Category: 343338-28-3

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

Nie, Xiao-Di published the artcileA diastereoselective approach to amino alcohols and application for divergent synthesis of dolastatin 10, Formula: C4H11NOS, the main research area is amino alc enantioselective diastereoselective synthesis; chiral imine radical addition benzyloxymethylsulfonyl pyridine catalyst samarium diiodide; dolastatin synthesis antitumor agent chirality peptide coupling.

A diastereoselective approach to obtain amino alcs. through SmI2-induced radical addition of chiral imine with 2-(benzyloxymethylsulfonyl)pyridine is described. This approach was easily used for the synthesis of non-natural amino acid (I) hydrochloride, a flexible key fragment whose utility was demonstrated in the divergent synthesis of dolastatin 10 and its nine analogs were obtained.

Organic Chemistry Frontiers published new progress about Addition reaction catalysts (SmI2). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Formula: C4H11NOS.

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

Mendes, Joseane A. published the artcileEnantioselective Synthesis, DFT Calculations, and Preliminary Antineoplastic Activity of Dibenzo 1-Azaspiro[4.5]decanes on Drug-Resistant Leukemias, Product Details of C4H11NOS, the main research area is diastereoselective addition magnesium bromide chiral imine tetralone type ketone; dibenzo azaspirodecane preparation sulfinamide derivative intermediate arylation; azaspiro compound DFT calculation antineoplastic activity drug resistant leukemia.

The addition of 2-bromobenzylmagnesium bromide to chiral N-tert-butanesulfinyl imines derived from tetralone-type ketones proceeds with high levels of diastereocontrol. The resulting sulfinamide derivatives were transformed into dibenzoazaspiro compounds after a palladium-catalyzed intramol. N-arylation. DFT calculations have been performed to rationalize the stereochem. course of the reaction. Similar results have been obtained considering either di-Et ether or toluene as a solvent, in both cases in an excellent agreement with exptl. findings. NCI topol. calculations have also been used to evidence crucial noncovalent interactions. In addition, the azaspiro compounds reduced the viability of chronic myeloid leukemia cells in the micromolar range. Notably, both the halogen-substituted (R)- and (S)-I (R = F, X = CH2) and I (R = Br, X = CH2) as well as (R)-I (R = H, X = S) were at least two times more effective on a multidrug-resistant derivative than on the parental cell line, exerting a collateral sensitivity effect.

Journal of Organic Chemistry published new progress about Addition reaction, stereoselective. 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

Kaczorek, Dorota published the artcileHighly stereoselective synthesis of non-racemic 3-substituted dihydro-benzo[de]isoquinolinones via an addition-cyclization-substitution method, Related Products of amides-buliding-blocks, the main research area is dihydrobenzoisoquionlinone preparation enantioselective; sulfinylimine preparation Grignard reagent addition cyclization substitution reaction.

Substituted dihydrobenzo[de]isoquinolinones (R/S)-I (R = Me, Bu, Ph, 2-methoxy Ph, etc.) were synthesized via diastereoselective addition of Grignard reagents RMgBr to the N-tert-butylsulfinylimine (R/S)-II derived from 1,8-naphthaldehydic Me ester, followed by cyclization and substitution at the sulfur atom. The products were obtained in 25-98% yield and with enantiomeric excess of 46-99%.

Tetrahedron Letters published new progress about Addition reaction, stereoselective. 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