Category: amides-buliding-blocks

Drug repositioning of tranilast to sensitize a cancer therapy by targeting cancer-associated fibroblast was written by Ochi, Kosuke;Suzawa, Ken;Thu, Yin Min;Takatsu, Fumiaki;Tsudaka, Shimpei;Zhu, Yidan;Nakata, Kentaro;Takeda, Tatsuaki;Shien, Kazuhiko;Yamamoto, Hiromasa;Okazaki, Mikio;Sugimoto, Seiichiro;Shien, Tadahiko;Okamoto, Yoshiharu;Tomida, Shuta;Toyooka, Shinichi. And the article was included in Cancer Science in 2022.Synthetic Route of C18H17NO5 This article mentions the following:

Cancer-associated fibroblasts (CAFs) are a major component of the tumor microenvironment that mediate resistance of cancer cells to anticancer drugs. Tranilast is an antiallergic drug that suppresses the release of cytokines from various inflammatory cells. In this study, we investigated the inhibitory effect of tranilast on the interactions between non-small cell lung cancer (NSCLC) cells and the CAFs in the tumor microenvironment. Three EGFR-mutant NSCLC cell lines, two KRAS-mutant cell lines, and three CAFs derived from NSCLC patients were used. To mimic the tumor microenvironment, the NSCLC cells were cocultured with the CAFs in vitro, and the mol. profiles and sensitivity to mol. targeted therapy were assessed. Crosstalk between NSCLC cells and CAFs induced multiple biol. effects on the NSCLC cells both in vivo and in vitro, including activation of the STAT3 signaling pathway, promotion of xenograft tumor growth, induction of epithelial-mesenchymal transition (EMT), and acquisition of resistance to mol.-targeted therapy, including EGFR-mutant NSCLC cells to osimertinib and of KRAS-mutant NSCLC cells to selumetinib. Treatment with tranilast led to inhibition of IL-6 secretion from the CAFs, which, in turn, resulted in inhibition of CAF-induced phospho-STAT3 upregulation. Tranilast also inhibited CAF-induced EMT in the NSCLC cells. Finally, combined administration of tranilast with mol.-targeted therapy reversed the CAF-mediated resistance of the NSCLC cells to the mol.-targeted drugs, both in vitro and in vivo. Our results showed that combined administration of tranilast with mol.-targeted therapy is a possible new treatment strategy to overcome drug resistance caused by cancer-CAF interaction. In the experiment, the researchers used many compounds, for example, 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8Synthetic Route of C18H17NO5).

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

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

Reinforcement of hydrogen peroxide bleaching of bamboo pulp was written by Li, Peiyi;Zhang, Meiyun;Xia, Xinxing;Lin, Chuntao. And the article was included in Advanced Materials Research (Durnten-Zurich, Switzerland) in 2012.Application In Synthesis of N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) This article mentions the following:

Magnesium-based alkalis and the Chelants (tetra acetyl ethylene diamine (TAED), Sodium Citrate and Opal) for hydrogen peroxide bleaching of bamboo pulp were investigated in this paper. The results showed that the optimal conditions of hydrogen peroxide bleaching of bamboo pulp were as follows: H₂O₂ 4%, Mg(OH)₂:NaOH=25%, Sodium Citrate 1%, Opal 1.5%, TAED:H₂O₂=0.67, temperature 60°C, and time 90 min. Under the optimum conditions, the brightness of bamboo pulp can be enhanced from 41.2% ISO to 78.2% ISO, while the brightness of bleached pulp by using the Mg(OH)₂-based alkalis was higher than by using NaOH as the alkali source. It can be seen that Sodium Citrate, Opal, and TAED activated H₂O₂ bleaching needed lower reaction temperature, shorter time, and got better brightness and alleviated environment pollution, compared with the conventional H₂O₂ bleaching of the same pulp. 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. 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 N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide)

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

Low-temperature bleaching of cotton induced by glucose oxidase enzymes and hydrogen peroxide activators was written by Tavccer, Petra Forte. And the article was included in Biocatalysis and Biotransformation in 2012.Computed Properties of C10H16N2O4 This article mentions the following:

Glucose oxidase enzymes were used to produce hydrogen peroxide from glucose and oxygen in aqueous solutions Different working conditions, i.e., temperature, aeration with liquefied air, presence of cotton fiber and time of enzyme activity, were tested in order to obtain a solution with the highest possible concentration of hydrogen peroxide. The hydrogen peroxide produced was transformed into different peracids which could bleach the cotton fabric under mild conditions, at a pH between 7 and 8 and at a temperature of around 60°C. The conversion or activation of hydrogen peroxide was conducted with the bleach activators TAED, NOBS and TBBC. The concentrations of hydrogen peroxide and peracids in the solutions were measured with sodium thiosulfate titrations The results indicated that the formation of hydrogen peroxide with glucose oxidase was effective under optimal conditions, which are 50°C, pH 4.6 and aeration. Convenient activators for the conversion of hydrogen peroxide into peracids were TAED and TBBC, which enabled attainment of a relatively high degree of whiteness at pH 7.5 and temperature 50°C. Using the activator NOBS under these conditions did not provide enough peracid to markedly improve whiteness. 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. 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 freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Computed Properties of C10H16N2O4

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

1,3,4-Trisubstituted pyrrolidine CCR5 receptor antagonists. Part 4: Synthesis of N-1 acidic functionality affording analogues with enhanced antiviral activity against HIV was written by Lynch, Christopher L.;Hale, Jeffrey J.;Budhu, Richard J.;Gentry, Amy L.;Mills, Sander G.;Chapman, Kevin T.;MacCoss, Malcolm;Malkowitz, Lorraine;Springer, Martin S.;Gould, Sandra L.;DeMartino, Julie A.;Siciliano, Salvatore J.;Cascieri, Margaret A.;Carella, Anthony;Carver, Gwen;Holmes, Karen;Schleif, William A.;Danzeisen, Renee;Hazuda, Daria;Kessler, Joseph;Lineberger, Janet;Miller, Michael;Emini, Emilio A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2002.Computed Properties of C6H12N2O4 This article mentions the following:

A series of α-(pyrrolidin-1-yl)acetic acids I [R¹ = H, Me, Me₂CH, cyclopropyl, cyclobutylmethyl, cyclohexyl, Ph, etc.; R² = Ph(CH₂)₃, 4-FC₆H₄; R³ = H, HO] was prepared and investigated as selective and potent antivirals against HIV. Several of the pyrrolidine zwitterions demonstrated reasonable in vitro properties, enhanced antiviral activities and improved pharmacokinetic profiles over the lead pyrrolidine. In the experiment, the researchers used many compounds, for example, N1,N2-Dimethoxy-N1,N2-dimethyloxalamide (cas: 106675-70-1Computed Properties of C6H12N2O4).

N1,N2-Dimethoxy-N1,N2-dimethyloxalamide (cas: 106675-70-1) 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.Computed Properties of C6H12N2O4

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

Salicylamide in urine after intake of acetylsalicylic acid due to degradation of salicylic acid conjugates was written by Besserer, Kurt;Tiess, Detlef;Kala, Maria. And the article was included in Z Zagadnien Nauk Sadowych in 2000.Recommanded Product: N,N-Diethylsalicylamide This article mentions the following:

In addition to the well-known acetylsalicylic acid metabolites, salicylamide (SA) was detected in urine from healthy persons after intake of acetylsalicylic acid. SA was found in the Et₂O extracts of urine after alkalinization by ammonia solution SA was identified by gas chromatog.-mass spectrometry. Further examination showed that SA was present in urine only after alkalinization by ammonia solution and not after alkalinization by NaHCO₃ or Na₂CO₃. When dimethyl-, diethyl- or dibutylamine was used for the alkalinization of the urine, the corresponding salicylic acid dialkylamides were detected. Further anal. led to the conclusion that ester-type salicylic acid glucuronide conjugates undergo degradation by hydrolytic amination to form the corresponding amides. This gives the possibility of a specific demonstration of the presence of ester-type glucuronide conjugates. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Recommanded Product: N,N-Diethylsalicylamide).

N,N-Diethylsalicylamide (cas: 19311-91-2) 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. 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.Recommanded Product: N,N-Diethylsalicylamide

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

Antidiabetic Potential of Sinigrin Against Streptozotocin-Induced Diabetes via Modulating Inflammation and Oxidative Stress was written by Zhang, Jing;Wang, Shuling. And the article was included in Applied Biochemistry and Biotechnology in 2022.Quality Control of 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide This article mentions the following:

Diabetes mellitus (DM) is a common metabolic disorder which arises due to the improper carbohydrate metabolism, decreased secretion/activity of insulin, and genetic abnormalities, which result in the increased blood glucose level generally known as hyperglycemia. Diabetes holds an increased global prevalence in each year and is responsible for increased morbidity and mortality rates. Hence, the current investigation focusses to assess the antidiabetic potential of sinigrin on diabetic animal model through the suppression of inflammation. Diabetes was initiated to the animals via administering streptozotocin (STZ) and supplemented with the sinigrin at 25- and 50-mg/kg dose via oral route. The diabetic rats demonstrated the elevated glucose, food and water intake, kidney and liver weights, and reduced bodyweight and depleted insulin status. The sinigrin treatment remarkably improved and modulated these changes in diabetic animals. Addnl., the sinigrin supplementation also modulated the changes in glucose-6-phosphatase; fructose 1,6-bisphosphatase; AST; ALT; creatinine; and inflammatory mediators in the STZ-provoked diabetic animals. The levels of hexokinase, protein, and antioxidants also improved by the sinigrin treatment. The histol. investigations of pancreas also witnessed the therapeutic actions of sinigrin, which is supported by the findings of biochem. examinations Therefore, it was clear that the sinigrin supplementation displayed remarkable antidiabetic effect on STZ-initiated diabetic animals via modulating inflammation and other biochem. changes, which recommends that sinigrin could be a talented candidate for diabetes management in the future. In the experiment, the researchers used many compounds, for example, 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8Quality Control 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. 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. 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 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide

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

Deep Eutectic Solvent Mediated Carbonylation of Amines and Alcohols by Using Dimethyl Carbonate: Selective Symmetrical Urea and Organic Carbonate Synthesis was written by Karimi, Farzaneh;Shariatipour, Monire;Heydari, Akbar. And the article was included in ChemistrySelect in 2021.HPLC of Formula: 2387-23-7 This article mentions the following:

This work presented one-pot synthesis of sym. organic carbonates and ureas by employing cheap and biodegradable deep eutectic solvent as the catalyst and reaction media. The effect of different reaction parameters such as temperature, DMC/amines and alcs. ratio and reaction time were investigated on the reaction efficiency. This new protocol provided a simple, fast, and sustainable approach and proceeded with high efficiency with aliphatic and aromatic amines and alcs. as well. Finally, applicability of this methodol. was also examined for reaction of nucleophiles such as Ph hydrazine and Ph glycine with di-Me carbonate. Interestingly, it was found that this reaction system obtained good yields of product for both of them. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7HPLC of Formula: 2387-23-7).

1,3-Dicyclohexylurea (cas: 2387-23-7) 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.HPLC of Formula: 2387-23-7

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

Copper-Catalyzed Coupling Reaction of (Hetero)Aryl Chlorides and Amides was written by De, Subhadip;Yin, Junli;Ma, Dawei. And the article was included in Organic Letters in 2017.Application of 10268-06-1 This article mentions the following:

Cu₂O/N,N’-bis(thiophen-2-ylmethyl)oxalamide is established to be an effective catalyst system for Goldberg amidation with inferior reactive (hetero)aryl chlorides, which have not been efficiently documented by Cu-catalysis to date. The reaction is well liberalized toward a variety of functionalized (hetero)aryl chlorides and a wide range of aromatic and aliphatic primary amides in good to excellent yields. Furthermore, the arylation of lactams and oxazolidinones is achieved. The present catalytic system also accomplished an intramol. cross-coupling product. In the experiment, the researchers used many compounds, for example, 2-(2-Chlorophenyl)acetamide (cas: 10268-06-1Application of 10268-06-1).

2-(2-Chlorophenyl)acetamide (cas: 10268-06-1) 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 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.Application of 10268-06-1

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

Actual contamination of the Danube and Sava Rivers at Belgrade (2013) was written by Antonijevic, Milan D.;Arsovic, Marija;Caslavsky, Josef;Cvetkovic, Vesna;Dabic, Predrag;Franko, Mladen;Ilic, Gordana;Ivanovic, Milena;Ivanovic, Nevena;Kosovac, Milica;Medic, Dragana;Najdanovic, Slobodan;Nikolic, Milica;Novakovic, Jovana;Radovanovic, Tatjana;Ranic, Durdina;Sajatovic, Dojan;Spijunovic, Gorica;Stankov, Ivana;Tosovic, Jelena;Trebse, Polonca;Vasiljevic, Olivera;Schwarzbauer, Jan. And the article was included in Journal of the Serbian Chemical Society in 2014.Application In Synthesis of N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) This article mentions the following:

This study was focussed on a comprehensive investigation on the state of pollution of the Danube and Sava Rivers in the region of Belgrade. Different complementary anal. approaches were employed covering both i) organic contaminants in the river water by target analyses of hormones and neonicotinoids as well as non-target screening analyses and ii) heavy metals in the sediments. Finally, some common water quality parameters were analyzed. The overall state of pollution is on a moderate level. Bulk parameters did not reveal any unusual observations. Moreover, quantification of preselected organic contaminants did not indicate to elevated pollution. More significant contaminations were registered for chromium, nickel, zinc and partially copper in sediments with values above the target values according to Serbian regulations. Lastly, non-target screening anal. revealed a wider spectrum of organic contaminants comprising pharmaceuticals, tech. additives, personal care products and pesticides. The study presented a comprehensive view on the state of pollution of the Sava and Danube Rivers and is the base for setting up further monitoring programs. As a superior outcome, it was illustrated how different chem. analyses can result in different assessments of the river quality. A comparison of target and non-target analyses pointed to potential misinter-pretation of the real state of pollution. 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. 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. 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.Application In Synthesis of N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide)

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

Regioselective synthesis of C3 alkylated and arylated benzothiophenes was written by Shrives, Harry J.;Fernandez-Salas, Jose A.;Hedtke, Christin;Pulis, Alexander P.;Procter, David J.. And the article was included in Nature Communications in 2017.Synthetic Route of C11H15NO2 This article mentions the following:

The method for completely regioselective, metal-free C3 C-H functionalization of benzothiophenes e.g., I that utilizes synthetically unexplored benzothiophene S-oxides II (R¹ = H, 5-NO₂, 6-Br, etc.; R² = H, CO₂CH₃, CN, etc.), readily available from straightforward oxidation of benzothiophenes such as 5-bromobenzo[b]thiophene, 2-phenylbenzo[b]thiophene, 2-methylbenzo[b]thiophene, etc. and phenols such as p-cresol, 4-iodophenol, 4-nitrophenol, etc./propargyl silanes such as trimethyl(allyl)silane, trimethyl(2-bromoallyl)silane, 2-((trimethylsilyl)methyl)allyl acetate, etc. and allyl silanes such as propargyl silane, hex-1-yne-1,3-diylbis(trimethylsilane), hept-2-yn-1-yltrimethylsilane, etc. was described. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Synthetic Route of C11H15NO2).

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. 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.Synthetic Route of C11H15NO2

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