Category: amides-buliding-blocks

Intermolecular 1,4-Carboamination of Conjugated Dienes Enabled by Cp*Rh^III-Catalyzed C-H Activation was written by Pinkert, Tobias;Wegner, Tristan;Mondal, Shobhan;Glorius, Frank. And the article was included in Angewandte Chemie, International Edition in 2019.Computed Properties of C9H10BrNO2 This article mentions the following:

A protocol for the three-component 1,4-carboamination of dienes is described. Synthetically versatile Weinreb amides were coupled with 1,3-dienes and readily available dioxazolones as the nitrogen source using [Cp*RhCl₂]₂-catalyzed C-H activation to deliver the 1,4-carboaminated products. This transformation proceeds under mild reaction conditions and affords the products with high levels of regio- and E-selectivity. Mechanistic investigations suggest an intermediate Rh^III-allyl species is trapped by an electrophilic amidation reagent in a redox-neutral fashion. In the experiment, the researchers used many compounds, for example, 4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2Computed Properties of C9H10BrNO2).

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. 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.Computed Properties of C9H10BrNO2

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

Therapeutic effect of ethinylestradiol in castration-resistant prostate cancer was written by Nakano, Taito;Kadono, Yoshifumi;Iwamoto, Hiroaki;Yaegashi, Hiroshi;Iijima, Masashi;Kawaguchi, Shohei;Nohara, Takahiro;Shigehara, Kazuyoshi;Izumi, Koujl;Mizkami, Atsushi. And the article was included in Anticancer Research in 2020.Application of 53902-12-8 This article mentions the following:

Background/Aim: The best sequential treatment for castration-resistant prostate cancer (CRPC) remains unclear. This study evaluated the therapeutic effects of ethinylestradiol (EE) on CRPC. Patients and Methods: A total of 80 patients with CRPC, treated with 0.5-15 mg/day of EE, were retrospectively assessed. Results: The ntedian duration from the initial treatment to the beginning of EE was 48.3 mo. A decline in the prostate-specific antigen (PSA)from the baseline was noted in 60 patients (75%) and a >50% PSA decline in 27 patients (34%). The median time ofPSA progression, overall survival, and cancer-specific survival after EE were 5.60 mo, 24.00 mo, and 27.93 mo, resp. Conclusion: EE administration for CRPC showed a relatively high PSA response regardless of timing of sequential treatment. The frequency of cardiovascular adverse events was not significantly high. EE administration is a potential treatment option for CRPC. In the experiment, the researchers used many compounds, for example, 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8Application of 53902-12-8).

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. 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 of 53902-12-8

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

Predictably Selective (sp³)C-O Bond Formation through Copper Catalyzed Dehydrogenative Coupling: Facile Synthesis of Dihydro-oxazinone Derivatives was written by Modak, Atanu;Dutta, Uttam;Kancherla, Rajesh;Maity, Soham;Bhadra, Mohitosh;Mobin, Shaikh M.;Maiti, Debabrata. And the article was included in Organic Letters in 2014.COA of Formula: C11H15NO2 This article mentions the following:

An intramol. dehydrogenative (sp³)C-O bond formation in salicylamides can be initiated by an active Cu/O₂ species to generate pharmaceutically relevant dihydrooxazinones. E.g., in presence of CuCl₂ and pyridine in m-xylene at 130 °C, dehydrogenative coupling of salicylamide derivative (I) gave 90% 2H-benz[e][1,3]oxazin-4(3H)-one derivative (II). Exptl. findings suggest that stereoelectronic parameters in both coupling partners are controlling factors for site selectivity in bond formation. Mechanistic investigations including isotope labeling and kinetic studies helped us to propose a catalytic cycle. The method provides a convenient synthesis of an investigational new medicine CX-614, which has potential in finding treatment for Parkinson’s and Alzheimer’s diseases. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2COA of Formula: C11H15NO2).

N,N-Diethylsalicylamide (cas: 19311-91-2) 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.COA of Formula: C11H15NO2

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

Synthesis of N-derivatives of p-quinonimines was written by Titov, E. A.;Avdeenko, A. P.. And the article was included in Zhurnal Organicheskoi Khimii in 1972.Formula: C13H13NO3S This article mentions the following:

N,2-Bis(benzenesulfonyl)- and N-benzenesulfonyl-2-chloro-1,4-naphthaquinone imine and N-benzenesulfonyl-2,6-dichloro-1,4-benzoquinone imine were prepared in ≤95.5% yield by treating the corresponding sulfonamido phenols with either HNO3 or NaNO2-HOAc. -PhSO2NHC10-H6OH-1 was converted to 54.2% 4-benzenesulfonamido-1,2-naphthoquinone by the former procedure and 65.0% N-benzenesulfonyl-1,4-naphthoquinone imine by the latter. N-(2,4-Dinitrophenyl)-4-aminophenol was oxidized by Pb(OAc)4 in HOAc to the corresponding quinone imine, which gave N-(2,4-dinitrophenyl)-2-chloro-4-aminophenol (I) with HCl-HOAc; N-(2,4-dinitrophenyl)-2,6-dichloro-4-aminophenol and -1,4-benzoquinone imine were prepared analogously from I. -Benzenesulfonamido- and 4-(p-toluenesulfonamido)-2-nitrophenol were prepared by nitration of the parent sulfonamido phenols using NaNO2-HOAc. -Benzenesulfonamido- and 1-(p-toluenesulfonamido)naphthalene gave mixtures of the resp. 2- and 4-nitro derivatives with HCl-NaNO2, with the latter predominating. In the experiment, the researchers used many compounds, for example, N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6Formula: C13H13NO3S).

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. 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.Formula: C13H13NO3S

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

Poly(amidoamine) dendronized hollow fiber membranes: Synthesis, characterization, and preliminary applications as drug delivery devices was written by Zhang, Qian;Wang, Na;Xu, Tongwen;Cheng, Yiyun. And the article was included in Acta Biomaterialia in 2012.Recommanded Product: Sodium (S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioate This article mentions the following:

Poly(amidoamine) (PAMAM) dendrons were prepared from hollow fiber membranes (HFM) consisting of bromomethylated poly(2,6-dimethyl-1,4-phenylene oxide) (BPPO) in a stepwise manner. The prepared HFM were characterized by Fourier transform IR spectroscopy, elemental anal., and SEM. The drug loading efficiency and release behavior of the PAMAM dendronized HFM were evaluated using sodium salicylate, sodium methotrexate, and Congo red as model drugs. The results suggest that PAMAM dendronized HFM can be effectively loaded with a variety of drugs and prolong the release of these drugs. The drug loading and release characteristics of the HFM depend on the generation of PAMAM dendrons grafted on the membranes. The prepared PAMAM dendronized BPPO HFM are promising scaffolds in drug delivery and tissue engineering. In the experiment, the researchers used many compounds, for example, Sodium (S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioate (cas: 7413-34-5Recommanded Product: Sodium (S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioate).

Sodium (S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioate (cas: 7413-34-5) 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.Recommanded Product: Sodium (S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioate

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

Design, synthesis, and biological evaluation of aryl N-methoxyamide derivatives as GPR119 agonists was written by Jang, Yoon Kyung;Lee, Kyu Myung;Jung, Kwan-Young;Kang, Seung Kyu;Pagire, Suvarna H.;Lee, Jun Mi;Pagire, Haushabhau S.;Kim, Kwang Rok;Bae, Myung Ae;Lee, Hohjai;Rhee, Sang Dal;Ahn, Jin Hee. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.Recommanded Product: 192436-83-2 This article mentions the following:

A series of N-methoxyamide derivatives was identified and evaluated as GPR119 agonists. Several N-methoxyamides with thienopyrimidine and pyridine scaffolds showed potent GPR119 agonistic activities. Among them, compound I displayed good in vitro activity and potency. Moreover, compound I lowered glucose excursion in mice in an oral glucose tolerance test and increased GLP-1 secretion in intestinal cells. In the experiment, the researchers used many compounds, for example, 4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2Recommanded Product: 192436-83-2).

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

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

Using Affinity To Provide Long-Term Delivery of Antiangiogenic Drugs in Cancer Therapy was written by Rivera-Delgado, Edgardo;von Recum, Horst A.. And the article was included in Molecular Pharmaceutics in 2017.SDS of cas: 53902-12-8 This article mentions the following:

Antiangiogenic drugs encompass many of the different cancer drugs currently under clin. investigation. One of the drawbacks of antiangiogenic therapy, though, is that upon cessation of drug treatment tumors can recur with an accelerated growth rate. In this study we investigate the capacity of using affinity interactions between a polymer made from cyclodextrin and four antiangiogenic drugs, tranilast, SU5416, 2-methoxyestradiol, and silibinin, with the ultimate goal of creating delivery profiles on the order of antiangiogenic processes (needing weeks, rather than hours of delivery). In these systems, release rate is dependent on affinity, so using in silico mol. docking studies followed by surface plasmon resonance we determined that silibinin possesses the highest affinity among the drugs screened. Silibinin also showed a differential binding affinity among various cyclodextrins tested, with a greater affinity toward the larger mol. pocket of γ-cyclodextrin than for β-cyclodextrin. Release studies confirmed this affinity to translate into a slower, more sustained release of silibinin. Similarly we found this trend in the release of tranilast. Then using U87 human glioblastoma cells in a mouse xenograft model, we showed that affinity-based cyclodextrin polymers loaded with silibinin showed substantially longer release rates than nonaffinity control polymers; however, both were capable of inhibiting tumor growth in the time frame studied. From this work we showed three different, but chem. similar, polymers, each with a different release rate. Future work is on evaluating longer term tumor models where this longer release rate from affinity delivery systems might have addnl. advantages over polymers dependent only on diffusion. In the experiment, the researchers used many compounds, for example, 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8SDS of cas: 53902-12-8).

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

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

Distribution and degradation of [3H]-methotrexate after intravenous and cerebral intraventricular injection in primates was written by Kimelberg, Harold K.;Biddlecome, Sandra M.;Bourke, Robert S.. And the article was included in Cancer Research in 1977.Electric Literature of C20H20N8Na2O5 This article mentions the following:

Four h after either a single injection or continuous infusion of Na methotrexate (Na I) [7413-34-5] plus purified [3′,5′,9(n3-3H]I in cynomolgus or rhesus monkeys, 80 to 98% of the 3H radioactivity present in the plasma was found not to represent intact I. The percentage of 3H-containing I products in the urine after 4 h was considerably less, although more variable. This variability seemed to be related variability in the amount of the total dose excreted. Non-I products were also found in selected tissues and the percentage of intact I found 4 h after i.v. injection varied from 2 to 26%. The percentage of intact I was routinely measured by comparing the values obtained using the dihydrofolate reductase assay with values based on the specific activity of [3′,5′,9(n)-3H]I. Results obtained by diethylaminoethyl column chromatog. on a few samples, however, showed good agreement with results from the reductase assay. [3′,5′,9(N)-3H]I products appeared in peaks eluting from the diethylaminoethyl column both earlier and later than the I peak, with the earlier peaks being present in only small amounts in the urine. After continuous i.v. infusion, only 2% or less of the radioactivity found in the cerebrospinal fluid after 4 h represented intact I, with the remaining radioactivity eluting much earlier than I. In contrast, after direct injection into the left lateral ventricle, all the 3H radioactivity in both cerebrospinal fluid and brain tissue represented intact I for up to 4 h after injection. The appearance of I products in the plasma and selected tissues of these primates a short time after i.v. injection is compared to other work in exptl. animals and man and suggests a greater metabolism of I than was previously suspected. In the experiment, the researchers used many compounds, for example, Sodium (S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioate (cas: 7413-34-5Electric Literature of C20H20N8Na2O5).

Sodium (S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioate (cas: 7413-34-5) 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.Electric Literature of C20H20N8Na2O5

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

Targeting Cancer Stem Cells with Repurposed Drugs to Improve Current Therapies was written by Fong, Dunne;Christensen, Chase T.;Chan, Marion M.. And the article was included in Recent Patents on Anti-Cancer Drug Discovery in 2021.Quality Control of 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid This article mentions the following:

Background: Cancer is a multistep process involving genetic and epigenetic changes in the somatic genome. Genetic mutations as well as environmental factors lead to the initiation, promotion, and progression of cancer. Metastasis allows cancer cells to spread via circulatory and lymphatic systems; secondary tumorigenesis typically leads to a fatal outcome. Recent exptl. evidence suggests that Cancer Stem Cells (CSCs) play a pivotal role in tumor progression. A tumor is heterogeneous and composed of different cell types. CSCs are a subpopulation of tumor cells possessing abilities to self-renew and differentiate. Objective: The aim of this study was to present repurposed drugs, and potential candidates, that can serve as anticancer medications intended to target resistant cancer cells, i.e. CSCs. Methods: Research publications, FDA filings, and patents have been reviewed for repurposed drugs or drug combinations that can act to improve cancer treatment and care. Results: Drugs that act against CSCs include ones approved for treatment of diabetes (metformin & thiazolidinediones), parasitic diseases (chloroquine, niclosamide, mebendazole & pyrvinium), psychotic disorders (thioridazine, clomipramine & phenothiazines), alcoholism (disulfiram), lipid disorder (statins), inflammatory diseases (tranilast, auranofin, acetaminophen & celecoxib), antibiotics (azithromycin), and other disorders. Current research findings advocate the existence of beneficial effects by combining these repurposed drugs, and also through their complementary use with conventional cancer therapies. Conclusion: Repurposing FDA-approved medications towards cancer care, by targeting the resistant CSCs, will allow for a quicker, cheaper development and approval process. A larger drug library available to physicians will allow for increased efficacy during both first-line and recurrent cancer treatments. In the experiment, the researchers used many compounds, for example, 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8Quality Control 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. 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.Quality Control of 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid

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

Aza-Knoevenagel-type condensation of secondary amides: direct access to N-monosubstituted β,β-difunctionalized enamines was written by Huang, Pei-Qiang;Ou, Wei;Ye, Jian-Liang. And the article was included in Organic Chemistry Frontiers in 2015.Reference of 13255-50-0 This article mentions the following:

An efficient approach to N-monosubstituted β,β-difunctionalized enamines, a class of versatile building blocks for the synthesis of bioactive compounds, was reported. The method was based on the triflic anhydride-mediated direct aza-Knoevenagel-type condensation of secondary amides with active methylene compounds The reaction showed good chemoselectivity and functional group tolerance. A number of title compounds were synthesized in good to excellent yields in one pot from readily available starting materials. In the experiment, the researchers used many compounds, for example, 4-Formyl-N-isopropylbenzamide (cas: 13255-50-0Reference of 13255-50-0).

4-Formyl-N-isopropylbenzamide (cas: 13255-50-0) 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.Reference of 13255-50-0

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