Category: amides-buliding-blocks

The Directed Ortho Metalation-Ullmann Connection. A New Cu(I)-Catalyzed Variant for the Synthesis of Substituted Diaryl Ethers was written by Kalinin, Alexey V.;Bower, Justin F.;Riebel, Peter;Snieckus, Victor. And the article was included in Journal of Organic Chemistry in 1999.Application of 19311-91-2 This article mentions the following:

CuPF₆(MeCN)₄ catalyzed the ortho metalation-Ullmann reaction of o-halo benzamides and sulfonamides with phenols, thiophenols, or PhCH₂NH₂. E.g., reaction of 2-IC₆H₄CONHEt with PhSH gave 97% 2-PhSC₆H₄CONHEt. The reactions are conducted in the presence of Cs₂CO₃ as base. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Application of 19311-91-2).

N,N-Diethylsalicylamide (cas: 19311-91-2) 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)Nâ€?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 cmâˆ?. 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 19311-91-2

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

Bridelia ferruginea Benth. (Euphorbiaceae) mitigates oxidative imbalance and lipotoxicity, with concomitant modulation of insulin signaling pathways via GLUT4 upregulation in hepatic tissues of diabetic rats was written by Oyebode, Olajumoke A.;Erukainure, Ochuko L.;Chuturgoon, Anil A.;Ghazi, Terisha;Naidoo, Pragalathan;Chukwuma, Chika I.;Islam, Shahidul Md.. And the article was included in Journal of Ethnopharmacology in 2022.Name: 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide This article mentions the following:

Bridelia ferruginea Benth. (Euphorbiaceae) is among the medicinal plants commonly used for the management of type 2 diabetes (T2D) and its complications. The hepato-therapeutic effect of the butanol fraction of Bridelia ferruginea leaves was investigated in diabetic rats The butanol fraction of B. ferruginea was given to type 2 diabetic rats at both low and high doses (150 and 300 mg/kg bodyweight, respectivley), while metformin and glibenclamide served as the standard anti-diabetic drugs. A normal toxicol. group was administered a high dose of the fraction. At the end of the expremental period, the rats were sacrificed, and their livers and psoas muscle collected. The liver was assayed for oxidative stress markers, liver glycogen content, lipid metabolite profile (using GC-MS) and their metabolic pathways were analyzed using the MetaboAnalyst 5.0 online server. The expression of GLUT4 was also assayed in the liver and muscle as well as the identification of signaling pathways associated with GLUT4 expression using the Enrichr online server. In silico mol. docking was used to investigate the mol. interactions of some postulated compound found in B. ferruginea with GLUT4. The ability of the fraction to stimulate muscle glucose uptake was determined in isolated rat psoas muscle ex vivo. Treatment with the high dose of fraction caused an inhibition of lipid peroxidation as well as the elevation of catalase, SOD, glutathione reductase and glutathione peroxidase activities in the rat liver. There was an increased expression of GLUT4 in livers and muscles of diabetic rats following treatment with B. ferruginea. Treatment with the fraction also caused inactivation of diabetes-activated pathways and changes in the distribution of the hepatic lipid metabolites. Mol. docking anal. revealed strong mol. interactions of pyrogallol and sitosterol with GLUT4. These data illustrate the hepato-protective effect of B. ferruginea in diabetic rats which compare favorably with the tested anti-diabetic drugs (metformin and glibenclamide). In the experiment, the researchers used many compounds, for example, 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8Name: 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. 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′Râ€? or, equivalently, an acyl (alkanoyl) group RC(=O)âˆ?joined to an amine group. The presence of the amide group –C(=O)Nâ€?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 cmâˆ?. 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.Name: 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide

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

Neuropharmacological effects of methotrexate perfused through the cerebrospinal fluid system of the Rhesus monkey was written by Shepard, Robert F.;Merker, Philip C.;Walker, Michael D.;Gilles, Floyd H.. And the article was included in Cancer Research in 1976.Safety of Sodium (S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioate This article mentions the following:

Thirteen adult Rhesus monkeys were repeatedly perfused through the ventriculocisternal or ventriculolumbar spaces with Elliott’s B solution containing various concentrations of Na methotrexate (I Na salt) [7413-34-5] and trace amounts of 3H-I and 14C-inulin. The concentrations of I ranged from 4.8 to 0.15 mg/ml representing perfusion dosages of 551 to 16 mg/m2. The average steady-state concentration out-concentration in (Co/Ci) value for I was 0.78 for the ventriculocisternal and 0.66 for the ventriculolumbar routes. I treatments did not significantly affect mean inulin steady-state Co/Ci values or CSF formation rate. With the exception of a monkey perfused with I at an inflow concentration of 4.8 mg/ml, body weight, food intake, and urine output, analyzed at weekly intervals, generally were not remarkably affected by I perfusions. In 5 monkeys perfused with I in concentrations of 4.8 to 0.6 mg/ml, gross neurol. toxicity was observed, principally in the form of seizures and hypokinesia during perfusion series with occasional residual motor deficit. Significant cerebral damage was associated with the brains of two monkeys perfused with I at concentrations of 2.4 and 0.6 mg/ml and 2 monkeys perfused at concentrations of 1.2 and 0.3 mg/ml; 3 of the 4 animals displayed signs of gross neurotoxicity, and 2 animals developed permanent motor deficits. However, the extent to which neurotoxic signs could be attributed solely to I was difficult to judge because some changes in central nervous system morphol. were associated with the mechanical aspects of the procedure. Overall behavioral performance as measured by a visual pattern discrimination reinforced by avoidance or escape from an elec. shock was not significantly affected by repeated perfusions of I (0.6 mg/ml) in 2 monkeys not otherwise studied in detail. In the experiment, the researchers used many compounds, for example, Sodium (S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioate (cas: 7413-34-5Safety of Sodium (S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioate).

Sodium (S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioate (cas: 7413-34-5) 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 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.Safety of Sodium (S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioate

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

An efficient synthesis of Weinreb amides and ketones via palladium nanoparticles on ZIF-8 catalysed carbonylative coupling was written by Thanh Dang, Tuan;Chen, Anqi;Majeed Seayad, Abdul. And the article was included in RSC Advances in 2014.Synthetic Route of C9H10BrNO2 This article mentions the following:

The heterogeneously catalyzed carbonylative coupling reactions such as aminocarbonylation and Suzuki-carbonylation are reported using Pd nanoparticles supported on ZIF-8 for efficient and environmentally attractive synthesis of Weinreb amides ArC(O)N(CH₃)OCH₃ [Ar = 4-CH₃C₆H₄, 3,4,5-(OCH₃)₃C₆H₂, pyridin-3-yl, pyrimidin-5-yl, etc.] and ketones from aryl bromides ArBr or iodides ArI. The catalyst is air stable, offers high activity with very low palladium leaching and is recyclable. The presence of a phosphine ligand was required when ArBr were used as substrates, while no ligand was necessary when ArI were used. In the experiment, the researchers used many compounds, for example, 4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2Synthetic Route of C9H10BrNO2).

4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2) 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. 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.Synthetic Route of C9H10BrNO2

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

Pemetrexed-conjugated hyaluronan for the treatment of malignant pleural mesothelioma was written by Amano, Yuki;Ohta, Seiichi;Sakura, Kazuma L.;Ito, Taichi. And the article was included in European Journal of Pharmaceutical Sciences in 2019.Synthetic Route of C13H24N2O This article mentions the following:

Pemetrexed (PMX) is a multi-targeted antifolate drug used for the treatment of malignant pleural mesothelioma (MPM) and non-small cell lung cancer. Hyaluronan (HA) in blood is well known as a disease marker of MPM. We synthesized PMX-conjugated hyaluronan (HA-ADH-PMX) for the first time to develop a novel anticancer chemotherapeutic agent. HAs with different mol. weights (76 and 130 kDa) were first derivatized with adipic dihydrazide (ADH) and then conjugated to PMX. The obtained HA-ADH-PMX retained inhibitory activity against folate metabolism enzymes; thymidylate synthase was inhibited to the same extent as native PMX, whereas the inhibition constant against dihydrofolate reductase was 3.3% for 76 kDa HA-ADH-PMX and 12% for 130 kDa HA-ADH-PMX when compared with that of native PMX. The in vitro cytotoxicity of HA-ADH-PMX from both mol. weights against MPM cell lines was lower than that of native PMX. On the other hand, intrapleural administration of 76 kDa HA-ADH-PMX resulted in a survival rate of MPM model mice comparable to that with native PMX, suggesting the potential for future MPM therapy. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Synthetic Route of C13H24N2O).

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′Râ€? or, equivalently, an acyl (alkanoyl) group RC(=O)âˆ?joined to an amine group. In simple aromatic amides, fragmentation occurs on both sides of the carbonyl group. If a hydrogen is available in N-substituted aromatic amides, it tends to migrate and form an aromatic amine and the loss of a ketene.Synthetic Route of C13H24N2O

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

Oxidation-reduction potentials of N-(arenesulfonyl)quinonimine-arenesulfonamidophenol systems was written by Dubina, V. L.;Burmistrov, K. S.. And the article was included in Zhurnal Organicheskoi Khimii in 1977.Name: N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide This article mentions the following:

Oxidation-reduction potentials (EN) were determined for 11 N-(4-hydroxyphenyl)arenesulfonamides, 3 N-(4-hydroxy-1-naphthyl)benzenesulfonamides, and 5 N-(2-hydroxyphenyl)benzenesulfonamides in a (AcO)4Pb system. Residual (AcO)4Pb was titrated with 0.5M AcONa in glacial AcOH. The highest EN, 0.887 v for N-(4-chloro-2-hydroxyphenyl)benzenesulfonamide, was only 0.014 v higher than the EN for its 5-chloro isomer. In the experiment, the researchers used many compounds, for example, N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6Name: N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide).

N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6) 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. 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.Name: N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide

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

Investigation of a homogeneous activating ozonation method in the rinsing procedure of cotton fabric dyed with reactive dye [Erratum to document cited in CA155:354636] was written by Mao, Ya-Hong;Guan, Yu;Luo, Deng-Hong;Zheng, Qing-Kang;Feng, Xi-Ning;Wang, Xiu-Xing. And the article was included in Coloration Technology in 2011.Synthetic Route of C10H16N2O4 This article mentions the following:

On page 265, in Table 7, in row 2, in column 4, the Peak II chem. formula, “C₄H₆ozone”, was incorrectly given, and should read: “C₄H₆O₃“. The correct version of the table is given. In the experiment, the researchers used many compounds, for example, N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) (cas: 10543-57-4Synthetic Route of C10H16N2O4).

N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) (cas: 10543-57-4) 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.Synthetic Route of C10H16N2O4

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

Inhibition of Human Alcohol Dehydrogenases by Formamides was written by Schindler, John F.;Berst, Kristine B.;Plapp, Bryce V.. And the article was included in Journal of Medicinal Chemistry in 1998.Related Products of 58644-54-5 This article mentions the following:

Human alc. dehydrogenase (HsADH) comprises class I (α, β, and γ), class II (π), and class IV (σ) enzymes. Selective inhibitors of the enzymes could be used to prevent the metabolism of alcs. that form toxic products. Formamides are unreactive analogs of aldehydes and bind to the enzyme-NADH complex [Ramaswamy, S.; Scholze, M.; Plapp, B. V. Biochem. 1997, 36, 3522-3527]. They are uncompetitive inhibitors against varied concentrations of alc., and this makes them effective even with saturating concentrations of alcs. Mol. modeling led to the design and synthesis of a series of cyclic, linear, and disubstituted formamides. Evaluation of 23 compounds provided structure-function information and selective inhibitors for the enzymes, which have overlapping but differing substrate specificities. Monosubstituted formamides are good inhibitors of class I and II enzymes, and disubstituted formamides are selective for the α enzyme. Selective inhibitors, with K_i values at pH 7 and 25 °C of 0.33-0.74 μM, include N-cyclopentyl-N-cyclobutylformamide for HsADH α, N-benzylformamide for HsADH β₁, N-1-methylheptylformamide for HsADH γ₂, and N-heptylformamide for HsADH σ and HsADH β₁. In the experiment, the researchers used many compounds, for example, N-Cyclopropylformamide (cas: 58644-54-5Related Products of 58644-54-5).

N-Cyclopropylformamide (cas: 58644-54-5) 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 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.Related Products of 58644-54-5

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

New development for combined bioscouring and bleaching of cotton-based fabrics was written by Hebeish, Ali;Hashem, Mohamed;Shaker, Nihal;Ramadan, Mohamed;El-Sadek, Bahiya;Hady, Marwa Abdel. And the article was included in Carbohydrate Polymers in 2009.Application of 10543-57-4 This article mentions the following:

A thorough investigation into conditions appropriate for effecting combined eco-friendly bioscouring and/or bleaching of cotton-based fabrics was undertaken. Fabrics used include cotton, gray mercerized cotton, cotton/polyester blend 50/50 and cotton/polyester blend 35/65. The four cotton-based fabric were subjected to bioscouring by single use of alk. pectinase enzymes or by using binary mixtures of alk. pectinase and cellulase enzymes under a variety of conditions. Results of bioscouring show that, the bioscoured substrates exhibit fabrics performances which are comparable with these of the conventional alkali scouring. Incorporation of EDTA in the bioscouring with a mixture of alk. pectinase and cellulase improves the performance of the bioscoured fabrics. Addition of β-cyclodextrin to the bioscouring solution using alk. pectinase in admixtures with cellulase acts in favor of tech. properties and performance of the bioscoured fabrics. Concurrent bioscouring and bleaching by in situ formed peracetic acid using tetraacetylethylenediamine (TAED) and H₂O₂ was also investigated. The results reveal unequivocally that the environmentally sound technol. brought about by current development is by far the best. The new development involves a single-stage process for full purification/preparation of cotton textiles. The new development at its best comprises treatment of the fabric with an aqueous formulation consisting of alk. pectinase enzyme (2 g/L), TAED (15 g/L), H₂O₂ (5 g/L), nonionic wetting agent (0.5 g/L) and sodium silicate (2 g/L). The treatment is carried out at 60 °C for 60 min. Beside the advantages of the new development with respect to major tech. fabric properties, it is eco-friendly and reproducible. This advocates the new development for mill trials. In the experiment, the researchers used many compounds, for example, N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) (cas: 10543-57-4Application of 10543-57-4).

N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) (cas: 10543-57-4) 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. 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 10543-57-4

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

Study on structure-activity relationship of mutation-dependent herbicide resistance acetohydroxyacid synthase through 3D-QSAR and mutation was written by Yu, ZhiHong;Niu, CongWei;Ban, ShuRong;Wen, Xin;Xi, Zhen. And the article was included in Chinese Science Bulletin in 2007.SDS of cas: 82097-01-6 This article mentions the following:

Seventy-four sulfonylureas were synthesized and tested for their inhibitory activity against the whole enzyme of E. coli acetohydroxyacid synthase (AHAS, EC 2.2.1.6) isoenzyme II, and 3D-QSAR analyses were performed based on these inhibitory activities. The binding conformation of chlorimuron-Et, a com. herbicidal AHAS inhibitor, in the crystal structure of AHAS complex was extracted and used as template to build the initial three-dimensional structure of other sulfonylureas, and then all structures were fully geometrically optimized. After systematic optimization of the alignment rule, mol. orientation, grid space and attenuation factor, two satisfactory models with excellent performances (CoMFA: q² = 0.735, r² = 0.954, n = 7, r²_pred = 0.832; CoMSIA: q² = 0.721, r² = 0.913, n = 8, r²_pred = 0.844) were established. By mapping the 3D contour maps of CoMFA and CoMSIA models into the possible inhibitory active site in the crystal structure of catalytic subunit of yeast AHAS, a plausible binding model for AHAS, with best fit QSAR in the literature so far, was proposed. The results of 3D-QSAR were further utilized to interpret resistance of site-directed mutants. A relative activity index (RAI) for AHAS enzyme mutant was defined for the first time to relate the 3D-QSAR and resistance of mutants. This study, for the first time, demonstrated that combination of 3D-QSAR and enzyme mutation can be used to decipher the mol. basis of ligand-receptor interaction mechanism. This study refined our understanding of the ligand-receptor interaction and resistance mechanism in AHAS-sulfonylurea system, and provided basis for designing new potent herbicides to combat the herbicide resistance. In the experiment, the researchers used many compounds, for example, 2-(2-Chloroethoxy)benzenesulfonamide (cas: 82097-01-6SDS of cas: 82097-01-6).

2-(2-Chloroethoxy)benzenesulfonamide (cas: 82097-01-6) 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. 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.SDS of cas: 82097-01-6

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