November 2022 - Page 48 of 81 - Indole Building Blocks

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.

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

Yao, Chun-Hsu’s team published research in Journal of Medicinal Chemistry in 2011-01-13 | CAS: 41910-64-9

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.

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.

Zhang, Hailong’s team published research in Organic Letters in 2014-05-02 | CAS: 41910-64-9

Organic Letters published new progress about Amination catalysts. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Product Details of C8H8ClN.

Zhang, Hailong published the artcileConstruction of the N1-C3 Linkage Stereogenic Centers by Catalytic Asymmetric Amination Reaction of 3-Bromooxindoles with Indolines, Product Details of C8H8ClN, the main research area is nickel catalyst asym amination bromooxindole indoline.

The catalytic asym. amination reaction of 3-bromooxindoles with indolines for the construction of the N1-C3 linkage stereogenic centers has been realized for the first time. E.g., in presence of Ni(OAc)2, ligand (I), and DABCO in MTBE, amination of 3-bromooxindole derivative (II) with indoline gave 87% III. Moreover, the racemic substrates (3-substituted indolines) were also applicable under the same chiral conditions. The newly developed method conveniently led to a formal synthesis of (+)-psychotrimine.

Vangveravong, Suwanna’s team published research in Bioorganic & Medicinal Chemistry in 2010-07-15 | CAS: 5654-92-2

Bioorganic & Medicinal Chemistry published new progress about Dopamine 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, Recommanded Product: N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine.

Vangveravong, Suwanna published the artcileSynthesis and characterization of selective dopamine D2 receptor antagonists. 2. Azaindole, benzofuran, and benzothiophene analogs of L-741,626, Recommanded Product: N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, the main research area is dopamine D2 receptor antagonist indole benzofuran benzothiophene preparation SAR.

A series of indole, 7-azaindole, benzofuran, and benzothiophene compounds have been prepared and evaluated for affinity at D2-like dopamine receptors. These compounds share structural elements with the classical D2-like dopamine receptor antagonists haloperidol, N-methylspiperone and benperidol. Two new compounds, 4-(4-iodophenyl)-1-((4-methoxy-1H-indol-3-yl)methyl)piperidin-4-ol (6) and 4-(4-iodophenyl)-1-((5-methoxy-1H-indol-3-yl)methyl)piperidin-4-ol (7), were found to have high affinity to and selectivity for D2 vs. D3 receptors. Changing the aromatic ring system from an indole to other heteroaromatic ring systems reduced the D2 binding affinity and the D2 vs. D3 selectivity.

Fu, Li Qiang’s team published research in Chinese Chemical Letters in 2012 | CAS: 366453-21-6

Chinese Chemical Letters published new progress about Antibacterial agents. 366453-21-6 belongs to class indole-building-block, name is 4-Hydroxy-2,3-dihydroisoindol-1-one, and the molecular formula is C8H7NO2, Recommanded Product: 4-Hydroxy-2,3-dihydroisoindol-1-one.

Fu, Li Qiang published the artcileSynthesis and antibacterial activity of pleuromutilin derivatives with novel C(14) side chain, Recommanded Product: 4-Hydroxy-2,3-dihydroisoindol-1-one, the main research area is pleuromutilin derivative synthesis antibacterial agent.

In order to find novel antibacterial agents with superior antibacterial activity and overcoming multidrug resistance, a series of pleuromutilin derivatives with novel C(14) side chain were synthesized and evaluated for their in vitro antibacterial activities. The results of antibacterial activities indicated that most of the derivatives showed potent activities against Gram-pos. organisms. In particular, compound I exhibited the most potent inhibitory activity compared with pleuromutilin and linezoid, emerged as potential mol. for further investigation.

Zheng, Xudong’s team published research in Tetrahedron in 2019-11-29 | CAS: 1677-47-0

Tetrahedron published new progress about Antibacterial agents. 1677-47-0 belongs to class indole-building-block, name is 4,5-Dichloroisatin, and the molecular formula is C8H3Cl2NO2, Related Products of indole-building-block.

Zheng, Xudong published the artcileSynthesis of substituted tryptanthrin via aryl halides and amines as antitumor and anti-MRSA agents, Related Products of indole-building-block, the main research area is tryptanthrin derivative synthesis aryl halide amine antitumor anti MRSA.

The natural alkaloid, tryptanthrin (indolo[2,1-b]quinazoline-6,12-dione, I), and its analogs are found to exhibit potent antitumor and anti-MRSA activities. An efficient and convenient method has been developed for the synthesis of tryptanthrin D-ring derivatives through the reaction of substituted tryptanthrins and secondary amines in moderate to good yields. Some of the new compounds exhibited antitumor activities against the human tumor cell lines A549, HCT116 and MDA-MB-231, with mean IC50 values at low micromolar levels. In addition, some of the compounds showed excellent anti-MRSA activities and were more effective than vancomycin, with MIC values of 0.31-1.25 μg/mL for Mu50,RN4220, and Newman strains.

Williams, John D.’s team published research in Bioorganic & Medicinal Chemistry in 2013-12-15 | CAS: 104291-81-8

Bioorganic & Medicinal Chemistry published new progress about Antibacterial agents. 104291-81-8 belongs to class indole-building-block, name is Ethyl 6-cyano-1H-indole-2-carboxylate, and the molecular formula is C12H10N2O2, Recommanded Product: Ethyl 6-cyano-1H-indole-2-carboxylate.

Williams, John D. published the artcilePotent and broad-spectrum antibacterial activity of indole-based bisamidine antibiotics: Synthesis and SAR of novel analogs of MBX 1066 and MBX 1090, Recommanded Product: Ethyl 6-cyano-1H-indole-2-carboxylate, the main research area is indole bisamidine preparation antibacterial antibiotic; Amidine; Antibacterial; Antibiotic; Broad-spectrum; Cadogan–Sundberg reaction; Imidazoline; Indole; McMurry reductive homocoupling reaction; Reissert indole synthesis; Tetrahydropyrimidine.

The prevalence of drug-resistant bacteria in the clinic has propelled a concerted effort to find new classes of antibiotics that will circumvent current modes of resistance. The authors have previously described a set of bisamidine antibiotics that contains a core composed of two indoles and a central linker. The first compounds of the series, MBX 1066 and MBX 1090, have potent antibacterial properties against a wide range of Gram-pos. and Gram-neg. bacteria. The authors have conducted a systematic exploration of the amidine functionalities, the central linker, and substituents at the indole 3-position to determine the factors involved in potent antibacterial activity. Some of the newly synthesized compounds have even more potent and broad-spectrum activity than MBX 1066 and MBX 1090.

Knepper, Kerstin’s team published research in Organic Letters in 2003-08-07 | CAS: 57663-18-0

Organic Letters published new progress about Solid phase synthesis. 57663-18-0 belongs to class indole-building-block, name is Methyl 2-methyl-1H-indole-5-carboxylate, and the molecular formula is C11H11NO2, HPLC of Formula: 57663-18-0.

Knepper, Kerstin published the artcileBartoli Indole Synthesis on Solid Supports, HPLC of Formula: 57663-18-0, the main research area is indolecarboxylate Bartoli synthesis solid phase.

Bartoli indole synthesis was performed on solid supports. Starting from Merrifield resin, immobilization of five nitrobenzoic acids was performed. Addition of four different alkenyl Grignard reagents and basic cleavage leads to substituted Me indolecarboxylates in excellent purities. Features of this reaction are the stability of halide groups, ester moieties, and tolerance of o,o’-unsubstituted nitro resins. Heck and Sonogashira reactions are also possible with immobilized indoles.

Golovko, T. V.’s team published research in Russian Chemical Bulletin in 2008-01-31 | CAS: 1009-27-4

Russian Chemical Bulletin published new progress about Condensation reaction. 1009-27-4 belongs to class indole-building-block, name is 2-Ethoxy-1H-indole, and the molecular formula is C10H11NO, Category: indole-building-block.

Golovko, T. V. published the artcileNew synthesis of pyrido[4,3-b]indoles (γ-carbolines) on the basis of indolin-2-one lactim ether, Category: indole-building-block, the main research area is indolinone lactim ether malononitrile condensation; oxindole lactim ether malononitrile condensation; pyridoindole preparation; gamma carboline preparation; pyrimidocarboline preparation.

Condensation of indolin-2-one (oxindole) lactim ether with H2C(CN)2 leads to 2-dicyanomethylidene-2,3-dihydroindole. Subsequent reaction with DMF di-Et acetal [or HC(OEt)3] and further cyclization affords 4-cyanopyrido[4,3-b]indoles (γ-carbolines). 3-Amino-4-cyanopyrido[4,3-b]indole was used in the synthesis of substituted pyrimido[4,5-c]-γ-carbolines.

Jiang, Zhigan’s team published research in Bioorganic & Medicinal Chemistry Letters in 2014-09-01 | CAS: 13523-93-8

Bioorganic & Medicinal Chemistry Letters published new progress about Aspergillus fumigatus. 13523-93-8 belongs to class indole-building-block, name is 4-(Benzyloxy)-1-methyl-1H-indole, and the molecular formula is C16H15NO, Recommanded Product: 4-(Benzyloxy)-1-methyl-1H-indole.

Jiang, Zhigan published the artcileScaffold hopping of sampangine: discovery of potent antifungal lead compound against Aspergillus fumigatus and Cryptococcus neoformans, Recommanded Product: 4-(Benzyloxy)-1-methyl-1H-indole, the main research area is antifungal sampangine derivative; Antifungal activity; Sampangine; Scaffold hopping.

Discovery of novel antifungal agents against Aspergillus fumigatus and Cryptococcus neoformans remains a significant challenge in current antifungal therapy. Here, the antifungal natural product sampangine (I) was used as the lead compound for novel antifungal drug discovery. D-ring scaffold hopping derivatives were designed and synthesized to improve antifungal activity and water solubility Among them, the thiophene derivative S2 showed broad-spectrum antifungal activity, particularly for Aspergillus fumigatus and Cryptococcus neoformans. Moreover, compound S2 also revealed better water solubility than sampangine, which represents a promising antifungal lead compound for further structural optimization.