14/11/2022 - Indole Building Blocks

Li, Xiaomeng’s team published research in Journal of Organic Chemistry in 2018-03-02 | CAS: 13523-93-8

Journal of Organic Chemistry published new progress about Aromatic ethers Role: RCT (Reactant), RACT (Reactant or Reagent). 13523-93-8 belongs to class indole-building-block, name is 4-(Benzyloxy)-1-methyl-1H-indole, and the molecular formula is C16H15NO, Product Details of C16H15NO.

Li, Xiaomeng published the artcileHydrochloric Acid-Promoted Intermolecular 1,2-Thiofunctionalization of Aromatic Alkenes, Product Details of C16H15NO, the main research area is hydrochloric acid promoted thiofunctionalization aromatic alkene arylsulfenylphthalimide nucleophile.

An efficient method for making 1,2-thiofunctionalized products via the difunctionalization of aromatic alkenes was developed. In this method, cheap and readily available hydrochloric acid was used to promote 1,2-thiofunctionalization of aryl alkenes with N-arylsulfenylphthalimide and different types of nucleophiles. Importantly, extension of nucleophiles can reach aryl ethers, indoles, and carboxylic acids with good reactivity. This practical and convenient method has broad substrate scope and high yields under metal-free and mild conditions. Furthermore, we achieved conversion and application for making sulfoxide and sulfone by oxidation

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

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].

Koenig, Stefan G.’s team published research in Tetrahedron Letters in 2010-12-15 | CAS: 104291-81-8

Tetrahedron Letters published new progress about Amino esters Role: RCT (Reactant), RACT (Reactant or Reagent) (amido-). 104291-81-8 belongs to class indole-building-block, name is Ethyl 6-cyano-1H-indole-2-carboxylate, and the molecular formula is C12H10N2O2, Formula: C12H10N2O2.

Koenig, Stefan G. published the artcileA ligand-free, copper-catalyzed cascade sequence to indole-2-carboxylic esters, Formula: C12H10N2O2, the main research area is indole carboxylic ester preparation ligand free substituent effect; haloaryl aldehyde glycine amido ester heterocyclization copper catalyst.

A variety of indole-2-carboxylic esters, e.g. I, are accessible in yields up to 61% through a ligand-free, copper-catalyzed reaction of a series of com. available 2-halo aryl aldehydes with benign glycine amidoesters, including the common reagent Et acetamidoacetate. This one-pot, three-reaction format allows ready entry to the desired heterocycles from starting substrates in the reactivity order of iodo > bromo ≥ chloro substituents. An assortment of functional groups is tolerated, adding to the generality of this methodol.

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.

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.

Bellezza, Delia’s team published research in European Journal of Organic Chemistry in 2019 | CAS: 69622-40-8

European Journal of Organic Chemistry published new progress about Alkyl aryl ketones Role: RCT (Reactant), RACT (Reactant or Reagent) (Chloromethyl). 69622-40-8 belongs to class indole-building-block, name is 2-(tert-Butyl)-5-chloro-1H-indole, and the molecular formula is C12H14ClN, Name: 2-(tert-Butyl)-5-chloro-1H-indole.

Bellezza, Delia published the artcilePalladium-Catalyzed C-C Ring Closure in α-Chloromethylimines: Synthesis of 1H-Indoles, Name: 2-(tert-Butyl)-5-chloro-1H-indole, the main research area is chloromethylimine palladium phosphine ring closure catalyst; indole preparation.

The C-C ring closure of α-chloromethyl alkyl or aryl N-aryl imines catalyzed with 1 to 10 % Pd(OAc)2/P(p-tolyl)3 afford efficiently 2-aryl- and 2-alkyl-1H-indoles. The heterocyclization reaction involves the initial formation of [2-(arylimino)ethyl]palladium(II) chloride complexes with subsequent C-H activation of the aromatic amine ring. Readily or com. available α-chloromethyl-aryl or -alkyl ketones are used as the precursors. Functionalized indoles at the benzene ring are obtained when the imines are derived from substituted anilines.

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.

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.

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.

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.