Category: 5654-92-2

Benghiat, Eric published the artcileSynthesis of S-3-indolemethyl derivatives of 5′-deoxy-5′-thioadenosine, Synthetic Route of 5654-92-2, the main research area is indolylmethylthiodeoxyadenosine; adenosine indolylmethylthiodeoxy.

The title compounds (I; R = H, Me) were prepared by reaction of the appropriate 3-indolemethyl thioacetate with 5′-deoxy-5′-chloroadenosine in basic media. 5′-Deoxy-5′-(3-indolemethylthio)adenosines unsubstituted at the indolic nitrogen, cannot be prepared via this route due to facile conversion of the precursor 3-indolemethylthiol derivative to the corresponding 3,3′-diindolemethyl sulfide.

Journal of Heterocyclic Chemistry published new progress about indolylmethylthiodeoxyadenosine; adenosine indolylmethylthiodeoxy. 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, Synthetic Route 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

Eskola, Olli published the artcileSynthesis of 3-[[4-(4-[18F]fluorophenyl)piperazin-1-yl]methyl]-1H-pyrrolo[2,3-b]pyridine, Quality Control of 5654-92-2, the main research area is fluorophenylpiperazinylmethylpyrrolopyridine preparation biodistribution.

3-[[4-(4-[18F]fluorophenyl)piperazin-1-yl]methyl]-1H-pyrrolo[2,3-b]pyridine, a candidate to image dopamine D4 receptors, was synthesized via electrophilic fluorination of a trimethylstannyl precursor with high specific radioactivity [18F]F2. The precursor was obtained by a facile four-step synthetic approach; the trimethylstannyl leaving group was introduced by displacement of iodine utilizing palladium catalysis and hexamethyldistannane in an inert solvent. The total radiosynthesis time was 50 min, including purification and formulation for injection. Decay corrected radiochem. yield was <1% as calculated from the amount of [18F]F- produced. Specific radioactivity at the end of synthesis was 12.8-16.4 GBq/μmol. Radiochem. purity was 88-92%. Ex vivo studies in rats showed homogeneous distribution of radioactivity within rat brain. Journal of Labelled Compounds & Radiopharmaceuticals published new progress about fluorophenylpiperazinylmethylpyrrolopyridine preparation biodistribution. 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

Sanchez-Obregon, Ruben published the artcileSynthesis of a potential fluorescence probe, (-)-(R)-7-azatryptophan, via alkylation of the (1R,4R)-camphor imine of tert-butylglycinate, COA of Formula: C10H13N3, the main research area is azatryptophan; bornylidenaminoacetate alkylation iodomethylazaindole.

The synthesis of (-)-(R)-7-azatryptophan (I) from com. available 7-azaindole is described. The key step involved the diastereoselective alkylation of the bornylideneaminoacetate II with 1-(tert-butoxycarbonyl-3-(iodomethyl)-7-azaindole. The alkylation, conducted at -100° in THF/HMPA using KN(SiMe3)2 as the base, afforded imine III in >98% diastereomeric excess. Hydrolysis and deprotection of III gave I.

Canadian Journal of Chemistry published new progress about azatryptophan; bornylidenaminoacetate alkylation iodomethylazaindole. 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, COA of Formula: C10H13N3.

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

Baader, Manuel published the artcileCharacterization of the properties of a selective, orally bioavailable autotaxin inhibitor in preclinical models of advanced stages of liver fibrosis, Recommanded Product: N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, the main research area is autotaxin inhibitor bioavailability pharmacokinetics hepatitis liver fibrosis.

Autotaxin (ATX) is a secreted phospholipase which hydrolyzes lysophosphatidylcholine to generate lysophosphatidic acid (LPA). The extracellular signalling mol. LPA exerts its biol. actions through activation of six GPCRs expressed in various cell types including fibroblasts. Multiple preclin. studies using knockout animals, LPA receptor antagonists or ATX inhibitors have provided evidence for a potential role of the ATX/LPA axis in tissue fibrosis. Despite growing evidence for a correlation between ATX levels and the degree of fibrosis in chronic liver diseases, including viral hepatitis and hepatocellular carcinoma, the role of ATX in non-alc. steatohepatitis (NASH) remains unclear. The relevance of ATX in the pathogenesis of liver fibrosis was investigated by oral administration of Ex_31, a selective ATX inhibitor, in a 10 wk model of carbon tetrachloride-induced liver injury and in a 14 wk model of choline-deficient amino acid-defined diet-induced liver injury in rats. Oral administration of Ex_31, a selective ATX inhibitor, at 15 mg·kg-1 twice daily in therapeutic intervention mode resulted in efficient ATX inhibition and more than 95% reduction in plasma LPA levels in both studies. Treatment with Ex_31 had no effect on biomarkers of liver function, inflammation, or fibrosis and did not result in histol. improvements in diseased animals. Our findings question the role of ATX in the pathogenesis of hepatic fibrosis and the potential of small mol. ATX inhibitors for the treatment of patients with NASH and advanced stages of liver fibrosis.

British Journal of Pharmacology published new progress about Apoptosis. 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.

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

Dalziel, Michael E. published the artcileRegioselective Functionalization of 7-Azaindole by Controlled Annular Isomerism: The Directed Metalation-Group Dance, Product Details of C10H13N3, the main research area is regioselective functionalization azaindole annular isomerism directed metalation group migration; deuterium; heterocycles; lithiation; regioselectivity; synthetic methods.

The regioselective functionalization of 7-azaindole by controlled annular isomerism employing a directed metalation-group migration is reported. The N7 carbamoyl azaindoles undergo regioselective metalation and quenching with an electrophile to furnish C6-substituted derivatives which, in the presence of a catalytic amount of ClCONR2 promotes a carbamoyl group shift or dance from N7 to N1. A second directed metalation/electrophile quench sequence leads to 2,6-substituted azaindoles. Optimization of the metalation conditions for C2 and C6, sep. and iteratively, is presented. Using the directed metalation group dance strategy, a late-stage deuteration of an antipsychotic drug is described. Overall, the controlled migration of the carbamoyl directing group allows multiple functionalization events of the bioactive azaindole scaffold.

Angewandte Chemie, International Edition published new progress about Carbamoyl group. 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.

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

Iwaki, Yuzo published the artcileONO-8430506: A Novel Autotaxin Inhibitor That Enhances the Antitumor Effect of Paclitaxel in a Breast Cancer Model, Safety of N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, the main research area is ONO 8430506 autotaxin inhibitor preparation paclitaxel breast cancer.

Lysophosphatidic acid (LPA) is a bioactive lipid mediator that elicits a number of biol. functions, including smooth muscle contraction, cell motility, proliferation, and morphol. change. LPA is endogenously produced by autotaxin (ATX) from extracellular lysophosphatidylcholine (LPC) in plasma. Herein, we report our medicinal chem. effort to identify a novel and highly potent ATX inhibitor, ONO-8430506 (20), with good oral availability. To enhance the enzymic ATX inhibitory activity, we designed several compounds by structurally comparing our hit compound with the endogenous ligand LPC. Further optimization to improve the pharmacokinetic profile and enhance the ATX inhibitory activity in human plasma resulted in the identification of ONO-8430506 (20), which enhanced the antitumor effect of paclitaxel in a breast cancer model.

ACS Medicinal Chemistry Letters 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, Safety of N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine.

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

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.

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.

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

Kulagowski, Janusz J. published the artcile3-[[4-(4-Chlorophenyl)piperazin-1-yl]methyl]-1H-pyrrolo[2,3-b]pyridine: An Antagonist with High Affinity and Selectivity for the Human Dopamine D4 Receptor, Category: indole-building-block, the main research area is dopamine D4 receptor chlorophenylpiperazinylmethyl pyrrolopyridine.

A topol. similarity search of the Merck sample collection using known dopamine agonists and antagonists as probe structures identified indole I as having modest binding selectivity for cloned human dopamine D4 receptors over D2 and D3 subtypes. Optimization of the amino side chain and introduction of a nitrogen atom into the indole nucleus resulted in L-745,870 (II), having high D4 affinity (Ki 0.43 nM) with 2200 and >5000-fold selectivity over D2 and D3 receptors, resp. Also identified in the course of this work was the piperidinol III which demonstrated the opposite selectivity, being 100-fold binding selective for the D2 receptor.

Journal of Medicinal Chemistry published new progress about Dopamine D4 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, Category: indole-building-block.

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

See, Cheng Shang published the artcileDiscovery of the cancer cell selective dual acting anti-cancer agent (Z)-2-(1H-indol-3-yl)-3-(isoquinolin-5-yl)acrylonitrile (A131), Application of N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, the main research area is indolyl isoquinolinyl acrylonitrile analogs preparation cancer mitosis autophagy; Antimitotic; Antiproliferative; Antitumor; Tumor-selective.

Selective targeting of cancer cells over normal cells is a key objective of targeted therapy. However few approaches achieve true mechanistic selectivity resulting in debilitating side effects and dose limitation. In this work we describe the discovery of A131 (4a), a new agent with an unprecedented dual mechanism of action targeting both mitosis and autophagy. Compound 4a was first identified in a phenotypic screen in which HeLa cells treated with 4a manifested mitotic arrest along with formation of multiple vesicles. Further investigations showed that 4a causes an increase in mitotic marker pH3 and autophagy marker LC3. Importantly 4a induces cell death in cancer cells while sparing normal cells which regrow after 4a is removed. Dual activities against pH3 and LC3 markers are required for cancer cell selectivity. An extensive SAR investigation confirmed 4a as the optimal dual inhibitor with potency against a panel of 30 cancer cell lines (average antiproliferative GI50 1.5μM). In a mouse model of paclitaxel-resistant colon cancer, 4a showed 74% tumor growth inhibition when administered at a dose of 20mg/kg IP twice a day.

European Journal of Medicinal Chemistry published new progress about Antiproliferative 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, Application of N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine.

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