylate, and the molecular formula is C11H11NO2, Synthetic Route of 57663-18-0.

Lamotte, Yann published the artcileSynthesis and biological activities of novel indole derivatives as potent and selective PPARγ modulators, Synthetic Route of 57663-18-0, the main research area is biphenylcarboxylic acid indolylmethyl preparation peroxisome proliferator activated receptor modulator; acid biphenylcarboxylic indolylmethyl preparation PPAR gamma modulator potency SAR; indolylmethyl biphenylcarboxylic acid preparation antidiabetic PPAR partial agonist activity.

Starting from the structure of Telmisartan, a new series of potent and selective PPARγ modulators was identified. The synthesis, in vitro and in vivo evaluation of the most potent compounds were reported and the X-ray structure of compound I bound to the PPARγ ligand binding domain was described.

Ambrogio, Ilaria’s team published research in Tetrahedron in 2009-10-31 | CAS: 57663-18-0

Tetrahedron published new progress about Heterocyclic compounds, nitrogen Role: SPN (Synthetic Preparation), PREP (Preparation). 57663-18-0 belongs to class indole-building-block, name is Methyl 2-methyl-1H-indole-5-carboxylate, and the molecular formula is C11H11NO2, Name: Methyl 2-methyl-1H-indole-5-carboxylate.

Ambrogio, Ilaria published the artcile3-(o-Trifluoroacetamidoaryl)-1-propargylic esters: common intermediates for the palladium-catalyzed synthesis of 2-aminomethyl-, 2-vinylic, and 2-alkylindoles, Name: Methyl 2-methyl-1H-indole-5-carboxylate, the main research area is amino methyl indole preparation; vinyl indole preparation; alkyl indole preparation.

3-(O-Trifluoroacetamidoaryl)-1-propargylic esters have been used as common synthetic intermediates for the preparation of a variety of 3-unsubstituted 2-substituted indoles. Treating Et 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates unsubstituted or containing an aryl substituent at the propargylic carbon with piperazines and Pd(PPh3)4 in THF at 80 °C affords 2-(piperazin-1-ylmethyl)indoles in excellent yields. Good to excellent yields of 2-aminomethylindoles are also obtained with other secondary amines. Et 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates bearing an alkyl substituent at the propargylic carbon and Et 3-(o-trifluoroacetamidoaryl)-1-propargylic acetates disubstituted at the propargylic carbon give 2-vinylic indoles with the Pd(OAc)2/PPh3 combination and Et3N in THF at 80 °C. Formation of 2-vinylic indoles is quite stereoselective, generating trans vinylic derivatives, at least with the substrates that we have investigated. In the presence of formic acid, Et3N, and Pd(PPh3)4 in MeCN at 80 °C, Et 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates afford 2-alkylindoles in good to excellent yields.

Ren, Albert’s team published research in Bioorganic & Medicinal Chemistry Letters in 2020-03-01 | CAS: 41910-64-9

Bioorganic & Medicinal Chemistry Letters published new progress about 5-HT2A receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Synthetic Route of 41910-64-9.

Ren, Albert published the artcileDiscovery of a lead series of potent benzodiazepine 5-HT2C receptor agonists with high selectivity in functional and binding assays, Synthetic Route of 41910-64-9, the main research area is food intake reduction 5HT2C receptor agonists lead; 5-HT(2C) receptor; Agonist; GPCR; Lead identification.

A series of potential new 5-HT2 receptor scaffolds based on a simplification of the clin. studied, 5-HT2CR agonist vabicaserin, were designed. An in vivo feeding assay early in our screening process played an instrumental part in the lead identification process, leading us to focus on a 6,5,7-tricyclic scaffold. A subsequent early SAR investigation provided potent agonists of the 5-HT2C receptor that were highly selective in both functional and binding assays, had good rat PK properties and that significantly reduced acute food intake in the rat.

Zhang, Liying’s team published research in Scientific Reports in 2017-01-29 | CAS: 800401-68-7

Scientific Reports published new progress about Amino acids Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 800401-68-7 belongs to class indole-building-block, name is 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid, and the molecular formula is C8H5ClN2O2, Application of 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid.

Zhang, Liying published the artcileNovel Liver-targeted conjugates of Glycogen Phosphorylase Inhibitor PSN-357 for the Treatment of Diabetes: Design, Synthesis, Pharmacokinetic and Pharmacological Evaluations, Application of 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid, the main research area is diabetes glycogen phosphorylase liver conjugate PSN inhibitor pharmacokinetics.

PSN-357, an effective glycogen phosphorylase (GP) inhibitor for the treatment for type 2 diabetics, is hampered in its clin. use by the poor selectivity between the GP isoforms in liver and in skeletal muscle. In this study, by the introduction of cholic acid, 9 novel potent and liver-targeted conjugates of PSN-357 were obtained. Among these conjugates, conjugate 6 exhibited slight GP inhibitory activity (IC50 = 31.17 μM), good cellular efficacy (IC50 = 13.39 μM) and suitable stability under various conditions. The distribution and pharmacokinetic studies revealed that conjugate 6 could redistribute from plasma to liver resulting in a considerable higher exposure of PSN-357 metabolizing from 6 in liver (AUC liver/AUC plasma ratio was 18.74) vs that of PSN-357 (AUC liver/AUC plasma ratio was 10.06). In the in vivo animal study of hypoglycemia under the same dose of 50 mg/kg, conjugate 6 exhibited a small but significant hypoglycemic effects in longer-acting manners, that the hypoglycemic effects of 6 is somewhat weaker than PSN-357 from administration up to 6 h, and then became higher than PSN-357 for the rest time of the test. Those results indicate that the liver-targeted glycogen phosphorylase inhibitor may hold utility in the treatment of type 2 diabetes.

Zhang, Chunhui’s team published research in Organic Letters in 2018-05-04 | CAS: 74572-29-5

Organic Letters published new progress about Aralkyl amines Role: RCT (Reactant), RACT (Reactant or Reagent) (primary). 74572-29-5 belongs to class indole-building-block, name is 5-Chloroisoindolin-1-one, and the molecular formula is C8H6ClNO, Formula: C8H6ClNO.

Zhang, Chunhui published the artcilePalladium-Catalyzed Direct C-H Carbonylation of Free Primary Benzylamines: A Synthesis of Benzolactams, Formula: C8H6ClNO, the main research area is primary benzylamine carbon monoxide carbonylation palladium; benzolactam preparation; palladium carbonylation.

A protocol for palladium-catalyzed C-H carbonylation of readily available free primary benzylamines using NH2 as the chelating group under an atm. pressure of CO has been achieved, providing a general, atom- and step-economic approach to benzolactams, an important structural motif found in many biol. active compounds Application of this new method is also exemplified in the concise syntheses of two bioactive mols, e.g., (R)-PD 172939.

Benghiat, Eric’s team published research in Synthesis in 1982-12-31 | CAS: 5654-92-2

Synthesis published new progress about Amino acids Role: SPN (Synthetic Preparation), 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, Safety of N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine.

Benghiat, Eric published the artcilePreparation of S-(3-indolylmethyl) derivatives of mercapto amino acids, Safety of N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, the main research area is indolylmethyl mercapto amino acid; cysteine indolylmethyl; homocysteine indolylmethyl.

Title compounds I (X = CH, R = H, Me; R1 = H, Me; X = N, R = R1 = H; n = 1, 2) were prepared by treating indoles II (X = CH, R = H, Me; X = N, R = R1 = H; R2 = NMe2; X = CH, R = Me, R1 = H, Me, R2 = N+Me3 I-) with DL-HS(CH2)nCH(NH2)CO2H in aqueous NaOH. I (n = 2) were also prepared by treating the appropriate II with thialactone DL-III. I (X = CH, R = R1 = H, n = 2) was also prepared by treating II (X, R, R1 = same, R2 = N+Me3 I-) with DL-[HO2CCH(NH2)CH2CH2S].

Larsen, Matthew A.’s team published research in Journal of the American Chemical Society in 2014-03-19 | CAS: 5654-92-2

Journal of the American Chemical Society published new progress about Borylation (regioselective). 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, Product Details of C10H13N3.

Larsen, Matthew A. published the artcileIridium-Catalyzed C-H Borylation of Heteroarenes: Scope, Regioselectivity, Application to Late-Stage Functionalization, and Mechanism, Product Details of C10H13N3, the main research area is iridium catalyzed carbon hydrogen borylation heteroarene regioselectivity functionalization mechanism; tetramethylphenanthroline iridium catalyzed heteroarene borylation regioselectivity computational study.

A study on the iridium-catalyzed C-H borylation of heteroarenes is reported. Several heteroarenes containing multiple heteroatoms were amenable to C-H borylation catalyzed by the combination of an iridium(I) precursor and tetramethylphenanthroline. The investigations of the scope of the reaction led to the development of powerful rules for predicting the regioselectivity of borylation, foremost of which is that borylation occurs distal to nitrogen atoms. One-pot functionalizations are reported of the heteroaryl boronate esters formed in situ, demonstrating the usefulness of the reported methodol. for the synthesis of complex heteroaryl structures. Application of this methodol. to the synthesis and late-stage functionalization of biol. active compounds is also demonstrated. Mechanistic studies show that basic heteroarenes can bind to the catalyst and alter the resting state from the olefin-bound complex observed during arene borylation to a species containing a bound heteroarene, leading to catalyst deactivation. Studies on the origins of the observed regioselectivity show that borylation occurs distal to N-H bonds due to rapid N-H borylation, creating an unfavorable steric environment for borylation adjacent to these bonds. Computational studies and mechanistic studies show that the lack of observable borylation of C-H bonds adjacent to basic nitrogen is not the result of coordination to a bulky Lewis acid prior to C-H activation, but the combination of a higher-energy pathway for the borylation of these bonds relative to other C-H bonds and the instability of the products formed from borylation adjacent to basic nitrogen.

Soderberg, Bjorn C. G.’s team published research in Tetrahedron in 2003-10-27 | CAS: 57663-18-0

Tetrahedron published new progress about Cyclization. 57663-18-0 belongs to class indole-building-block, name is Methyl 2-methyl-1H-indole-5-carboxylate, and the molecular formula is C11H11NO2, Synthetic Route of 57663-18-0.

Soderberg, Bjorn C. G. published the artcileIntramolecular cyclization reactions of unsaturated amino Fischer chromium carbenes forming indoles and quinolines, Synthetic Route of 57663-18-0, the main research area is thermally induced intramol annulation alkenylphenylamino substituted Fischer chromium carbene; solvent effect intramol annulation alkenylphenylamino substituted Fischer chromium carbene; steric effect intramol annulation alkenylphenylamino substituted Fischer chromium carbene; inductive effect intramol annulation alkenylphenylamino substituted Fischer chromium carbene; electronic effect intramol annulation alkenylphenylamino substituted Fischer chromium carbene; aminostyrene intramol annulation alkenylphenylamino substituted Fischer chromium carbene; thermal decomposition intramol annulation alkenylphenylamino substituted Fischer chromium carbene; carbonyl alkylidene amino chromium Fischer carbene preparation intramol cyclization; amino carbonyl alkylidene chromium Fischer carbene preparation intramol cyclization; dubamine amino carbonyl alkylidene chromium Fischer carbene intramol cyclization; quinoline amino carbonyl alkylidene chromium Fischer carbene intramol cyclization; quinolinecarboxylic amino carbonyl alkylidene chromium Fischer carbene intramol cyclization; indole amino carbonyl alkylidene chromium Fischer carbene intramol cyclization; indolecarboxylic amino carbonyl alkylidene chromium Fischer carbene intramol cyclization.

A thermally induced intramol. annulation reaction of N-(2-alkenylphenyl)amino substituted Fischer chromium carbenes has been extensively examined The carbene complexes were prepared in moderate to good yields by reaction of 2-aminostyrenes with intermediately formed acyloxy substituted carbenes. Upon heating, the thermally labile carbenes decomposed producing indoles and quinolines as the major products. The product distribution was found to be highly dependent on the substitution pattern and electronic properties of the starting material, and on the solvent used. The reaction of pentacarbonyl[1-[[2-ethenyl-3-(methoxycarbonyl)phenyl]amino]ethylidene]chromium gave 2-methyl-1H-indole-4-carboxylic acid Me ester. The reaction of pentacarbonyl[1-[[2-(1-methylethenyl)phenyl]amino]ethylidene]chromium gave 2,4-dimethylquinoline and 1,2,3,4-tetrahydro-2,4-dimethylquinoline.