Category: amides-buliding-blocks

Design, synthesis and biological activity of ethyl 2-(N-substituted-arylsulfonamido)-2-oxo-acetate was written by Wang, Bao-lei;Wu, Jing;He, Feng-qi;Li, Yong-hong;Li, Zheng-ming. And the article was included in Chemical Research in Chinese Universities in 2008.Electric Literature of C9H13NO2S This article mentions the following:

Thirteen new Et 2-(N-substituted-arylsulfonamido)-2-oxo-acetates, based on the structure of ketol-acid reductoisomerase (KARI) inhibitor IpOHA, were designed and synthesized. Their structures were established on the basis of ¹H NMR, IR, MS, and elemental analyses. The bioassay result reveals that the structural changes from hydroxyl group on the N atom of IpOHA to arylsulfonyl groups does not enhance the inhibitory activity of the compounds to KARI in vitro. Compounds 2-(N-isopropyl/phenyl/p-chlorophenyl-(2-nitrophenyl/p-methylphenyl/phenyl)sulfonamido)-2-oxo-acetates are more effective than IpOHA against the monocotyledonous barnygrass at 100 μg/mL in herbicidal tests. In the experiment, the researchers used many compounds, for example, N-Isopropylbenzenesulfonamide (cas: 5339-69-5Electric Literature of C9H13NO2S).

N-Isopropylbenzenesulfonamide (cas: 5339-69-5) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. Amides can be recrystallised from large quantities of water, ethanol, ethanol/ether, aqueous ethanol, chloroform/toluene, chloroform or acetic acid. The likely impurities are the parent acids or the alkyl esters from which they have been made. The former can be removed by thorough washing with aqueous ammonia followed by recrystallisation, whereas elimination of the latter is by trituration or recrystallisation from an organic solvent.Electric Literature of C9H13NO2S

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

One-pot sequential combination of multi-component and multi-catalyst: synthesis of 5-aminobenzofurans from aminophenol and ketene acetals was written by Yang, Cheng-Wen;Bai, Yue-Xia;Zhang, Ni-Tao;Zeng, Cheng-Chu;Hu, Li-Ming;Tian, Hong-Yu. And the article was included in Tetrahedron in 2012.Electric Literature of C13H13NO3S This article mentions the following:

The reaction between p-aminophenols and various ketene acetals in the presence of hypervalent iodine is described. The results show that 2- and 3-substituted 5-sulfonamidobenzofurans, e.g., I, are obtained in moderate to good yields from p-aminophenols and ketene acetals. In the experiment, the researchers used many compounds, for example, N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6Electric Literature of C13H13NO3S).

N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6) belongs to amides. Amides can be viewed as a derivative of a carboxylic acid RC(=O)OH with the hydroxyl group –OH replaced by an amine group −NR′R″; or, equivalently, an acyl (alkanoyl) group RC(=O)− joined to an amine group. The presence of the amide group –C(=O)N– is generally easily established, at least in small molecules. It can be distinguished from nitro and cyano groups in IR spectra. Amides exhibit a moderately intense νCO band near 1650 cm−1. By 1H NMR spectroscopy, CONHR signals occur at low fields. In X-ray crystallography, the C(=O)N center together with the three immediately adjacent atoms characteristically define a plane.Electric Literature of C13H13NO3S

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

Design of inhibitors from the three-dimensional structure of alcohol dehydrogenase. Chemical synthesis and enzymic properties was written by Freudenreich, Charles;Samama, Jean Pierre;Biellmann, Jean Francois. And the article was included in Journal of the American Chemical Society in 1984.Category: amides-buliding-blocks This article mentions the following:

Inhibitors of liver alc. dehydrogenase were designed from the 3-dimensional structure of the enzyme. The ligand to the catalytic Zn(II) is an amide group or, better, a formamide group. With the latter function, a H-bond between the NH groups and the hydroxyl group of serine-48 may be formed. The hydrophobic substrate binding site brings structural restraints. α-ω Bifunctional mols. show good inhibitory properties possibly due to the interactions with polar residues at the entrance of the substrate. In the experiment, the researchers used many compounds, for example, 2-(2-Chlorophenyl)acetamide (cas: 10268-06-1Category: amides-buliding-blocks).

2-(2-Chlorophenyl)acetamide (cas: 10268-06-1) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. Amides can be recrystallised from large quantities of water, ethanol, ethanol/ether, aqueous ethanol, chloroform/toluene, chloroform or acetic acid. The likely impurities are the parent acids or the alkyl esters from which they have been made. The former can be removed by thorough washing with aqueous ammonia followed by recrystallisation, whereas elimination of the latter is by trituration or recrystallisation from an organic solvent.Category: amides-buliding-blocks

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

PEGylated ethyl cellulose micelles as a nanocarrier for drug delivery was written by Singam, Amarnath;Killi, Naresh;Patel, Pratikshkumar R.;Gundloori, Rathna V. N.. And the article was included in RSC Advances in 2021.Product Details of 2387-23-7 This article mentions the following:

Natural polymers provide a better alternative to synthetic polymers in the domain of drug delivery systems (DDSs) because of their renewability, biocompatibility, and low immunogenicity; therefore, they are being studied for the development of bulk/nanoformulations. Likewise, current methods for engineering natural polymers into micelles are in their infancy, and in-depth studies are required using natural polymers as controlled DDSs. Accordingly, in our present study, a new micellar DDS was synthesized using Et cellulose (EC) grafted with polyethylene glycol (PEG); it was characterized, its properties, cell toxicity, and hemocompatibility were evaluated, and its drug release kinetics were demonstrated using doxorubicin (DOX) as a model drug. Briefly, EC was grafted with PEG to form the amphiphilic copolymers EC-PEG1 and EC-PEG2 with varying PEG concentrations, and nano-micelles were prepared with and without the drug (DOX) via a dialysis method; the critical micelle concentrations (CMCs) were recorded to be 0.03 mg mL-1 and 0.00193 mg mL-1 for EC-PEG1 and EC-PEG2, resp. The physicochem. properties of the resp. nano-micelles were evaluated via various characterization techniques. The morphologies of the nano-micelles were analyzed via transmission electron microscopy (TEM), and the average size of the nano-micelles was recorded to be ∼80 nm. In vitro, drug release studies were done for 48 h, where 100% DOX release was recorded at pH 5.5 and 52% DOX release was recorded at pH 7.4 from the micelles. In addition, cytotoxicity studies suggested that DOX-loaded micelles were potent in killing MDA-MB-231 and MCF-7 cancer cells, and the blank micelles were non-toxic toward cancerous and normal cells. A cellular uptake study via fluorescence microscopy indicated the internalization of DOX-loaded micelles by cancer cells, delivering the DOX into the cellular compartments. Based on these studies, we concluded that the developed material should be studied further via in vivo studies to understand its potential as a controlled DDS to treat cancer. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Product Details of 2387-23-7).

1,3-Dicyclohexylurea (cas: 2387-23-7) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. Amides can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Product Details of 2387-23-7

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

Microbicidal action of heat, detergents and active oxygen bleach as components of laundry hygiene was written by Brands, Britta;Brinkmann, Angelina;Bloomfield, Sally;Bockmuehl, Dirk P.. And the article was included in Tenside, Surfactants, Detergents in 2016.Application In Synthesis of N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) This article mentions the following:

It is known that decreasing temperatures in laundry can have a significant impact on the hygiene efficacy of laundering. This study used suspension tests to investigate the microbicidal effects of heat, detergent, and activated oxygen bleach and their contributions to laundry hygiene. Heat at 60° contributes significantly to the microbicidal action, while detergent only has limited effects. Activated oxygen bleach strongly enhances the microbicidal action and thus has the potential to compensate for the loss of antimicrobial efficacy due to temperature decrease. This effect varied with the test strain and the temperature, and further work is needed to determine whether it is possible to achieve a hygiene effectiveness equivalent to that at 60° across both fungal and bacterial strains. In the experiment, the researchers used many compounds, for example, N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) (cas: 10543-57-4Application In Synthesis of N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide)).

N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) (cas: 10543-57-4) belongs to amides. 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. Tertiary amides, with the important exception of N,N-dimethylformamide, exhibit low solubility in water. Amides can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Application In Synthesis of N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide)

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

Carbonylative C-C Bond Activation of Aminocyclopropanes Using a Temporary Directing Group Strategy was written by Wang, Gang-Wei;Sokolova, Olga O.;Young, Tom. A.;Christodoulou, Ektor M. S.;Butts, Craig P.;Bower, John F.. And the article was included in Journal of the American Chemical Society in 2020.Reference of 2387-23-7 This article mentions the following:

Temporary directing groups (TDGs) underpin a range of C-C bond activation methodologies; however, the use of TDGs for the regiocontrolled activation of cyclopropane C-C bonds is underdeveloped. In this report, we show how an unusual ring contraction process can be harnessed for TDG-based carbonylative C-C bond activations of cyclopropanes. The method involves the transient installation of an isocyanate-derived TDG, rather than relying on carbonyl condensation events as used in previous TDG-enabled C-C bond activations. For example, carbonylative ring expansion and contraction of nonracemic cyclopropylurea I yielded nonracemic lactam II. The carbonylative C-C activation reaction was used in tandem with Pictet-Spengler, intramol. Diels-Alder, and alkene-alkyne coupling reactions to yield fused lactams such as III, IV, and V. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Reference of 2387-23-7).

1,3-Dicyclohexylurea (cas: 2387-23-7) belongs to amides. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. Ionic, or saltlike, amides are strongly alkaline compounds ordinarily made by treating ammonia, an amine, or a covalent amide with a reactive metal such as sodium.Reference of 2387-23-7

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

Occurrences of Tire Rubber-Derived Contaminants in Cold-Climate Urban Runoff was written by Challis, J. K.;Popick, H.;Prajapati, S.;Harder, P.;Giesy, J. P.;McPhedran, K.;Brinkmann, M.. And the article was included in Environmental Science & Technology Letters in 2021.Application of 2387-23-7 This article mentions the following:

Recent findings that 2-anilo-5-[(4-methylpentan-2-yl)amino]cyclohexa-2,5-diene-1,4-dione (6PPD-quinone), the transformation product of a common tire rubber antioxidant, is acutely toxic in stormwater-impacted streams has highlighted the need for a better understanding of contaminants in urban runoff. This study represents one of the first reports of 6PPD-quinone and other tire rubber-derived compounds in stormwater and snowmelt of a cold-climate Canadian city (Saskatoon, 2019-2020). Semiquantification of the five target compounds, N,N′-diphenylguanidine (DPG), N,N-dicyclohexylmethylamine (DCA), N,N′-dicyclohexylurea (DCU), 1-cyclohexyl-3-phenylurea (CPU), and 6PPD-quinone, revealed DPG was most abundant, with average concentrations of 60 μg L^-1 in stormwater and 1 μg L^-1 in snowmelt. Maximum observed concentrations of DPG were greater than 300 μg L^-1, equivalent to loadings of 15 kg from a single rain event. These concentrations of DPG represent some of the highest reported in urban runoff globally. 6PPD-Quinone was detected in 57% (12/21) of stormwater samples with a mean concentration of approx. 600 ng L-1 (2019) and greater than 80% (28/31) of snowmelt samples with mean concentrations of 80-370 ng L-1 (2019 and 2020). Concentrations of 6PPD-quinone exceeded the acute LC₅₀ for coho salmon (0.8-1.2 μg L^-1) in greater than 20% of stormwater samples. Mass loadings of all target chems. correlated well with roads and residential land-use area. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Application of 2387-23-7).

1,3-Dicyclohexylurea (cas: 2387-23-7) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. Amides are stable compounds. The lower-melting members (such as acetamide) can be readily purified by fractional distillation. Most amides are solids which have low solubilities in water.Application of 2387-23-7

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

Parallel synthesis of 1,2,3-thiadiazoles employing a “Catch and Release” strategy was written by Hu, Yonghan;Baudart, Sylvie;Porco, John A. Jr.. And the article was included in Journal of Organic Chemistry in 1999.COA of Formula: C9H10BrNO2 This article mentions the following:

A very efficient hybrid solution-/solid phase sequence for the synthesis of 1,2,3-thiadiazoles employing “resin capture” of ketones without the need for chromatog. was developed. Cyclative cleavage of resin-bound sulfonylhydrazones was accomplished using thionyl chloride to afford 1,2,3-thiadiazoles. Stille coupling of resin-bound intermediates was also demonstrated. In the experiment, the researchers used many compounds, for example, 4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2COA of Formula: C9H10BrNO2).

4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. Amides are not in general accessible by the direct condensation of amines with carboxylic acids for two reasons: first, both components are readily deactivated by a transfer of a proton from the acid to the amine and second, the hydroxy unit on the carbonyl of the acid is a relatively poor leaving group. Nevertheless, the formation of five- and six-membered rings is often surprisingly simple provided that other factors can be brought into play to assist in the condensation.COA of Formula: C9H10BrNO2

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

Heterogeneous Pd-Catalyzed Efficient Synthesis of Imidazolones via Dehydrogenative Condensation between Ureas and 1,2-Diols was written by Arango-Daza, Juan Camilo;Lluna-Galan, Carles;Izquierdo-Aranda, Luis;Cabrero-Antonino, Jose R.;Adam, Rosa. And the article was included in ACS Catalysis in 2022.Application of 2387-23-7 This article mentions the following:

A heterogeneously catalyzed protocol for the acceptorless dehydrogenative condensation between N,N’-disubstituted ureas and 1,2-diols to afford imidazolones was developed. Palladium nanoaggregates stabilized onto an alumina matrix with suitable acidic properties, namely, [Pd/Al2O3], was designed and successfully applied as efficient and reusable heterogeneous nanocatalyst for this relevant transformation. The methodol. developed showed its wide applicability through the synthesis of more than 25 imidazolones with moderate to good yields, reaching a turnover number (TON) of up to 19444 and a initial turnover frequency (TOF₀) > 290 h^-1. The active nanostructured catalyst was fully characterized [X-ray diffraction (XRD), high-resolution transmission electron microscopy (HR-TEM), high-resolution scanning transmission electron microscopy (HR-STEM), energy-dispersive X-ray (EDX), Raman spectroscopy, temperature-programmed reduction (TPR), temperature-programmed desorption (TPD)-NH3, TPD-CO2, XPS, Brunauer-Emmett-Teller (BET) area], and mechanistic studies were performed. Moreover, other related Pd-based nanomaterials composed of different acidic or basic inorganic supports were synthesized and extensively compared in this reaction. These studies revealed that the presence of Pd nanoparticles with a wide range of sizes (average particle size 2.8 nm) over a metal oxide support with a high d. of acid sites is a key point for the good activity of the material, γ-Al₂O₃ being the optimum support. Furthermore, a Pd-Zn cooperation effect was described for the dehydrogenative condensation of unactivated 1,2-diols, including ethylene glycol, with ureas. Two Pd-Zn bimetallic materials ([Pd/ZnO] and [Pd(5%)-Zn(5%)/A_l2O₃]) were also designed and characterized properly. These materials, as well as the [Pd/Al₂O₃] system in combination with catalytic amounts of ZnO, showed good activity and selectivity in the acceptorless dehydrogenative condensation between ureas and unactivated 1,2-diols. The heterogeneous nature of all of the described catalytic systems was demonstrated, and the reusability of the catalysts was proven. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Application of 2387-23-7).

1,3-Dicyclohexylurea (cas: 2387-23-7) belongs to amides. Amides can be viewed as a derivative of a carboxylic acid RC(=O)OH with the hydroxyl group –OH replaced by an amine group −NR′R″; or, equivalently, an acyl (alkanoyl) group RC(=O)− joined to an amine group. Amides can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Application of 2387-23-7

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

Mechanochemical Divergent Syntheses of Oxindoles and α-Arylacylamides via Controllable Construction of C-C and C-N Bonds by Copper and Piezoelectric Materials was written by Lv, Honggui;Xu, Xinyue;Li, Jing;Huang, Xiaobo;Fang, Guoyong;Zheng, Lifei. And the article was included in Angewandte Chemie, International Edition in 2022.HPLC of Formula: 5339-69-5 This article mentions the following:

The divergent syntheses of α-arylacylamides Ar(C)R¹R²C(O)NHAr/Alkyl (Ar = Ph, 2,3-dihydro-1-benzofuran-5-yl, naphthalen-1-yl, thiophen-2-yl, etc.; R¹ = Me, H; R² = Me, F; R¹R² = cyclobutyl; Alkyl = Me, 2-methylpropyl, butyl) and oxindoles I (R³ = Me; R⁴ = Me; R³R⁴ = cyclobutyl; Alkyl = Me, 2-methylpropyl) via mechanoredox chem. by using easily accessible α-bromo N-sulfonyl amides ArS(O)₂(N)alkylC(O)CR²R³X as starting materials were present. The system consists of a catalytic amount of Cu^II precatalyst and piezoelec. materials. The highly polarized BaTiO₃ or PbTiO₃ under mech. agitation can act as an electron donor to realize the recycling of Cu^II and Cu^I. Control experiments and d. functional theory calculations have been performed to support the proposed mechanistic rationale for the cascade reactions. In the experiment, the researchers used many compounds, for example, N-Isopropylbenzenesulfonamide (cas: 5339-69-5HPLC of Formula: 5339-69-5).

N-Isopropylbenzenesulfonamide (cas: 5339-69-5) belongs to amides. Amides include many other important biological compounds, as well as many drugs like paracetamol, penicillin and LSD. Low-molecular-weight amides, such as dimethylformamide, are common solvents. Amides can be recrystallised from large quantities of water, ethanol, ethanol/ether, aqueous ethanol, chloroform/toluene, chloroform or acetic acid. The likely impurities are the parent acids or the alkyl esters from which they have been made. The former can be removed by thorough washing with aqueous ammonia followed by recrystallisation, whereas elimination of the latter is by trituration or recrystallisation from an organic solvent.HPLC of Formula: 5339-69-5

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