Tag: M.W=250-300

Race, Nicholas J. published the artcileEnantioselective C2-Alkylation of Indoles through a Redox-Relay Heck Reaction of 2-Indole Triflates, Application of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one, the publication is Chemistry – A European Journal (2019), 25(2), 512-515, database is CAplus and MEDLINE.

A palladium-catalyzed enantioselective redox-relay Heck reaction of 2-indole triflates and disubstituted alkenes is reported. This process combines readily available indole triflates with a variety of alkenes to afford a range of indole derivatives bearing a stereocenter adjacent to C2. Enantioselectivity is achieved through use of a simple pyridine-oxazoline ligand. Tuning the electronics of the indole, through judicious choice of N-protecting group, is required to ensure selective β-hydride elimination away from the indole core. Utility of this method is highlighted in a modular formal synthesis of an S1P₁ agonist precursor developed by Merck.

Chemistry – A European Journal published new progress about 837392-64-0. 837392-64-0 belongs to indole-building-block, auxiliary class Indoline,Boronic acid and ester,Amide,Boronate Esters, name is 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one, and the molecular formula is C14H18BNO3, Application of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Mertins, Kristin published the artcileCatalytic borylation of o-xylene and heteroarenes via C-H activation, SDS of cas: 683229-62-1, the publication is Journal of Molecular Catalysis A: Chemical (2004), 207(1), 21-25, database is CAplus.

Ir and Rh complexes catalyze the borylation of xylene and different heteroarenes using pinacolborane via C-H activation. Various five-membered heterocycles such as thiophene, pyrrole, thionaphthene, and indole derivatives yield the borylated products in moderate to good yields. In general, the reactions proceed with high selectivity to give borylation ortho to the heteroatom.

Journal of Molecular Catalysis A: Chemical published new progress about 683229-62-1. 683229-62-1 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Ether,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 5-Methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C15H20BNO3, SDS of cas: 683229-62-1.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Zhang, Dengyou published the artcileSynthesis and biological evaluation of 2-amino-5-aryl-3-benzylthiopyridine scaffold based potent c-Met inhibitors, Application of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one, the publication is Bioorganic & Medicinal Chemistry (2013), 21(21), 6804-6820, database is CAplus and MEDLINE.

A series of 2-amino-N-benzylpyridine-3-carboxamides, 2-amino-N-benzylpyridine-3-sulfonamides and 2-amino-3-benzylthiopyridines against c-Met were designed by means of bioisosteric replacement and docking anal. Optimization of the 2-amino-3-benzylthiopyridine scaffold led to the identification of compound I displaying c-Met inhibition with an IC₅₀ up to 7.7 nM. In the cytotoxic evaluation, compound I effectively inhibited the proliferation of c-Met addictive human cancer cell lines (IC₅₀ from 0.19 to 0.71 μM) and c-Met activation-mediated cell metastasis. At a dose of 100 mg/Hg, I evidently inhibited tumor growth (45%) in NIH-3T3/TPR-Met xenograft model. Of note, I could overcome c-Met-activation mediated gefitinib-resistance, which indicated its potential use for drug combination. Taken together, 2-amino-3-benzylthiopyridine scaffold was first disclosed and exhibited promising pharmacol. profiles against c-Met, which left room for further exploration.

Bioorganic & Medicinal Chemistry published new progress about 837392-64-0. 837392-64-0 belongs to indole-building-block, auxiliary class Indoline,Boronic acid and ester,Amide,Boronate Esters, name is 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one, and the molecular formula is C17H29BO2, Application of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Bremer, Paul T. published the artcilePicolinic acids as β-exosite inhibitors of botulinum neurotoxin A light chain, Quality Control of 1256358-95-8, the publication is Chemical Communications (Cambridge, United Kingdom) (2016), 52(84), 12521-12524, database is CAplus and MEDLINE.

In developing small-mol. inhibitors of botulinum neurotoxin serotype A light chain (BoNT/A LC), substituted picolinic acids were identified. Extensive investigation into the SAR of the picolinic acid scaffold revealed 5-(1-butyl-4-chloro-1H-indol-2-yl)picolinic acid (I), which possessed low micromolar activity against BoNT/A. Kinetic and docking studies demonstrated binding of I to the β-exosite: a largely unexplored site on the LC that holds therapeutic relevance for botulism treatment.

Chemical Communications (Cambridge, United Kingdom) published new progress about 1256358-95-8. 1256358-95-8 belongs to indole-building-block, auxiliary class Indole,Chloride,Boronic acid and ester,Boronic Acids,Boronate Esters, name is 4-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C14H17BClNO2, Quality Control of 1256358-95-8.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Bremer, Paul T. published the artcilePicolinic acids as β-exosite inhibitors of botulinum neurotoxin A light chain, Formula: C14H17BFNO2, the publication is Chemical Communications (Cambridge, United Kingdom) (2016), 52(84), 12521-12524, database is CAplus and MEDLINE.

In developing small-mol. inhibitors of botulinum neurotoxin serotype A light chain (BoNT/A LC), substituted picolinic acids were identified. Extensive investigation into the SAR of the picolinic acid scaffold revealed 5-(1-butyl-4-chloro-1H-indol-2-yl)picolinic acid (I), which possessed low micromolar activity against BoNT/A. Kinetic and docking studies demonstrated binding of I to the β-exosite: a largely unexplored site on the LC that holds therapeutic relevance for botulism treatment.

Chemical Communications (Cambridge, United Kingdom) published new progress about 1256359-96-2. 1256359-96-2 belongs to indole-building-block, auxiliary class Indole,Fluoride,Boronic acid and ester,Boronic Acids,Boronate Esters,Boronate Esters, name is 4-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C14H17BFNO2, Formula: C14H17BFNO2.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Nemoto, Tetsuhiro published the artcileCatalytic Asymmetric Total Synthesis of Tangutorine, HPLC of Formula: 167015-84-1, the publication is Organic Letters (2010), 12(4), 872-875, database is CAplus and MEDLINE.

The first enantioselective total synthesis of (-)-tangutorine (I) was achieved via a Pd-catalyzed asym. allylic amination using a chiral diaminophosphine oxide (DIAPHOX) preligand as the key step.

Organic Letters published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C15H20N2O2, HPLC of Formula: 167015-84-1.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Savall, Brad M. published the artcileDiscovery of Imidazo[1,2-a]pyrazines and Pyrazolo[1,5-c]pyrimidines as TARP γ-8 Selective AMPAR Negative Modulators, Formula: C14H18BNO3, the publication is ACS Medicinal Chemistry Letters (2019), 10(3), 267-272, database is CAplus and MEDLINE.

This report discloses the discovery and characterization of imidazo[1,2-a]pyrazines and pyrazolo[1,5-c]pyrimidines as selective neg. modulators of α-amino-3-hydroxy-5-methylisoxazole-4-propionate receptors (AMPARs) associated with transmembrane AMPAR regulatory protein γ-8. Imidazopyrazine 5 was initially identified as a promising γ-8 selective high-throughput screening hit, and subsequent structure-activity relationship optimization yielded subnanomolar, brain penetrant leads. Replacement of the imidazopyrazine core with an isosteric pyrazolopyrimidine scaffold improved microsomal stability and efflux liabilities to provide 26(I), JNJ-61432059. Following oral administration, 26 exhibited time- and dose-dependent AMPAR/γ-8 receptor occupancy in mouse hippocampus, which resulted in robust seizure protection in corneal kindling and pentylenetetrazole (PTZ) anticonvulsant models.

ACS Medicinal Chemistry Letters published new progress about 837392-64-0. 837392-64-0 belongs to indole-building-block, auxiliary class Indoline,Boronic acid and ester,Amide,Boronate Esters, name is 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one, and the molecular formula is C14H18BNO3, Formula: C14H18BNO3.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Wang, Cong-Shuai published the artcileDesign of C3-Alkenyl-Substituted 2-Indolylmethanols for Catalytic Asymmetric Interrupted Nazarov-Type Cyclization, HPLC of Formula: 100123-25-9, the publication is Advanced Synthesis & Catalysis (2018), 360(5), 846-851, database is CAplus.

The C3-alkenyl-substituted 2-indolylmethanols were designed as a new class of substrates for catalytic asym. interrupted Nazarov-type cyclizations. In the presence of a chiral phosphoric acid as a mild chiral Bronsted acid, the interrupted Nazarov-type cyclization of C3-alkenyl-substituted 2-indolylmethanols I (R¹ = Ph, 4-ClC₆H₄, 2-FC₆H₄, etc.; R² = Ph, 3-FC₆H₄, 3-MeC₆H₄; R³ = H, Cl, Br, MeO) with nucleophiles R⁴H (R⁴ = 3-indolyl, 2-hydroxy-1-naphthyl, etc.) occurred smoothly to construct cyclopenta[b]indole frameworks II with generally excellent diastereo- and enantioselectivities (up to >95:5 dr, >99% ee).

Advanced Synthesis & Catalysis published new progress about 100123-25-9. 100123-25-9 belongs to indole-building-block, auxiliary class Indole,Bromide,Ester,Aldehyde, name is Ethyl 5-bromo-3-formyl-1H-indole-2-carboxylate, and the molecular formula is C6H5F4NO3S, HPLC of Formula: 100123-25-9.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Ma, Yan-rong published the artcileAn LC-MS/MS analytical method for the determination of uremic toxins in patients with end-stage renal disease, Synthetic Route of 2642-37-7, the publication is Journal of Pharmaceutical and Biomedical Analysis (2020), 113551, database is CAplus and MEDLINE.

End-stage renal disease (ESRD) is the last stage of chronic kidney disease, characterized by the progressive accumulation of uremic toxins (UTs). Hemodialysis is the standard approach to remove UTs from the body. Creatinine and urea levels are important indexes of hemodialysis effectiveness, but the utility of those markers to estimate the removal of UTs, especially protein-binding UTs is limited. We developed an LC-MS/MS method for the quantification of UTs and to provide markers for evaluating hemodialysis effectiveness. These substances were extracted from serum samples after acetonitrile precipitation of protein and then separated on a HILIC column. The flow rate was 0.6 mL/min with a run time of 8.0 min for the neg. ion mode and pos. ion mode each. In this study 26 UTs were determined in normal subjects and in patients with ESRD before and after hemodialysis; serum levels were significantly higher in patients with ESRD than in subjects with normal renal function. A significant decrease in a variety of serum UTs were observed in patients after dialysis treatment, but no change in the levels of orotic acid, CMPF, kynurenic acid, p-cresol sulfate, phenyl-β-D-glucuronide, 4-ethylphenyl sulfate and 3-indolyl-β-D-glucopyranoside was found. These results show that some UTs could not be completely removed by hemodialysis. In addition, some biomarkers of different types of UTs are proposed for evaluating hemodialysis effectiveness.

Journal of Pharmaceutical and Biomedical Analysis published new progress about 2642-37-7. 2642-37-7 belongs to indole-building-block, auxiliary class Indole,Salt,Sulfonate,Inhibitor,Inhibitor, name is Potassium 1H-indol-3-yl sulfate, and the molecular formula is C8H6KNO4S, Synthetic Route of 2642-37-7.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Wang, Guanghui published the artcileDouble N,B-Type Bidentate Boryl Ligands Enabling a Highly Active Iridium Catalyst for C-H Borylation, Recommanded Product: 2-Methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, the publication is Journal of the American Chemical Society (2015), 137(25), 8058-8061, database is CAplus and MEDLINE.

Boryl ligands hold promise in catalysis due to their very high electron-donating property. In this communication double N,B-type boryl anions were designed as bidentate ligands to promote an sp² C-H borylation reaction. A sym. pyridine-containing tetraaminodiborane(4) compound was readily prepared as the ligand precursor that could be used, in combination with [Ir(OMe)(COD)]₂, to in situ generate a highly active catalyst for a broad range of (hetero)arene substrates including highly electron-rich and/or sterically hindered ones. This work provides the 1st example of a bidentate boryl ligand in supporting homogeneous organometallic catalysis.

Journal of the American Chemical Society published new progress about 919119-59-8. 919119-59-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2-Methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C5H6BNO2, Recommanded Product: 2-Methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles