Tag: M.W=100-150

Li, Bowen published the artcileNickel-Catalyzed Asymmetric Hydrogenation of N-Sulfonyl Imines, Application In Synthesis of 343338-28-3, the main research area is asym hydrogenation sulfonyl imine nickel catalyst quinoxaline phosphine ligand; amines; asymmetric catalysis; hydrogenation; nickel; reaction mechanisms.

An efficient nickel-catalyzed asym. hydrogenation of N-tert-Bu-sulfonyl imines was developed with excellent yields and enantioselectivities using (R,R)-QuinoxP*, I, as a chiral ligand. The use of a much lower catalyst loading (0.0095 mol %, S/C=10500) represents the highest catalytic activity for the Ni-catalyzed asym. hydrogenations reported so far. Mechanistic studies suggest that a coordination equilibrium exists between the nickel salt and its complex, and that excess nickel salt promotes the formation of the active Ni-complex, and therefore improved the efficiency of the hydrogenation. The catalytic cycle was also investigated by calculations to determine the origin of the enantioselectivity. An extensive network of numerous weak attractive interactions was found to exist between the catalyst and substrate in the transition state and may also contribute to the high catalytic activity.

Angewandte Chemie, International Edition published new progress about Enantioselective synthesis. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Application In Synthesis of 343338-28-3.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Thakur, Nimisha published the artcileEnantiomeric impurities in chiral catalysts, auxiliaries, and synthons used in enantioselective syntheses. Part 5, COA of Formula: C4H11NOS, the main research area is chiral catalyst synthon enantioselective enantiomeric impurity; chiral separation; enantiomeric excess; enantiomeric impurity; enantioselective syntheses.

The enantiomeric excess of chiral starting materials is one of the important factors determining the enantiopurity of products in asym. synthesis. Fifty-one com. available chiral reagents used as building blocks, catalysts, and auxiliaries in various enantioselective syntheses were assayed for their enantiomeric purity. The test results were classified within five impurities level (ie, <0.01%, 0.01%-0.1%, 0.1%-1%, 1%-10%, >10%). Previously from 1998 to 2013, several reports have been published on the enantiomeric composition of more than 300 chiral reagents. This series of papers is necessitated by the fact that new reagents are forthcoming and that the enantiomeric purity of the same reagent can vary from batch to batch and/or from supplier to supplier. This report presents chiral liquid chromatog. (LC) and gas composition(GC) methods to sep. enantiomers of chiral compounds and evaluate their enantiomeric purities. The accurate and efficient LC anal. was done using newly introduced superficially porous particle (SPP 2.7μm) based chiral stationary phases (TeicoShell, VancoShell, LarihcShell-P, and NicoShell).

Chirality published new progress about Enantioselective synthesis. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, COA of Formula: C4H11NOS.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Wilding, Birgit published the artcileInvestigating the phosphinic acid tripeptide mimetic DG013A as a tool compound inhibitor of the M1-aminopeptidase ERAP1, Quality Control of 343338-28-3, the main research area is phosphinic acid tripeptide mimetic enantioselective synthesis inhibitor aminopeptidase ERAP1; peptidomimetic phosphinic acid library synthesis tool probe; chirality condensation protection phospha Michael addition epimerization resolution; enzyme inhibitor structure activity drug discovery target permeability; ERAP1 DG013A bound crystal structure mol docking antitumor agent; Chemical probe; DG013A; ERAP1; M1-aminopeptidase; Permeability.

ERAP1 is a zinc-dependent M1-aminopeptidase that trims lipophilic amino acids from the N-terminus of peptides. Owing to its importance in the processing of antigens and regulation of the adaptive immune response, dysregulation of the highly polymorphic ERAP1 has been implicated in autoimmune disease and cancer. To test this hypothesis and establish the role of ERAP1 in these disease areas, high affinity, cell permeable and selective chem. probes are essential. DG013A 1, is a phosphinic acid tripeptide mimetic inhibitor with reported low nanomolar affinity for ERAP1. However, this chemotype is a privileged structure for binding to various metal-dependent peptidases and contains a highly charged phosphinic acid moiety, so it was unclear whether it would display the high selectivity and passive permeability required for a chem. probe. Therefore, we designed a new stereoselective route to synthesize a library of DG013A 1 analogs to determine the suitability of this compound as a cellular chem. probe to validate ERAP1 as a drug discovery target.

Bioorganic & Medicinal Chemistry Letters published new progress about (Benzyloxy)carbonyl group. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Quality Control of 343338-28-3.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Kokkonda, Praveen published the artcileTotal Synthesis of (+)-epi-Condyfoline, Related Products of amides-buliding-blocks, the main research area is asym total synthesis epi condyfoline; Michael Mannich annulation sulfinyl metallodienamine epi condyfoline synthesis; cyclization tosyloxy sulfinamide epi condyfoline synthesis; spirocyclization thioacetal epi condyfoline synthesis.

Herein, we report the first asym. total synthesis of aspidospermatan indole alkaloid (+)-epi-condyfoline in 15 steps from com. available 2-methylindole-3-carboxaldehyde. Key steps include (1) our domino Michael/Mannich annulation method of N-sulfinyl metallodienamines to set three contiguous stereocenters, (2) LiHMDS-mediated cyclization of an ω-tosyloxy N-sulfinamide to prepare the signature indole-fused 2-azabicyclo[3.3.1]nonane framework, and (3) DMTSF-promoted spirocyclization of a dithioacetal intermediate to access the final pyrrolidine ring. Functional group manipulations delivered the targeted alkaloid (+)-epi-condyfoline (1) in 13 steps and 1.25% overall yield from N-sulfinylimine.

Organic Letters published new progress about Chiral auxiliary (sulfinamide). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Related Products of amides-buliding-blocks.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Cinelli, Maris A. published the artcileCorrection to Nitrile in the Hole: Discovery of a Small Auxiliary Pocket in Neuronal Nitric Oxide Synthase Leading to the Development of Potent and Selective 2-Aminoquinoline Inhibitors [Erratum to document cited in CA166:529893], Safety of (S)-2-Methylpropane-2-sulfinamide, the main research area is aminoquinoline derivative preparation nNOS inhibitor neurodegenerative disorder erratum.

In the original publication on Page 3975, Under the paragraph heading “”Inhibitor Complex Crystal Preparation””, lines 9-10 state “”… for human eNOS, 12-15% PEG3350, 0.1 M Bis-Tris, pH 6.5, …”” should read “”… for human eNOS, 12-15% PEG3350, 0.1 M Bis-Tris, pH 7.5, …””; the correction is provided here.

Journal of Medicinal Chemistry published new progress about Central nervous system agents. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Safety of (S)-2-Methylpropane-2-sulfinamide.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Mazur, Marzena published the artcileDevelopment of Dual Chitinase Inhibitors as Potential New Treatment for Respiratory System Diseases, Related Products of amides-buliding-blocks, the main research area is aminotriazolyl piperidin amine preparation chitinases inhibitor respiratory system disease.

Acidic mammalian chitinase (AMCase) and chitotriosidase-1 (CHIT1) are two enzymically active proteins produced by mammals capable of cleaving the glycosidic bond in chitin. Based on the clin. findings and animal model studies, involvement of chitinases has been suggested in several respiratory system diseases including asthma, COPD, and idiopathic pulmonary fibrosis. Exploration of structure-activity relationships within the series of 1-(3-amino-1H-1,2,4-triazol-5-yl)-piperidin-4-amines, which was earlier identified as a scaffold of potent AMCase inhibitors, led us to discover highly active dual (i.e., AMCase and CHIT1) inhibitors with very good pharmacokinetic properties. Among them, compound 30 was shown to reduce the total number of cells in bronchoalveolar lavage fluid of mice challenged with house dust mite extract after oral administration (50 mg/kg, qd). In addition, affinity toward the hERG potassium channel of compound 30 was significantly reduced when compared to the earlier reported chitinase inhibitors.

Journal of Medicinal Chemistry published new progress about Allergic respiratory disease. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Related Products of amides-buliding-blocks.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Madron du Vigne, Adrien published the artcileChiral Cyclic Alkyl Amino Carbene (CAAC) Transition-Metal Complexes: Synthesis, Structural Analysis, and Evaluation in Asymmetric Catalysis, HPLC of Formula: 343338-28-3, the main research area is chiral cyclic alkyl amino carbene CAAC transition metal complex; asym catalysis chiral cyclic alkyl amino carbene transition metal; conjugate borylation asym alpha beta unsaturated ester copper carbene; crystal mol structure cyclic alkyl amino carbene transition metal.

Despite recent advances in the field of cyclic alkyl amino carbenes (CAACs) including a few complementary synthetic strategies affording CAACs with various substitution patterns, the application potential of chiral CAACs to efficiently catalyze asym. organometallic transformations remains largely underdeveloped. Herein, authors describe a convenient and robust route that incorporates common chiral primary amine allowing access of a broad range of chiral CAACs precursors. The corresponding transition-metal complexes with Cu, Au, Ru, Rh, Ir, and Pd were obtained in a straightforward manner. The steric parameters of the complexes were comprehensively collected by x-ray single-crystal anal. to serve as a source of information for further ligand design. The preliminary application potential of the copper CAAC complexes was tested in asym. conjugate borylation of an α,β-unsaturated ester providing 89:11 er, thus illustrating the potential of chiral CAACs in asym. catalysis.

Organometallics published new progress about Borylation (asym. conjugate). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, HPLC of Formula: 343338-28-3.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Xiao, Miao published the artcileTransition-Metal-Free Hydrogen Autotransfer: Diastereoselective N-Alkylation of Amines with Racemic Alcohols, Quality Control of 343338-28-3, the main research area is diastereoselective alkylation amines alc chiral amine synthesis; alcohols; alkylation; amines; deuterium; reaction mechanisms.

A practical method for the synthesis of α-chiral amines by alkylation of amines with alcs. in the absence of any transition-metal catalysts has been developed. Under the co-catalysis of a ketone and NaOH, racemic secondary alcs. reacted with Ellman’s chiral tert-butanesulfinamide by a hydrogen autotransfer process to afford chiral amines with high diastereoselectivities (up to >99:1) [e.g., 1-phenylethanol + (R)-(+)-tert-butanesulfinamide → I (70%, > 95:5 d.r.) in presence of acetophenone and NaOH in toluene]. Broad substrate scope and up to a 10 g scale production of chiral amines were demonstrated. The method was applied to the synthesis of chiral deuterium-labeled amines with high deuterium incorporation and optical purity, including examples of chiral deuterated drugs. The configuration of amine products is found to be determined solely by the configuration of the chiral tert-butanesulfinamide regardless of that of alcs., and this is corroborated by DFT calculations Further mechanistic studies showed that the reaction is initiated by the ketone catalyst and involves a transition state similar to that proposed for the Meerwein-Ponndorf-Verley (MPV) reduction, and importantly, it is the interaction of the sodium cation of the base with both the nitrogen and oxygen atoms of the sulfinamide moiety that makes feasible, and determines the diastereoselectivity of, the reaction.

Angewandte Chemie, International Edition published new progress about Alkylation catalysts, stereoselective. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Quality Control of 343338-28-3.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Bendelsmith, Andrew J. published the artcileEnantioselective Synthesis of α-Allyl Amino Esters via Hydrogen-Bond-Donor Catalysis, Synthetic Route of 343338-28-3, the main research area is chloro glycinate enantioselective allylation squaramide catalyst allylstannane allylsilane; allyl amino ester chiral preparation.

Chiral-squaramide-catalyzed enantio- and diastereoselective synthesis of α-allyl amino esters is reported. The optimized protocol provides access to N-carbamoyl-protected amino esters via nucleophilic allylation of readily accessible α-chloro glycinates. A variety of useful α-allyl amino esters were prepared, including crotylated products bearing vicinal stereocenters that are inaccessible through enolate alkylation, with high enantioselectivity (up to 97% ee) and diastereoselectivity (>10:1). The reactions display 1st-order kinetic dependence on both the α-chloro glycinate and the nucleophile, consistent with rate-limiting C-C bond formation. Computational anal. of the uncatalyzed reaction predicts an energetically inaccessible iminium intermediate, and a lower energy concerted SN2 mechanism.

Journal of the American Chemical Society published new progress about Allylation kinetics (stereoselective). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Synthetic Route of 343338-28-3.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Bester, Stephanie M. published the artcileStructural and mechanistic bases for a potent HIV-1 capsid inhibitor, Product Details of C4H11NOS, the main research area is GS 6207 preparation antiviral HIV1 capsid inhibitor.

The potent HIV-1 capsid inhibitor GS-6207 is an investigational principal component of long-acting antiretroviral therapy. We found that GS-6207 inhibits HIV-1 by stabilizing and thereby preventing functional disassembly of the capsid shell in infected cells. X-ray crystallog., cryo-electron microscopy, and hydrogen-deuterium exchange experiments revealed that GS-6207 tightly binds two adjoining capsid subunits and promotes distal intra- and inter-hexamer interactions that stabilize the curved capsid lattice. In addition, GS-6207 interferes with capsid binding to the cellular HIV-1 cofactors Nup153 and CPSF6 that mediate viral nuclear import and direct integration into gene-rich regions of chromatin. These findings elucidate structural insights into the multimodal, potent antiviral activity of GS-6207 and provide a means for rationally developing second-generation therapies.

Science (Washington, DC, United States) published new progress about Anti-HIV agents (anti-HIV-1 agents). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Product Details of C4H11NOS.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics