Category: amides-buliding-blocks

Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogs of N-methylformamide was written by Gate, E. Nicholas;Threadgill, Michael D.;Stevens, Malcolm F. G.;Chubb, David;Vickers, Lisa M.;Langdon, Simon P.;Hickman, John A.;Gescher, Andreas. And the article was included in Journal of Medicinal Chemistry in 1986.Application of 58644-54-5 This article mentions the following:

HCONHR (R = Me, CD₃, Et, CH₂CH₂Cl, cyclopropyl, CH₂CF₃, CH₂OH, CH₂OEt, CH₂NMe₂), HCONRMe (R = Me, CH₂OH, CH₂OAc, CH₂OBz), R¹CONHMe (R¹ = Me, CF₃, Ph, NHMe), R¹CONMe₂ (R¹ = Me, NMe₂), R¹CONHCH₂OH (R¹ = CCl₃, Ph), HCONMeOH, H₂NCONHOH, R¹CSNMe₂ (R¹ = H, NMe₂), (MeNH)₂CS, (MeNH)₂C:NH, RR²NC(:X)H [R, R² = H, Me; RR² = CH₂CH₂OCH₂CH₂; X = CHNO₂, C(CN)₂, CMeCHO] were prepared These compounds have been tested for activity against the M5076 ovarian sarcoma and the TLX5 lymphoma in mice. HCONHMe was by far the most potent agent with activity against both tumors. Some other compounds showed weak activity, but there is a rigorous structural requirement for activity and most analogs were inactive. Certain members of the series exist as equilibrium mixtures of rotamers about the amide or pro-amide bonds as shown by NMR. In the experiment, the researchers used many compounds, for example, N-Cyclopropylformamide (cas: 58644-54-5Application of 58644-54-5).

N-Cyclopropylformamide (cas: 58644-54-5) 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. 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.Application of 58644-54-5

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

Discovery of a New Isoxazole-3-hydroxamate-Based Histone Deacetylase 6 Inhibitor SS-208 with Antitumor Activity in Syngeneic Melanoma Mouse Models was written by Shen, Sida;Hadley, Melissa;Ustinova, Kseniya;Pavlicek, Jiri;Knox, Tessa;Noonepalle, Satish;Tavares, Mauricio T.;Zimprich, Chad A.;Zhang, Guiping;Robers, Matthew B.;Barinka, Cyril;Kozikowski, Alan P.;Villagra, Alejandro. And the article was included in Journal of Medicinal Chemistry in 2019.SDS of cas: 2670-38-4 This article mentions the following:

Isoxazole is a five-membered heterocycle that is widely used in drug discovery endeavors. Here, the authors report the design, synthesis, and structural and biol. characterization of SS-208, a novel HDAC6-selective inhibitor containing the isoxazole-3-hydroxamate moiety as a zinc-binding group as well as a hydrophobic linker. A crystal structure of the Danio rerio HDAC6/SS-208 complex reveals a bidentate coordination of the active-site zinc ion that differs from the preferred monodentate coordination observed for HDAC6 complexes with phenylhydroxamate-based inhibitors. While SS-208 has minimal effects on the viability of murine SM1 melanoma cells in vitro, it significantly reduced in vivo tumor growth in a murine SM1 syngeneic melanoma mouse model. These findings suggest that the antitumor activity of SS-208 is mainly mediated by immune-related antitumor activity as evidenced by the increased infiltration of CD8+ and NK+ T cells and the enhanced ratio of M1 and M2 macrophages in the tumor microenvironment. In the experiment, the researchers used many compounds, for example, 3,4-Dichlorobenzamide (cas: 2670-38-4SDS of cas: 2670-38-4).

3,4-Dichlorobenzamide (cas: 2670-38-4) 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.SDS of cas: 2670-38-4

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

Identification of organic xenobiotics in urban aquatic environments using time-of-flight mass spectrometry was written by Jernberg, Joonas;Pellinen, Jukka;Rantalainen, Anna-Lea. And the article was included in Science of the Total Environment in 2013.Recommanded Product: 10543-57-4 This article mentions the following:

Qual. non-target and post-target anal. methods using gas chromatog.-time-of-flight mass spectrometry were applied for analyzing neutral and acidic organic xenobiotics in urban and suburban water samples. Ten water samples representing wastewater, stormwater and surface water matrixes were collected and concentrated using solid phase extraction Compound identification was performed using a spectral deconvolution program, accurate mass measurements and comparisons with library spectra. The non-target and post-target analyses identified 36 and 18 compounds, resp. The identification of 10 compounds was afterwards confirmed with standard compounds Organophosphate esters were the most abundant compound group detected. The combination of non-target and post-target analyses proved a useful tool in the tentative identification of xenobiotics in water samples. Post-target anal. can complement non-target anal. results at low analyte concentrations Results showed that several organic xenobiotics originate in urban areas and accumulate in the environment. The wastewater sample produced the highest number of identified compounds, but most of these compounds were also found in stormwater samples from the city center. Nearly all the compounds in wastewater were addnl. detected in the surface water sample taken 3 Km downstream from the wastewater effluent discharge point. Only a few xenobiotics were otherwise detected in the surface water samples. In the experiment, the researchers used many compounds, for example, N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) (cas: 10543-57-4Recommanded Product: 10543-57-4).

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. 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: 10543-57-4

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

Design and synthesis of α-glucosidase inhibitor having DNA cleaving activity was written by Hakamata, Wataru;Yamamoto, Emiko;Muroi, Makoto;Mochizuki, Masataka;Kurihara, Masaaki;Okuda, Haruhiro;Fukuhara, Kiyoshi. And the article was included in Journal of Applied Glycoscience in 2006.Safety of N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide This article mentions the following:

Apoptosis, or programmed cell death, is a mechanism by which cells undergo death to control cell proliferation or in response to DNA damage. The present study was designed to explore small mol. apoptosis inducers for antitumor agents. The synthesis of 4-sulfonylphenyl α-D-glucopyranoside derivatives 1-6 and 4-(sulfonylamino)phenyl α-D-glucopyranoside derivatives 7-12, endoplasmic reticulum (ER)-targeted small mols. that were designed to induce apoptosis from ER stress by ER glucosidase inhibition and DNA damage is described. Compounds 6 and 12, with a terminal 2-naphthyl group, indicated inhibitions of α-glucosidases from S. cerevisiae (IC₅₀ = 51.7 μM and IC₅₀ = 74.1 μM) and B. stearothermophilus (IC₅₀ = 60.1 μM and IC₅₀ = 89.1 μM). Moreover, compound 12 strongly induced the DNA strand breakage condition. When compounds 1-12 were assayed for their ability to inhibit processing by glucosidases at the cellular level, no effects on glycoprotein processing were observed In the experiment, the researchers used many compounds, for example, N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6Safety of N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide).

N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6) 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.Safety of N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide

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

Novel and Direct Transformation of Methyl Ketones or Carbinols to Primary Amides by Employing Aqueous Ammonia was written by Cao, Liping;Ding, Jiaoyang;Gao, Meng;Wang, Zihua;Li, Juan;Wu, Anxin. And the article was included in Organic Letters in 2009.Recommanded Product: 3,4-Dichlorobenzamide This article mentions the following:

A novel and direct transformation of aryl, heteroaryl, vinyl, or ethynyl Me ketones or carbinols to corresponding primary amides has been developed. An iodine-NH₃·H₂O system was proven to be efficient for this reaction and afforded the expected products with good yields in aqueous media. A tandem Lieben-Haller-Bauer reaction mechanism was involved in this type of reaction and is proposed for the first time. In the experiment, the researchers used many compounds, for example, 3,4-Dichlorobenzamide (cas: 2670-38-4Recommanded Product: 3,4-Dichlorobenzamide).

3,4-Dichlorobenzamide (cas: 2670-38-4) 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.Recommanded Product: 3,4-Dichlorobenzamide

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

Esophageal cancer stem cells are suppressed by tranilast, a TRPV2 channel inhibitor was written by Shiozaki, Atsushi;Kudou, Michihiro;Ichikawa, Daisuke;Fujiwara, Hitoshi;Shimizu, Hiroki;Ishimoto, Takeshi;Arita, Tomohiro;Kosuga, Toshiyuki;Konishi, Hirotaka;Komatsu, Shuhei;Okamoto, Kazuma;Marunaka, Yoshinori;Otsuji, Eigo. And the article was included in Journal of Gastroenterology in 2018.Synthetic Route of C18H17NO5 This article mentions the following:

Background: Recent evidence suggests that the targeting of membrane proteins specifically activated in cancer stem cells (CSCs) is an important strategy for cancer therapy. The objectives of the present study were to investigate the expression and activity of ion-transport-related mols. in the CSCs of esophageal squamous cell carcinoma. Methods: Cells exhibiting strong aldehyde dehydrogenase 1 family member A1 (ALDH1A1) activity were isolated from TE8 cells by fluorescence-activated cell sorting, and CSCs were then generated with the sphere formation assay. The gene expression profiles of CSCs were examined by microarray anal. Results: Among TE8 cells, ALDH1A1 mRNA and protein levels were higher in CSCs than in non-CSCs. The CSCs obtained were resistant to cisplatin and had the ability to redifferentiate. The results of the microarray anal. revealed that the expression of 50 genes encoding plasma membrane proteins was altered in CSCs, whereas that of several genes related to ion channels, including transient receptor potential vanilloid 2 (TRPV2), was upregulated. The TRPV2 inhibitor tranilast was more cytotoxic at a lower concentration in CSCs than in non-CSCs, and effectively decreased the number of tumorspheres. Furthermore, tranilast significantly decreased the cell population that strongly expressed ALDH1A1 among TE8 cells. Conclusions: The results of the present study suggest that TRPV2 is involved in the maintenance of CSCs, and that its specific inhibitor, tranilast, has potential as a targeted therapeutic agent against esophageal squamous cell carcinoma. 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. 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. 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 C18H17NO5

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

Oxidation decoloration kinetics of C.I. direct Blue 108 in activated oxygen bleach systems was written by Zhu, Yang;Tang, Ren-Cheng. And the article was included in Advanced Materials Research (Durnten-Zurich, Switzerland) in 2011.SDS of cas: 10543-57-4 This article mentions the following:

The decoloration behaviors of C.I. Direct Blue 108 in two activated oxygen bleach systems (PB/TAED and PC/TAED) were investigated. It was found that the decoloration kinetics of the dye in the two systems followed the first-order kinetic model and the rate constants calculated by linear regression increased significantly with increasing temperature The activation energies for the decoloration in PB/TAED and PC/TAED systems were 63.34 and 58.10 kJ/mol, resp. Moreover, the highest decoloration rate constant was obtained at pH 9 in the two systems. The kinetic model had not changed with temperature and pH in the two systems. In the experiment, the researchers used many compounds, for example, N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) (cas: 10543-57-4SDS of cas: 10543-57-4).

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

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

Mild and Efficient Copper-Catalyzed Amination of Aryl Bromides with Primary Alkylamines was written by Kwong, Fuk Yee;Buchwald, Stephen L.. And the article was included in Organic Letters in 2003.Electric Literature of C11H15NO2 This article mentions the following:

An efficient copper-catalyzed amination of aryl bromides with primary alkylamines was developed that uses com. available diethylsalicylamide as the ligand. This amination reaction can be performed at 90 °C in good yield. A variety of functional groups are compatible with these reaction conditions. Preliminary results show that this reaction can be carried out under solvent-free conditions with comparable yields. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Electric Literature 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. 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.Electric Literature of C11H15NO2

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

Microwave-Assisted Beckman Rearrangement by Cu(II)/Triazine-Based Dendrimer as an Efficacious Recoverable Nano-Catalyst Under Solvent-Free Conditions was written by Ghoreishi, Somayeh;Moeinpour, Farid. And the article was included in Polycyclic Aromatic Compounds.Product Details of 2670-38-4 This article mentions the following:

An efficient solvent-less procedure has been expanded to synthesis primary amides through Beckman rearrangement using Cu(II)/hydroxyl terminated triazine-based dendrimer (Cu(II)/TD) as a proficient heterogeneous nano-catalyst. The Cu(II)/TD nano-catalyst was recognized using TEM, FT-IR, TGA, SEM, EDS, XRD and ICP techniques. The deploying of this new nano-catalyst provides the synthesis of assorted primary amides in outstanding yields through a simple working-up method in a short-term reaction under green conditions in the absence of dangerous and poisonous organic solvents. The Cu(II)/TD catalyst was able to reprocessed and recovered many times without considerable failure of its performance. In the experiment, the researchers used many compounds, for example, 3,4-Dichlorobenzamide (cas: 2670-38-4Product Details of 2670-38-4).

3,4-Dichlorobenzamide (cas: 2670-38-4) 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. 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 2670-38-4

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

Doxorubicin Impairs Smooth Muscle Cell Contraction: Novel Insights in Vascular Toxicity was written by Bosman, Matthias;Kruger, Dustin N.;Favere, Kasper;Wesley, Callan D.;Neutel, Cedric H. G.;Van Asbroeck, Birgit;Diebels, Owen R.;Faes, Bart;Schenk, Timen J.;Martinet, Wim;De Meyer, Guido R. Y.;Van Craenenbroeck, Emeline M.;Guns, Pieter-Jan D. F.. And the article was included in International Journal of Molecular Sciences in 2021.Related Products of 53902-12-8 This article mentions the following:

Clin. and animal studies have demonstrated that chemotherapeutic doxorubicin (DOX) increases arterial stiffness, a predictor of cardiovascular risk. Despite consensus about DOX-impaired endothelium-dependent vasodilation as a contributing mechanism, some studies have reported conflicting results on vascular smooth muscle cell (VSMC) function after DOX treatment. The present study aimed to investigate the effects of DOX on VSMC function. To this end, mice received a single injection of 4 mg DOX/kg, or mouse aortic segments were treated ex vivo with 1 μM DOX, followed by vascular reactivity evaluation 16 h later. Phenylephrine (PE)-induced VSMC contraction was decreased after DOX treatment. DOX did not affect the transient PE contraction dependent on Ca2+ release from the sarcoplasmic reticulum (0 mM Ca2+), but it reduced the subsequent tonic phase characterised by Ca2+ influx. These findings were supported by similar angiotensin II and attenuated endothelin-1 contractions. The involvement of voltage-gated Ca2+ channels in DOX-decreased contraction was excluded by using levcromakalim and diltiazem in PE-induced contraction and corroborated by similar K+ and serotonin contractions. Despite the evaluation of multiple blockers of transient receptor potential channels, the exact mechanism for DOX-decreased VSMC contraction remains elusive. Surprisingly, DOX reduced ex vivo but not in vivo arterial stiffness, highlighting the importance of appropriate timing for evaluating arterial stiffness in DOX-treated patients. In the experiment, the researchers used many compounds, for example, 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8Related Products of 53902-12-8).

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

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