Category: amides-buliding-blocks

Chiral Silver Phosphate Catalyzed Transformation of ortho-Alkynylaryl Ketones into 1H-Isochromene Derivatives through an Intramolecular-Cyclization/Enantioselective-Reduction Sequence was written by Terada, Masahiro;Li, Feng;Toda, Yasunori. And the article was included in Angewandte Chemie, International Edition in 2014.Recommanded Product: 4-Bromo-N-methoxy-N-methylbenzamide This article mentions the following:

The transformation of ortho-alkynylaryl ketones I (R¹ = Me, n-Pr, i-Bu, Ph, 4-BrC₆H₄, etc.; R² = n-Bu, Ph, 4-MeC₆H₄, etc.; R³ = H, F) through a cyclization/enantioselective reduction sequence in the presence of a chiral silver phosphate catalyst afforded 1H-isochromenes II in high yields with fairly good to high enantioselectivities. An asym. synthesis of the 9-oxabicyclo[3.3.1]nona-2,6-diene framework, which has been found in some biol. active mols., is presented as a demonstration of the synthetic utility of this method. In the experiment, the researchers used many compounds, for example, 4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2Recommanded Product: 4-Bromo-N-methoxy-N-methylbenzamide).

4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2) 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. 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: 4-Bromo-N-methoxy-N-methylbenzamide

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

Mechanistic Insight Facilitates Discovery of a Mild and Efficient Copper-Catalyzed Dehydration of Primary Amides to Nitriles Using Hydrosilanes was written by Liu, Richard Y.;Bae, Minwoo;Buchwald, Stephen L.. And the article was included in Journal of the American Chemical Society in 2018.Electric Literature of C13H24N2O This article mentions the following:

Metal-catalyzed silylative dehydration of primary amides is an economical approach to the synthesis of nitriles. A copper-hydride(CuH)-catalyzed process is reported that avoids a typically challenging 1,2-siloxane elimination step, thereby dramatically increasing the rate of the overall transformation relative to alternative metal-catalyzed systems. This new reaction proceeds at ambient temperature, tolerates a variety of metal-, acid-, or base-sensitive functional groups and can be performed using a simple ligand, inexpensive siloxanes and low catalyst loading. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Electric Literature of C13H24N2O).

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

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

Iron-Catalysed Remote C(sp³)-H Azidation of O-Acyl Oximes and N-Acyloxy Imidates Enabled by 1,5-Hydrogen Atom Transfer of Iminyl and Imidate Radicals: Synthesis of γ-Azido Ketones and β-Azido Alcohols was written by Torres-Ochoa, Ruben O.;Leclair, Alexandre;Wang, Qian;Zhu, Jieping. And the article was included in Chemistry – A European Journal in 2019.Recommanded Product: N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide This article mentions the following:

In the presence of a catalytic amount of iron(III) acetylacetonate [Fe(acac)₃], the reaction of structurally diverse ketoxime esters with trimethylsilyl azide (TMSN₃) afforded γ-azido ketones in good to excellent yields. This unprecedented distal γ-C(sp³)-H bond azidation reaction went through a sequence of reductive generation of an iminyl radical, 1,5-hydrogen atom transfer (1,5-HAT) and iron-mediated redox azido transfer to the translocated carbon radical. TMSN₃ served not only as a nitrogen source to functionalize the unactivated C(sp³)-H bond, but also as a reductant to generate the catalytically active Fe^II species in situ. Based on the same principle, a novel β-C(sp³)-H functionalization of alcs. via N-acyloxy imidates was subsequently realized, leading, after hydrolysis of the resulting ester, to β-azido alcs., which are important building blocks in organic and medicinal chem. In the experiment, the researchers used many compounds, for example, N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7Recommanded Product: N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide).

N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7) 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.Recommanded Product: N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide

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

Discovery of 4-amino-2-(thio)phenol derivatives as novel protein kinase and angiogenesis inhibitors for the treatment of cancer: Synthesis and biological evaluation. was written by Xu, Fuming;Zhang, Lei;Jia, Yuping;Wang, Xuejian;Li, Xiaoguang;Wen, Qingli;Zhang, Yingjie;Xu, Wenfang. And the article was included in European Journal of Medicinal Chemistry in 2013.Synthetic Route of C13H13NO3S This article mentions the following:

A novel series of 4-amino-2-(thio)phenol derivatives were well synthesized. The preliminary biol. test revealed that several compounds displayed high specific protein kinase and angiogenesis inhibitory activities compared with previous work mainly because of the substitution of sulfonamide structure for amide fragment. Among which, compound I was identified to inhibit protein kinase B/AKT (IC₅₀ = 1.26 μM) and ABL tyrosine kinase (IC₅₀ = 1.50 μM) effectively. Meanwhile, compound I demonstrated competitive in vitro antiangiogenic activities to Pazopanib in both human umbilical vein endothelial cell (HUVEC) tube formation assay and the rat thoracic aorta rings test. In the experiment, the researchers used many compounds, for example, N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6Synthetic Route of C13H13NO3S).

N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6) 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 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 C13H13NO3S

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

Ligand-Promoted Alkynylation of Aryl Ketones: A Practical Tool for Structural Diversity in Drugs and Natural Products was written by Xu, Hui;Ma, Biao;Fu, Zunyun;Li, Han-Yuan;Wang, Xing;Wang, Zhen-Yu;Li, Ling-Jun;Cheng, Tai-Jin;Zheng, Mingyue;Dai, Hui-Xiong. And the article was included in ACS Catalysis in 2021.Quality Control of 3-Fluoro-N-methoxy-N-methylbenzamide This article mentions the following:

A palladium-catalyzed ligand-promoted alkynation of unstrained aryl ketones RC(O)R¹ (R = naphthalen-2-yl, 1-benzothiophen-5-yl, 4-(2H-1,2,3-triazol-2-yl)benzen-1-yl, etc.; R¹ = Me, n-Pr, Ph, etc.) have been reported. The protocol allows the alkynation to be carried out in a one-pot procedure with broad functional-group tolerance and substrate scope for the synthesis of aryl-/terminal alkynes RCCR² (R² = 2-fluorophenyl, naphthalen-2-yl, thiophen-2-yl, etc.) and RCCH. The potential applications of this protocol in drug discovery and chem. biol. are further demonstrated by late-stage diversification of a number of pharmaceuticals and natural products e.g., I. More importantly, two different biol. important fragments R³CCR⁴ (R = 3-methoxy-4-([(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy)benzen-1-yl, 6-[3-(adamantan-1-yl)-4-methoxyphenyl]naphthalen-2-yl; R⁴ = 4-(dipropylsulfamoyl)phenyl) derived from a pharmaceutical and natural product could be connected by the consecutive alkynation of ketones CH₃(CH₂)₂C(O)R⁴. Distinct from aryl halides in conventional Sonogashira reactions, the protocol provides a practical tool for the 1,2-bifunctionalization of aryl ketone (1-[(17β)-17-(acetyloxy)estra-1,3,5(10)-trien-2-yl]ethanone) by merging ketone-directed ortho-C-H activation with ligand-promoted ipso-Ar-C(O) alkynation. In the experiment, the researchers used many compounds, for example, 3-Fluoro-N-methoxy-N-methylbenzamide (cas: 226260-01-1Quality Control of 3-Fluoro-N-methoxy-N-methylbenzamide).

3-Fluoro-N-methoxy-N-methylbenzamide (cas: 226260-01-1) 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. 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 3-Fluoro-N-methoxy-N-methylbenzamide

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

Tranilast inhibits TGF-β1-induced epithelial-mesenchymal transition and invasion/metastasis via the suppression of Smad4 in human lung cancer cell lines was written by Takahashi, Koji;Menju, Toshi;Nishikawa, Shigeto;Miyata, Ryo;Tanaka, Satona;Yutaka, Yojiro;Yamada, Yoshito;Nakajima, Daisuke;Hamaji, Masatsugu;Ohsumi, Akihiro;Chen-Yoshikawa, Toyofumi Fengshi;Sato, Toshihiko;Sonobe, Makoto;Date, Hiroshi. And the article was included in Anticancer Research in 2020.Safety of 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid This article mentions the following:

Background/Aim: Transforming growth factor β1 (TGF-β1) is an important epithelial-mesenchymal transition (EMT) activator that regulates the expression of E-cadherin and vimentin through Smad signalling. Tranilast is an anti-allergic drug that inhibits TGF-β1, and is used in the treatment of keloids and hypertrophic scars. We investigated whether tranilast inhibits TGF-β1-induced EMT and invasiveness in human non-small cell lung cancer cell lines. Materials and Methods: We examined the effects of tranilast treatment on EMT markers, TGF-β1/Smad signalling, and cell invasiveness in A549 and PC14 cells. Tumors from a mouse orthotopic lung cancer model with or without tranilast treatment were also immunohistochem. evaluated. Results: Tranilast increased E-cadherin expression via Smad4 suppression and inhibited cell invasion in TGF-β1-stimulated cells. Tranilast treatment of the in vivo mouse model reduced the pleural dissemination of cancer cells and suppressed vimentin and Smad4 expression. Conclusion: Tranilast inhibited TGF-β1-induced EMT and cellular invasion/metastasis by suppressing Smad4 expression in cancer cells. In the experiment, the researchers used many compounds, for example, 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8Safety of 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid).

2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8) 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. The presence of the amide group –C(=O)N– is generally easily established, at least in small molecules. It can be distinguished from nitro and cyano groups in IR spectra. Amides exhibit a moderately intense νCO band near 1650 cm−1. By 1H NMR spectroscopy, CONHR signals occur at low fields. In X-ray crystallography, the C(=O)N center together with the three immediately adjacent atoms characteristically define a plane.Safety of 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid

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

N,N’-Dimethoxy-N,N’-dimethylethanediamide: a useful α-oxo-N-methoxy-N-methylamide and 1,2-diketone synthon was written by Sibi, Mukund P.;Sharma, Rajiv;Paulson, Kevin L.. And the article was included in Tetrahedron Letters in 1992.COA of Formula: C6H12N2O4 This article mentions the following:

N,N‘-Dimethoxy-N,N‘-dimethylethanediamide (I) on treatment with one to two equivalent of alkyl, aryl, and benzyl Grignard reagents provide α-oxo-N-methoxy-N-methylamides in good to excellent yields and on reaction with excess aryllithiums furnish moderate to good yields of sym. 1,2-diaryl ketones. Thus, I was treated with PhMgBr or 4-MeC₆H₄Li in THF to give 95% PhCOCONMeOMe or 86% 4-MeC₆H₄COCOC₆H₄Me-4, resp. In the experiment, the researchers used many compounds, for example, N1,N2-Dimethoxy-N1,N2-dimethyloxalamide (cas: 106675-70-1COA of Formula: C6H12N2O4).

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

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

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-Mediated Tandem Oxidative Annulation for Preparing 2,2-Disubstituted 2,3-Dihydroquinazolin-4(1H)-ones was written by Cheng, Dongping;Yan, Xianhang;Pu, Yueqi;Shen, Jing;Xu, Xiaoliang;Yan, Jizhong. And the article was included in European Journal of Organic Chemistry in 2021.Synthetic Route of C7H7ClN2O This article mentions the following:

An efficient tandem oxidative annulation for the synthesis of 2,2-disubstituted 2,3-dihydroquinazolin-4(1H)-ones via DDQ-mediated dual cross-dehydrogenative-coupling (CDC) reactions is described. This transformation proceeds from easily available o-aminobenzamides and 1,3-diarylpropenes under mild conditions, and the corresponding products are obtained in moderate to excellent yields. In the experiment, the researchers used many compounds, for example, 6-Chloro-2-aminobenzamide (cas: 54166-95-9Synthetic Route of C7H7ClN2O).

6-Chloro-2-aminobenzamide (cas: 54166-95-9) 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. 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.Synthetic Route of C7H7ClN2O

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

Synthesis, crystal structure and herbicidal activity of novel sulfonylureas containing triazolinone moiety was written by Pan, Li;Chen, Youwei;Liu, Zhuo;Li, Yonghong;Li, Zhengming. And the article was included in Youji Huaxue in 2013.Product Details of 82097-01-6 This article mentions the following:

In order to search for efficient sulfonylurea herbicides, the title compounds were designed by introducing triazolinones into some known sulfonylurea structures. 23 Novel sulfonylurea compounds had been synthesized and characterized by ¹H NMR, HRMS and X-ray diffraction. Herbicidal activities of title compounds were determined by pot-culture method. IC₅₀ values of some effective sulfonylurea compounds were tested by culture dish method. It was found that compound I attained the super-active level which was comparable to the controls as triasulfuron and cinosulfuron. It was worthy to note that compound I had potent inhibitory activity against Echinochloa crusgalli by pot-culture method at 3.75 g/ha. In the experiment, the researchers used many compounds, for example, 2-(2-Chloroethoxy)benzenesulfonamide (cas: 82097-01-6Product Details of 82097-01-6).

2-(2-Chloroethoxy)benzenesulfonamide (cas: 82097-01-6) belongs to amides. Compared to amines, amides are very weak bases and do not have clearly defined acid–base properties in water. On the other hand, amides are much stronger bases than esters, aldehydes, and ketones. 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.Product Details of 82097-01-6

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

Metformin versus glyburide in treatment and control of gestational diabetes mellitus: a systematic review with meta-analysis. was written by Oliveira, Marina Martins de;Andrade, Kayan Felipe de Oliveira;Lima, Giovanni Henrique Silva;Rocha, Thiago Casali. And the article was included in Einstein (Sao Paulo, Brazil) in 2022.Category: amides-buliding-blocks This article mentions the following:

OBJECTIVE: To compare the major outcomes of use of metformin and glyburide in treatment of gestational diabetes mellitus. METHODS: Studies published in English, in the last 10 years, in the databases MEDLINE®, SciELO, LILACS and Cochrane Library were analyzed, and randomized controlled trials were selected. Health Sciences Descriptors were used to compose the search phrase, and the keywords “Gestational diabetes”, “Glyburide”, “Metformin” and their variations were searched in the Medical Subject Headings. PRISMA systematization was used to prepare this review, and a meta-analysis was conducted aiming to mathematically show the results of fasting blood glucose, postprandial blood glucose, birth weight and weight gain during pregnancy after using metformin and glyburide. RESULTS: The studies evaluated birth weight, neonatal hypoglycemia, mode of delivery, need for intensive care, Apgar score, macrosomia, fasting glucose, postprandial glucose and weight gain during pregnancy. In 60% of studies, there were no statistically significant differences regarding safety and efficacy of administration of metformin and glyburide. Meta-analysis demonstrated the absence of statistical differences between these drugs in fasting blood glucose (p=0.821), postprandial blood glucose (p=0.217) and birth weight (p=0.194). However, significant differences were shown in weight gain during pregnancy (p=0.036). CONCLUSION: The methods are effective, but the adverse effects of glyburide are more common; therefore, the use of metformin should be recommended, if in monotherapy. In the experiment, the researchers used many compounds, for example, 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8Category: amides-buliding-blocks).

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. 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.Category: amides-buliding-blocks

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