Category: amides-buliding-blocks

The presence of unauthorized ingredients in dietary supplements: An analysis of the risk warning data in Korea was written by Shin, Dasom;Kwon, Jeongeun;Kang, Hui-Seung;Suh, Junghyuck;Lee, Eunju. And the article was included in Journal of Food Composition and Analysis in 2022.Application In Synthesis of 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide This article mentions the following:

The Ministry of Food and Drug Safety (MFDS) has identified that numerous dietary supplements contain unapproved (hidden, undeclared, and unauthorized) ingredients that could be unsafe. The aim of this study is to summarize the presence of unapproved ingredients in dietary supplements based on the warning dataset released by the MFDS from 2010 to 2019. The warning data were extracted from the alert system on the MFDS′s website. The highest number (ratio) of products found in the dataset were marketed for sexual enhancement [770 (43.3%)], weight-loss [690 (38.8%)], muscular strengthening [243 (13.7%)], or relaxing [76 (4.3%)]. A total of 1779 products contained one or more unapproved ingredients. The most common unauthorized compounds were icariin, sildenafil, and tadalafil for sexual enhancement, yohimbine, sibutramine, and sennoside for weight loss, and yohimbine and icariin for muscular strengthening, and melatonin and 5-hydroxytryptophan for relaxing products, resp. Unapproved ingredients continue to be identified in dietary supplements, especially those marketed for sexual enhancement or weight loss, even after warnings by regulatory authorities. The unauthorized compounds in these dietary supplements have potential adverse health effects on consumers owing to accidental misuse, overuse, interaction with other medications, underlying health conditions, or other pharmaceuticals within the supplement. Our study reviewed potential health issues concerning the main unapproved ingredients to contribute to the understanding of adulteration in dietary supplements. The result of this study can be used to elucidate adulteration trends of unapproved ingredients in dietary supplements. In the experiment, the researchers used many compounds, for example, 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8Application In Synthesis of 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide).

5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8) belongs to amides. Compared to amines, amides are very weak bases and do not have clearly defined acid–base properties in water. On the other hand, amides are much stronger bases than esters, aldehydes, and ketones. 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 In Synthesis of 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide

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

Weinreb Amide Directed Versatile C-H Bond Functionalization under (η⁵-Pentamethylcyclopentadienyl)cobalt(III) Catalysis was written by Kawai, Kentaro;Bunno, Youka;Yoshino, Tatsuhiko;Matsunaga, Shigeki. And the article was included in Chemistry – A European Journal in 2018.Recommanded Product: 3-Fluoro-N-methoxy-N-methylbenzamide This article mentions the following:

The (η⁵-pentamethylcyclopentadienyl)cobalt(III) (Cp*Co^III)-catalyzed C-H bond functionalization of aromatic, heteroaromatic and α,β-unsaturated Weinreb amides was explored. The C-H allylation using allyl carbonate and a perfluoroalkene/oxidative alkenylation with Et acrylate/iodination using N-iodosuccinimide and amidation with dioxazolones were catalyzed by Cp*Co(CO)I₂ in presence of cationic silver salt and silver acetate to afford various synthetically useful building blocks like RC(O)N(Me)(OMe) [R = 2-H₂C=CHCH₂C₆H₄, MeC=CHCH=CHCO₂Et, 2-I-C₆H₄, etc.]. Mechanistic studies of C-H allylation disclosed that the C-H activation step was rate determining and virtually irreversible. In the experiment, the researchers used many compounds, for example, 3-Fluoro-N-methoxy-N-methylbenzamide (cas: 226260-01-1Recommanded Product: 3-Fluoro-N-methoxy-N-methylbenzamide).

3-Fluoro-N-methoxy-N-methylbenzamide (cas: 226260-01-1) 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 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.Recommanded Product: 3-Fluoro-N-methoxy-N-methylbenzamide

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

Synthesis and properties of new non-symmetric liquid crystal dimers containing mandelic acid and cyano group was written by Yao, Miao;Chen, Xin-shi;Dong, Liang;Wan, Xin-yi;Xian, Yu-pei;Yao, Dan-shu;Hu, Jian-she;Tian, Mei. And the article was included in Liquid Crystals in 2018.Name: 1,3-Dicyclohexylurea This article mentions the following:

Four non-sym. dimers containing mandelic acid as the chiral core I [R = H, cyano, (4-cyanophenyl)], II were synthesized. Chem. structures and liquid crystal (LC) properties of the dimers were characterised by FTIR, ¹H-NMR, differential scanning calorimetry (DSC), thermogravimetric anal. (TG) and polarised optical microscopy (POM). The results indicated that the rigidity and conformation of the mols. of the dimers played important effects on their mesophase properties. I [R = H] did not display any mesophase, I [R = cyano, (4-cyanophenyl)] exhibited nematic (N) phases, while II displayed cholesteric (ch) phase, which indicated that chiral mandelic acid could induce cholesteric phase, but some attention should be paid to the mol. conformation to obtain cholesteric phase. For the four dimers, melting temperature (Tm) increased first and then decreased, inferring that mol. conformation played a more important effect besides mol. weight and rigidity. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Name: 1,3-Dicyclohexylurea).

1,3-Dicyclohexylurea (cas: 2387-23-7) 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.Name: 1,3-Dicyclohexylurea

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

Discovery of Potent, Selective, and Orally Bioavailable Alkynylphenoxyacetic Acid CRTH2 (DP2) Receptor Antagonists for the Treatment of Allergic Inflammatory Diseases was written by Crosignani, Stefano;Pretre, Adeline;Jorand-Lebrun, Catherine;Fraboulet, Gaele;Seenisamy, Jeyaprakashnarayanan;Augustine, John Kallikat;Missotten, Marc;Humbert, Yves;Cleva, Christophe;Abla, Nada;Daff, Hamina;Schott, Olivier;Schneider, Manfred;Burgat-Charvillon, Fabienne;Rivron, Delphine;Hamernig, Ingrid;Arrighi, Jean-Francois;Gaudet, Marilene;Zimmerli, Simone C.;Juillard, Pierre;Johnson, Zoe. And the article was included in Journal of Medicinal Chemistry in 2011.Electric Literature of C8H10FNO2S This article mentions the following:

New phenoxyacetic acid antagonists of CRTH2 are described. Following the discovery of a hit compound, I, by a focused screening, high protein binding was identified as its main weakness. Optimization aimed at reducing serum protein binding led to the identification of several compounds that showed not only excellent affinities for the receptor (41 compounds with K_i < 10 nM) but also excellent potencies in a human whole blood assay (IC₅₀ < 100 nM; PGD2-induced eosinophil shape change). Addnl. optimization of the pharmacokinetic characteristics led to the identification of several compounds suitable for in vivo testing. Of these, II (R¹ = n-Pr, R² = Me; R¹ = n-Pr, R² = F) were tested in two different pharmacol. models (acute FITC-mediated contact hypersensitivity and ovalbumin-induced eosinophilia models) and found to be active after oral dosing (10 and 30 mg/kg). In the experiment, the researchers used many compounds, for example, 4-Fluoro-N,N-dimethylbenzenesulfonamide (cas: 383-31-3Electric Literature of C8H10FNO2S).

4-Fluoro-N,N-dimethylbenzenesulfonamide (cas: 383-31-3) 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. 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 C8H10FNO2S

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

Rhodium-Catalyzed C-H Olefination of Aryl Weinreb Amides was written by Wang, Yan;Li, Chao;Li, Yan;Yin, Feng;Wang, Xi-Sheng. And the article was included in Advanced Synthesis & Catalysis in 2013.SDS of cas: 116332-61-7 This article mentions the following:

A rhodium(III)-catalyzed oxidative C-H olefination directed by Weinreb amides, a class of well developed versatile building blocks in organic synthesis, has been developed with air as the terminal oxidant. The reactions proceed with excellent reactivity, good functional group tolerance and high yields. In the experiment, the researchers used many compounds, for example, N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7SDS of cas: 116332-61-7).

N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7) belongs to amides. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well. Thus amides can participate in hydrogen bonding with water and other protic solvents; the oxygen atom can accept hydrogen bonds from water and the N–H hydrogen atoms can donate H-bonds. 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.SDS of cas: 116332-61-7

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

Asymmetric synthesis of aryl/vinyl alkyl carbinol esters via Ni-catalyzed reductive arylation/vinylation of 1-chloro-1-alkanol esters was written by Sun, Deli;Tao, Xianghua;Ma, Guobin;Wang, Jifen;Chen, Yunrong. And the article was included in Chemical Science in 2022.Quality Control of 4-Bromo-N-methoxy-N-methylbenzamide This article mentions the following:

An asym. Ni-catalyzed cross-electrophile coupling approach to prepare enantioenriched aryl/vinyl alkyl carbinol esters RC(O)OC(R¹)R² [R = 4-methylphenyl, iso-Pr, naphthalen-2-yl, etc.; R¹ = 4-(methoxycarbonyl)phenyl, 2H-1,3-benzodioxol-5-yl, cyclopent-1-en-1-yl, etc; R² = Et, 2-phenylethyl, 4-methoxy-4-oxobutyl, etc.] through arylation/vinylation of easily accessible racemic 1-chloro-1-alkanol esters RC(O)OC(Cl)R² with aryl/vinyl electrophiles R¹X (X = Br, I, OTf) was reported. The method features a broad substrate scope as demonstrated by more than 60 examples including the challenging chiral allylic esters. It tolerates a wide array of functional groups including alkenyl, carbonyl and free hydroxyl groups that may not survive in conventional carbonyl reduction and addition methods. The synthetic utility of the present work was showcased by facile preparation of a few key intermediates and the modification of chiral drugs and naturally occurring compounds Finally, an efficient one-pot procedure for this method was described. In the experiment, the researchers used many compounds, for example, 4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2Quality Control of 4-Bromo-N-methoxy-N-methylbenzamide).

4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2) 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. As a result of interactions such as these, the water solubility of amides is greater than that of corresponding hydrocarbons. These hydrogen bonds are also have an important role in the secondary structure of proteins.Quality Control of 4-Bromo-N-methoxy-N-methylbenzamide

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

Synthesis and pharmacological properties of some 2,5-substituted isopropyl and hydroxyethylpiperazinylpyridines was written by Thunus, L.. And the article was included in Annales Pharmaceutiques Francaises in 1977.Name: 6-Chloro-N,N-dimethylnicotinamide This article mentions the following:

Pyridylpiperazines I (R = CONR2R3, SO2NR2R3; R1 = CHMe2, CH2CH2OH; R2 = H, R3 = H, Me, Et, CHMe2; NR2R3 = NMe2, NEt2, pyrrolidino, piperidino, morpholino, 4-methylpiperazino) were obtained in 65-95% yield by treating piperazines with chloropyridines. I are devoid of pharmacol. activity. In the experiment, the researchers used many compounds, for example, 6-Chloro-N,N-dimethylnicotinamide (cas: 54864-83-4Name: 6-Chloro-N,N-dimethylnicotinamide).

6-Chloro-N,N-dimethylnicotinamide (cas: 54864-83-4) 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 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.Name: 6-Chloro-N,N-dimethylnicotinamide

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

Synthesis of biaryl ketones by arylation of Weinreb amides with functionalized Grignard reagents under thermodynamic control vs. kinetic control of N,N-Boc₂-amides was written by Li, Guangchen;Szostak, Michal. And the article was included in Organic & Biomolecular Chemistry in 2020.Recommanded Product: 116332-61-7 This article mentions the following:

A highly efficient method for chemoselective synthesis of biaryl ketones by arylation of Weinreb amides (N-methoxy-N-methylamides) with functionalized Grignard reagents was reported. This protocol offers rapid entry to functionalized biaryl ketones after Mg/halide exchange with i-PrMgCl·LiCl under operationally-simple and practical reaction conditions. The scope of the method was highlighted in >40 examples, including bioactive compounds and pharmaceutical derivatives Collectively, this transition-metal-free approach offers a major advantage over the recently established cross-coupling of amides by oxidative addition of N-C(O) bonds. Considering the utility of amide acylation reactions in modern synthesis, we expect that this method will be of broad interest. In the experiment, the researchers used many compounds, for example, N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7Recommanded Product: 116332-61-7).

N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7) 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.Recommanded Product: 116332-61-7

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

The predominance of endothelium-derived relaxing factors and beta-adrenergic receptor pathways in strong vasorelaxation induced by 4-hydroxybenzaldehyde in the rat aorta was written by Loh, Yean Chun;Oo, Chuan Wei;Tew, Wan Yin;Wen, Xu;Wei, Xu;Yam, Mun Fei. And the article was included in Biomedicine & Pharmacotherapy in 2022.Application In Synthesis of 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide This article mentions the following:

4-Hydroxybenzaldehyde (4HB), known as ρ-hydroxybenzaldehyde, is commonly present in traditional Chinese medicine herb, most frequently used for hypertension treatment. This research aims to determine the potency of 4HB’s vasorelaxant action. In the study, the vasodilation effect of 4HB was evaluated using in vitro isolated rat aortic rings assay. The aortic rings were pre-incubated with resp. antagonists before being pre-contracted with phenylephrine (PE) and challenged with various concentrations of 4HB for mechanistic action studies. R_max (maximal vasodilation) and pEC₅₀ (neg. logarithm of half-maximal effective concentration) values of each experiment were determined for comparison purposes. 4HB caused vasodilation on endothelium-intact aortic rings which pre-contracted with PE (pEC₅₀ = 3.53 ± 0.05, R_max = 100.95 ± 4.25%) or potassium chloride (pEC₅₀ = 2.96 ± 0.13, R_max = 72.13 ± 4.93%). The vasodilation effect of 4HB was significantly decreased in the absence of an endothelium (pEC₅₀ = 2.21 ± 0.25, R_max = 47.96 ± 4.16%). The atropine, 4-aminopyridine, Nω-nitro–arginine Me ester, glibenclamide, and propranolol significantly reduced the vasorelaxation effect of 4HB. Besides that, 4HB blocked the voltage-operated calcium channel (VOCC) and regulated the intracellular Ca²⁺ release from the sarcoplasmic reticulum (SR) in the aortic ring. Thus, the results indicated that 4HB exerted its vasodilatory effect via cGMP and β2 pathways, M₃-dependent PLC/IP₃ pathways, and potassium and calcium channels. In the experiment, the researchers used many compounds, for example, 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8Application In Synthesis of 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide).

5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8) 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. As a result of interactions such as these, the water solubility of amides is greater than that of corresponding hydrocarbons. These hydrogen bonds are also have an important role in the secondary structure of proteins.Application In Synthesis of 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide

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

Sulfated-Tungstate-Catalyzed Synthesis of Ureas/Thioureas via Transamidation and Synthesis of Forchlorofenuron was written by Wagh, Ganesh D.;Pathare, Sagar P.;Akamanchi, Krishnacharya G.. And the article was included in ChemistrySelect in 2018.Application of 2387-23-7 This article mentions the following:

N, N’-Disubstituted ureas and thioureas were efficiently and expeditiously synthesized by transamidation reaction between unsubstituted or monosubstituted ureas/thioureas and amines under solvent-free condition using sulfated tungstate as a heterogeneous mild solid acid catalyst. This protocol offered several advantages such as wide substrate scope, providing both sym. and unsym. ureas and thioureas, solvent-free reaction, recyclability of the catalyst and a simple work-up procedure. Application of the methodol. was demonstrated through simple and one step synthesis of forchlorofenuron [1-(2-chloropyridine-4-yl)-3-phenylurea] (CPPU), an approved plant growth regulator. 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. 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.Application of 2387-23-7

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