M.W=100-150 Archives - Page 29 of 180 - Amides-buliding-blocks

Losasso, Valeria’s team published research in Biophysical Journal in 121 | CAS: 1453-82-3

Biophysical Journal published new progress about 1453-82-3. 1453-82-3 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is Isonicotinamide, and the molecular formula is C6H6N2O, Formula: C6H6N2O.

Losasso, Valeria published the artcileSmall molecules enhance the potency of natural antimicrobial peptides, Formula: C6H6N2O, the publication is Biophysical Journal (2022), 121(3), 491-501, database is CAplus and MEDLINE.

The skin-associated microbiome plays an important role in general well-being and in a variety of treatable skin conditions. In this regard, endogenous antimicrobial peptides have both a direct and indirect role in determining the composition of the microbiota. We demonstrate here that certain small mol. species can amplify the antimicrobial potency of naturally occurring antimicrobial peptides. In this study, we have used niacinamide, a form of vitamin B3 naturally found in foods and widely used in cosmetic skincare products, and two of its structural analogs, to investigate their cooperativity with the human antimicrobial peptide LL37 on the bacterium Staphylococcus aureus. We observed a clear synergistic effect of niacinamide and, to some extent, N-methylnicotinamide, whereas isonicotinamide showed no significant cooperativity with LL37. Adaptively biased mol. dynamics simulations using simplified model membrane substrates and single peptides revealed that these mols. partition into the headgroup region of an anionic bilayer used to mimic the bacterial membrane. The simulated effects on the phys. properties of the simulated model membrane are well correlated with exptl. activity observed in real biol. assays despite the simplicity of the model. In contrast, these mols. have little effect on zwitterionic bilayers that mimic a mammalian membrane. We conclude that niacinamide and N-methylnicotinamide can therefore potentiate the activity of host peptides by modulating the phys. properties of the bacterial membrane, and to a lesser extent through direct interactions with the peptide. The level of cooperativity is strongly dependent on the detailed chem. of the additive, suggesting an opportunity to fine-tune the behavior of host peptides.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Liu, Fangyao’s team published research in Macromolecular Chemistry and Physics in 216 | CAS: 2479-62-1

Macromolecular Chemistry and Physics published new progress about 2479-62-1. 2479-62-1 belongs to amides-buliding-blocks, auxiliary class Monomers,Acrylamide Monomers, name is N-(2-Amino-2-oxoethyl)acrylamide, and the molecular formula is C5H8N2O2, Synthetic Route of 2479-62-1.

Liu, Fangyao published the artcileThermoresponsive Gold Nanoparticles with Positive UCST-Type Thermoresponsivity, Synthetic Route of 2479-62-1, the publication is Macromolecular Chemistry and Physics (2015), 216(4), 460-465, database is CAplus.

Trithiocarbonate end-functionalized poly(N-acryloylglycinamide) (PNAGA), synthesized via reversible addition-fragmentation transfer (RAFT) polymerization of different mol. weights, is grafted onto gold nanoparticles (AuNPs) by ligand exchange in phosphate-buffered saline. The PNAGA-grafted AuNPs display upper critical solution temperature (UCST)-type transitions: stable colloidal distribution and aggregation above and below the cloud points, resp. Cloud points of PNAGA are not affected by the grafting procedure, and PNAGA@AuNPs show similar cloud points as that of the trithiocarbonate end-functionalized free-PNAGAs used for grafting. The UCST-type phase transition is reversible for many cycles. The reversible control of the phase transition is proved by turbidity measurements and UV-vis spectroscopy, as well as by transmission electron microscopy (TEM).

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Seuring, Jan’s team published research in Macromolecules (Washington, DC, United States) in 45 | CAS: 2479-62-1

Macromolecules (Washington, DC, United States) published new progress about 2479-62-1. 2479-62-1 belongs to amides-buliding-blocks, auxiliary class Monomers,Acrylamide Monomers, name is N-(2-Amino-2-oxoethyl)acrylamide, and the molecular formula is C17H18N2O6, Category: amides-buliding-blocks.

Seuring, Jan published the artcileFirst Example of a Universal and Cost-Effective Approach: Polymers with Tunable Upper Critical Solution Temperature in Water and Electrolyte Solution, Category: amides-buliding-blocks, the publication is Macromolecules (Washington, DC, United States) (2012), 45(9), 3910-3918, database is CAplus.

We present a powerful universal and versatile approach for the synthesis of polymers that show a UCST in water. Up to now only a few polymers were known that show an upper critical solution temperature (UCST) in water. This study establishes general requirements to obtain polymers with a UCST in water as well as electrolyte solution It is demonstrated that old homo- and copolymer systems like poly(methacrylamide) and poly(acrylamide-co-acrylonitrile) can exhibit a UCST in water and how polymers with a tunable UCST can be synthesized by copolymerization of acrylamide and acrylonitrile, monomers that are industrially produced on large scales. Controlled increase of the UCST by copolymerization of acrylamide with varying amounts of acrylonitrile was shown, and it could be varied between 6 and 60 °C. The hysteresis between the cloud point upon cooling and heating was very small with only 1-2 °C in most cases. The cloud points in pure water were similar to the cloud points measured in phosphate buffered saline. Also, it is possible to prepare highly concentrated thermo-responsive polymer solutions without gel formation.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Zhou, Li’s team published research in Angewandte Chemie, International Edition in 2021-01-11 | CAS: 343338-28-3

Angewandte Chemie, International Edition published new progress about Helicity. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Recommanded Product: (S)-2-Methylpropane-2-sulfinamide.

Zhou, Li published the artcileSelective Synthesis of Single-Handed Helical Polymers from Achiral Monomer and a Mechanism Study on Helix-Sense-Selective Polymerization, Recommanded Product: (S)-2-Methylpropane-2-sulfinamide, the main research area is helicity conformation single handed polyphenyl isocyanide preparation; chiral polymers; helix; helix-sense-selective polymerization; living polymerization; polymers.

Inspired by the exquisite helixes in nature, fabrication of helical materials with controlled handedness has attracted considerable attention. Herein, the authors report on precise synthesis of single left- and right-handed helical polyisocyanides through living polymerization of achiral monomers using chiral palladium catalysts under helix-sense-selective manner. Mechanism study revealed that the yielded helixes with opposite handedness showed different activity of the living chain end. The helix with unfavored handedness was self-terminated, while the one with favored handedness showed high activity and could undergo chain propagation to form a high mol. weight polymer with maintained single-handed helicity.

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

Zhang, Shu-Wei’s team published research in Journal of Medicinal Chemistry in 2020-01-23 | CAS: 343338-28-3

Journal of Medicinal Chemistry published new progress about Amidation. 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.

Zhang, Shu-Wei published the artcileSynthesis and in Vitro and in Vivo Biological Evaluation of Tissue-Specific Bisthiazole Histone Deacetylase (HDAC) Inhibitors, Product Details of C4H11NOS, the main research area is bisthiazole derivative preparation anticancer HDAC inhibitor.

A series of bisthiazole-based hydroxamic acids as novel potent HDAC inhibitors was developed during our previous work. In the present work, a new series of highly potent bisthiazole-based compounds were designed and synthesized. Among the prepared compounds, compound I, which contains an α-(S)-methyl-substituted benzyl group, displays potent inhibitory activity toward human HDACs and several cancer cells lines. Compound I has a favorable PK profile and high tissue distribution specificity in the colon, as well as good efficacy in the AOM-DSS mouse model for colitis-associated colonic tumorigenesis.

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

Kawada, Takuma’s team published research in Journal of Organic Chemistry in 2022-07-01 | CAS: 343338-28-3

Journal of Organic Chemistry published new progress about Amination. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Category: amides-buliding-blocks.

Kawada, Takuma published the artcileAsymmetric Transfer Hydrogenative Amination of Benzylic Ketones Catalyzed by Cp*Ir(III) Complexes Bearing a Chiral N-(2-Picolyl)sulfonamidato Ligand, Category: amides-buliding-blocks, the main research area is amine preparation chemoselective diastereoselective enantioselective; benzylic ketone asym transfer hydrogenative amination iridium complex catalyst.

A convenient asym. reductive amination of benzylic ketones (α-arylated ketones) catalyzed by newly designed Cp*Ir complexes bearing a chiral N-(2-picolyl)sulfonamidato ligand was developed. Using readily available β-amino alcs. as chiral aminating agents, a range of benzo-fused and acyclic ketones were successfully reduced with formic acid in methanol at 40°C to afford amines with favorable chemo- and diastereoselectivities. The amino alc.-derived chiral auxiliary was easily removed by mild periodic oxidants, leading to optically active primary β-arylamines without erosion of the optical purity (up to 97% ee). The excellent catalytic performance was retained even upon lowering the amount of catalyst to a substrate/catalyst (S/C) ratio of 20,000, and the amination could be performed on a large scale exceeding 100 g. The precise hydride transfer to iminium species generated from the ketonic substrate and the chiral amine counterpart was suggested by the mechanistic studies on stoichiometric reactions of isolable hydridoiridium complexes and model intermediates such as N,O-acetal, enamine, and iminium compounds

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

Li, Chun-Tian’s team published research in Organic Letters in 2019-10-18 | CAS: 343338-28-3

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

Li, Chun-Tian published the artcileRearrangement of N-tert-Butanesulfinyl Enamines for Synthesis of Enantioenriched α-Hydroxy Ketone Derivatives, Formula: C4H11NOS, the main research area is acyclic tertiary hydroxy sulfenyloxy ketone preparation enantioselective; tert butanesulfinyl ketimine methyl triflate cascade enamination methylation rearrangement.

Treating chiral N-tert-butanesulfinyl ketimines with potassium hexamethyldisilazide (or potassium tert-butoxide) and Me triflate gives N-methylated N-tert-butanesulfinyl enamine intermediates that undergo stereoselective [2,3]-rearrangement to afford α-sulfenyloxy ketones I (R = Ph, iPr, 2-furyl, etc.; R’ = Me, allyl, Bn, etc.) with excellent enantiopurities. This cascade of enamination-N-methylation-rearrangement was even used to generate acyclic tertiary α-hydroxy ketones, II bearing two α-substituents showing negligible differences in bulkiness, such as Me and Et groups.

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

Kamimura, Akio’s team published research in Polymer Degradation and Stability in 2019-02-28 | CAS: 343338-28-3

Polymer Degradation and Stability published new progress about Chirality. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Recommanded Product: (S)-2-Methylpropane-2-sulfinamide.

Kamimura, Akio published the artcileA study on the stereochemistry of direct conversion of polyamides to hydroxyesters using monomeric secondary chiral amines as a model compound, Recommanded Product: (S)-2-Methylpropane-2-sulfinamide, the main research area is stereochem mechanism polyamide hydroxyester secondary chiral amine model compound.

Stereochem. of direct conversion of polyamides to hydroxyesters was investigated using model compounds Optically active secondary-alkyl amines underwent the conversion to corresponding secondary alcs. in moderate yields by treatment with supercritical methanol in the presence of glycolic acid. The reaction progressed through almost completely stereochem. inversion to give secondary alcs. in high yields. The substitution reaction of amino group to hydroxyl group progressed through SN2 transition state accompanying with stereoinversion.

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

Zhang, Yaqi’s team published research in ChemistrySelect in 2019 | CAS: 343338-28-3

ChemistrySelect published new progress about Chirality. 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.

Zhang, Yaqi published the artcileEnantioselective Syntheses of Axially Chiral Phosphonates or Phosphine Oxides via Asymmetric Suzuki Reactions with Chiral Sulfinamide Monophosphine Ligands, Synthetic Route of 343338-28-3, the main research area is stereoselective Suzuki chiral sulfinamide phosphine oxide phosphonate chiral preparation.

A class of chiral sulfinamide monophosphine ligands Ming-Phos were firstly employed in the asym. Suzuki coupling reactions. Using the in-situ formed catalyst from PdCl2 and (R, SS)-M07, 22 axially chiral phosphonates or phosphine oxides were successfully synthesized in 29-99% yields with up to 98% ee. This method provides a simple and efficient protocol for the synthesis of axially chiral biaryl monophosphine oxides.

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

Nimje, Roshan Y.’s team published research in Organic Process Research & Development in 2021-07-16 | CAS: 343338-28-3

Organic Process Research & Development published new progress about Cyanation. 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.

Nimje, Roshan Y. published the artcileDevelopment of a Stereoselective and Scalable Synthesis for the Potent Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitor, BMT-297376; N-((R)-1-((cis)-4-(3-(Difluoromethyl)-2-methoxypyridin-4-yl)cyclohexyl)propyl)-6-methoxynicotinamide, Quality Control of 343338-28-3, the main research area is difluoromethyl methoxypyridinyl cyclohexyl methoxynicotinamide preparation enantioselective indoleamine dioxygenase inhibitor.

The current work describes a stereoselective and scalable route to N-((R)-1-((cis)-4-(3-(difluoromethyl)-2-methoxypyridin-4-yl)cyclohexyl)propyl)-6-methoxynicotinamide I from readily available 1,4-dioxaspiro[4.5]decan-8-one. The developed process encompasses an efficient 1,4-trans-selective synthesis of (trans)-4-(3-(difluoromethyl)-2-methoxypyridin-4-yl)cyclohexyl methanesulfonate as the key intermediate and the use of Ellman sulfinamine methodol. to install an alkyl amine in a stereoselective manner. Various synthetic routes were screened to accomplish a stereoselective and scalable protocol to access the title compound I. This advancement enabled a competent route to the title compound in an enantioselective, safe, cost-effective, and scalable manner.

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