M.W=250-300归档 - Heterocyclic Building Blocks-Thiazole

Chow, Wing-Kin’s team published research in Chemistry – A European Journal in 17 | CAS: 791614-90-9

Chemistry – A European Journal published new progress about 791614-90-9. 791614-90-9 belongs to thiazole, auxiliary class Boronate Esters,Boronic acid and ester,Boronic acid and ester, name is 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole, and the molecular formula is C14H18BNO2S, Computed Properties of 791614-90-9.

Chow, Wing-Kin published the artcilePalladium-Catalyzed Borylation of Aryl Mesylates and Tosylates and Their Applications in One-Pot Sequential Suzuki-Miyaura Biaryl Synthesis, Computed Properties of 791614-90-9, the publication is Chemistry – A European Journal (2011), 17(25), 6913-6917, S6913/1-S6913/47, database is CAplus and MEDLINE.

Palladium-catalyzed borylation with the N-methyl-2-(2′-dicyclohexylphosphino-5′-methoxyphenyl)indole (MeO-CM-Phos) ligand of ten aryl tosylates and twelve aryl mesylates gave the corresponding pinacol aryl boronates in 63% to 97% yield. The reaction conditions are mild and provide excellent functional-group compatibility (e.g., CN, CHO, COOMe, ketone, NH₂, benzodioxole, quinolyl, benzothiazole or NH-indole). E.g., reaction of 3-cyanophenyl mesylate with bis(pinacolato)diboron afforded pinacol (3-benzonitrile) boronate in 97% yield. The Pd/MeO-CM-phos catalyst system allows one-pot sequential reactions in the preparation of unsym. biaryls. Four biaryls were prepared by one-pot two-step and one-pot three-step transformations of aryl tosylates and 3-cyanophenol, resp.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Zhang, Peng’s team published research in Bioorganic & Medicinal Chemistry in 18 | CAS: 791614-90-9

Bioorganic & Medicinal Chemistry published new progress about 791614-90-9. 791614-90-9 belongs to thiazole, auxiliary class Boronate Esters,Boronic acid and ester,Boronic acid and ester, name is 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole, and the molecular formula is C65H82N2O18S2, COA of Formula: C14H18BNO2S.

Zhang, Peng published the artcileStructure-activity relationships in a novel series of 7-substituted-aryl quinolines and 5-substituted-aryl benzothiazoles at the metabotropic glutamate receptor subtype 5, COA of Formula: C14H18BNO2S, the publication is Bioorganic & Medicinal Chemistry (2010), 18(9), 3026-3035, database is CAplus and MEDLINE.

The metabotropic glutamate receptor subtype 5 (mGluR5) has been implicated in numerous neuropsychiatric disorders including addiction. We have discovered that the rigid diaryl alkyne template, derived from the potent and selective noncompetitive mGluR5 antagonist 2-methyl-6-(phenylethynyl)pyridine (MPEP), can serve to guide the design of novel quinoline analogs and pharmacophore optimization has resulted in potent mGluR5 noncompetitive antagonists (EC₅₀ range 60-100 nM) in the quinoline series.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Kulkarni, Santosh S.’s team published research in Bioorganic & Medicinal Chemistry Letters in 17 | CAS: 791614-90-9

Bioorganic & Medicinal Chemistry Letters published new progress about 791614-90-9. 791614-90-9 belongs to thiazole, auxiliary class Boronate Esters,Boronic acid and ester,Boronic acid and ester, name is 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole, and the molecular formula is C14H18BNO2S, Synthetic Route of 791614-90-9.

Kulkarni, Santosh S. published the artcileDiscovery of heterobicyclic templates for novel metabotropic glutamate receptor subtype 5 antagonists, Synthetic Route of 791614-90-9, the publication is Bioorganic & Medicinal Chemistry Letters (2007), 17(11), 2987-2991, database is CAplus and MEDLINE.

Investigation of a series of heterobicyclic compounds with essential pharmacophoric features of the metabotropic glutamate receptor 5 (mGluR5) antagonists MPEP and MTEP provided novel structural templates with sub-micromolar affinities at the mGluR5. Compound I showed antagonist activity (IC₅₀ = 0.26 μM) in the functional assay measuring hydrolysis of phosphoinositide and may provide a new lead for further SAR investigation.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

He, Zhi-Tao’s team published research in Journal of the American Chemical Society in 140 | CAS: 791614-90-9

Journal of the American Chemical Society published new progress about 791614-90-9. 791614-90-9 belongs to thiazole, auxiliary class Boronate Esters,Boronic acid and ester,Boronic acid and ester, name is 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole, and the molecular formula is C14H18BNO2S, Application In Synthesis of 791614-90-9.

He, Zhi-Tao published the artcileTrimethylphosphate as a Methylating Agent for Cross Coupling: A Slow-Release Mechanism for the Methylation of Arylboronic Esters, Application In Synthesis of 791614-90-9, the publication is Journal of the American Chemical Society (2018), 140(49), 17197-17202, database is CAplus and MEDLINE.

Tri-Me phosphate acted as an effective source of Me groups; in the presence of CuI, and LiI, (MeO)₃P(:O) underwent chemoselective coupling with arylpinacolboronates mediated by LiOt-Bu in 1,3-dimethylimidazolidin-2-one (DMI) to yield methylarenes in higher yields than related coupling reactions using either Me iodide or Me tosylate. The methylation reaction was used in tandem with iridium-catalyzed regioselective borylation with bis(pinacolato)diboron to provide a one-pot methylation reaction for arenes, and for trideuteromethylation of arylpinacoboronates using tris(trideuteromethyl) phosphate. The chemoselectivity of the reaction was tested using additives possessing various functional groups (robustness screen); unprotected amines, alcs., and amides and terminal alkynes were not tolerated. The methylation of 1-naphthylpinacolboronate was demonstrated on a 200 mmol scale. The kinetics of the methylation and its dependence on Li⁺ and I^– ions was determined and a mechanism suggested. Me iodide is released slowly upon reaction of tri-Me phosphate with iodide; the low concentration of MeI enables selective reaction with arylcopper intermediates generated from the arylboronate rather than with other nucleophiles, while binding of tert-butoxide to the pinacolboronate reactants inhibits reaction of MeI with tert-butoxide.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Wang, Xin’s team published research in Organic Letters in 21 | CAS: 791614-90-9

Organic Letters published new progress about 791614-90-9. 791614-90-9 belongs to thiazole, auxiliary class Boronate Esters,Boronic acid and ester,Boronic acid and ester, name is 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole, and the molecular formula is C16H10O5, Formula: C14H18BNO2S.

Wang, Xin published the artcileA Monophosphine Ligand Derived from Anthracene Photodimer: Synthetic Applications for Palladium-Catalyzed Coupling Reactions, Formula: C14H18BNO2S, the publication is Organic Letters (2019), 21(20), 8158-8163, database is CAplus and MEDLINE.

Herein, we present an air-stable dianthracenyl monophosphine ligand (diAnthPhos) which can be prepared in two steps from com. available anthracene derivatives The ligand exhibits excellent efficiency for palladium-catalyzed coupling reactions. In particular, Miyaura borylation of heterocycle-containing electrophiles can be facilitated employing the diAnthPhos ligand with a broad substrate scope and low catalyst loading. The valuable synthetic utility of the new ligand is further demonstrated by a one-pot Miyaura borylation/Suzuki coupling protocol for heteroaryl-containing substrates.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Zhao, Haiwei’s team published research in Angewandte Chemie, International Edition in 61 | CAS: 791614-90-9

Angewandte Chemie, International Edition published new progress about 791614-90-9. 791614-90-9 belongs to thiazole, auxiliary class Boronate Esters,Boronic acid and ester,Boronic acid and ester, name is 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole, and the molecular formula is C14H14N2O2, Category: thiazole.

Zhao, Haiwei published the artcile[Ph₄P]⁺[Cu(CF₂H)₂]^–: A Powerful Difluoromethylating Reagent Inspired by Mechanistic Investigation, Category: thiazole, the publication is Angewandte Chemie, International Edition (2022), 61(42), e202210151, database is CAplus and MEDLINE.

The quest of the active species in copper-mediated difluoromethylation of aryl halides led to the discovery of a powerful difluoromethylating reagent [Ph₄P]⁺[Cu(CF₂H)₂]^–. [Ph₄P]⁺[Cu(CF₂H)₂]^– complex was able to difluoromethylate a variety of electrophiles including electron-deficient and electron-rich aryl iodides, heteroaryl iodides, activated heteroaryl bromides, chloride and aryl bromides with a directing group, as well as other electrophiles such as alkenyl iodide, benzyl bromides, allyl bromides, alkyl iodide, allyl carbonates and acid chloride. In addition, in the presence of an oxidant, [Ph₄P]⁺[Cu(CF₂H)₂]^– complex reacted with various lithium nbutyl arylboronic acid pinacol esters, alkyne and heteroarene. Moreover, [Ph₄P]⁺[Cu(CF₂H)₂]^– complex could transmetalate the difluoromethyl reagent to other metals such as [Ph₄P]⁺[CuCl₂]^– complex and [(DPPF)PdCl₂].

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Larsen, Matthew A.’s team published research in Journal of the American Chemical Society in 136 | CAS: 791614-90-9

Larsen, Matthew A. published the artcileIridium-Catalyzed C-H Borylation of Heteroarenes: Scope, Regioselectivity, Application to Late-Stage Functionalization, and Mechanism, HPLC of Formula: 791614-90-9, the publication is Journal of the American Chemical Society (2014), 136(11), 4287-4299, database is CAplus and MEDLINE.

A study on the iridium-catalyzed C-H borylation of heteroarenes is reported. Several heteroarenes containing multiple heteroatoms were amenable to C-H borylation catalyzed by the combination of an iridium(I) precursor and tetramethylphenanthroline. The investigations of the scope of the reaction led to the development of powerful rules for predicting the regioselectivity of borylation, foremost of which is that borylation occurs distal to nitrogen atoms. One-pot functionalizations are reported of the heteroaryl boronate esters formed in situ, demonstrating the usefulness of the reported methodol. for the synthesis of complex heteroaryl structures. Application of this methodol. to the synthesis and late-stage functionalization of biol. active compounds is also demonstrated. Mechanistic studies show that basic heteroarenes can bind to the catalyst and alter the resting state from the olefin-bound complex observed during arene borylation to a species containing a bound heteroarene, leading to catalyst deactivation. Studies on the origins of the observed regioselectivity show that borylation occurs distal to N-H bonds due to rapid N-H borylation, creating an unfavorable steric environment for borylation adjacent to these bonds. Computational studies and mechanistic studies show that the lack of observable borylation of C-H bonds adjacent to basic nitrogen is not the result of coordination to a bulky Lewis acid prior to C-H activation, but the combination of a higher-energy pathway for the borylation of these bonds relative to other C-H bonds and the instability of the products formed from borylation adjacent to basic nitrogen.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Boutard, Nicolas’s team published research in ChemMedChem in 14 | CAS: 791614-90-9

ChemMedChem published new progress about 791614-90-9. 791614-90-9 belongs to thiazole, auxiliary class Boronate Esters,Boronic acid and ester,Boronic acid and ester, name is 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole, and the molecular formula is C14H18BNO2S, COA of Formula: C14H18BNO2S.

Boutard, Nicolas published the artcileDiscovery and structure-activity relationships of N-aryl 6-aminoquinoxalines as potent PFKFB3 kinase inhibitors, COA of Formula: C14H18BNO2S, the publication is ChemMedChem (2019), 14(1), 169-181, database is CAplus and MEDLINE.

Energy and biomass production in cancer cells are largely supported by aerobic glycolysis in what is called the Warburg effect. The process is regulated by key enzymes, among which phosphofructokinase PFK-2 plays a significant role by producing fructose-2,6-biphosphate; the most potent activator of the glycolysis rate-limiting step performed by phosphofructokinase PFK-1. Herein, the synthesis, biol. evaluation and structure-activity relationship of novel inhibitors of 6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 3 (PFKFB3), which is the ubiquitous and hypoxia-induced isoform of PFK-2, are reported. X-ray crystallog. and docking were instrumental in the design and optimization of a series of N-aryl 6-aminoquinoxalines. The most potent representative, N-(4-methanesulfonylpyridin-3-yl)-8-(3-methyl-1-benzothiophen-5-yl)quinoxalin-6-amine, displayed an IC₅₀ of 14 nM for the target and an IC₅₀ of 0.49 μM for fructose-2,6-biphosphate production in human colon carcinoma HCT116 cells. This work provides a new entry in the field of PFKFB3 inhibitors with potential for development in oncol.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Smith, Adrian L.’s team published research in Journal of Medicinal Chemistry in 58 | CAS: 791614-90-9

Journal of Medicinal Chemistry published new progress about 791614-90-9. 791614-90-9 belongs to thiazole, auxiliary class Boronate Esters,Boronic acid and ester,Boronic acid and ester, name is 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole, and the molecular formula is C7H13NO2, Quality Control of 791614-90-9.

Smith, Adrian L. published the artcileDiscovery of 1H-Pyrazol-3(2H)-ones as Potent and Selective Inhibitors of Protein Kinase R-like Endoplasmic Reticulum Kinase (PERK), Quality Control of 791614-90-9, the publication is Journal of Medicinal Chemistry (2015), 58(3), 1426-1441, database is CAplus and MEDLINE.

The structure-based design and optimization of a novel series of selective PERK inhibitors are described resulting in the identification of I as a potent, highly selective, and orally active tool compound suitable for PERK pathway biol. exploration both in vitro and in vivo.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Okumura, Kazuro’s team published research in Bulletin of the Chemical Society of Japan in 1996-08-31 | 96929-05-4

Bulletin of the Chemical Society of Japan published new progress about Peptide analogs Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, Recommanded Product: Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate.

Okumura, Kazuro; Ito, Akio; Saito, Hiroyuki; Nakamura, Yutaka; Shin, Chung-gi published the artcile< Dehydrooligopeptides. XIV. Syntheses of 2-[(Z)-1-aminoalken-1-yl]oxazole-4-carboxylic acid and the main common skeleton of thiostrepton peptide antibiotics A10255G and A10255J.>, Recommanded Product: Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate, the main research area is dehydrooligopeptide preparation thiostrepton peptide antibiotic intermediate.

Precursor (I) to title cyclopeptide antibiotics (II; R = Q1, Q2) is constructed from novel 2-[(Z)-1-amino-1-propen-1-yl]oxazole-4-carboxylic acids (III; R1 = Me, Me2CH, Ph; R2 = H, Me) and 2-(1-aminomethyl)- and 2[(S)-1-aminoethyl]thiazole-4-carboxylic acid residues.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica