Category: amides-buliding-blocks

Ru-catalyzed highly enantioselective hydrogenation of α-keto Weinreb amides was written by Zhao, Meng Meng;Li, Wan Fang;Ma, Xin;Fan, Wei Zheng;Tao, Xiao Ming;Li, Xiao Ming;Xie, Xiao Min;Zhang, Zhao Guo. And the article was included in Science China: Chemistry in 2013.Synthetic Route of C6H12N2O4 This article mentions the following:

Asym. hydrogenation of α-keto Weinreb amides was realized with [Ru((S)-Sunphos)(benzene)Cl]Cl as the catalyst and CeCl₃·7H₂O as reagent. A series of enantiopure α-hydroxy Weinreb amides (up to 97% ee) have been obtained. A catalytic amount of CeCl₃·7H₂O is essential for the high reactivity and enantioselectivity and the ratio of CeCl₃·7H₂O to [Ru((S)-Sunphos)(benzene)Cl]Cl plays an important role in the hydrogenation reaction. The synthesis of the target compounds was achieved using (η⁶-benzene)chloro[1,1′-[(4S)-2,2,2′,2′-tetramethyl[4,4′-bi-1,3-benzodioxole]-5,5′-diyl]bis[1,1-diphenylphosphine-κP]]ruthenium chloride (1:1) as efficient catalyst. Starting materials thus used included N-Methoxy-N-methyl-α-oxobenzeneacetamide, N-methoxy-N-methyl-α-oxo-2-thiopheneacetamide (thiophene Weinreb oxo amide), N-methoxy-N-methyl-2-oxopropanamide, N-methoxy-N-methyl-α-oxobenzenepropanamide. The title compounds thus formed included (+)-α-hydroxy-N-methoxy-N-methylbenzeneacetamide, (αR)-α-hydroxy-N-methoxy-N-methylbenzenepropanamide, etc. In the experiment, the researchers used many compounds, for example, N1,N2-Dimethoxy-N1,N2-dimethyloxalamide (cas: 106675-70-1Synthetic Route of C6H12N2O4).

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

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

Zinc(II) Triflate-Controlled 1,3-Dipolar Cycloadditions of C-(2-Thiazolyl)nitrones: Application to the Synthesis of a Novel Isoxazolidinyl Analog of Tiazofurin was written by Chiacchio, Ugo;Rescifina, Antonio;Saita, Maria G.;Iannazzo, Daniela;Romeo, Giovanni;Mates, Juan A.;Tejero, Tomas;Merino, Pedro. And the article was included in Journal of Organic Chemistry in 2005.Computed Properties of C6H13NO3 This article mentions the following:

The cycloaddition reaction between C-(2-thiazolyl) nitrones and allylic alc. takes place with complete exo selectivity when the reactions are carried out in the presence of 1 equiv of zinc triflate. The rate of the reaction is increased enormously under microwave irradiation The use of a chiral dipolarophile allowed application of the methodol. to the synthesis of a hitherto unknown enantiomerically pure isoxazolidinyl analog of the C-nucleoside tiazofurin. In the experiment, the researchers used many compounds, for example, 2,2-Diethoxyacetamide (cas: 61189-99-9Computed Properties of C6H13NO3).

2,2-Diethoxyacetamide (cas: 61189-99-9) 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 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.Computed Properties of C6H13NO3

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

Anodic Oxidation and Organocatalysis: Direct Regio- and Stereoselective Access to meta-Substituted Anilines by α-Arylation of Aldehydes was written by Jensen, Kim L.;Franke, Patrick T.;Nielsen, Lasse T.;Daasbjerg, Kim;Joergensen, Karl Anker. And the article was included in Angewandte Chemie, International Edition in 2010.SDS of cas: 1146-43-6 This article mentions the following:

An anodic oxidation/organocatalytic protocol for α-arylation of aldehydes using substituted electron-rich aromatic compounds provided meta-substituted anilines, e.g. I, in good yields with excellent enantioselectivities. 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. Amides include many other important biological compounds, as well as many drugs like paracetamol, penicillin and LSD. Low-molecular-weight amides, such as dimethylformamide, are common solvents. Amides are stable compounds. The lower-melting members (such as acetamide) can be readily purified by fractional distillation. Most amides are solids which have low solubilities in water.SDS of cas: 1146-43-6

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

Copper(I)-catalyzed site-selective C(sp³)-H bond chlorination of ketones, (E)-enones and alkylbenzenes by dichloramine-T was written by Jin, Jianwen;Zhao, Yichao;Kyne, Sara Helen;Farshadfar, Kaveh;Ariafard, Alireza;Chan, Philip Wai Hong. And the article was included in Nature Communications in 2021.Electric Literature of C10H10F3NO2 This article mentions the following:

Here, a copper(I)-catalyzed synthetic method for the efficient site-selective C(sp³)-H bond chlorination of ketones, (E)-enones and alkylbenzenes by dichloramine-T at room temperature were reported. A key feature of the broad substrate scope is tolerance to unsaturation, which would normally pose an immense challenge in chemoselective aliphatic C-H bond functionalization. By unlocking dichloramine-T’s potential as a chlorine radical atom source, the product site-selectivities achieved were among the most selective in alkane functionalization and should find widespread utility in chem. synthesis. This was exemplified by the late-stage site-selective modification of a number of natural products and bioactive compounds and gram-scale preparation and formal synthesis of two drug mols. In the experiment, the researchers used many compounds, for example, N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7Electric Literature of C10H10F3NO2).

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

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

Metabolism of procarbazine (N-isopropyl-α-(2-methylhydrazino)-p-toluamide hydrochloride) was written by Prough, R. A.;Coomes, M. W.;Cummings, S. W.;Wiebkin, P.. And the article was included in Advances in Experimental Medicine and Biology in 1982.Application In Synthesis of 4-Formyl-N-isopropylbenzamide This article mentions the following:

The liver microsomal metabolism of procarbazine (I) [366-70-1] was studied in various liver microsomal preparations from rats. A scheme is suggested for I metabolism in which the intermediate azoprocarbazine  [2235-59-8] is transformed by independent pathways to methylating agents via 2 azoxy derivatives or to CH₄  [74-82-8] via some other reactive intermediate. In the experiment, the researchers used many compounds, for example, 4-Formyl-N-isopropylbenzamide (cas: 13255-50-0Application In Synthesis of 4-Formyl-N-isopropylbenzamide).

4-Formyl-N-isopropylbenzamide (cas: 13255-50-0) belongs to amides. Compared to amines, amides are very weak bases and do not have clearly defined acid–base properties in water. On the other hand, amides are much stronger bases than esters, aldehydes, and ketones. Amides can be recrystallised from large quantities of water, ethanol, ethanol/ether, aqueous ethanol, chloroform/toluene, chloroform or acetic acid. The likely impurities are the parent acids or the alkyl esters from which they have been made. The former can be removed by thorough washing with aqueous ammonia followed by recrystallisation, whereas elimination of the latter is by trituration or recrystallisation from an organic solvent.Application In Synthesis of 4-Formyl-N-isopropylbenzamide

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

Zinc Powder Catalysed Formylation and Urealation of Amines Using CO₂ as a C1 Building Block was written by Du, Chongyang;Chen, Yaofeng. And the article was included in Chinese Journal of Chemistry in 2020.Name: 1,3-Dicyclohexylurea This article mentions the following:

The zinc powder catalyzed formylation and urealation of secondary amines e.g., N-methylaniline and primary aromatic amines RNH₂ (R = Ph, 2,4,6-trimethylphenyl, cyclohexyl, etc.) with CO₂ and (EtO)₃SiH under solvent-free condition were reported. Using 2 mol% zinc powder as the catalyst, a series of secondary amines, both the aromatic ones and the aliphatic ones can be formylated into formamides e.g., N-methyl-N-phenylformamide. When primary aromatic amines were used as the substrates, the reactions produce urea derivatives RNHC(O)NHR. The electronic and steric effects from the substrates on the formylation and urealation reactions were observed and discussed. The recovery and reusability of zinc powder were investigated, showing that zinc powder can be reused in the formylation reaction without loss of catalytic activity. The anal. on the reactants/products mixture after filtering out the zinc powder showed that zinc concentration in the mixture is low to 1 ppm. The pathways for the formylation and urealation of amines with this catalytic system were also investigated and related to the different substrates. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Name: 1,3-Dicyclohexylurea).

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 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.Name: 1,3-Dicyclohexylurea

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

The screening of emerging micropollutants in wastewater in Sol Plaatje Municipality, Northern Cape, South Africa was written by Oluwalana, Abimbola E.;Musvuugwa, Tendai;Sikwila, Stephen T.;Sefadi, Jeremia S.;Whata, Albert;Nindi, Mathew M.;Chaukura, Nhamo. And the article was included in Environmental Pollution (Oxford, United Kingdom) in 2022.Safety of 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide This article mentions the following:

Although pollutants pose environmental and human health risks, the majority are not routinely monitored and regulated. Organic pollutants emanate from a variety of sources, and can be classified depending on their chem. and environmental fate. Classification of pollutants is important because it informs fate processes and apposite removal technologies. The occurrence of emerging contaminants (ECs) in water bodies is a source of environmental and human health concern globally. Despite being widely reported, data on the occurrence of ECs in South Africa are scarce. Specifically, ECS in wastewater in the Northern Cape in South Africa are understudied. In this study, various ECs were screened in water samples collected from three wastewater treatment plants (WWTPs) in the province. The ECs were detected using liquid chromatog. coupled to high resolution Orbitrap mass spectrometry following Oasis HLB solid-phase extraction The main findings were: (1) there is a wide variety of ECs in the WWTPs, (2) physico-chem. properties such as pH, total dissolved solids, conductivity, and dissolved organic content showed reduced values in the outlet compared to the inlet which confirms the presence of less contaminants in the treated wastewater, (3) specific UV absorbance of less than 2 was observed in the WWTPs samples, suggesting the presence of natural organic matter (NOM) that is predominantly non-humic in nature, (4) most of the ECs were recalcitrant to the treatment processes, (5) pesticides, recreational drugs, and analgesics constitute a significant proportion of pollutants in wastewater, and (6) NOM removal ranged between 35 and 90%. Consequently, a comprehensive database of ECs in wastewater in Sol Plaatje Municipality was created. Since the detected ECs pose ecotoxicol. risks, there is a need to monitor and quantify ECs in WWTPs. These data are useful in selecting suitable monitoring and control strategies at WWTPs. 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. Compared to amines, amides are very weak bases and do not have clearly defined acid–base properties in water. On the other hand, amides are much stronger bases than esters, aldehydes, and ketones. Amides can be recrystallised from large quantities of water, ethanol, ethanol/ether, aqueous ethanol, chloroform/toluene, chloroform or acetic acid. The likely impurities are the parent acids or the alkyl esters from which they have been made. The former can be removed by thorough washing with aqueous ammonia followed by recrystallisation, whereas elimination of the latter is by trituration or recrystallisation from an organic solvent.Safety of 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide

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

Oxidative metabolism of N-isopropyl-α-(2-methylhydrazino)-p-toluamide hydrochloride (procarbazine) by rat liver microsomes was written by Dunn, Danny L.;Lubet, Ronald A.;Prough, Russell A.. And the article was included in Cancer Research in 1979.Electric Literature of C11H13NO2 This article mentions the following:

The oxidative metabolism of procarbazine-HCl (I) [366-70-1] by rat liver microsomes was studied by 3 different biochem. assays. The major, stable microsomal metabolite produced was the azo derivative, N-isopropyl-α-(2-methylazo)-p-toluamide [2235-59-8], which can undergo a rapid chem. conversion to an aldehyde, p-formyl-N-isopropylbenzamide [13255-50-0], and methylhydrazine upon the addition of acid. The rate of metabolism could most conveniently be determined spectrophotometrically by reacting the resultant methylhydrazine with p-dimethylaminobenzaldehyde. Rates of metabolism ranged from 13.4 to 14.1 nmol/min/mg of microsomal protein. Inhibitor and induction studies indicated that the cytochrome P-450-dependent monooxygenase [9038-14-6] system is responsible for this oxidation reaction. Several possible mechanisms were considered. The azo derivative of I was further oxidized to 2 isomeric azoxy derivatives, N-isopropyl-α-(2-methyl-NNO-azoxy)-p-toluamide [66944-55-6] and N-isopropyl-α-(2-methyl-ONN-azoxy)-p-toluamide [66944-56-7], at a metabolic rate 10-15% as large as the rate of I oxidation In addition, the affinity of the azo derivative for the monooxygenase was high relative to that of the parent hydrazine. The reaction was inhibited by cytochrome P-450 inhibitors and was sensitive to the in vitro addition of several thiono-S-containing compounds The azoxy compounds were also metabolized by microsomal fractions from liver and yielded p-formyl-N-isopropylbenzamide as a product. This complex in vitro metabolic scheme is analogous to the in vivo metabolism of 1,2-dimethylhydrazine and suggests that I may be metabolically activated to yield alkylating agents capable of expressing carcinogenic and/or toxic effects by a mechanism common for at least these 2 N,N‘-disubstituted hydrazines. In the experiment, the researchers used many compounds, for example, 4-Formyl-N-isopropylbenzamide (cas: 13255-50-0Electric Literature of C11H13NO2).

4-Formyl-N-isopropylbenzamide (cas: 13255-50-0) belongs to amides. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. Amides are stable compounds. The lower-melting members (such as acetamide) can be readily purified by fractional distillation. Most amides are solids which have low solubilities in water.Electric Literature of C11H13NO2

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

Synthesis and Biological Evaluation of Benzophenone Derivatives as Potential HIV-1 Inhibitors was written by Song, Zhendong;Wang, Ping;Huang, Shanshan;Wang, Changyuan;Wang, Rui-Rui;Yang, Liu-Meng;Zhen, Yuhong;Liu, Kexin;Zheng, Yong-Tang;Ma, Xiaodong. And the article was included in Medicinal Chemistry (Sharjah, United Arab Emirates) in 2017.Application of 53297-70-4 This article mentions the following:

Although a number of agents can achieve high response in acquired immunodeficiency syndrome (AIDS) patients, safer and more active HIV inhibitors are still needed for the growing number of patients infected with resistant HIV virus strains. GW678248 is one of the most potent benzophenone derivatives, exhibiting high potency against a panel of HIV- 1 virus (wild-type, K103N mutant, Y181C, etc.) at 1 nmol/L concentrations However, the safety issues associated with rash and liver metabolic enzymes ultimately led to discontinue its further deve-lopment. As a continuation of our structural modifications on this template, in this manuscript, a new series of benzophenones are described as potential HIV inhibitors. All the title mols. were synthesized according to the routes in Scheme 1 and Scheme 2, and were tested for anti-HIV-1 activity using the MTT method. In the mol. simulation, the docking program of AutoDock 4.0.1 in parallel with the default parameters were used. A series of novel benzophenone derivatives (BPs) with nanomolar anti-HIV-1 activity were identified. Of these inhibitors, analog 10i (EC50 = 2.9 nmol/L), the most active inhibitor, was comparable to the lead compound GW678248 in inhibiting the wild-type HIV-1 virus. Addnl., analog 13b, which not only exhibited strong inhibitory activity against the HIV-1 virus (EC50 = 4.2 nmol/L), but also has very low cytotoxicity with a TI value of more than 219178.1 was also discovered. This study led to the identification of a series of benzophenone derivatives with nanomolar level of anti-HIV-1 activity. Analogs 10i and 13b, with low cytotoxicity along with high activity are worthy of further development. In the experiment, the researchers used many compounds, for example, 4-Amino-3-methylbenzenesulfonamide (cas: 53297-70-4Application of 53297-70-4).

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. 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 of 53297-70-4

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

Synthesis of 1,2,3-benzotriazin-4-one derivatives containing spirocyclic indoline-2-one moieties and their nematicidal evaluation was written by Wang, Gao-Lei;Chen, Xi;Chang, Ya-Ning;Du, Dan;Li, Zhong;Xu, Xiao-Yong. And the article was included in Chinese Chemical Letters in 2015.Reference of 119023-25-5 This article mentions the following:

To discover new chemotypes of nematicides with proper toxicol. profiles, a series of novel 1,2,3-benzotriazin-4-one derivatives were synthesized and further bioevaluated. The bioassay results showed that most of the synthesized compounds were endowed with moderate to good control efficacy against Meloidogyne incognita at 10.0 mg/L in vivo. Among them, compounds 1-(4-(4-oxo-7-methoxylbenzo[d][1,2,3]triazin-3(4H)-yl)butyl)spiro[indoline-3,2′-[1,3]dioxolan]-2-one and 1-(4-(4-oxo-7-nitrobenzo[d][1,2,3]triazin-3(4H)-yl)butyl)spiro[indoline-3,2′-[1,3]dioxolan]-2-one displayed 100% inhibitory activities at this concentration, which implied that they could be used as lead compounds for promising nematicides. In the experiment, the researchers used many compounds, for example, 2-Amino-4-fluorobenzamide (cas: 119023-25-5Reference of 119023-25-5).

2-Amino-4-fluorobenzamide (cas: 119023-25-5) 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.Reference of 119023-25-5

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