Category: indole-building-block

Yao, Chun-Hsu published the artcileDiscovery of Novel N-β-D-Xylosyl-indole Derivatives as Sodium-Dependent Glucose Co-transporter 2 (SGLT2) Inhibitors for the Management of Hyperglycemia in Diabetes, SDS of cas: 41910-64-9, the main research area is aryl C glycoside preparation antidiabetic; human xyloside indole SGLT2 inhibitor hyperglycemia diabetes antidiabetic preparation.

A novel series of N-linked β-D-xylosides were synthesized and evaluated for inhibitory activity against sodium-dependent glucose co-transporter 2 (SGLT2) in a cell-based assay. Of these, the β-D-xylopyranosyl-1H-indole I (R = 4-chlorocyclopropylbenzyl) was the most potent inhibitor, with an EC50 value similar to that of the natural SGLT2 inhibitor phlorizin. Further studies in Sprague-Dawley (SD) rats indicated that I significantly increased urine glucose excretion in a dose-dependent manner with oral administration. The antihyperglycemic effect of I was also observed in streptozotocin (STZ) induced diabetic SD rats. These results described here are a good starting point for further investigations into N-glycoside SGLT2 inhibitors.

Journal of 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, SDS of cas: 41910-64-9.

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

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.

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.

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, 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.

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.

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

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.

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.

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

Masters, Kye-Simeon published the artcileortho-Bromo(propa-1,2-dien-1-yl)arenes: Substrates for domino reactions, Application of Methyl 2-methyl-1H-indole-5-carboxylate, the main research area is indole preparation; bromopropadienylarene amine amide domino reaction Pd catalyst.

O-Bromo(propa-1,2-dien-1-yl)arenes exhibit novel and orthogonal reactivity under Pd catalysis in the presence of secondary amines to form enamines (concerted Pd insertion, intramol. carbopalladation, and terminative Buchwald-Hartwig coupling) and of amides to form indoles (addition, Buchwald-Hartwig cyclization, and loss of the acetyl group). The substrates for these reactions can be accessed in a reliable and highly selective two-step process from 2-bromoaryl bromides.

Journal of Organic Chemistry published new progress about Addition reaction. 57663-18-0 belongs to class indole-building-block, name is Methyl 2-methyl-1H-indole-5-carboxylate, and the molecular formula is C11H11NO2, Application of Methyl 2-methyl-1H-indole-5-carboxylate.

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

Kumar, G. Santosh published the artcileCatalyst-free synthesis of 3-hydroxy-3-(alkyl/aryl)indolin-2-ones by addition of organoaluminum reagents to isatins, SDS of cas: 1677-47-0, the main research area is isatin organoaluminum reagent addition; alkyl hydroxyindolinone preparation; phenyl hydroxyindolinone preparation.

An efficient synthesis of 3-hydroxy-3-(alkyl/aryl)indol-2-one derivatives I (R = H, Me, Bn; R1 = H, Cl, Br; R2 = H, Cl, Br, I, F, OCF3, NO2; R3 = H, Cl, Br) has been described by the reactions of isatin with organoaluminum reagents. The reaction is very rapid and yields are high. The protocol is applicable for substituted isatins as well as a variety of organoaluminums.

Tetrahedron Letters published new progress about Addition reaction. 1677-47-0 belongs to class indole-building-block, name is 4,5-Dichloroisatin, and the molecular formula is C8H3Cl2NO2, SDS of cas: 1677-47-0.

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

Li, Xiang published the artcileAerobic Transition-Metal-Free Visible-Light Photoredox Indole C-3 Formylation Reaction, Quality Control of 13523-93-8, the main research area is indole TMEDA oxygen Rose Bengal visible light photoredox formylation; formyl indole regioselective preparation.

An aerobic visible-light-promoted indole C-3 formylation reaction catalyzed by Rose Bengal has been developed. This transition-metal-free process employs mol. oxygen as the terminal oxidant and uses TMEDA as the one-carbon source through C-N bond cleavage. The reaction is compatible with a variety of functional groups.

ACS Catalysis published new progress about C-N bond cleavage. 13523-93-8 belongs to class indole-building-block, name is 4-(Benzyloxy)-1-methyl-1H-indole, and the molecular formula is C16H15NO, Quality Control of 13523-93-8.

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

Sirisoma, Nilantha published the artcileDiscovery of substituted N’-(2-oxoindolin-3-ylidene)benzohydrazides as new apoptosis inducers using a cell- and caspase-based HTS assay, Computed Properties of 1677-47-0, the main research area is antitumor oxoindolinylidenebenzohydrazide preparation apoptosis neoplasm.

The discovery of a series of substituted N’-(2-oxoindolin-3-ylidene)benzohydrazides as inducers of apoptosis using a proprietary cell- and caspase-based ASAP HTS assay is reported. Through SAR studies, N’-(4-bromo-5-methyl-2-oxoindolin-3-ylidene)-3,4,5-trimethoxybenzohydrazide (3g) was identified as a potent apoptosis inducer with an EC50 value of 0.24 μM in human colorectal carcinoma HCT116 cells, more than a 40-fold increase in potency from the initial screening hit N’-(5-bromo-2-oxoindolin-3-ylidene)-3,4,5-trimethoxybenzohydrazide (2a). Compound 3g also was found to be highly active in a growth inhibition assay with a GI50 value of 0.056 μM in HCT116 cells. A group of potentially more aqueous soluble analogs were prepared and found to be highly active. Among them, compound 4e incorporating a Me piperazine moiety was found to have EC50 values of 0.17, 0.088 and 0.14 μM in human colorectal carcinoma cells HCT116, hepatocellular carcinoma cancer SNU398 cells and human colon cancer RKO cells, resp. Compounds 3g and 4e were found to function as inhibitors of tubulin polymerization

Bioorganic & Medicinal Chemistry Letters published new progress about Antitumor agents. 1677-47-0 belongs to class indole-building-block, name is 4,5-Dichloroisatin, and the molecular formula is C8H3Cl2NO2, Computed Properties of 1677-47-0.

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

Cho, Er-Chieh published the artcileRing size changes in the development of class I HDAC inhibitors, Application of Methyl 2-methyl-1H-indole-5-carboxylate, the main research area is thienylbenzamide anticancer SAR HDAC inhibitor docking; HDAC; Thienylbenzamides; colon cancer; ring transformation.

Five pathways involving different ring structures led to generation of fourteen thienylbenzamides which display the structure-activity relationships of class I HDAC inhibitors. All the synthesized compounds inhibit HDAC1 and HDAC2 selectively over other isoforms and many inhibit DLD1 and HCT116 cells more effectively than a parent compound Compounds and inhibit HCT116 cells by activation of the apoptosis pathway.

Journal of Enzyme Inhibition and Medicinal Chemistry published new progress about Antitumor agents. 57663-18-0 belongs to class indole-building-block, name is Methyl 2-methyl-1H-indole-5-carboxylate, and the molecular formula is C11H11NO2, Application of Methyl 2-methyl-1H-indole-5-carboxylate.

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

Nimbarte, Vijaykumar D. published the artcileSynthesis and in Vitro Evaluation of Novel 5-Nitroindole Derivatives as c-Myc G-Quadruplex Binders with Anticancer Activity, Quality Control of 5654-92-2, the main research area is human cervical cancer anticancer cMyc; G-quadruplex binders; c-Myc; nitroindoles; oncogene promoters, reactive oxygen species, structure-activity relationships.

Lead-optimization strategies for compounds targeting c-Myc G-quadruplex (G4) DNA are being pursued to develop anticancer drugs. Here, we investigate the structure-activity- relationship (SAR) of a newly synthesized series of mols. based on the pyrrolidine-substituted 5-nitro indole scaffold to target G4 DNA. Our synthesized series allows modulation of flexible elements with a structurally preserved scaffold. Biol. and biophys. analyses illustrate that substituted 5-nitroindole scaffolds bind to the c-Myc promoter G-quadruplex. These compounds downregulate c-Myc expression and induce cell-cycle arrest in the sub-G1/G1 phase in cancer cells. They further increase the concentration of intracellular reactive oxygen species. NMR spectra show that three of the newly synthesized compounds interact with the terminal G-quartets (5′- and 3-ends) in a 2 : 1 stoichiometry.

ChemMedChem published new progress about Antitumor agents. 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, Quality Control of 5654-92-2.

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