Category: amides-buliding-blocks

Polymeric micelles loaded with glyburide and vanillic acid: I. Formulation development, in-vitro characterization and bioavailability studies was written by Kaur, Jaskiran;Gulati, Monica;Famta, Paras;Corrie, Leander;Awasthi, Ankit;Saini, Sumant;Khatik, Gopal L.;Bettada, Vidya G.;Madhunapantula, SubbaRao V.;Paudel, Keshav Raj;Gupta, Gaurav;Chellappan, Dinesh Kumar;Arshad, Mohammed F.;Adams, Jon;Gowthamarajan, Kuppusamy;Dua, Kamal;Hansbro, Philip M.;Singh, Sachin Kumar. And the article was included in International Journal of Pharmaceutics (Amsterdam, Netherlands) in 2022.Name: 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide This article mentions the following:

The co-formulation of glyburide (Gly) and vanillic acid (VA) as such in the form of nanomedicine has never been explored to treat metabolic diseases including type 2 diabetes mellitus. Both the drugs possess dissolution rate-limited oral bioavailability leading to poor therapeutic efficacy. Hence, co-loading these drugs into a nanocarrier could overcome their poor oral bioavailability related challenges. Owing to this objective, both drugs were co-loaded in amphiphilic polymeric micelles (APMs) and evaluated for their biopharmaceutical outcomes. The APMs were prepared using mPEG-b-PCL/CTAB as a copolymer-surfactant system via the liquid antisolvent precipitation (LAP) method. The design of these APMs were optimized using Box Behnken Design by taking various process/formulation based variables to achieve the desired micellar traits. The release of both the drugs from the optimized co-loaded APMs was compared in different media and displayed a remarkable sustained release profile owing to their hydrophobic interactions with the PCL core. The in vitro cytotoxicity study of co-loaded APMs on Caco-2 cells revealed 70 % cell viability in a concentration-dependent manner. The preventive effects of Gly and VA co-loaded in APMs on glucose uptake was studied in insulin-responsive human HepG2 cells treated with high glucose. The co-loading of both the drugs in optimized APMs exhibited synergistic glucose-lowering activity (p < 0.001) than raw drugs with low cytotoxicity on HepG2 cells within the test concentration This could be attributed to an increase in the relative oral bioavailability of both the drugs in APMs i.e., 868 % for Gly and 87 % for VA resp. In the experiment, the researchers used many compounds, for example, 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8Name: 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. 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.Name: 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide

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

Manganese oxalate – a Bio-inspired bleach catalyst was written by Reinhardt, G.;Best, M.;Ladwig, M.. And the article was included in SOFW Journal in 2011.Reference of 10543-57-4 This article mentions the following:

Sustainability driven trends to lower temperatures and shorter washing times require the use of alternative bleaches in automatic dishwashing applications. α-Manganese oxalate dihydrate, a synthetic analog of the mineral Lindbergite, offers a new proposition for a low temperature bleach catalyst in automatic dishwashing detergents. In combination with sodium percarbonate, the biodegradable catalyst enables tea stain removal at temperatures below 50°C where common bleaches fail. Storage stable co-granules comprising the catalyst in combination with the activator tetraacetyl ethylenediamine offer excellent tea stain removal while ensuring a high level of hygiene even at low temperatures In the experiment, the researchers used many compounds, for example, N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) (cas: 10543-57-4Reference of 10543-57-4).

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

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

Functional characterization and comparison of human and mouse organic anion transporter 1 as drugs and pesticides uptake carrier was written by Floerl, Saskia;Kuehne, Annett;Hagos, Yohannes. And the article was included in European Journal of Pharmaceutical Sciences in 2022.COA of Formula: C23H28ClN3O5S This article mentions the following:

The organic anion transporter 1 (OAT1) is mainly expressed in proximal tubule cells, where it mediates the renal uptake of endogenous and exogenous compounds Thereby, it has enormous clin. relevance particularly in drug-drug interactions. The aim of the present in vitro study was to elucidate potential species dependent disparity of human and mouse OAT1 in handling of structural diverse drugs and pesticides. A basic functional comparison of the two transporters showed a similar time-dependent uptake of the substrate para-aminohippuric acid (PAH), the affinity (Km) was 94μM for hOAT1 and 32μM for mOat1. Inhibition experiments for hOAT1 and mOat1 provided IC50 values for glibenclamide of 5.1 and 6.4μM and for probenecid of 31 and 11μM. Than the interaction of hOAT1 and mOat1 with 23 drugs and 13 pesticides was examined Three pesticides and thirteen drugs showed high inhibitory potency of 50% or more to both transporters. Furthermore, we identified rosiglitazone as a differential active inhibitor, with stronger inhibitory properties (IC50) to mOat1 (7.7μM) than to hOAT1 (31μM), and olmesartan with the most pronounced difference: The IC50 of hOAT1 (0.40μM) was 48-fold lower than of mOat1 (19μM). In conclusion, we found a strong correlation for the inhibitory effects of most drugs and pesticides on human and mouse OAT1. But the example of olmesartan shows that species differences have to be considered when extrapolating data from mouse to human. In the experiment, the researchers used many compounds, for example, 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8COA of Formula: C23H28ClN3O5S).

5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8) 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 can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.COA of Formula: C23H28ClN3O5S

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

Discovery of 1,1′-Biphenyl-4-sulfonamides as a New Class of Potent and Selective Carbonic Anhydrase XIV Inhibitors was written by La Regina, Giuseppe;Coluccia, Antonio;Famiglini, Valeria;Pelliccia, Sveva;Monti, Ludovica;Vullo, Daniela;Nuti, Elisa;Alterio, Vincenzo;De Simone, Giuseppina;Monti, Simona Maria;Pan, Peiwen;Parkkila, Seppo;Supuran, Claudiu T.;Rossello, Armando;Silvestri, Romano. And the article was included in Journal of Medicinal Chemistry in 2015.Synthetic Route of C9H10BrNO2 This article mentions the following:

New 1,1′-biphenylsulfonamides were synthesized and evaluated as inhibitors of the ubiquitous human carbonic anhydrase isoforms I, II, IX, XII, and XIV using acetazolamide (AAZ) as reference compound The 1,1′-biphenylsulfonamides inhibited all the isoforms, with K_i values in the nanomolar range of concentration, and were superior to AAZ against all of them. X-ray crystallog. and mol. modeling studies on the adducts that compound I, the most potent hCA XIV inhibitor of the series (K_i = 0.26 nM), formed with the five hCAs, provided insight into the mol. determinants responsible for the high affinity of this mol. toward the target enzymes. The results pave the way to the development of 1,1′-biphenylsulfonamides as a new class of highly potent hCA XIV inhibitors. In the experiment, the researchers used many compounds, for example, 4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2Synthetic Route 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. 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.Synthetic Route of C9H10BrNO2

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

Tranilast-induced stress alleviation in solid tumors improves the efficacy of chemo- and nanotherapeutics in a size-independent manner was written by Papageorgis, Panagiotis;Polydorou, Christiana;Mpekris, Fotios;Voutouri, Chrysovalantis;Agathokleous, Eliana;Kapnissi-Christodoulou, Constantina P.;Stylianopoulos, Triantafyllos. And the article was included in Scientific Reports in 2017.Application In Synthesis of 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid This article mentions the following:

Accumulation of mech. stresses during cancer progression can induce blood and lymphatic vessel compression, creating hypo-perfusion, hypoxia and interstitial hypertension which decrease the efficacy of chemo- and nanotherapies. Stress alleviation treatment has been recently proposed to reduce mech. stresses in order to decompress tumor vessels and improve perfusion and chemotherapy. However, it remains unclear if it improves the efficacy of nanomedicines, which present numerous advantages over traditional chemotherapeutic drugs. Furthermore, we need to identify safe and well-tolerated pharmaceutical agents that reduce stress levels and may be added to cancer patients’ treatment regimen. Here, we show math. and with a series of in vivo experiments that stress alleviation improves the delivery of drugs in a size-independent manner. Importantly, we propose the repurposing of tranilast, a clin. approved anti-fibrotic drug as stress-alleviating agent. Using two orthotopic mammary tumor models, we demonstrate that tranilast reduces mech. stresses, decreases interstitial fluid pressure (IFP), improves tumor perfusion and significantly enhances the efficacy of different-sized drugs, doxorubicin, Abraxane and Doxil, by suppressing TGFβ signaling and expression of extracellular matrix components. Our findings strongly suggest that repurposing tranilast could be directly used as a promising strategy to enhance, not only chemotherapy, but also the efficacy of cancer nanomedicine. 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 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 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 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid

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

Removing polysaccharides-and saccharides-related coloring impurities in alkyl polyglycosides by bleaching with the H₂O₂/TAED/NaHCO₃ system was written by Yanmei, Liu;Jinliang, Tao;Jiao, Sun;Wenyi, Chen. And the article was included in Carbohydrate Polymers in 2014.Computed Properties of C10H16N2O4 This article mentions the following:

The effect of H₂O₂/TAED/NaHCO₃ system, namely NaHCO₃ as alk. agent with the (tetra acetyl ethylene diamine (TAED)) TAED-activated peroxide system, bleaching of alkyl polyglycosides solution was studied by spectrophotometry. The results showed that the optimal bleaching conditions about H₂O₂/TAED/NaHCO₃ system bleaching of alkyl polyglycosides solution were as follows: molar ratio of TAED to H₂O₂ was 0.06, addition of H₂O₂ was 8.6%, addition of NaHCO₃ was 3.2%, bleaching temperature of 50-65 °C, addition of MgO was 0.13%, and bleaching time was 8 h. If too much amount of NaHCO₃ was added to the system and maintained alk. pH, the bleaching effect would be greatly reduced. Fixing molar ratio of TAED to H₂O₂ and increasing the amount of H₂O₂ were beneficial to improve the whiteness of alkyl polyglycosides, but adding too much amount of H₂O₂ would reduce the transparency. In the TAED-activated peroxide system, NaHCO₃ as alk. agent and buffer agent, could overcome the disadvantage of producing black precipitates when NaOH as alk. agent. In the experiment, the researchers used many compounds, for example, N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) (cas: 10543-57-4Computed Properties of C10H16N2O4).

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.Computed Properties of C10H16N2O4

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

Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one containing 4,5-dihydrothiazole-2-thiol derivatives against Meloidogyne incognita was written by Chen, Xiulei;Zhou, Zhen;Li, Zhong;Xu, Xiaoyong. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 2020.Application In Synthesis of 6-Chloro-2-aminobenzamide This article mentions the following:

A series of novel 1,2,3-benzotriazin-4-one derivatives containing 4,5-dihydrothiazole-2-thiol I (R = H, 5-OMe, 7-F, 8-NO₂, etc.) was synthesized. The bioassay results showed that compounds I (R = 7-OMe, 6-NO₂, 7-Cl (A)) exhibited good control efficacy against the cucumber root-knot nematode disease caused by Meloidogyne incognita at the concentration of 10.0 mg L^-1 in vivo. Compound (A) showed excellent nematicidal activity with inhibition 68.3% at a concentration of 1.0 mg L^-1. It suggested that the structure of 1,2,3-benzotriazin-4-one containing 4,5-dihydro-thiazole-2-thiol could be optimized further. In the experiment, the researchers used many compounds, for example, 6-Chloro-2-aminobenzamide (cas: 54166-95-9Application In Synthesis of 6-Chloro-2-aminobenzamide).

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. 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 In Synthesis of 6-Chloro-2-aminobenzamide

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

Quantification and method validation of dicyclohexylurea content in fosaprepitant dimeglumine drug substance by reverse phase HPLC was written by Kishore, M. V.;Sivarao, T.;Srinivas, K. Rama;Satyendranath, Ch. V.;Kumar, Vundavilli Jagadeesh;Kumar, K. S. R. Pavan;Sreenivas, N.. And the article was included in International Journal of Pharmaceutical Sciences and Research in 2020.Computed Properties of C13H24N2O This article mentions the following:

A simple, sensitive, and rapid reverse phase High-Pressure Liquid Chromatog. (HPLC) method was developed and validated for the quantification of residual Dicyclohexylurea in Fosaprepitant dimeglumine drug substance at trace level. The method was optimized on Zorbax Eclipse XDB-C8, 250 mm x 4.6 mm, 5μm with column oven temperature maintaining at 35°C with flow rate at 0.7 mL/min. Mobile Phase was prepared by a mixture of phosphate buffer pH 7.0 ((0.68 g of Potassium dihydrogen orthophosphate in 1000 mL of water) and Acetonitrile in the ratio of 53:47 volume/volume), the injection volume is 20μl, the detector wavelength is 205 nm. The developed, optimized method was further validated in accordance with ICH, and the method is found to be specific, sensitive, accurate, and precise. The Limit of detection (LOD) and Limit of quantification (LOQ) for dicyclohexylurea are 20μg/g and 60μg/g, resp. The method validation exptl. results are discussed in detail in this research paper. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Computed Properties of C13H24N2O).

1,3-Dicyclohexylurea (cas: 2387-23-7) 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. 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.Computed Properties of C13H24N2O

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

Mass spectrometry-based metabolomics approach to reveal differential compounds in pufferfish soups: Flavor, nutrition, and safety was written by Bi, Hongyan;Cai, Dandan;Zhang, Rutan;Zhu, Yiwen;Zhang, Danni;Qiao, Liang;Liu, Yuan. And the article was included in Food Chemistry in 2019.HPLC of Formula: 2387-23-7 This article mentions the following:

Some Eastern Asian countries deem pufferfish – especially its muscle – a culinary delight. Herein, mol. mass fingerprinting of soups prepared by Takifugu flavidus, Takifugu obscurus and Takifugu rubripes was established via matrix-assisted laser desorption/ionization – mass spectrometry (MALDI MS). Soup samples were directly analyzed by MALDI MS to collect mass spectra within 0-700 Da in a quick way, followed by principal component anal. to distinguish the different soups and to find out the distinctive compounds among the soups. High performance liquid chromatog. – tandem MS (HPLC-MS/MS) was applied to identify the compounds Nineteen compounds were identified from the HPLC-MS/MS data by using METLIN database. Through literature mining, we found that these compounds are closely related to the flavor, nutrition, and safety of pufferfish soups. This method can also be used as a facile way to distinguish between different pufferfish fillets when morphol. characters have been damaged or destroyed. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7HPLC of Formula: 2387-23-7).

1,3-Dicyclohexylurea (cas: 2387-23-7) 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 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.HPLC of Formula: 2387-23-7

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

Ortho- and Para-Selective Ruthenium-Catalyzed C(sp²)-H Oxygenations of Phenol Derivatives was written by Liu, Weiping;Ackermann, Lutz. And the article was included in Organic Letters in 2013.Name: N,N-Diethylsalicylamide This article mentions the following:

Versatile ruthenium catalysts allowed for efficient direct oxygenations of aryl carbamates under remarkably mild reaction conditions to provide o-hydroxy products, e.g., I. In addition to chelation-assisted C-H activation, the optimized ruthenium catalyst proved amenable to para-selective hydroxylations of anisoles without Lewis basic directing groups. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Name: N,N-Diethylsalicylamide).

N,N-Diethylsalicylamide (cas: 19311-91-2) 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.Name: N,N-Diethylsalicylamide

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