Tag: M.W=100-150

Roy, Sudeshna; Sileikyte, Justina; Schiavone, Marco; Neuenswander, Benjamin; Argenton, Francesco; Aube, Jeffrey; Hedrick, Michael P.; Chung, Thomas D. Y.; Forte, Michael A.; Bernardi, Paolo; Schoenen, Frank J. published the artcile< Discovery, Synthesis, and Optimization of Diarylisoxazole-3-carboxamides as Potent Inhibitors of the Mitochondrial Permeability Transition Pore>, Application In Synthesis of 29027-20-1, the main research area is diarylisoxazole carboxamide preparation mitochondrial permeability transition pore inhibitor human; structure activity relationship; calcium retention capacity; mitochondria; muscular dystrophy; permeability transition; zebrafish.

The mitochondrial permeability transition pore (mtPTP) is a Ca2+-requiring mega-channel which, under pathol. conditions, leads to the deregulated release of Ca2+ and mitochondrial dysfunction, ultimately resulting in cell death. Although the mtPTP is a potential therapeutic target for many human pathologies, its potential as a drug target is currently unrealized. Herein, an optimization effort initiated around hit, 5-(3-hydroxyphenyl)-N-(3,4,5-trimethoxyphenyl)isoxazole-3-carboxamide, which was found to possess promising inhibitory activity against mitochondrial swelling (EC50<0.39 M) and showed no interference on the inner mitochondrial membrane potential (rhodamine 123 uptake EC50>100 M) is described. This enabled the construction of a series of picomolar mtPTP inhibitors that also potently increase the calcium retention capacity of the mitochondria. Finally, the therapeutic potential and in vivo efficacy of one of the most potent analogs, N-(3-chloro-2-methylphenyl)-5-(4-fluoro-3-hydroxyphenyl)isoxazole-3-carboxamide, was validated in a biol. relevant zebrafish model of collagen VI congenital muscular dystrophies.

ChemMedChem published new progress about Aromatic amines Role: RCT (Reactant), RACT (Reactant or Reagent). 29027-20-1 belongs to class chlorides-buliding-blocks, and the molecular formula is C7H8ClN, Application In Synthesis of 29027-20-1.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Chang, Chun-Wei; Wu, Chia-Hui; Lin, Mei-Huei; Liao, Pin-Hsuan; Chang, Chun-Chi; Chuang, Hsiao-Han; Lin, Su-Ching; Lam, Sarah; Verma, Ved Prakash; Hsu, Chao-Ping; Wang, Cheng-Chung published the artcile< Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity>, SDS of cas: 128-09-6, the main research area is predicted stereocontrolled glycosylation relative reactivity thioglycoside; carbohydrates; diastereoselectivity; glycosylation.

Stereocontrolled chem. glycosylation remains a major challenge despite vast efforts reported over many decades and so far still mainly relies on trial and error. Now it is shown that the relative reactivity value (RRV) of thioglycosides is an indicator for revealing stereoselectivities according to four types of acceptors. Mechanistic studies show that the reaction is dominated by two distinct intermediates: glycosyl triflates and glycosyl halides from N-halosuccinimide (NXS)/TfOH. The formation of glycosyl halide is highly correlated with the production of α-glycoside. These findings enable glycosylation reactions to be foreseen by using RRVs as an α/β-selectivity indicator and guidelines and rules to be developed for stereocontrolled glycosylation.

Angewandte Chemie, International Edition published new progress about Diastereoselective synthesis. 128-09-6 belongs to class chlorides-buliding-blocks, and the molecular formula is C4H4ClNO2, SDS of cas: 128-09-6.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Sisco, Edward; Barnes, Korry L. published the artcile< Design, Synthesis, and Biological Evaluation of Novel 1,3-Oxazole Sulfonamides as Tubulin Polymerization Inhibitors>, Application In Synthesis of 29027-20-1, the main research area is oxazolyl sulfonamide preparation antitumor SAR tubulin polymerization inhibitor; cyclopropyl oxazolyl benzenesulfonyl chloride amine coupling reaction.

A series of novel 1,3-oxazole sulfonamides I (R = 4-FC6H4NH2, -CH2CH2SO2Me, 1-Naph, etc; R’ = H, Me)were constructed and screened for their potential to inhibit cancer cell growth. These compounds were evaluated against the full NCI-60 human tumor cell lines, with the majority exhibiting promising overall growth inhibitory properties. They displayed high specificity within the panel of leukemia cell lines vs. all other lines tested. When examined in the dose-response assay, GI50 values fell within the low micromolar to nanomolar ranges. 1,3-Oxazole sulfonamide I (R = 4-Cl-3-CF3C6H3NH2, R’ = H) displayed the best average growth inhibition, whereas the 2-chloro-5-methylphenyl and 1-naphthyl substituents on the sulfonamide nitrogen proved to be the most potent leukemia inhibitors with mean GI50 values of 48.8 and 44.7 nM, resp. In vitro tubulin polymerization experiments revealed that this class of compounds effectively binds to tubulin and induces the depolymerization of microtubules within cells.

ACS Medicinal Chemistry Letters published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 29027-20-1 belongs to class chlorides-buliding-blocks, and the molecular formula is C7H8ClN, Application In Synthesis of 29027-20-1.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Zhang, Yuanyuan; Liang, Yaoyu; Zhao, Xiaodan published the artcile< Chiral Selenide-Catalyzed, Highly Regio- and Enantioselective Intermolecular Thioarylation of Alkenes with Phenols>, Related Products of 128-09-6, the main research area is chiral phenol preparation regioselective enantioselective diastereoselective; alkene phenol thiosuccinimide three component thioarylation chiral selenide catalyst.

Enantioselective electrophilic three-component thioarylation of alkenes by chiral selenide catalysis with free phenols as arylating sources is disclosed. A variety of chiral phenols, e.g., I, were prepared in high regio-, enantio-, and diastereoselectivities. Mechanistic studies revealed that this transformation went through carbon nucleophilic attack to give the products rather than the process of intramol. rearrangement of phenolic ether intermediates. The application of this organocatalytic method in the alkylation of methoxy-substituted benzenes elucidated its generality.

ACS Catalysis published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 128-09-6 belongs to class chlorides-buliding-blocks, and the molecular formula is C4H4ClNO2, Related Products of 128-09-6.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Riley, Kevin E.; Murray, Jane S.; Fanfrlik, Jindrich; Rezac, Jan; Sola, Ricardo J.; Concha, Monica C.; Ramos, Felix M.; Politzer, Peter published the artcile< Halogen bond tunability I: the effects of aromatic fluorine substitution on the strengths of halogen-bonding interactions involving chlorine, bromine, and iodine>, Related Products of 1435-43-4, the main research area is halogen bond tunability iodine aromatic fluorine substitution strength bonding; chlorine bromine halogen bond.

In the past several years, halogen bonds are relevant in crystal engineering and biomedical applications. One of the reasons for the utility of these types of noncovalent interactions in the development of, for example, pharmaceutical ligands is that their strengths and geometric properties are very tunable. That is, substitution of atoms or chem. groups in the vicinity of a halogen can have a very strong effect on the strength of the halogen bond. The authors study halogen-bonding interactions involving aromatically-bound halogens (Cl, Br, and I) and a carbonyl oxygen. The properties of these halogen bonds are modulated by substitution of aromatic hydrogens with fluorines, which are very electroneg. These types of substitutions have dramatic effects on the strengths of the halogen bonds, leading to interactions that can be up to 100% stronger. Very good correlations are obtained between the interaction energies and the magnitudes of the pos. electrostatic potentials (σ-holes) on the halogens. The substitution of fluorines in systems containing smaller halogens results in electrostatic potentials resembling those of systems with larger halogens, with correspondingly stronger interaction energies. Also aromatic fluorine substitutions affect the optimal geometries of the halogen-bonded complexes, often as the result of secondary interactions.

Journal of Molecular Modeling published new progress about Aryl halides Role: PEP (Physical, Engineering or Chemical Process), PRP (Properties), PROC (Process). 1435-43-4 belongs to class chlorides-buliding-blocks, and the molecular formula is C6H3ClF2, Related Products of 1435-43-4.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Bera, Shyamal Kanti; Mal, Prasenjit published the artcile< Mechanochemical-Cascaded C-N Cross-Coupling and Halogenation Using N-Bromo- and N-Chlorosuccinimide as Bifunctional Reagents>, Category: chlorides-buliding-blocks, the main research area is phenanthridinone derivative preparation crystal structure mol; biphenyl carboxamide halosuccinimide cascade cross coupling halogenation.

Direct synthesis of halo-substituted phenanthridinone derivatives I [R = Cl, Br, I; R1 = H, 3-Me, 3-F, etc.; R2 = H, 8-Me; R3 = OMe, Ph] was achieved via cascade C-N bond formation and subsequent halogenation reactions of N-halosuccinimides with N-methoxy-[1,1′-biphenyl]-2-carboxamides. During the reactions, NBS/NCS first assisted the oxidative C-N coupling reaction and subsequently promoted a halogenation reaction. Thus, the role of NBS/NCS was established to be bifunctional. This protocol offered a mild, solvent-free, convenient, one-pot synthesis of compounds I.

Journal of Organic Chemistry published new progress about Aromatic amides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 128-09-6 belongs to class chlorides-buliding-blocks, and the molecular formula is C4H4ClNO2, Category: chlorides-buliding-blocks.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Li, Jia; Li, Yu-An; Wu, Ge; Zhang, Xu published the artcile< Metal-free aminohalogenation of quinones with alkylamines and NXS at room temperature>, Category: chlorides-buliding-blocks, the main research area is halo amino naphthalenedione preparation; naphthoquinone amine aminohalogenation; NXS; aminohalogenation; metal-free; quinones; radical reactions.

A simple and practical strategy for intermol. aminohalogenation of quinone with alkyl amines and NXS was developed for preparation of halo(amino)naphthalenediones I [X = H, Cl, Br, I; R1 = Me; R2 = 2-cyanoethyl, (4-bromophenyl)methyl, phenethyl, (3S)-3-(2-methylphenoxy)-3-phenyl-propyl; R1 = R2 = (CH2)2O(CH2)2, (CH2)2CH(OH)(CH2)2, (CH2)2CH(CO2Me)(CH2)2], in which haloamines generated in situ were employed as bifunctional reagents. The reaction system was reliable, efficient and wide in substrate range, which was suitable for the two-fold aminochlorination of 1, 4-benzoquinones, large-scale reaction and late-stage modification of pharmaceuticals.

Frontiers in Chemistry (Lausanne, Switzerland) published new progress about Halogenation (amino). 128-09-6 belongs to class chlorides-buliding-blocks, and the molecular formula is C4H4ClNO2, Category: chlorides-buliding-blocks.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Sun, Caocao; Yin, Guoyin published the artcile< Integrating aryl chlorides into nickel-catalyzed 1,1-difunctionalization of alkenes>, Application of C6H3ClF2, the main research area is secondary benzyl boronate preparation regioselective; alkene aryl chloride bispinacolatodiboron difunctionalization nickel catalyst.

Herein, a first achievement in 1,1-difunctionalization of alkenes RCH=CH2 (R = hexyl, cyclohexyl, 3-(1H-pyrrol-1-yl)propyl, 9H-carbazol-9-ylmethyl, etc.) with aryl chlorides ArCl (Ar = Ph, 2,4-difluorophenyl, 1-[(tert-butoxy)(oxo)methane]-1H-indol-6-yl, 2H-1,3-benzodioxol-5-yl, etc.) as coupling partners was reported. The success is predominantly ascribed to the judicious selection of 1,2-diamine ligand. This study provides an efficient protocol for the synthesis of secondary benzyl boronates RCH2CH(R1)Ar (R1 = tetramethyl-1,3,2-dioxaborolan-2-yl) from easily accessible feedstock chems. Furthermore, the distinguished features of this method include excellent 1,1-regio- and chemoselectivity, good functional group tolerance and easily-operational catalytic reaction conditions.

Chinese Chemical Letters published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 1435-43-4 belongs to class chlorides-buliding-blocks, and the molecular formula is C6H3ClF2, Application of C6H3ClF2.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Pleschke, A.; Marhold, A.; Schneider, M.; Kolomeitsev, A.; Roschenthaler, G.-V. published the artcile< Halex reactions of aromatic compounds catalysed by 2-azaallenium, carbophosphazenium, aminophosphonium and diphosphazenium salts: a comparative study>, Computed Properties of 1435-43-4, the main research area is fluoride aryl preparation; chloride aryl halogen exchange azaallenium carbophosphazenium aminophosphonium diphosphazenium catalyst.

One of the most common methods to introduce fluorine into aromatic compounds is the well-investigated halogen-exchange (Halex) reaction, in which chloro- and bromoaroms. activated towards nucleophilic substitution, react with a fluoride source to yield the corresponding fluoroarenes. In general, the reaction is supported by phase-transfer catalysts. The new classes of compounds, I (X = C, R = Me; X = Et2NP, R = Et), were found to be active phase-transfer catalysts allowing for substitution of even weakly activated halogens.

Journal of Fluorine Chemistry published new progress about Aryl chlorides Role: RCT (Reactant), RACT (Reactant or Reagent). 1435-43-4 belongs to class chlorides-buliding-blocks, and the molecular formula is C6H3ClF2, Computed Properties of 1435-43-4.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Qu, Zheng-Wang; Zhu, Hui; Grimme, Stefan published the artcile< Mechanistic Insights for Aniline-Catalyzed Halogenation Reactions>, Recommanded Product: 1-Chloropyrrolidine-2,5-dione, the main research area is anisole halosuccinimide aniline catalyst halogenation reaction mechanism.

Lewis base catalyzed electrophilic aromatic halogenation using N-halosuccinimides (NsX; X=Cl, Br, I) under mild conditions has attracted much attention, but the detailed mechanism remains elusive. Using the aniline MesNH2 and anisole PhOMe as the typical base catalyst and aromatic substrate, resp., a novel mechanism is revealed by extensive DFT calculations The autogenic protonation of imine XMes=NH (via Mes=NH+ mediated dimerization of MesNH2) is crucial to initialize the electrophilic halonium X+ transfer to nucleophilic substrates. It is shown that the aniline MesNH2 and more basic imine XMes=NH may act as efficient halonium X+ and proton H+ shuttles, resp., connected by the arenium XMesNH2+. Non-coordinating MesNH3+ salts are suggested as efficient catalyst for electrophilic iodination. Without suitable stabilization of the highly basic anion Ns-, the generally accepted concept of Lewis base catalyst as simple X+ shuttle will never work efficiently due to a high thermodn. barrier. In general, autogenic or addnl. acid additives should be used for more efficient Lewis base catalyzed halogenation.

ChemCatChem published new progress about Free energy. 128-09-6 belongs to class chlorides-buliding-blocks, and the molecular formula is C4H4ClNO2, Recommanded Product: 1-Chloropyrrolidine-2,5-dione.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics