Category: amides-buliding-blocks

Tranilast inhibits angiotensin II-induced myocardial fibrosis through S100A11/ transforming growth factor-β (TGF-β1)/Smad axis was written by Chen, Youquan;Huang, Ming;Yan, Yi;He, Dequan. And the article was included in Bioengineered in 2021.Product Details of 53902-12-8 This article mentions the following:

Tranilast has an ameliorative effect on myocardial fibrosis (MF), but the specific mechanism has not been studied. S100A11 is a key regulator of collagen expression in MF. In this paper, we will study the regulatory roles of Tranilast and S100A11 in MF. After the introduction of angiotensin II (AngII) to Human cardiac fibroblasts (HCF), Tranilast was administered. CCK-8 kit was used to detect cell viability. Wound Healing assay detected cell migration, and Western blot was used to detect the expression of migration-related proteins and proteins related to extracellular matrix synthesis. The expression of α-SMA was detected by immunofluorescence (IF). The expression of S100A11 was detected by qPCR and Western blot, and then S100A11 was overexpressed by cell transfection technol., so as to explore the mechanism by which Tranilast regulated MF. In addition, the expression of TGF-β1/Smad pathway related proteins was detected by Western blot. Tranilast inhibited Ang II-induced over-proliferation, migration and fibrosis of human cardiac fibroblasts (HCF), and simultaneously significantly decreased S100A11 expression was observed Overexpression of S100A11 reversed the inhibition of Tranilast on AngII-induced over-proliferation, migration, and fibrosis in HCF, accompanied by activation of the TGF-β1/Smad pathway. Overall, Tranilast inhibits angiotensin II-induced myocardial fibrosis through S100A11/TGF-β1/Smad axis. In the experiment, the researchers used many compounds, for example, 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8Product Details of 53902-12-8).

2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8) 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 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 53902-12-8

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

Formation of the Tertiary Sulfonamide C(sp³)-N Bond Using Alkyl Boronic Ester via Intramolecular and Intermolecular Copper-Catalyzed Oxidative Cross-Coupling was written by Kim, Dong Sun;Lee, Hong Geun. And the article was included in Journal of Organic Chemistry in 2021.Synthetic Route of C9H13NO2S This article mentions the following:

A synthetic strategy for the formation of C(sp³)-N bonds, particularly through a Cu-catalyzed oxidative cross-coupling, is rare. Herein, the authors report a novel synthetic approach for the preparation of tertiary sulfonamides via Cu-catalyzed intra- and intermol. oxidative C(sp³)-N cross-coupling reactions. This method allows the use of the readily available C(sp³)-based pinacol boronate as a substrate and the tolerance of a wide range of functional groups under mild reaction conditions. The success of this strategy relies on the unprecedented additive effects of silanol and NaIO₄. In the experiment, the researchers used many compounds, for example, N-Isopropylbenzenesulfonamide (cas: 5339-69-5Synthetic Route of C9H13NO2S).

N-Isopropylbenzenesulfonamide (cas: 5339-69-5) 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. 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 C9H13NO2S

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

One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides was written by Davies, Alyn T.;Curto, John M.;Bagley, Scott W.;Willis, Michael C.. And the article was included in Chemical Science in 2017.Electric Literature of C9H10BrNO2 This article mentions the following:

A mild, efficient synthesis of sulfonyl fluorides from aryl and heteroaryl bromides utilizing palladium catalysis is described. The process involves the initial palladium-catalyzed sulfonylation of aryl bromides using DABSO as an SO₂ source, followed by in situ treatment of the resultant sulfinate with the electrophilic fluorine source NFSI. This sequence represents the first general method for the sulfonylation of aryl bromides, and offers a practical, one-pot alternative to previously described synthesis of sulfonyl fluorides, allowing rapid access to these biol. important mols. Excellent functional group tolerance is demonstrated, with the transformation successfully achieved on a number of active pharmaceutical ingredients, and their precursors. The preparation of peptide-derived sulfonyl fluorides is also demonstrated. In the experiment, the researchers used many compounds, for example, 4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2Electric Literature 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. 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.Electric Literature of C9H10BrNO2

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

Tranilast Blunts the Hypertrophic and Fibrotic Response to Increased Afterload Independent of Cardiomyocyte Transient Receptor Potential Vanilloid 2 Channels was written by Koch, Sheryl E.;Nieman, Michelle L.;Robbins, Nathan;Slone, Samuel;Worley, Mariah;Green, Lisa C.;Chen, Yamei;Barlow, Alexandria;Tranter, Michael;Wang, HongSheng;Lorenz, John N.;Rubinstein, Jack. And the article was included in Journal of Cardiovascular Pharmacology in 2018.COA of Formula: C18H17NO5 This article mentions the following:

Tranilast is clin. indicated for the treatment of allergic disorders and is also a nonselective blocker of the transient receptor potential vanilloid 2 (TRPV2) channel. Previous studies have found that it has protective effects in various animal models of cardiac disease. The laboratory has found that genetic deletion of TRPV2 results in a blunted hypertrophic response to increased afterload; thus, this study tested the hypothesis that tranilast through cardiomyocyte TRPV2 blockade can inhibit the hypertrophic response to pressure overload in vivo through transverse aortic constriction and ex vivo through isolated myocyte studies. The in vivo studies demonstrated that tranilast blunted the fibrotic response to increased afterload and, to a lesser extent, the hypertrophic response. After 4 wk, this blunting was associated with improved cardiac function, although at 8 wk, the cardiac function deteriorated similarly to the control group. Finally, the in vitro studies demonstrated that tranilast was not inhibiting these responses at the cardiomyocyte level. In conclusion, it demonstrated that tranilast blunting of the fibrotic and hypertrophic response occurs independently of cardiac TRPV2 channels and may be cardioprotective in the short term but not after prolonged administration. In the experiment, the researchers used many compounds, for example, 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8COA of Formula: C18H17NO5).

2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8) 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 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.COA of Formula: C18H17NO5

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

Ring-Opening Fluorination of Isoxazoles was written by Komatsuda, Masaaki;Ohki, Hugo;Kondo, Hiroki Jr.;Suto, Ayane;Yamaguchi, Junichiro. And the article was included in Organic Letters in 2022.Synthetic Route of C10H10F3NO2 This article mentions the following:

A series of tertiary fluorinated carbonyls I [R¹ = Ph, 2-naphthyl, 2-thienyl, etc.; R² = Me, nBu, (CH₂)₂Ph, etc.] was developed via ring-opening fluorination of isoxazoles by using an electrophilic fluorinating agent (Selectfluor) followed by deprotonation. This method featured mild reaction conditions, good functional group tolerance and a simple exptl. procedure. Diverse transformations of the resulting α-fluorocyanoketones were also demonstrated, furnished a variety of fluorinated compounds In the experiment, the researchers used many compounds, for example, N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7Synthetic Route of C10H10F3NO2).

N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7) 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 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 C10H10F3NO2

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

Dose-dependent Spasmolytic, Bronchodilator, and Hypotensive Activities of Panicum miliaceum L. was written by Saqib, Fatima;Al-Huqail, Arwa Abdulkreem;Asma, Memona;Chicea, Liana;Hogea, Mircea;Irimie, Marius;Gavris, Claudia. And the article was included in Dose-Response in 2022.Recommanded Product: 10238-21-8 This article mentions the following:

Panicum miliaceum L. is a medicinally effective plant used in indigenous system of medicine for a variety of ailments. However, there is no comprehensive study explaining its effectiveness in gastrointestinal tract, respiratory, and cardiovascular system ailments. This study was designed to validate the pharmacol. basis for the folkloric use of Panicum miliaceum L. in diarrhea, asthma, and hypertension. Panicum miliaceum extract was analyzed to detect the presence of bioactive compounds by HPLC. The isolated rabbit jejunum, trachea, and aorta were used for in vitro experiments using tissue bath assembly coupled with Power Lab data acquisition system to explore their relative effects. In-vivo experiments were performed for anti-diarrheal activity. HPLC anal. revealed the presence of gallic acid, butylated hydroxytoluene, catechin, and quercetin. Concentration dependent activities were observed by relaxing K⁺ (low) induced contractions having spasmolytic effect with EC50 = .358 ± .052, bronchodilator (EC50 = 2.483 ± .05793), and vasorelaxant (EC50 = .383 ± .063), probably due to the ATP dependent potassium channel activation. It was confirmed through pre-exposure of glibenclamide (specific ATP-dependent K⁺ channel blocker) having similarities with cromakalim. Pm. Cr revealed its antidiarrheal via in vivo experiments on rats. This study indicates that Panicum miliaceum has antidiarrheal, spasmolytic, bronchodilator, and vasorelaxant activities probably due to the ATP dependent K⁺ channel activation. 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: 10238-21-8).

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. 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.Recommanded Product: 10238-21-8

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

Synthesis, characterization and desalination study of novel PSAB and mPSAB blend membranes with Polysulfone (PSf) was written by Padaki, Mahesh;Isloor, Arun M.;Ismail, Ahmad Fauzi;Abdullah, M. S.. And the article was included in Desalination in 2012.Synthetic Route of C7H10N2O2S This article mentions the following:

The present paper describes the synthesis of poly sulfonyl amino benzamide (PSAB) and methyalated poly sulfonyl amino benzamide (mPSAB) polymer, using terephthalic acid chloride and substituted 4-amino-1-benzensulfonmide in N-methyl-2-pyrrolidone. Polymers were characterized by FT-IR, NMR and GPC. Polysulfone composite membranes were prepared using these novel polymers by DIPS (Diffusion Induced Phase Separation) method. These composite membranes are useful for water purification with special emphasis on sea water desalination. Newly prepared membranes were studied for salt rejection, water flux, mol. weight cut off by PEG solution, effect of the pH on water swelling and salt rejection and flux decline was also studied. 30 to 70% of the salt rejection was observed in all membranes. Effect of the dilution on salt rejection was studied using different concentration of NaCl solution varying from 1000 ppm to 3500 ppm. All the membranes showed 80% rejection for PEG having 1000 Da mol. weight Contact angle and water swelling was measured to determine hydrophilicity of the membrane. Water swelling and salt rejection in different pH was also studied. In the experiment, the researchers used many compounds, for example, 4-Amino-3-methylbenzenesulfonamide (cas: 53297-70-4Synthetic Route of C7H10N2O2S).

4-Amino-3-methylbenzenesulfonamide (cas: 53297-70-4) 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. 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 C7H10N2O2S

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

Characterization of the contamination fingerprint of wastewater treatment plant effluents in the Henares River Basin (central Spain) based on target and suspect screening analysis was written by Lopez-Herguedas, N.;Gonzalez-Gaya, B.;Castelblanco-Boyaca, N.;Rico, A.;Etxebarria, N.;Olivares, M.;Prieto, A.;Zuloaga, O.. And the article was included in Science of the Total Environment in 2022.Reference of 10238-21-8 This article mentions the following:

The interest in contaminants of emerging concern (CECs) has increased lately due to their continued emission and potential ecotoxicol. hazards. Wastewater treatment plants (WWTPs) are generally not capable of eliminating them and are considered the main pathway for CECs to the aquatic environment. The number of CECs in WWTPs effluents is often so large that complementary approaches to the conventional target anal. need to be implemented. Within this context, multitarget quant. anal. (162 compounds) and a suspect screening (>40,000 suspects) approaches were applied to characterize the CEC fingerprint in effluents of five WWTPs in the Henares River basin (central Spain) during two sampling campaigns (summer and autumn). The results indicated that 76% of the compounds quantified corresponded to pharmaceuticals, 21% to pesticides and 3% to industrial chems. Apart from the 82 compounds quantified, suspect screening increased the list to 297 annotated compounds Significant differences in the CEC fingerprint were observed between summer and autumn campaigns and between the WWTPs, being those serving the city of Alcala de Henares the ones with the largest number of compounds and concentrations Finally, a risk prioritization approach was applied based on risk quotients (RQs) for algae, invertebrates, and fish. Azithromycin, diuron, chlortoluron, clarithromycin, sertraline and sulfamethoxazole were identified as having the largest risks to algae. As for invertebrates, the compounds having the largest RQs were carbendazim, fenoxycarb and eprosartan, and for fish acetaminophen, DEET, carbendazim, caffeine, fluconazole, and azithromycin. The two WWTPs showing higher calculated Risk Indexes had tertiary treatments, which points towards the need of increasing the removal efficiency in urban WWTPs. Furthermore, considering the complex mixtures emitted into the environment and the low dilution capacity of Mediterranean rivers, we recommend the development of detailed monitoring plans and stricter regulations to control the chem. burden created to freshwater ecosystems. In the experiment, the researchers used many compounds, for example, 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8Reference of 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. 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.Reference of 10238-21-8

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

Validation of the CULTEX Radial Flow System for the assessment of the acute inhalation toxicity of airborne particles was written by Tsoutsoulopoulos, Amelie;Gohlsch, Katrin;Moehle, Niklas;Breit, Andreas;Hoffmann, Sebastian;Krischenowski, Olaf;Mueckter, Harald;Gudermann, Thomas;Thiermann, Horst;Aufderheide, Michaela;Steinritz, Dirk. And the article was included in Toxicology In Vitro in 2019.COA of Formula: C10H16N2O4 This article mentions the following:

The CULTEX Radial Flow System (RFS) is a modular in vitro system for the homogenous exposure of cells to airborne particles at the air-liquid interface (ALI). A former pre-validation study successfully demonstrated the general applicability of the CULTEX RFS and its transferability, stability and reproducibility. Based on these results, the methodol. was optimized, validated and prediction models for acute inhalation hazards were established. Cell viability of A549 cells after ALI exposure to 20 pre-selected test substances was assessed in three independent laboratories Cytotoxicity of test substances was compared to the resp. incubator controls and used as an indicator of toxicity. Substances were considered to exert an acute inhalation hazard when viability decreased below 50% (prediction model (PM) 50%) or 75% (PM 75%) at any of three exposure doses (25, 50 or 100 μg/cm²). Results were then compared to existing in vivo data and revealed an overall concordance of 85%, with a specificity of 83% and a sensitivity of 88%. Depending on the applied PM, the within-laboratory and between-laboratory reproducibility ranged from 90 to 100%. In summary, the CULTEX RFS was proven as a transferable, reproducible and well predictive screening method for the qual. assessment of the acute pulmonary cytotoxicity of airborne particles. In the experiment, the researchers used many compounds, for example, N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) (cas: 10543-57-4COA of Formula: C10H16N2O4).

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

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

Mass-spectrometric investigations on derivatives of phenylacetic acid. I. Loss of ortho substituents from ionized phenylacetamides was written by Lee, Dong Ung;Mayer, Klaus K.;Wiegrebe, Wolfgang;Lauber, Rolf;Schlunegger, Urs P.. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 1988.Quality Control of 2-(2-Chlorophenyl)acetamide This article mentions the following:

The mol. ions of 2-RC₆H₄CH₂CONR¹₂ (I; R = Cl, Br, NO₂; R¹ = H, Me) lost R to give strong [M-R]⁺ signals. I (R = MeO, cyano; R¹ = H, Me) lost R to a minor extent, while I (R = H, Me, F; R¹ = H; R = H, F, R¹ = Me) did not lose R. Also, Cl was not lost from the 3- and 4-chloro amides. Loss of a 2-NO₂ group was favored by an addnl. MeO substituent. Metastable-ion and collisional-activation spectra were discussed. In the experiment, the researchers used many compounds, for example, 2-(2-Chlorophenyl)acetamide (cas: 10268-06-1Quality Control of 2-(2-Chlorophenyl)acetamide).

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. 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.Quality Control of 2-(2-Chlorophenyl)acetamide

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