41910-64-9 | - Indole Building Blocks

Florvall, Lennart’s team published research in Journal of Medicinal Chemistry in 1986 | CAS: 41910-64-9

Journal of Medicinal Chemistry published new progress about monoamine oxidase inhibitor aminoethylindole; neuron selective aminoethylindole. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Product Details of C8H8ClN.

Florvall, Lennart published the artcileSelective monoamine oxidase inhibitors. 3. Cyclic compounds related to 4-aminophenethylamine. Preparation and neuron-selective action of some 5-(2-aminoethyl)-2,3-dihydroindoles, Product Details of C8H8ClN, the main research area is monoamine oxidase inhibitor aminoethylindole; neuron selective aminoethylindole.

Nine (aminoethyl)dihydroindoles I (R = Me, Et; R1, R3 = H, Me; R2 = H, Cl, Me; R4 = H, Et) were prepared and tested as monoamine oxidase (MAO) inhibitors in vitro and in vivo. I are selective MAO-A inhibitors in vitro, the most active compounds, 5-[1-(2-aminopropyl)]-2,3-dihydro-4-methylindole acetate (II), 5-[1-(2-aminopropyl)]-4-chloro-2,3-dihydroindole acetate, 5-[1-(2-aminopropyl)]-2,3-dihydro-1-ethyl-4-methylindole tartrate (III), 5-[1-(2-aminopropyl)]-2,3-dihydro-1-ethyl-6-methylindole tartrate, and 5-[1-(2-aminobutyl)]-4-chloro-2,3-dihydroindole acetate being equipotent with amiflamine. II, III, 5-[1-(2-aminopropyl)]-2,3-dihydroindole acetate (IV), and 5-[1-(2-amino-2-methylpropyl)]-2,3-dihydroindole acetate were very potent inhibitors of MAO in serotonergic and/or noradrenergic nerve terminals in the rat brain in vivo, inhibiting MAO within these neurons at doses 1/10 of those required to inhibit MAO in other neurons or cells. IV was also a potent and selective inhibitor of MAO within dopaminergic nerve terminals in vivo.

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

Bremer, Paul T.’s team published research in Journal of Medicinal Chemistry in 2017-01-12 | CAS: 41910-64-9

Journal of Medicinal Chemistry published new progress about Botulism. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, HPLC of Formula: 41910-64-9.

Bremer, Paul T. published the artcileNewly Designed Quinolinol Inhibitors Mitigate the Effects of Botulinum Neurotoxin A in Enzymatic, Cell-Based, and ex Vivo Assays, HPLC of Formula: 41910-64-9, the main research area is quinolinol sulfonamide preparation botulinum neurotoxin inhibitor botulism.

Botulinum neurotoxin A (BoNT/A) is one of the most deadly toxins, and is the etiol. agent of the potentially fatal condition, botulism. Herein, the authors investigated 8-hydroxyquinoline (quinolin-8-ol) as a potential inhibitor scaffold for preventing the deadly neurochem. effects of the toxin. Quinolinols are known chelators that can disrupt the BoNT/A metalloprotease zinc-containing active site, thus impeding its proteolysis of the endogenous protein substrate, synaptosomal-associated protein 25 (SNAP-25). Using this information, the structure-activity relationship (SAR) of the quinolinol-5-sulfonamide scaffold was explored through preparation of a crude sulfonamide library, and evaluating the library in a BoNT/A LC enzymic assay. Potency optimization of the sulfonamide hit compounds was undertaken as informed by docking studies, granting a lead compound with a submicromolar Ki. These quinolinol analogs demonstrated inhibitory activity in a cell-based model for SNAP-25 cleavage and an ex vivo assay for BoNT/A-mediated muscle paralysis.

Bakke, Jan’s team published research in Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry in 1974 | CAS: 41910-64-9

Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry published new progress about Cyclization. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, SDS of cas: 41910-64-9.

Bakke, Jan published the artcileNew syntheses of substituted indoles, SDS of cas: 41910-64-9, the main research area is indole chloro phenyl; phenethyl chloride nitro cyclization; cyclization nitrophenethyl chloride.

The indoles I (R = H, 4-Cl, 6-Cl, 4-NH2) were prepd by cyclizing RC6H3(CH2CH2Cl)(NO2)-1,2 (R = H, 6-Cl, 4-Cl, 6-O2N) with Fe and dehydration of the resulting dehydroindole with Pd/C. o-O2NC6H4Me was condensed with PhCHO to give o-O2NC6H4CH2(O)HPh which was oxidized with concentrated HNO3 and the product cyclized by catalytic reduction to give 2-phenylindole.

Yang, Guoqiang’s team published research in Journal of the American Chemical Society in 2014-07-30 | CAS: 41910-64-9

Journal of the American Chemical Society published new progress about Acetoxylation. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Formula: C8H8ClN.

Yang, Guoqiang published the artcilePd(II)-Catalyzed meta-C-H Olefination, Arylation, and Acetoxylation of Indolines Using a U-Shaped Template, Formula: C8H8ClN, the main research area is regioselective meta carbon hydrogen bond olefination indoline palladium catalyst; acetoxylation indoline palladium catalyst; arylation indoline palladium catalyst.

Meta-C-H olefination, arylation, and acetoxylation of indolines have been developed using nitrile-containing templates. The combination of a monoprotected amino acid ligand and the nitrile template attached at the indolinyl nitrogen via a sulfonamide linkage is crucial for the meta-selective C-H functionalization of electron-rich indolines that are otherwise highly reactive toward electrophilic palladation at the para-positions. A wide range of synthetically important and advanced indoline analogs are selectively functionalized at the meta-positions.

Haase, F.’s team published research in Tetrahedron Computer Methodology in 1990 | CAS: 41910-64-9

Tetrahedron Computer Methodology published new progress about Computer program. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Formula: C8H8ClN.

Haase, F. published the artcileHeterocyclic reaction design with RDSS, Formula: C8H8ClN, the main research area is computer generated synthetic design heterocyclic compound; RDSS computer program design synthesis heterocycle.

The paper gives a brief description of the synthesis planning computer program RDSS and deals with experience made in application to heterocyclic reactions, e.g., the synthesis of 4-hydroxyindole. The program version RDSS V4.1 was tested after completing a new synthon recognition program. A knowledge base consisting of some general synthesis rules and specialized heterocyclic mechanisms were built up to support this task. The results ensure that the knowledge based system RDSS may be a helpful tool for organic synthesis design.

Certal, Victor’s team published research in Bioorganic & Medicinal Chemistry Letters in 2014-03-15 | CAS: 41910-64-9

Bioorganic & Medicinal Chemistry Letters published new progress about Antitumor agents. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, COA of Formula: C8H8ClN.

Certal, Victor published the artcilePreparation and optimization of new 4-(2-(indolin-1-yl)-2-oxoethyl)-2-morpholinothiazole-5-carboxylic acid and amide derivatives as potent and selective PI3Kβ inhibitors, COA of Formula: C8H8ClN, the main research area is indolinyloxoethylmorpholinothiazole carboxylic acid amide derivative phosphatidylinositol kinase inhibitor antitumor; PI3Kβ; PTEN; Thiazole; pAKT.

In the authors’ continuous efforts to identify and develop novel targeted cancer treatments, a new morpholino-thiazole scaffold active against PI3Kβ was identified. This Letter reports the optimization of this compound class to develop PI3Kβ isoform-selective inhibitors with suitable pharmacol. properties.

Certal, Victor’s team published research in Journal of Medicinal Chemistry in 2014-02-13 | CAS: 41910-64-9

Journal of Medicinal Chemistry published new progress about Antitumor agents. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Recommanded Product: 4-Chloroindoline.

Certal, Victor published the artcileDiscovery and Optimization of Pyrimidone Indoline Amide PI3Kβ Inhibitors for the Treatment of Phosphatase and Tensin Homologue (PTEN)-Deficient Cancers, Recommanded Product: 4-Chloroindoline, the main research area is PI3Kbeta phosphatase tensin homolog PTEN neoplasm structure activity preparation.

Compelling mol. biol. publications have reported the implication of phosphoinositide kinase PI3Kβ in PTEN-deficient cell line growth and proliferation. These findings supported a scientific rationale for the development of PI3Kβ-specific inhibitors for the treatment of PTEN-deficient cancers. This paper describes the discovery of 2-[2-(2,3-dihydro-indol-1-yl)-2-oxo-ethyl]-6-morpholin-4-yl-3H-pyrimidin-4-one and the optimization of this new series of active and selective pyrimidone indoline amide PI3Kβ inhibitors. 2-[2-(2-Methyl-2,3-dihydro-indol-1-yl)-2-oxo-ethyl]-6-morpholin-4-yl-3H-pyrimidin-4-one (I), identified following a carefully designed Me scan, displayed improved physicochem. and in vitro pharmacokinetic properties. Structural biol. efforts enabled the acquisition of the first x-ray cocrystal structure of p110β with the selective inhibitor compound I bound to the ATP site. The nonplanar binding mode described herein is consistent with observed structure-activity relationship for the series. Compound I demonstrated significant in vivo activity in a UACC-62 xenograft model in mice, warranting further preclin. investigation. Following successful development, compound 28 entered phase I/Ib clin. trial in patients with advanced cancer.

Wang, Pei-Long’s team published research in Advanced Synthesis & Catalysis in 2016 | CAS: 41910-64-9

Advanced Synthesis & Catalysis published new progress about C-H bond activation. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Safety of 4-Chloroindoline.

Wang, Pei-Long published the artcilePalladium-Catalyzed C-7 Selective C-H Carbonylation of Indolines for Expedient Synthesis of Pyrroloquinazolinediones, Safety of 4-Chloroindoline, the main research area is pyrroloquinazolinedione preparation; carbon monoxide carbonylation indoline palladium catalyst.

A novel palladium-catalyzed C-7 selective C-H carbonylation of indolines with carbon monoxide for an expedient synthesis of pyrroloquinazolinediones, a structural motif with great potential in biol. active compounds, has been developed. Oxidation of the pyrroloquinazolinedione with 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) could easily afford the corresponding indole-based derivative in excellent yield.

Jiang, Xinpeng’s team published research in European Journal of Organic Chemistry in 2020-06-22 | CAS: 41910-64-9

European Journal of Organic Chemistry published new progress about C-H bond activation. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Name: 4-Chloroindoline.

Jiang, Xinpeng published the artcileFlavin/I2-Catalyzed Aerobic Oxidative C-H Sulfenylation of Aryl-Fused Cyclic Amines, Name: 4-Chloroindoline, the main research area is flavin iodine catalyst oxidative sulfenylation aryl fused cyclic amine.

We report an aerobic oxidative C-H sulfenylation of aryl-fused cyclic amines with various thiols catalyzed by flavin/I2 for the first time. While flavin I catalyzed the C-H sulfenylation of indolines to afford 3-sulfenylindoles, flavin II enabled transformations resulted in substitution at the position para to the N atom on the aryl ring to obtain 6-sulfenylquinolines. The advantages of this metal-free oxidative C-S coupling approach utilizing ambient oxygen as the terminal oxidant were that it was conducted under mild conditions with good atom-efficiency and excellent functional compatibility.

Sato, Kenjiro’s team published research in Bioorganic & Medicinal Chemistry in 2014-03-01 | CAS: 41910-64-9

Bioorganic & Medicinal Chemistry published new progress about Antidiabetic agents. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, COA of Formula: C8H8ClN.

Sato, Kenjiro published the artcileDiscovery of a novel series of indoline carbamate and indolinylpyrimidine derivatives as potent GPR119 agonists, COA of Formula: C8H8ClN, the main research area is indoline carbamate indolinylpyrimidine preparation GPR119 agonist; Conformation; GPCR; GPR119 agonist; Indoline; Type 2 diabetes mellitus.

GPR119 has emerged as an attractive target for antidiabetic agents. The authors identified a structurally novel GPR119 agonist that carries a 5-(methylsulfonyl)indoline motif as an early lead compound To generate more potent compounds of this series, structural modifications were performed mainly to the central alkylene spacer. Installation of a carbonyl group and a Me group on this spacer significantly enhanced agonistic activity, resulting in the identification of I. To further expand the chem. series of indoline-based GPR119 agonists, several heterocyclic core systems were introduced as surrogates of the carbamate spacer that mimic the presumed active conformation. This approach successfully produced an indolinylpyrimidine II, which has potent GPR119 agonist activity. In rat oral glucose tolerance tests, these two indoline-based compounds effectively lowered plasma glucose excursion and glucose-dependent insulin secretion after oral administration.