Category: amides-buliding-blocks

SDS of cas: 70-55-3In 2020 ,《Electrically-driven N(sp2)-C(sp2/3) bond cleavage of sulfonamides》 was published in ACS Sustainable Chemistry & Engineering. The article was written by Wetzel, Annica; Jones, Alan M.. The article contains the following contents:

The discovery and development of an unexpected elec.-driven N(sp2)-C(sp3) and N(sp2)-C(sp2) bond cleavage reaction alongside dehydrogenative C-O bond coupling reactions both in batch and flow conditions was reported. Intramol. trapping experiments with the diuretic hydrochlorothiazide, gave insight into the intermediacy of an N-sulfonyliminium ion en route to the related drug, chlorothiazide. Using only electrons as the oxidant, this was a green and sustainable technol. advance for sulfonamide deprotection chem. and drug metabolism studies.4-Methylbenzenesulfonamide(cas: 70-55-3SDS of cas: 70-55-3) was used in this study.

4-Methylbenzenesulfonamide(cas: 70-55-3) belongs to anime. To avoid the problem of multiple alkylation, methods have been devised for “blocking” substitution so that only one alkyl group is introduced. The Gabriel synthesis is one such method; it utilizes phthalimide, C6H4(CO)2NH, whose one acidic hydrogen atom has been removed upon the addition of a base such as KOH to form a salt.SDS of cas: 70-55-3

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

Sheng, Tao; Zhuang, Zhe; Wang, Zhen; Hu, Liang; Herron, Alastair N.; Qiao, Jennifer X.; Yu, Jin-Quan published an article in 2022. The article was titled 《One-Step Synthesis of β-Alkylidene-γ-lactones via Ligand-Enabled β,γ-Dehydrogenation of Aliphatic Acids》, and you may find the article in Journal of the American Chemical Society.Name: N-Methoxy-N-methylacetamide The information in the text is summarized as follows:

Ligand-enabled Pd-catalyzed regioselective α,β-dehydrogenation of carbonyl compounds via β-methylene C-H activation has recently emerged as a promising transformation. Herein, authors report the realization of β,γ-dehydrogenation and subsequent vinyl C-H olefination reactions of free carboxylic acids, thus providing a unique method for the structural diversification of aliphatic acids containing α-quaternary centers through sequential functionalizations of two β-C-H bonds and one γ-C-H bond. This tandem dehydrogenation-olefination-lactonization reaction offers a one-step preparation of β-alkylidene-γ-lactones, which are often difficult to prepare through conventional methods, from inexpensive and abundant free aliphatic acids. A variety of free aliphatic acids, such as isosteviol and grandiflorolic acid natural products, and olefins are compatible with the reported protocol. The newly designed bidentate oxime ether-pyridone and morpholine-pyridone ligands are crucial for this tandem reaction to proceed. Notably, these ligands also enable preferential methylene C-H activation over the previously reported, competing process of Me C-H bond olefination. In addition to this study using N-Methoxy-N-methylacetamide, there are many other studies that have used N-Methoxy-N-methylacetamide(cas: 78191-00-1Name: N-Methoxy-N-methylacetamide) was used in this study.

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. Large quantities of aliphatic amines are made synthetically. The most widely used industrial method is the reaction of alcohols with ammonia at a high temperature, catalyzed by metals or metal oxide catalysts (e.g., nickel or copper). Mixtures of primary, secondary, and tertiary amines are thereby produced.Name: N-Methoxy-N-methylacetamide

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

Hu, Yanhua; Zhang, Zhenfeng; Liu, Yangang; Zhang, Wanbin published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《Cobalt-Catalyzed Chemo- and Enantioselective Hydrogenation of Conjugated Enynes》.SDS of cas: 78191-00-1 The article contains the following contents:

Asym. hydrogenation is one of the most powerful methods for the preparation of single enantiomer compounds However, the chemo- and enantioselective hydrogenation of the relatively inert unsaturated group in substrates possessing multiple unsaturated bonds remains a challenge. We herein report a protocol for the highly chemo- and enantioselective hydrogenation of conjugated enynes while keeping the alkynyl bond intact. Mechanism studies indicate that the accompanying Zn2+ generated from zinc reduction of the CoII complex plays a critical role to initiate a plausible CoI/CoIII catalytic cycle. This approach allows for the highly efficient generation of chiral propargylamines (up to 99.9% ee and 2000 S/C) and further useful chem. transformations. In the experiment, the researchers used N-Methoxy-N-methylacetamide(cas: 78191-00-1SDS of cas: 78191-00-1)

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. Amine, any member of a family of nitrogen-containing organic compounds that is derived, either in principle or in practice, from ammonia (NH3). Naturally occurring amines include the alkaloids, which are present in certain plants; the catecholamine neurotransmitters (i.e., dopamine, epinephrine, and norepinephrine); and a local chemical mediator, histamine, that occurs in most animal tissues.SDS of cas: 78191-00-1

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

《Developmental toxicity of disinfection by-product monohaloacetamides in embryo-larval stage of zebrafish》 was published in Ecotoxicology and Environmental Safety in 2020. These research results belong to Ding, Xinliang; Zhu, Jingying; Zhang, Jie; Dong, Tianyu; Xia, Yankai; Jiao, Jiandong; Wang, Xinru; Zhou, Weijie. Quality Control of 2-Bromoacetamide The article mentions the following:

Developmental toxicity of disinfection byproduct monohaloacetamides in embryo-larval stage of zebrafish. Results showed that 80 mg/L CAcAm and 40 mg/L BAcAm significantly decreased the hatching rate, IAcAm decreased the hatching rate and delayed the hatching process in a concentration-dependent manner with an EC50 of 16.37 mg/L at 72 hpf. The frequency and severity order of morphol. abnormalities increased with the raised exposure concentrations and prolonged exposure time, and the corresponding EC50 at 96 hpf were 21.10, 9.77 and 16.60 mg/L for CAcAm, BAcAm and IAcAm, resp. MonoHAcAms exposure resulted in a time- and dose-dependent response in mortality and the calculated LC50 at 72 hpf were 38.44, 17.74 and 28.82 mg/L for CAcAm, BAcAm and IAcAm, resp. Based on EC50 for morphol. abnormalities and LC50, a toxicity rank order of BAcAm > IAcAm > CAcAm was observed Different degrees of hyperactivity and hypoactivity were observed from locomotor behavior anal. in larvae from ≤10.0 mg/L monoHAcAms exposure groups. The light-dark periodic change was disappeared in larvae of 10.0 mg/L BAcAm exposure group. In summary, our study showed that monoHAcAms were developmentally toxic to zebrafish even at very low concentrations and BAcAm exerted higher toxicity than IAcAm and CAcAm. These results will further our understanding of the toxicity of HAcAms and its potential toxicol. impact on human and ecol. environment. The results came from multiple reactions, including the reaction of 2-Bromoacetamide(cas: 683-57-8Quality Control of 2-Bromoacetamide)

2-Bromoacetamide(cas: 683-57-8) can be used in preparation of (2-carbamoylmethoxy-5-chloro-benzyl)-carbamic acid tert-butyl ester. It was aslo used as precursor to dehydropeptidase I inactivator.Quality Control of 2-Bromoacetamide

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

《Benzothiophene-2-carboxamide derivatives as SENPs inhibitors with selectivity within SENPs family》 was published in European Journal of Medicinal Chemistry in 2020. These research results belong to Wang, Zhongli; Liu, Yunqi; Zhang, Jianchen; Ullah, Shafi; Kang, Ning; Zhao, Yaxue; Zhou, Huchen. Reference of 2-Bromoacetamide The article mentions the following:

The SUMO (small ubiquitin-related modifier)-specific proteases (SENPs) are responsible for the cleavage of SUMO from its target proteins, thus play important roles in the dynamic SUMOylation and deSUMOylation processes. SENPs are related to a variety of human diseases including cancer and represent a new class of potential therapeutic targets with mechanism of action that is likely to be different from that of current clin. used drugs. However, potent inhibitors that are selective within the SENPs family members still remain a challenge due to their high homol. In order to demonstrate the feasibility of developing selective inhibitors within the SENPs family, we chose SENP1/2/5 as representatives, aiming to identify inhibitors with selectivity among the members. Starting from a hit compound ZCL951 from virtual screening, a series of benzothiophene-2-carboxamide inhibitors were designed based on the protein structures of SENP1, 2, and 5. First, an unoccupied hydrophobic pocket was first identified which led to IC50 as low as 0.56 μM. Furthermore, the ethylacetate 77 gave both submicromolar inhibitory activity and 33-fold selectivity for SENP2 vs. SENP5. They are the most potent and selective nonpeptidic inhibitor reported so far for the SENPs family, as far as we are aware. Their structure-activity relationship was also discussed. The results came from multiple reactions, including the reaction of 2-Bromoacetamide(cas: 683-57-8Reference of 2-Bromoacetamide)

2-Bromoacetamide(cas: 683-57-8) can be used in preparation of (2-carbamoylmethoxy-5-chloro-benzyl)-carbamic acid tert-butyl ester. It was aslo used as precursor to dehydropeptidase I inactivator.Reference of 2-Bromoacetamide

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

The author of 《Manganese-Catalyzed N-Alkylation of Sulfonamides Using Alcohols》 were Reed-Berendt, Benjamin G.; Morrill, Louis C.. And the article was published in Journal of Organic Chemistry in 2019. HPLC of Formula: 70-55-3 The author mentioned the following in the article:

An efficient manganese-catalyzed N-alkylation of sulfonamides has been developed. This borrowing hydrogen approach employs a well-defined and bench-stable Mn(I) PNP pincer precatalyst, allowing benzylic and simple primary aliphatic alcs. to be employed as alkylating agents. A diverse range of aryl and alkyl sulfonamides undergoes mono-N-alkylation in excellent isolated yields (32 examples, 85% average yield). After reading the article, we found that the author used 4-Methylbenzenesulfonamide(cas: 70-55-3HPLC of Formula: 70-55-3)

4-Methylbenzenesulfonamide(cas: 70-55-3) belongs to anime.Typically the presence of an amine functional group is deduced by a combination of techniques, including mass spectrometry as well as NMR and IR spectroscopies. 1H NMR signals for amines disappear upon treatment of the sample with D2O. In their infrared spectrum primary amines exhibit two N-H bands, whereas secondary amines exhibit only one.HPLC of Formula: 70-55-3

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

In 2019,Journal of the American Chemical Society included an article by Chen, Pan-Pan; Lucas, Erika L.; Greene, Margaret A.; Zhang, Shuo-Qing; Tollefson, Emily J.; Erickson, Lucas W.; Taylor, Buck L. H.; Jarvo, Elizabeth R.; Hong, Xin. Product Details of 70-55-3. The article was titled 《A Unified Explanation for Chemoselectivity and Stereospecificity of Ni-Catalyzed Kumada and Cross-Electrophile Coupling Reactions of Benzylic Ethers: A Combined Computational and Experimental Study》. The information in the text is summarized as follows:

Ni-catalyzed C(sp3)-O bond activation provides a useful approach to synthesize enantioenriched products from readily available enantioenriched benzylic alc. derivatives The control of stereospecificity is key to the success of these transformations. To elucidate the reversed stereospecificity and chemoselectivity of Ni-catalyzed Kumada and cross-electrophile coupling reactions with benzylic ethers, a combined computational and exptl. study is performed to reach a unified mechanistic understanding. Kumada coupling proceeds via a classic cross-coupling mechanism. Initial rate-determining oxidative addition occurs with stereoinversion of the benzylic stereogenic center. Subsequent transmetalation with the Grignard reagent and syn-reductive elimination produce the Kumada coupling product with overall stereoinversion at the benzylic position. The cross-electrophile coupling reaction initiates with the same benzylic C-O bond cleavage and transmetalation to form a common benzylnickel intermediate. However, the presence of the tethered alkyl chloride allows a facile intramol. SN2 attack by the benzylnickel moiety. This step circumvents the competing Kumada coupling, leading to the excellent chemoselectivity of cross-electrophile coupling. These mechanisms account for the observed stereospecificity of the Kumada and cross-electrophile couplings, providing a rationale for double inversion of the benzylic stereogenic center in cross-electrophile coupling. The improved mechanistic understanding will enable design of stereoselective transformations involving Ni-catalyzed C(sp3)-O bond activation. The experimental process involved the reaction of 4-Methylbenzenesulfonamide(cas: 70-55-3Product Details of 70-55-3)

4-Methylbenzenesulfonamide(cas: 70-55-3) belongs to anime. Nitrous acid converts secondary amines (aliphatic or aromatic) to N-nitroso compounds (nitrosamines): R2NH + HNO2 → R2N―NO. Some nitrosamines are potent cancer-inducing substances, and their possible formation is a serious consideration when nitrites, which are salts of nitrous acid, are present in foods or pharmaceutical preparations. Tertiary amines give rise to nitrosamines more slowly; an alkyl group is eliminated as an aldehyde or ketone, along with nitrous oxide, N2O.Product Details of 70-55-3

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

In 2018,Wessig, Pablo; John, Leonard; Mertens, Monique published 《Extending the Class of [1,3]-Dioxolo[4.5-f]benzodioxole (DBD) Fluorescent Dyes》.European Journal of Organic Chemistry published the findings.COA of Formula: C4H9NO2 The information in the text is summarized as follows:

Synthetic routes to a collection of new fluorescent dyes are described, which are based on the [1,3]-dioxolo[4.5-f]benzodioxole (DBD) core. By introducing different electron withdrawing groups in 4- and 8-position of the DBD moiety the emission wavelength could be adjusted over a large spectral range from blue to orange light. In the experimental materials used by the author, we found N-Methoxy-N-methylacetamide(cas: 78191-00-1COA of Formula: C4H9NO2)

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. Many important products require amines as part of their syntheses. Methylamine is utilized in the production of the analgesic meperidine (trade name Demerol) and the photographic developer Metol (trademark), and dimethylamine is used in the synthesis of the antihistamine diphenhydramine (trade name Benadryl), the solvent dimethylformamide (DMF), and the rocket propellant 1,1-dimethylhydrazine. The synthesis of the insect repellent N,N-diethyl-m-toluamide (DEET) incorporates diethylamine while that of the synthetic fibre Kevlar requires aromatic amines.COA of Formula: C4H9NO2

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

In 2017,Diehl, Julian; Brueckner, Reinhard published 《Synthesis of Enantiomerically Pure β-Hydroxy Ketones via β-Keto Weinreb Amides by a Condensation/Asymmetric-Hydrogenation/Acylation Sequence》.European Journal of Organic Chemistry published the findings.Product Details of 78191-00-1 The information in the text is summarized as follows:

An established route to enantiomerically pure β-hydroxy ketones proceeds through the asym. hydrogenation of β-keto esters, an ester/amide exchange, and the use of the resulting β-hydroxy amide for the acylation of an organometallic compound The authors shortened this route by showing that β-keto Weinreb amides are hydrogenated with up to 99% ee in the presence of [Me2NH2]+{[RuCl(S)-BINAP]2(μ-Cl)3}- (0.5 mol-%) at room temperature/5 bar. These Weinreb amides were prepared by seemingly obvious yet unprecedented condensations of lithiated N-methoxy-N-methylacetamide with carboxylic chlorides (51-87% yield). The resulting β-hydroxy Weinreb amides were used for the acylation of organolithium and Grignard reagents. They thus gave enantiomerically pure β-hydroxy ketones (28 examples). A selection of these compounds gave anti-1,3-diols after another C:O bond hydrogenation, or syn-1,3-diols by a Narasaka-Prasad reduction In the experiment, the researchers used N-Methoxy-N-methylacetamide(cas: 78191-00-1Product Details of 78191-00-1)

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. Amine, any member of a family of nitrogen-containing organic compounds that is derived, either in principle or in practice, from ammonia (NH3). Naturally occurring amines include the alkaloids, which are present in certain plants; the catecholamine neurotransmitters (i.e., dopamine, epinephrine, and norepinephrine); and a local chemical mediator, histamine, that occurs in most animal tissues.Product Details of 78191-00-1

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

In 2016,Harjani, Jitendra R.; Yap, Beow Keat; Leung, Eleanor W. W.; Lucke, Andrew; Nicholson, Sandra E.; Scanlon, Martin J.; Chalmers, David K.; Thompson, Philip E.; Norton, Raymond S.; Baell, Jonathan B. published 《Design, Synthesis, and Characterization of Cyclic Peptidomimetics of the Inducible Nitric Oxide Synthase Binding Epitope That Disrupt the Protein-Protein Interaction Involving SPRY Domain-Containing Suppressor of Cytokine Signaling Box Protein (SPSB) 2 and Inducible Nitric Oxide Synthase》.Journal of Medicinal Chemistry published the findings.Application of 71432-55-8 The information in the text is summarized as follows:

SPRY domain-containing suppressor of cytokine signaling box protein (SPSB) 2-deficient macrophages have been found to exhibit prolonged expression of inducible nitric oxide synthase (iNOS) and enhanced killing of persistent pathogens, suggesting that inhibitors of the SPSB2-iNOS interaction have potential as novel anti-infectives. In this study, we describe the design, synthesis, and characterization of cyclic peptidomimetic inhibitors of the SPSB2-iNOS interaction constrained by organic linkers to improve stability and druggability. SPR, ITC, and 19F NMR analyses revealed that the most potent cyclic peptidomimetic bound to the iNOS binding site of SPSB2 with low nanomolar affinity (KD 29 nM), a 10-fold improvement over that of the linear peptide DINNN (KD 318 nM), and showed strong inhibition of SPSB2-iNOS interaction in macrophage cell lysates. This study exemplifies a novel approach to cyclize a Type II β-turn linear peptide and provides a foundation for future development of this group of inhibitors as new anti-infectives. In the experiment, the researchers used tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8Application of 71432-55-8)

tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8) belongs to anime. Amine, any member of a family of nitrogen-containing organic compounds that is derived, either in principle or in practice, from ammonia (NH3). Naturally occurring amines include the alkaloids, which are present in certain plants; the catecholamine neurotransmitters (i.e., dopamine, epinephrine, and norepinephrine); and a local chemical mediator, histamine, that occurs in most animal tissues.Application of 71432-55-8

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