Month: December 2022

Inhibitory effect of tranilast on the myofibroblast differentiation of rat mesenchymal stem cells induced by transforming growth factor-beta1 in vitro was written by Tang, Wenxian;Zhang, Yuejuan;Tang, Lin;Zhang, Jun;Xiong, Lei;Wang, Baohe. And the article was included in Molecular Medicine Reports in 2018.Application In Synthesis of 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid This article mentions the following:

The results of the present study revealed that co-culturing with exogenous transforming growth factor (TGF)-beta1 can induce the transdifferentiation of cultured rat MSCs into myofibroblasts in vitro. Treatment of the MSCs with tranilast [N-(3′,4′-dimethoxycinnamoyl)-anthranilic acid] attenuated this fibrotic process. Immunocytochem. staining, western blot anal., reverse transcription-quant. polymerase chain reaction anal. and cell viability assays were performed in order to evaluate the mol. mechanisms underlying the effects of tranilast on TGF-beta1-mediated MSC-to-myofibroblast activation. The results demonstrated that TGF-beta1 upregulated the expression of a-smooth muscle actin (a-SMA) and collagen type I, and increased the phosphorylation of mothers against decapentaplegic homolog 3 (Smad3) and extracellular signal-regulated kinase 1/2 (ERK1/2) in the rat MSCs; by contrast, tranilast pretreatment downregulated their expression. Furthermore, the proliferation of MSCs induced by TGF-beta1 was decreased by pretreatment with tranilast. In conclusion, the results of the present study demonstrated that tranilast treatment markedly suppressed the TGF-beta1-induced differentiation of cultured rat MSCs into myofibroblasts, potentially by inhibiting the Smad3 and ERK1/2 signaling pathways. Therefore, this may be a potential antifibrotic therapeutic strategy, serving as an adjuvant treatment following transplantation of MSCs. In the experiment, the researchers used many compounds, for example, 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8Application In Synthesis of 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid).

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. 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.Application In Synthesis of 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid

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

Annulation-retro-Claisen cascade of bifunctional peroxides for the synthesis of lactone natural products was written by Xu, Qianlan;Li, Jialin;Li, Xuemin;Hu, Lin. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2022.Safety of N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide This article mentions the following:

A new and highly efficient annulation-retro-Claisen cascade, which involves the [4+1]- or [5+1]-annulation of α-benzoylacetates with bielectrophilic peroxides and a subsequent debenzoylation process under mild basic conditions, has been developed for the rapid construction of valuable tetrahydrofuran- and dihydropyran-2-carboxylates in good yields. By employing the new reaction, the unified total synthesis of γ- and δ-lactone natural products such as (±)-tanikolide, (±)-goniothalamins, (±)-7-epi-goniodiol, and (±)-plakolide A has been accomplished in 4-7 steps. In the experiment, the researchers used many compounds, for example, N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7Safety of N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide).

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.Safety of N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide

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

Tapwater Exposures, Effects Potential, and Residential Risk Management in Northern Plains Nations was written by Bradley, Paul M.;Romanok, Kristin M.;Smalling, Kelly L.;Focazio, Michael J.;Charboneau, Robert;George, Christine Marie;Navas-Acien, Ana;OLeary, Marcia;Red Cloud, Reno;Zacher, Tracy;Breitmeyer, Sara E.;Cardon, Mary C.;Cuny, Christa K.;Ducheneaux, Guthrie;Enright, Kendra;Evans, Nicola;Gray, James L.;Harvey, David E.;Hladik, Michelle L.;Kanagy, Leslie K.;Loftin, Keith A.;McCleskey, R. Blaine;Medlock-Kakaley, Elizabeth K.;Meppelink, Shannon M.;Valder, Joshua F.;Weis, Christopher P.. And the article was included in ACS ES&T Water in 2022.HPLC of Formula: 10238-21-8 This article mentions the following:

In the United States (US), private-supply tapwater (TW) is rarely monitored. This data gap undermines individual/community risk-management decision-making, leading to an increased probability of unrecognized contaminant exposures in rural and remote locations that rely on private wells. We assessed point-of-use (POU) TW in three northern plains Tribal Nations, where ongoing TW arsenic (As) interventions include expansion of small community water systems and POU adsorptive-media treatment for Strong Heart Water Study participants. Samples from 34 private-well and 22 public-supply sites were analyzed for 476 organics, 34 inorganics, and 3 in vitro bioactivities. 63 organics and 30 inorganics were detected. Arsenic, uranium (U), and lead (Pb) were detected in 54%, 43%, and 20% of samples, resp. Concentrations equivalent to public-supply maximum contaminant level(s) (MCL) were exceeded only in untreated private-well samples (As 47%, U 3%). Precautionary health-based screening levels were exceeded frequently, due to inorganics in private supplies and chlorine-based disinfection byproducts in public supplies. The results indicate that simultaneous exposures to co-occurring TW contaminants are common, warranting consideration of expanded source, point-of-entry, or POU treatment(s). This study illustrates the importance of increased monitoring of private-well TW, employing a broad, environmentally informative anal. scope, to reduce the risks of unrecognized contaminant exposures. 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 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.HPLC of Formula: 10238-21-8

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

A Catalytic Strategy for α,ω-Functionalization: NHC-Mediated Fragmentation/Umpolung Cascades to Access Hydroxytrifluoromethyl Ynones and Allenones was written by Selg, Christoph;Kraft, Fabian B.;Welcke, Linda;Zeitler, Kirsten. And the article was included in ChemCatChem in 2019.Product Details of 192436-83-2 This article mentions the following:

Herein we report an unprecedented, convenient NHC-catalyzed one-pot cascade reaction to afford α,ω-difunctionalized hydroxytrifluoromethyl alkynones and allenones in a single step. The critical fragile aliphatic aldehydes are introduced by a base-mediated in situ Grob-type fragmentation of their corresponding latent cyclic vinylogous hemiacetal triflate (VHAT) and γ-hydroxy vinyl triflate (GHVT) precursors, avoiding typical problems and losses upon isolation. The ‘demasked’ aldehydes are subsequently trapped by NHC-catalyzed umpolung and further metal-free C-C-cross-coupling to access a broad scope of terminally modified alkynyl or allenyl aliphatic, aromatic and heteroaromatic trifluoromethyl ketones as multifunctionalized, high-value building blocks for advanced synthetic applications. Addnl. synthetic utility of this approach is demonstrated with the possibility for asym. variants using chiral NHC-catalysts. In the experiment, the researchers used many compounds, for example, 4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2Product Details of 192436-83-2).

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. 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.Product Details of 192436-83-2

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

Methotrexate analogs. 19. Enhancement of the antitumor effect of methotrexate and 3′,5′-dichloromethotrexate by the use of lipid-soluble diesters was written by Rosowsky, A.;Yu, C. S.. And the article was included in Journal of Medicinal Chemistry in 1983.Reference of 7413-34-5 This article mentions the following:

The methotrexate (MTX) diesters I (R = CMe₃, PhCH₂, dodecyl, substituted benzyl, etc.) were prepared by esterification of the appropriate MTX salt with an alkyl or aralkyl halide in Me₂SO or DMF and evaluated in vivo against L1210 leukemia in mice. Methotrexate bis(2,6-dichlorobenzyl) ester (I; R = 2,6-dichlorobenzyl) [86669-36-5] and methotrexate bis(6-chloropiperonyl) ester (I; R = 6-chloropiperonyl) [86688-51-9] gave a 16% increase in median life span at 20 and 40 mg/kg, resp., values which are higher than those of MTX. Some 3′,5′-dichloromethotrexate (DCM) esters were also tested. The results indicate that MTX and DCM esters are not therapeutically equivalent in mice despite the high serum esterase activity in this species, and that an up to 10-fold reduction in total given dose is feasible by this approach. 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: 7413-34-5Reference of 7413-34-5).

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

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

Syntheses with α-metalated isocyanides, XXXI. 2-Oxazolines from α-metalated isocyanides and carbonyl compounds. A new synthesis of β-amino alcohols was written by Schoellkopf, Ulrich;Gerhart, Fritz;Hoppe, Inga;Harms, Ruediger;Hantke, Kurt;Scheunemann, Karl D.;Eilers, Eberhard;Blume, Ernst. And the article was included in Justus Liebigs Annalen der Chemie in 1976.Category: amides-buliding-blocks This article mentions the following:

α-Metalated isocyanides MCRR1NC [R = H, Me, Ph; R1 = H, Me, Ph, 4-MeOC6H4, pyridyl, PhS, PhCH2S, 4-MeC6H4S; RR1 = (CH2)2, (CH2)5 M = Li, K], prepared from HCRR1NC and BuLi, KOCMe3, or Li tetramethylpiperidide in THF, reacted at ∼-70° with carbonyl compounds R2COR3 [ R2 = e.g., Ph, PhCH:CH, H, 4-F3CC6H4; R3 = H, Me, Ph; R2R3 = (CH2)5] to give adducts MOCR2R3CRR1NC (I), which are in equilibrium with 2-metalated oxazolines II. Addition of MeOH to the reaction mixture gave oxazolines III, which are readily hydrolyzed to give β-amine alcs. III are preferably lithiated with BuLi in the 2 position. Depending on the electrophile, trapping experiments gave derivatives of either I or II. In the experiment, the researchers used many compounds, for example, N-Cyclopropylformamide (cas: 58644-54-5Category: amides-buliding-blocks).

N-Cyclopropylformamide (cas: 58644-54-5) 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. 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.Category: amides-buliding-blocks

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

Quantification of organic contaminants in urban stormwater by isotope dilution and liquid chromatography-tandem mass spectrometry was written by Hou, Fan;Tian, Zhenyu;Peter, Katherine T.;Wu, Christopher;Gipe, Alex D.;Zhao, Haoqi;Alegria, Ernesto A.;Liu, Fengmao;Kolodziej, Edward P.. And the article was included in Analytical and Bioanalytical Chemistry in 2019.Formula: C13H24N2O This article mentions the following:

Pollutants transported in urban stormwater runoff induce pervasive water quality degradation in receiving waters. To accurately characterize stormwater quality and treatment system performance across the range of possible contaminant characteristics, comprehensive multi-residue anal. methods are necessary. Here, we developed a solid-phase extraction (SPE) and high-performance liquid chromatog.-tandem mass spectrometry (HPLC-MS/MS) method to quantify representative stormwater-derived organic contaminants across multiple chem. classes, including vehicle-related chems., corrosion inhibitors, industrial chems., pesticides, pharmaceuticals and personal care products, and antioxidants. Extraction conditions, isotope-labeled internal standards, and LC-MS/MS parameters were optimized to enhance recovery, minimize matrix effects, and maximize selectivity and sensitivity. The developed method was sensitive (method quantification limits < 10 ng/L for > 80% of selected analytes) and accurate (mean relative recoveries in the range of 70-130%, with relative standard deviations < 25% for 77% of the analytes) for most of the analytes. The method was used to analyze samples collected from nine urban watersheds during a storm event; 62% of the 39 analytes were detected at least once at concentrations up to 540 ng/L (1,3-diphenylguanidine). Spatial trends in detection and concentration were observed for vehicle-related and industrial chems. that correlated with vehicle traffic. Total concentrations of pesticides suggested that residential uses could be more important sources than agriculture. This study illustrates the pervasive occurrence of a wide variety of stormwater-derived chems. in urban receiving waters and highlights the need to better understand their environmental fate and ecol. implications. [Figure not available: see fulltext.]. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Formula: 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. 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.Formula: C13H24N2O

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

Effective approach to ureas through organocatalyzed one-pot process was written by Wang, Mingliang;Han, Jilai;Si, Xiaojia;Hu, Yimin;Zhu, Jidong;Sun, Xun. And the article was included in Tetrahedron Letters in 2018.Reference of 2387-23-7 This article mentions the following:

An efficient approach to N,N’-unsym. substituted ureas ArN(R¹)C(O)NH(R²) (R¹ = H; R² = n-Bu, c-hexyl, Bn, etc.; Ar = 4-MeC₆H₄, 4-MeOC₆H₄, 4-F₃CC₆H₄, 3-BrC₆H₄) has been developed through the ammonolysis of N-Boc protected anilines with amines prompted by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). Moreover, a convenient protocol for the synthesis of the sym. N,N’-substituted ureas RNHC(O)NHR (R = Ph, 2-ClC₆H₄, 4-IC₆H₄, etc.) by one-pot diammonolysis of Boc₂O with amines catalyzed by DABCO has also been achieved. With broad substrate scope and mild conditions, these two methods demonstrate practical preparation of both unsym. and sym. ureas. 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. 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.Reference of 2387-23-7

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

Rapid and Simple Identification and Quantification of Components in Detergent Formulations by Nuclear Magnetic Resonance Spectroscopy was written by Hansen, Svend Hoime;Damhus, Ture;Brask, Jesper. And the article was included in Journal of Surfactants and Detergents in 2020.Application In Synthesis of N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) This article mentions the following:

A rapid, inexpensive, and simple high-resolution NMR spectroscopic method is outlined for determining the content of surfactants and other low-mol.-weight organic compounds in detergent formulations. With simple sample preparation, quant. results can be obtained from an internal standard and/or the method can be used as a fingerprint anal. of the surfactant composition The NMR sample is prepared by suspending the detergent sample in deuterated acetic acid and thus dissolving surfactants and other organic compounds Any content of carbonate will be liberated as CO₂, whereas other inorganic materials are removed by centrifugation. From one-dimensional ¹H and two-dimensional HSQC NMR spectra, the surfactant components and low-mol.-weight organic compounds can be identified from reference spectra. Intensities of signature signals in the one-dimensional ¹H NMR spectrum are used for quantification by comparing with an internal standard Furthermore, it is demonstrated how ³¹P NMR can be used to identify and quantify phosphonate-type chelators. In the experiment, the researchers used many compounds, for example, N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) (cas: 10543-57-4Application In Synthesis of N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide)).

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

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

Examining the evidence of non-monotonic dose-response in Androgen Receptor agonism high-throughput screening assay was written by Klimenko, Kyrylo. And the article was included in Toxicology and Applied Pharmacology in 2021.Category: amides-buliding-blocks This article mentions the following:

Modern High-Throughput Screening (HTS) techniques allow to determine in vitro bioactivity of tens of thousands of chems. within a relatively short period of time and tested compounds are usually interpreted as either active or inactive. The interpretation is mostly based on the assumption of monotonic dose-response. This approach ignores potential abnormal dose-response relationships, such as non-monotonic dose-response (NMDR). NMDR presents a serious challenge to toxicologists and pharmacologists, since they undermine the usefulness of such concepts as lowest-observed-adverse-effect level (LOAEL) and no-observed-adverse-effect level (NOAEL). The possible presence of the NMDR in Androgen receptor (AR) agonism was examined for a structurally diverse set of chems. (∼8 300 unique compounds) from Tox21 project library. The source of activity data is Tox21 AR agonism luciferase-based HTS on the MDA-MB-453 cell line. The examination of curve fitting for 35,328 dose-response data entries was based on modified version of existing criteria for determination of NMDR. The bias that arises from compounds’ cytotoxicity and interference with firefly luciferase protein was also studied. The examination has shown evidence of NMDR for several compounds, including known AR antagonists (e. g. Cyproterone acetate) and other known endocrine disruptors (e. g. Tranilast). Compounds were divided into 3 groups based on chem. class, known biol. activity profile and the shape of dose-response curve. The challenges of using HTS data to determine NMDR and benefits of this anal. are discussed. In the experiment, the researchers used many compounds, for example, 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8Category: amides-buliding-blocks).

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.Category: amides-buliding-blocks

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