Category: amides-buliding-blocks

Synthesis and Nematicidal Activities of 1,2,3-Benzotriazin-4-one Derivatives against Meloidogyne incognita was written by Wang, Gaolei;Chen, Xiulei;Deng, Yayun;Li, Zhong;Xu, Xiaoyong. And the article was included in Journal of Agricultural and Food Chemistry in 2015.Synthetic Route of C7H7FN2O This article mentions the following:

A series of novel 1,2,3-benzotriazin-4-one derivatives (I) where R is H, Cl, Br, etc.; and n = 1,2,3,or 4; were synthesized by the reaction of 3-bromoalkyl-1,2,3-benzotriazin-4-ones with potassium salt of 2-cyanoimino-4-oxothiazolidine in the presence of potassium iodide. Nematicidal assays in vivo showed that some of them exhibited good control efficacy against the cucumber root-knot nematode disease caused by Meloidogyne incognita, up to 100% at the concentration of 10.0 mg L^-1, which indicated that 1,2,3-benzotriazin-4-one derivatives might be potential for novel promising nematicides. The nematicidal activity was influenced by the combination of substituent type, substituted position, and linker length in the mol. The inhibition rate data at the concentrations of 5.0 and 1.0 mg L^-1 for the compounds with high inhibitory activities were also provided. When tested in vitro, none of them showed direct inhibition against M. incognita. The investigation of a significant difference between in vivo and in vitro data is in progress. In the experiment, the researchers used many compounds, for example, 2-Amino-4-fluorobenzamide (cas: 119023-25-5Synthetic Route of C7H7FN2O).

2-Amino-4-fluorobenzamide (cas: 119023-25-5) 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. 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.Synthetic Route of C7H7FN2O

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

Tariquidar analogues: synthesis by Cu^I-catalysed N/O-aryl coupling and inhibitory activity against the ABCB1 transporter was written by Egger, Michael;Li, Xuqin;Mueller, Christine;Bernhardt, Guenther;Buschauer, Armin;Koenig, Burkhard. And the article was included in European Journal of Organic Chemistry in 2007.Electric Literature of C11H15NO2 This article mentions the following:

Tariquidar analogs I (R = Br, MeOCH₂CH₂OCH₂CH₂NH, 4-morpholinyl, EtOCH₂CH₂O) are prepared as inhibitors of the ABCB1 transporter using copper-catalyzed coupling reactions of I (R = Br) with 2-(2-methoxyethoxy)ethylamine, morpholine, and 2-ethoxyethanol as the key steps. Ligands and catalysts are tried for the coupling of amines with 5-bromo-2-(tert-butoxycarbonylamino)benzoic acid. Attempted coupling of bis(2-(2-methoxyethoxy)ethyl)amine with I (R = Br) using either palladium or copper catalysts did not give the desired product. The lipophilicities of I (R = Br, MeOCH₂CH₂OCH₂CH₂NH, 4-morpholinyl, EtOCH₂CH₂O) and their inhibition of the ABCB1 transporter in the Kb-V1 human cancer cell line are determined; the lipophilicities of I (R = Br, MeOCH₂CH₂OCH₂CH₂NH, 4-morpholinyl, EtOCH₂CH₂O) correlate with their inhibition of the ABCB1 transporter. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Electric Literature of C11H15NO2).

N,N-Diethylsalicylamide (cas: 19311-91-2) 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. 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.Electric Literature of C11H15NO2

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

Selectivity in tosylation of p-aminophenol was written by Kurita, Keisuke. And the article was included in Chemistry & Industry (London, United Kingdom) in 1982.SDS of cas: 1146-43-6 This article mentions the following:

Tolylsulfonylation of p-H₂NC₆H₄OH with p-MeC₆H₄SO₂Cl in CH₂Cl₂ containing Et₃N at 25° for 2 h gave 81% p-MeC₆H₄SO₃C₆H₄NH₂–p (I), 6% p-MeC₆H₄SO₃C₆H₄(NHO₃SC₆H₄Me-p)-p (II), and 4% p-HOC₆H₄NHO₃SC₆H₄Me-p (III). With Me₃COK as base only 32% I was obtained. When pyridine was used III was the major product (76%), only 1 and 14% of I and II, resp., being obtained. In the presence of the weak base AcNMe₂, or in the absence of base, III was the sole product. In the experiment, the researchers used many compounds, for example, N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6SDS of cas: 1146-43-6).

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

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

Determination of the ionization constants of sulfonylureas in THF-water media by potentiometric titration and RPLC methods was written by Dereli, Dilara Basat;Alsancak, Abbase Guleren. And the article was included in Journal of the Iranian Chemical Society in 2022.Safety of 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide This article mentions the following:

In this study, the ionization constants (pK_a) of sulfonylurea group antidiabetic drugs (glibenclamide, gliclazide, glimepiride, and glipizide) were calculated, providing significant information about the physicochem. properties of the drugs. Potentiometric titration and reverse-phase liquid chromatog. were used to determine the ionization constants in THF-water media. The PKPOT and NLREG computer programs were used to evaluate the results. In addition, the aqueous pK_a values of the compounds were calculated using the Yasuda-Shedlovsky equation and mole fraction-pK_a extrapolation methods. When the potentiometric titration method was used, the aqueous pKa values of glibenclamide, gliclazide, glimepiride, and glipizide were calculated to be 6.002, 6.085, 6.106, and 6.016, resp., using the Yasuda-Shedlovsky equation, while the mole fraction-pK_a extrapolation method gave 6.013, 6.096, 6.117, and 6.027, resp. On the other hand, when the RPLC method was used, pKa values of 5.489, 5.732, 5.733, and 5.601, resp., were obtained with the Yasuda-Shedlovsky equation and mole fraction-pKa extrapolation gave 5.499, 5.742, 5.743, and 5.611, resp. The ionization constants obtained with these methods provide valuable information for researchers studying these active pharmaceutical compounds In the experiment, the researchers used many compounds, for example, 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8Safety 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 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 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.Safety of 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide

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

The antipsychotic aripiprazole induces peripheral antinociceptive effects through PI3Kγ/NO/cGMP/K_ATP pathway activation was written by Ferreira, Renata C.;de Almeida, Douglas L.;Duarte, Igor D. G.;Aguiar, Daniele C.;Moreira, Fabricio A.;Romero, Thiago R. L.. And the article was included in European Journal of Pain (Oxford, United Kingdom) in 2022.SDS of cas: 10238-21-8 This article mentions the following:

Aripiprazole is an antipsychotic drug used to treat schizophrenia and bipolar disorder. Recently, its peripheral analgesic component was evaluated, however, the mechanism involved in this effect is not fully established. Therefore, the aim of the study was to obtain pharmacol. evidence for the involvement of the nitric oxide system in the peripheral antinociceptive effect induced by aripiprazole. The hyperalgesia was induced via intraplantar injection of prostaglandin E₂ in mice and the nociceptive thresholds were evaluated using the paw pressure test. All drugs were injected locally into the right hind paw. The PI3K inhibitor (AS605240), but not rapamycin (mTOR kinase inhibitor), reversed the peripheral antinociceptive effect induced by Aripiprazole. Antinociception was antagonized by the non-selective inhibitor of the nitric oxide synthase (L-NOarg). The same response was observed using the selective iNOS, but not with the selective nNOS inhibitors. The selective guanylyl cyclase enzyme inhibitor (ODQ) and the non-selective potassium channel blocker tetraethylammonium were able to reverse the antinociceptive effect of aripiprazole. The same was seen using glibenclamide, an ATP-dependent K⁺ channel blocker. However, calcium-activated potassium channel blockers of small and high conductance, dequalinium chloride and paxilline, resp., did not reverse this effect. The injection of cGMP-specific phosphodiesterase type 5 inhibitor zaprinast, potentiated the antinociceptive effect induced by a low dose of aripiprazole. The results provide evidence that aripiprazole induces peripheral antinociceptive effects via PI3K/NO/cGMP/K_ATP pathway activation. In the experiment, the researchers used many compounds, for example, 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8SDS of cas: 10238-21-8).

5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8) 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. 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.SDS of cas: 10238-21-8

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

A facile semi-synthetic approach towards halogen-substituted aminobenzoic acid analogues of platensimycin was written by Qiu, Lin;Tian, Kai;Pan, Jian;Jiang, Lin;Yang, Hu;Zhu, Xiangcheng;Shen, Ben;Duan, Yanwen;Huang, Yong. And the article was included in Tetrahedron in 2017.Formula: C7H7FN2O This article mentions the following:

Platensimycin (PTM), produced by several strains of Streptomyces platensis, is a promising drug lead for infectious diseases and diabetes. The recent pilot-scale production of PTM from S. platensis SB12026 has set the stage for the facile semi-synthesis of a focused library of PTM analogs. In this study, gram-quantity of platensic acid (PTMA) was prepared by the sulfuric acid-catalyzed ethanolysis of PTM, followed by a mild hydrolysis in aqueous lithium hydroxide. Three PTMA esters were also obtained in near quant. yields in a single step, suggesting a facile route to make PTMA aliphatic esters. 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU)-catalyzed coupling of PTMA and 33 aminobenzoates resulted in the synthesis of 28 substituted aminobenzoate analogs of PTM, among which 26 of them were reported for the first time. Several of the PTM analogs showed weak antibacterial activity against methicillin-resistant Staphylococcus aureus. Our study supported the potential utility to integrate natural product biosynthetic and semi-synthetic approaches for structure diversification. In the experiment, the researchers used many compounds, for example, 2-Amino-4-fluorobenzamide (cas: 119023-25-5Formula: C7H7FN2O).

2-Amino-4-fluorobenzamide (cas: 119023-25-5) 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.Formula: C7H7FN2O

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

Sulfonylurea for improving neurological features in neonatal diabetes: A systematic review and meta-analyses was written by de Gouveia Buff Passone, Caroline;Giani, Elisa;Vaivre-Douret, Laurence;Kariyawasam, Dulanjalee;Berdugo, Marianne;Garcin, Laure;Beltrand, Jacques;Bernardo, Wanderley Marques;Polak, Michel. And the article was included in Pediatric Diabetes in 2022.Recommanded Product: 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide This article mentions the following:

Objective : In monogenic diabetes due to KCNJ11 and ABCC8 mutations that impair KATP- channel function, sulfonylureas improve long-term glycemic control. Although KATP channels are extensively expressed in the brain, the effect of sulfonylureas on neurol. function has varied widely. We evaluated published evidence about potential effects of sulfonylureas on neurol. features, especially epilepsy, cognition, motor function and muscular tone, visuo-motor integration, and attention deficits in children and adults with KCNJ11 and ABCC8-related neonatal-onset diabetes mellitus. Research Design and Methods : We conducted a systematic review and meta-analyses of the literature (PROSPERO, CRD42021254782), including individual-patient data, according to PRISMA, using RevMan software. We also graded the level of evidence. Results : We selected 34 of 776 publications. The evaluation of global neurol. function before and after sulfonylurea (glibenclamide) treatment in 114 patients yielded a risk difference (RD) of 58% (95%CI, 43%-74%; I² = 54%) overall and 73% (95%CI, 32%-113%; I² = 0%) in the subgroup younger than 4 years; the level of evidence was moderate and high, resp. EEG studies of epilepsy showed a RD of 56% (95%CI, 23%-89%; I² = 34%) in patients with KCNJ11 mutations, with a high quality of evidence. For hypotonia and motor function, the RDs were 90% (95%CI, 69%-111%; I² = 0%) and 73% (95%CI, 35%-111%; I² = 0%), resp., with a high level of evidence. Conclusions : Glibenclamide significantly improved neurol. abnormalities in patients with neonatal-onset diabetes due to KCNJ11 or ABCC8 mutations. Hypotonia was the symptom that responded best. Earlier treatment initiation was associated with greater benefits. In the experiment, the researchers used many compounds, for example, 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8Recommanded Product: 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′R″; or, equivalently, an acyl (alkanoyl) group RC(=O)− joined to an amine group. 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: 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide

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

Co(II)-Porphyrin Immobilized on Graphene Oxide: An Efficient Catalyst for the Beckmann Rearrangement was written by Ghadamyari, Zohreh;Khojastehnezhad, Amir;Seyedi, Seyed Mohammad;Shiri, Ali. And the article was included in ChemistrySelect in 2019.Safety of 3,4-Dichlorobenzamide This article mentions the following:

In this report, the synthesis of amides from aldoximes (Beckmann rearrangement) has been reported using cobalt(II) porphyrin covalently linked to graphene oxide as a nano heterogeneous catalyst. The prepared catalyst was characterized by applying of FT-IR, TGA, TEM, SEM, EDX, ICP and UV-Vis techniques. All anal. confirm the successful insertion of cobalt into the porphyrin ring and covalently linkage of Co-Porphyrin on the graphene oxide. Moreover, the prepared catalyst was applied in order to investigate its performance in the Beckmann rearrangement. This heterogeneous catalyst exhibited excellent catalytic efficiency with a high yield of products. Also, the suggested catalyst could be recycled for five runs without a dramatic decrease in its catalytic activity or metal leaching. In the experiment, the researchers used many compounds, for example, 3,4-Dichlorobenzamide (cas: 2670-38-4Safety of 3,4-Dichlorobenzamide).

3,4-Dichlorobenzamide (cas: 2670-38-4) 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. 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.Safety of 3,4-Dichlorobenzamide

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 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.Computed Properties of C10H16N2O4 This article mentions the following:

The textile dyeing process requires the consumption of large quantities of water, which includes huge amounts of colored wastewater. Usually the rinsing of dyed fabric and the treating of the dyeing house wastewater are separated The two independent processes not only increase the difficulty of wastewater treatment but also increase the costs of the treatment. In this paper, the ozone/tetraacetylethylenediamine active oxidation technol. was employed to rinse dyed fabric and to decolorise the rinsing wastewater simultaneously. The effects of the rinsing conditions on the decolorisation ratio and the COD Cr value of treated wastewater, and the K/S value, color difference, tensile strength and fastness of dyed samples were investigated. The results indicated that the decolorisation ratio of the rinsing effluent was greater than 80% and the COD Cr value decreased more than 58% by the ozone/tetraacetylethylenediamine rinsing process compared with that of traditional rinsing processes. Furthermore, the curve of decolorisation kinetics was in good agreement with a pseudo-first-order kinetic model. In addition, the decolorisation mechanism was also discussed after UV-visible and ultra performance liquid chromatograph-mass spectrometry analyses of the degraded dye mol. In the experiment, the researchers used many compounds, for example, N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) (cas: 10543-57-4Computed Properties of C10H16N2O4).

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

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

N-(2-(1H-indol-3-yl)ethyl)-2-(2-fluoro-[1,1”-biphenyl]-4-yl)propanamide was written by Manolov, Stanimir;Ivanov, Iliyan;Bojilov, And Dimitar. And the article was included in Molbank in 2021.Electric Literature of C13H24N2O This article mentions the following:

N-(2-(1H-Indol-3-yl)ethyl)-2-(2-fluoro-[1,1”-biphenyl]-4-yl)propanamide were prepared by a reaction between tryptamine and flurbiprofen, applying N,N”-dicyclohexylcarbodiimide, as a coupling agent. The obtained new amide has a fragment similar to Brequinar, a compound used in SARS-CoV-2 treatment trials. The newly synthesized compound was fully analyzed and characterized via ¹H, ¹³C-NMR, UV, IR, and mass spectral data. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Electric Literature of C13H24N2O).

1,3-Dicyclohexylurea (cas: 2387-23-7) 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.Electric Literature of C13H24N2O

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