Tag: 100-200

In 2019,Chemistry – A European Journal included an article by van Leest, Nicolaas P.; Grooten, Lars; van der Vlugt, Jarl Ivar; de Bruin, Bas. Category: amides-buliding-blocks. The article was titled 《Uncatalyzed Oxidative C-H Amination of 9,10-Dihydro-9-Heteroanthracenes: A Mechanistic Study》. The information in the text is summarized as follows:

A new method for the one-step C-H amination of xanthene and thioxanthene with sulfonamides is reported, without the need for any metal catalyst. A benzoquinone was employed as a hydride (or two-electron and one-proton) acceptor. Moreover, a previously unknown and uncatalyzed reaction between iminoiodanes and xanthene, thioxanthene and dihydroacridines (9,10-dihydro-9-heteroanthracenes or dihydroheteroanthracenes) is disclosed. The reactions proceed through hydride transfer from the heteroarene substrate to the iminoiodane or benzoquinone, followed by conjugate addition of the sulfonamide to the oxidized heteroaromatic compounds These findings may have important mechanistic implications for metal-catalyzed C-H amination processes involving nitrene transfer from iminoiodanes to dihydroheteroanthracenes. Due to the weak C-H bond, xanthene is an often-employed substrate in mechanistic studies of C-H amination reactions, which are generally proposed to proceed via metal-catalyzed nitrene insertion, especially for reactions involving nitrene or imido complexes that are less reactive (i.e., less strongly oxidizing). However, these substrates clearly undergo non-catalyzed (proton-coupled) redox coupling with amines, thus providing alternative pathways to the widely assumed metal-catalyzed pathways. In the experiment, the researchers used 4-Methylbenzenesulfonamide(cas: 70-55-3Category: amides-buliding-blocks)

4-Methylbenzenesulfonamide(cas: 70-55-3) belongs to anime. Aniline, ethanolamines, and several other amines are major industrial commodities used in making rubber, dyes, pharmaceuticals, and synthetic resins and fibres and for a host of other applications. Most of the numerous methods for the preparation of amines may be broadly divided into two groups: (1) chemical reduction (replacement of oxygen with hydrogen atoms in the molecule) of members of several other classes of organic nitrogen compounds and (2) reactions of ammonia or amines with organic compounds.Category: amides-buliding-blocks

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

In 2018,Thota, Ganesh Kumar; Sun, Gui-Jun; Deng, Tao; Li, Yi; Kang, Qiang published 《Enantioselective Conjugate Addition of 2-Acylimidazoles with Nitroalkenes Promoted by Chiral-at-Metal Rhodium(III) Complexes》.Advanced Synthesis & Catalysis published the findings.Formula: C4H9NO2 The information in the text is summarized as follows:

An enantioselective conjugate addition of 2-acylimidazoles with nitroalkenes catalyzed by chiral-at-metal rhodium(III) complex under mild reaction conditions was developed, affording versatile γ-nitro ketone skeletons in good yields with excellent enantioselectivities (up to >99% ee).N-Methoxy-N-methylacetamide(cas: 78191-00-1Formula: C4H9NO2) was used in this study.

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. Milder oxidation, using reagents such as NaOCl, can remove four hydrogen atoms from primary amines of the type RCH2NH2 to form nitriles (R―C≡N), and oxidation with reagents such as MnO2 can remove two hydrogen atoms from secondary amines (R2CH―NHR′) to form imines (R2C=NR′). Tertiary amines can be oxidized to enamines (R2C=CHNR2) by a variety of reagents.Formula: C4H9NO2

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

In 2018,Mackman, Richard L.; Steadman, Victoria A.; Dean, David K.; Jansa, Petr; Poullennec, Karine G.; Appleby, Todd; Austin, Carol; Blakemore, Caroline A.; Cai, Ruby; Cannizzaro, Carina; Chin, Gregory; Chiva, Jean-Yves C.; Dunbar, Neil A.; Fliri, Hans; Highton, Adrian J.; Hui, Hon; Ji, Mingzhe; Jin, Haolun; Karki, Kapil; Keats, Andrew J.; Lazarides, Linos; Lee, Yu-Jen; Liclican, Albert; Mish, Michael; Murray, Bernard; Pettit, Simon B.; Pyun, Peter; Sangi, Michael; Santos, Rex; Sanvoisin, Jonathan; Schmitz, Uli; Schrier, Adam; Siegel, Dustin; Sperandio, David; Stepan, George; Tian, Yang; Watt, Gregory M.; Yang, Hai; Schultz, Brian E. published 《Discovery of a potent and orally bioavailable cyclophilin inhibitor derived from the sanglifehrin macrocycle》.Journal of Medicinal Chemistry published the findings.Name: N-Methoxy-N-methylacetamide The information in the text is summarized as follows:

Cyclophilins are a family of peptidyl-prolyl isomerases that are implicated in a wide range of diseases including hepatitis C. Our aim was to discover through total synthesis an orally bioavailable, non-immunosuppressive cyclophilin (Cyp) inhibitor with potent anti-hepatitis C virus (HCV) activity that could serve as part of an all oral antiviral combination therapy. An initial lead (I) derived from the sanglifehrin A macrocycle was optimized using structure based design to produce a potent and orally bioavailable inhibitor (II). The macrocycle ring size was reduced by one atom, and an internal hydrogen bond drove improved permeability and drug-like properties. II demonstrates potent Cyp inhibition (Kd = 5 nM), potent anti-HCV 2a activity (EC50 = 98 nM), and high oral bioavailability in rat (100%) and dog (55%). The synthetic accessibility and properties of II support its potential as an anti-HCV agent and for interrogating the role of Cyp inhibition in a variety of diseases. In the experimental materials used by the author, we found N-Methoxy-N-methylacetamide(cas: 78191-00-1Name: N-Methoxy-N-methylacetamide)

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. The reaction of alkyl halides, R―X, where X is a halogen, or analogous reagents with ammonia (or amines) is useful with certain compounds. Not all alkyl halides are effective reagents; the reaction is sluggish with secondary alkyl groups and fails with tertiary ones. Its usefulness is largely confined to primary alkyl halides (those having two hydrogen atoms on the reacting site).Name: N-Methoxy-N-methylacetamide

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

The author of 《Mild Access to N-Formylation of Primary Amines using Ethers as C1 Synthons under Metal-Free Conditions》 were Mutra, Mohana Reddy; Dhandabani, Ganesh Kumar; Wang, Jeh-Jeng. And the article was published in Advanced Synthesis & Catalysis in 2018. Application of 4746-61-6 The author mentioned the following in the article:

A new synthetic protocol for the synthesis of N-formamide derivatives HC(O)NHR1 [R1 = C6H5, 3-ClC6H4, 3-NO2C6H4, etc.] was developed via N-formylation of primary amines using ethers as a C1 synthon under metal-free reaction conditions. The reaction was proceeded through C-H functionalization, C-O cleavage and C-N bond formation. Mechanistic studies disclosed that the reaction proceeds through a radical pathway. Synthesis of amino ethanones PhNHCH(R4)C(O)R2 [R2 = C6H5, 3-MeC6H4, 4-BrC6H4; R3 = tetrahydrofuran-2-yl, 1,4-dioxan-2-yl] were developed via α-alkylation of α-amino ketones with ethers. By replacing dioxane with Tetramethylethylenediamine (TMEDA) under standard conditions also gave the N-formamide derivatives HC(O)NHR1 in moderate yields. After reading the article, we found that the author used 2-Hydroxy-N-phenylacetamide(cas: 4746-61-6Application of 4746-61-6)

2-Hydroxy-N-phenylacetamide(cas: 4746-61-6) belongs to amides.Application of 4746-61-6 The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds.

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

Fiakpui, Charles Y.; Knaus, Edward E. published an article in Canadian Journal of Chemistry. The title of the article was 《An improved synthesis of 1,3-dihydro-1-methyl-5-phenyl-2H-pyrido[3,4-e]-1,4-diazepin-2-one via ortho-directed lithiation of 3-[(tert-butylcarbonyl)- and 3-[(tert-butoxycarbonyl)amino)pyridine]》.Formula: C10H14N2O The author mentioned the following in the article:

The ortho-directed lithiation of the title compounds I (R = CMe3, OCMe3) with alkyllithiums and benzoylation with PhCONEt2 followed by acid hydrolysis gave 63-66% 3-amino-4-benzoylpyridine (II). Amidation of R1NHCH2CO2H (R1 = PhCH2O2C, Me3CO2C) with II afforded[[(aminomethyl)carbonyl]amino]benzoylpyridines III (same R1). Acid-catalyzed hydrolysis and cyclocondensation of III, followed by methylation gave pyridodiazepinone IV in 36% overall yield from I.2,2-Dimehtyl-N-pyridin-3-yl-propionamide(cas: 70298-88-3Formula: C10H14N2O) was used in this study.

2,2-Dimehtyl-N-pyridin-3-yl-propionamide(cas: 70298-88-3) 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.Formula: C10H14N2O

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

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