Month: February 2023

Mechanochemical Synthesis of Primary Amides was written by Gomez-Carpintero, Jorge;Sanchez, J. Domingo;Gonzalez, J. Francisco;Menendez, J. Carlos. And the article was included in Journal of Organic Chemistry in 2021.Electric Literature of C6H13NO3 This article mentions the following:

Ball milling of aromatic, heteroaromatic, vinylic, and aliphatic esters RCOOEt (R = 3-fluorophenyl, 1,3-diethoxy-1,3-dioxopropan-2-yl, thiophen-2-yl, etc.) and 2-chromanone with ethanol and calcium nitride afforded the corresponding primary amides RC(O)NH₂in a transformation that was compatible with a variety of functional groups and maintained the integrity of a stereocenter α to carbonyl. This methodol. was applied to α-amino esters (S)-H₂NCH(CH₂R¹)C(O)OEt [R¹ = Ph, (methylsulfanyl)methyl] and N-Boc dipeptide esters (S)-(CH₃)₃COC(O)NHCH(CH₂R²)C(O)NHCH₂C(O)OEt (R² = H, Ph, 1H-indol-3-yl) and also to the synthesis of rufinamide, an antiepileptic drug. In the experiment, the researchers used many compounds, for example, 2,2-Diethoxyacetamide (cas: 61189-99-9Electric Literature of C6H13NO3).

2,2-Diethoxyacetamide (cas: 61189-99-9) 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 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.Electric Literature of C6H13NO3

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

The role of potassium channels in the proliferation and migration of endometrial adenocarcinoma HEC1-A cells was written by Erdem Kis, Emel;Tiftik, R. Nalan;Al Hennawi, Khairat;Un, Ismail. And the article was included in Molecular Biology Reports in 2022.HPLC of Formula: 10238-21-8 This article mentions the following:

Endometrial cancer is the most common gynecol. cancer in developed countries. Potassium channels, which have many types, are suggested to play a major role in cancer progression. However, their role in endometrial cancer has not been fully investigated. We aimed to demonstrate whether the ATP-sensitive potassium channel blocker glibenclamide, voltage-sensitive potassium channel blocker 4-aminopyridine, non-selective (voltage-sensitive and calcium-activated) potassium channels blocker tetraethylammonium and potassium chloride (KCl) have any effect on the proliferation and migration of HEC1-A cells. Methods and results: Proliferation and migration were evaluated by real-time cell anal. (xCELLigence system) and wound healing assays, resp. Proliferation was reduced by glibenclamide (0.1 and 0.2 mM, P < 0.05 and P < 0.01, resp.), 4-aminopyridine (10 and 20 mM, P < 0.001) and tetraethylammonium (10 and 20 mM, P < 0.01 and P < 0.001, resp.). However, KCl did not change the proliferation. Migration was reduced by glibenclamide (0.01, 0.1 and 0.2 mM, P < 0.001, P < 0.001 and P < 0.01, resp.) and 4-aminopyridine (10 and 20 mM, P < 0.05 and P < 0.01, resp.). Tetraethylammonium did not change migration. However, KCl reduced it (10, 25 and 50 mM, P < 0.05, P < 0.01 and P < 0.01, resp.). Both proliferation and migration were reduced by glibenclamide and 4-aminopyridine. However, tetraethylammonium only reduced proliferation and KCl only reduced migration. Potassium channels have an important role in HEC1-A cell proliferation and migration and potassium channel blockers needs to be further investigated for their therapeutic effect in endometrial cancer. In the experiment, the researchers used many compounds, for example, 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8HPLC of Formula: 10238-21-8).

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. 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.HPLC of Formula: 10238-21-8

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

Nonstrained γ-Butyrolactone to High-Molecular-Weight Poly(γ-butyrolactone): Facile Bulk Polymerization Using Economical Ureas/Alkoxides was written by Lin, Limiao;Han, Dongmei;Qin, Jiaxiang;Wang, Shuanjin;Xiao, Min;Sun, Luyi;Meng, Yuezhong. And the article was included in Macromolecules (Washington, DC, United States) in 2018.Recommanded Product: 1,3-Dicyclohexylurea This article mentions the following:

We disclose an efficient catalyst system of com. ureas/alkoxides for the challenging ring-opening polymerization (ROP) of bioderived “nonpolymerizable” γ-butyrolactone (γ-BL). This effective polymerization can not only be performed under mild conditions like bulk polymerization, higher monomer ratio, and elevated temperature (-20 °C comparing to -40 °C), but also obtains high-mol.-weight poly(γ-butyrolactone) (PγBL) (M_n up to 68.2 kg/mol). To our knowledge, this is a big progress in the research area of ROP of γ-BL, which provides a promising prospect for the industrial-scale methodol. of PγBL production Structural anal. including NMR and MALDI-TOF, along with mechanistic computational studies based on DFT calculations, show that urea anion acts as a bifunctional catalyst, which activates the alc. initiator and γ-BL before obeying an anionic polymerization Furthermore, the catalytic activities of ureas/alkoxides systems have been optimized using the ureas with electron-donating groups which are proved to have lower activation barrier by computational calculation In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Recommanded Product: 1,3-Dicyclohexylurea).

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′R″; or, equivalently, an acyl (alkanoyl) group RC(=O)− joined to an amine group. 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: 1,3-Dicyclohexylurea

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

Comparison of effectiveness and safety of insulin and oral hypoglycemic drugs in treatment of gestational diabetes mellitus and meta-analysis of 26 randomized controlled trials was written by Li, Chaolin;Gao, Can;Zhang, Xianqin;Zhang, Lin;Shi, Hao;Jia, Xu. And the article was included in Gynecological Endocrinology in 2022.Quality Control of 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide This article mentions the following:

Oral hypoglycemic drugs for the treatment of gestational diabetes mellitus (GDM) are still controversial because they can pass through the placenta. The purpose of this meta-anal. is to evaluate the safety and effectiveness of oral hypoglycemic drugs. PubMed, Ovid Embase, Web of Science, and Cochrane databases were systematically searched (inception to 20 Apr. 2021). Rev Man 5.0 was used to analyze the data. A random-effects model was used to compute the summary risk estimates There were 26 randomized controlled trials (RCTs) involving 4921 GDM patients which were included in this meta-anal. Compared with metformin, insulin had a significant increase in the risk of preeclampsia (odds ratio [OR], 1.61; 95% confidence interval [CI], 1.06 to 2.45; I²=40%; p < .05), hypertension (OR, 1.42; 95% CI, 1.02 to 1.99; I²=0%; p < .05), hypoglycemia (OR, 3.93; 95% CI, 1.27 to 12.19; I²=0%; p < .05), neonatal hypoglycemia (OR, 1.92; 95% CI, 1.34 to 2.76; I²=41%; p < .0001), neonatal jaundice (OR, 2.70; 95% CI, 1.12 to 6.52; I²=0%; p < .05), and Neonatal Intensive Care Unit Admission (OR, 1.46; 95% CI, 1.09 to 1.95; I²=39%; p < .05), but the risk of neonatal macrosomia (OR, 1.67; 95% CI, 1.12 to 2.40; I²=0%; p < .05) and neonatal injury (OR, 0.70; 95% CI, 0.55 to 0.89; I²=0%; p < .01) is lower. Metformin is comparable with insulin in glycemic control and neonatal outcomes and has the potential to replace insulin therapy in clin. practice. Glyburide is behind metformin and insulin, and more RCTs are needed to verify its safety. 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 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. 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.Quality Control of 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide

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

Photo-on-Demand Phosgenation Reactions with Chloroform for Selective Syntheses of N-Substituted Ureas and Isocyanates was written by Muranaka, Ryo;Liu, Yue;Okada, Itsuumi;Okazoe, Takashi;Tsuda, Akihiko. And the article was included in ACS Omega in 2022.Quality Control of 1,3-Dicyclohexylurea This article mentions the following:

Two new reaction processes involving the in situ oxidative photochem. conversion of CHCl₃ to COCl₂ allowed selective syntheses of N-substituted ureas and isocyanates from amines. (I) A CHCl₃ solution containing an amine and an organic base under O₂ bubbling provided the urea derivative under exposure to UV light generated from a low-pressure mercury lamp at 20-40°C. (II) A two-step reaction involving the oxidative photodecomposition of CHCl₃ at lower temperatures and subsequent sequential injections of an amine and organic base into the sample solution provided the isocyanate in high yield. The reaction processes of (I) and (II) capitalize on the solution conditions of [COCl₂] < [amine] and [COCl₂] > [amine], resp., to result in 1:2 and 1:1 reactions. In general, isocyanates, especially aromatic and haloalkyl ones, readily undergo hydrolysis in the presence of an organic base. However, with the advantage of synthesizing the isocyanates in CHCl₃ solvent, direct addition of monoalcs. and diols to the as-prepared sample solution containing the diisocyanate allowed the one-pot syntheses of biscarbamates and polyurethanes, resp. The reactions developed in this study are simple, safe, and inexpensive methods of synthesizing N-substituted ureas and isocyanates, and derivatives of isocyanates such as carbamates and polyurethanes. The present new methods can replace current synthetic methods using COCl₂ in both academia and industry. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Quality Control of 1,3-Dicyclohexylurea).

1,3-Dicyclohexylurea (cas: 2387-23-7) belongs to amides. The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds. Tertiary amides, with the important exception of N,N-dimethylformamide, exhibit low solubility in water. Amides can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Quality Control of 1,3-Dicyclohexylurea

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

Total synthesis of antibiotic althiomycin was written by Inami, Kaoru;Shiba, Tetsuo. And the article was included in Bulletin of the Chemical Society of Japan in 1985.Quality Control of 2,2-Diethoxyacetamide This article mentions the following:

Total synthesis of antibiotic althiomycin (I) was achieved staring from D-cysteine. The imide bond between thiazoline and the pyrrolinone part was constructed by coupling reaction of sodium salt of pyrrolinone with cysteine active ester or by photoreaction with diketene. The hydroxymethyl group attached on the carbon adjacent to C-2 of the thiazoline ring, was introduced by aldol condensation posterior to the thiazoline ring formation. The thiazole part was introduced in a final step in whole process of the total synthesis of the antibiotic. The synthetic althiomycin was identical with the natural antibiotic in all respects. In the experiment, the researchers used many compounds, for example, 2,2-Diethoxyacetamide (cas: 61189-99-9Quality Control of 2,2-Diethoxyacetamide).

2,2-Diethoxyacetamide (cas: 61189-99-9) 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.Quality Control of 2,2-Diethoxyacetamide

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

In vivo pharmacokinetic analyses of placental transfer of three drugs of different physicochemical properties in pregnant rats was written by Mehta, Darshan;Li, Miao;Nakamura, Noriko;Chidambaram, Mani;He, Xiaobo;Bryant, Matthew S.;Patton, Ralph;Davis, Kelly;Fisher, Jeffrey. And the article was included in Reproductive Toxicology in 2022.Application In Synthesis of 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide This article mentions the following:

Although the use of medication during pregnancy is common, information on exposure to the developing fetus and potential teratogenic effects is often lacking. This study used a rat model to examine the placental transfer of three small-mol. drugs with mol. weights ranging from approx. 300 to 800 Da with different physicochem. properties. Time-mated Sprague Dawley (Hsd:SD) rats aged 11-13 wk were administered either glyburide, rifaximin, or fentanyl at gestational day 15. Maternal blood, placentae, and fetuses were collected at 5 min, 30 min, 1 h, 4 h, 8 h, 24 h, 48 h, and 96 h post-dose. To characterize the rate and extent of placental drug transfer, we calculated several pharmacokinetic parameters such as maximum concentration (Cmax), time to maximum concentration (Tmax), area under the concentration-time curve (AUC), half-life (t1/2), clearance (CL), and volume of distribution (Vd) for plasma, placenta, and fetus tissues. The results indicated showed that fetal exposure was lowest for glyburide, accounting for only 2.2% of maternal plasma exposure as measured by their corresponding AUC ratio, followed by rifaximin (37.9%) and fentanyl (172.4%). The fetus/placenta AUC ratios were found to be 10.7% for glyburide, 11.8% for rifaximin, and 39.1% for fentanyl. These findings suggest that although the placenta acts as a protective shield for the fetus, the extent of protection varies for different drugs and depends on factors such as mol. weight, lipid solubility, transporter-mediated efflux, and binding to maternal and fetal plasma proteins. In the experiment, the researchers used many compounds, for example, 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8Application In Synthesis of 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide).

5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8) belongs to amides. Compared to amines, amides are very weak bases and do not have clearly defined acid–base properties in water. On the other hand, amides are much stronger bases than esters, aldehydes, and ketones. Amides can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Application In Synthesis of 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide

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

Reaction of electrogenerated cyanomethyl anion with cyclohexylisocyanate: synthesis of N-(cyclohexylcarbamoyl)acetamide. An unexpected product was written by Scarano, Vincenzo;Bortolami, Martina;Pandolfi, Fabiana;Petrucci, Rita;Rocco, Daniele;Zollo, Giuseppe;Feroci, Marta. And the article was included in Journal of the Electrochemical Society in 2020.Reference of 2387-23-7 This article mentions the following:

The contamination with H₂O of the cathodic ACN-Et₄NBF₄ solution gave the authors the opportunity to study alkyl isocyanate reactivity toward electrogenerated anions. The cathodic reduction of a ACN-Et₄NBF₄ solution gave both hydroxide and cyanomethyl anions. The reaction of the catholyte with cyclohexylisocyanate led to the exclusive formation of acetamidated product, with no traces of cyanomethylated one. On the contrary, when reacting with benzaldehyde only the cyanomethylated was isolated. Considering that the acetamidated product of benzaldehyde is reported to be unstable (thus its formation cannot be excluded), various experiments were carried out to understand the anomalous reactivity of cyclohexylisocyanate. Also, computational anal. allowed to state the higher stability of acetamidated product with respect to the cyanomethylated one. The possibility of a concerted reaction, instead of acetamide anion formation prior to the reaction, is still an open question. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Reference of 2387-23-7).

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

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

Chiral, Magnetic, and Photosensitive Liquid Crystalline Nanocomposites Based on Multifunctional Nanoparticles and Achiral Liquid Crystals was written by Poryvai, Anna;Smahel, Michal;Svecova, Marie;Nemati, Ahlam;Shadpour, Sasan;Ulbrich, Pavel;Ogolla, Timothy;Liu, Jiao;Novotna, Vladimira;Veverka, Miroslav;Vejpravova, Jana;Hegmann, Torsten;Kohout, Michal. And the article was included in ACS Nano in 2022.Application of 2387-23-7 This article mentions the following:

Nanoparticles serving as a multifunctional and multiaddressable dopant to modify the properties of liquid crystalline matrixes are developed by combining cobalt ferrite nanocrystals with organic ligands featuring a robust photosensitive unit and a source of chirality from the natural pool. These nanoparticles provide a stable nanocomposite when dispersed in achiral liquid crystals, giving rise to chiral supramol. structures that can respond to UV-light illumination, and, at the same time, the formed nanocomposite possesses strong magnetic response. We report on a nanocomposite that shows three addnl. functionalities (chirality and responsiveness to UV light and magnetic field) upon the introduction of a single dopant into achiral liquid crystals. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Application of 2387-23-7).

1,3-Dicyclohexylurea (cas: 2387-23-7) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. 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.Application of 2387-23-7

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

An α-Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung was written by Bauer, Adriano;Di Mauro, Giovanni;Li, Jing;Maulide, Nuno. And the article was included in Angewandte Chemie, International Edition in 2020.Application In Synthesis of 4-Bromo-N-methoxy-N-methylbenzamide This article mentions the following:

The reactivity of iodine(III) reagents towards nucleophiles is often associated with umpolung and cationic mechanisms. Herein, we report a general process converting a range of ketone derivatives into α-cyclopropanated ketones by oxidative umpolung [e.g., I → II (71%, d.r. > 95:5) + III (8%, d.r. > 95:5) in presence of PhIO.MsOH and BF₃.OEt₂]. Mechanistic investigation and careful characterization of side products revealed that the reaction follows an unexpected pathway and suggests the intermediacy of non-classical carbocations. In the experiment, the researchers used many compounds, for example, 4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2Application In Synthesis of 4-Bromo-N-methoxy-N-methylbenzamide).

4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2) 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.Application In Synthesis of 4-Bromo-N-methoxy-N-methylbenzamide

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