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1.
J Chromatogr A ; 1735: 465346, 2024 Oct 25.
Artigo em Inglês | MEDLINE | ID: mdl-39243587

RESUMO

The Soret effect is a significant factor in various scenarios, with thermodiffusion in binary systems serving as a common method for the study. Most research focuses rarely on the distribution characteristics of components in diffusion systems; and Soret coefficients in the porous media could not be obtained by typical methods based on the thermodiffusion column, which are particularly important in the field of oil and gas development. Moreover, experiments on ground conditions have struggled to determine the Soret coefficient accurately due to the convective effect caused by gravity differentiation. The thermodiffusion behavior of n-pentane (C5) and n-heptane (C7) binary mixtures in both bulk and porous media conditions have been investigated, aiming to provide corrected coefficients that mitigate the influence of gravity using theoretical derivation. A new method was proposed to calculate the Soret coefficients in this work by establishing a model based on gas chromatography technology. Dynamic variation of component concentration along the path was studied, and the corresponding Soret coefficients were calculated and analyzed in parallel. The results indicate that the concentration and temperature exhibit a logarithmic relationship with the distance from the heat source. The Soret coefficient values obtained from measurements in porous media are closer to the theoretically corrected values, which do not account for gravity effects. Additionally, as the permeability decreases, the counteracting effect of porous media on convection becomes more pronounced. Therefore, it presents a novel method for accurately measuring the Soret coefficient that ignores convection to some extent.


Assuntos
Heptanos , Heptanos/química , Cromatografia Gasosa/métodos , Porosidade , Difusão , Hidrocarbonetos/química , Hidrocarbonetos/análise , Temperatura , Modelos Químicos , Pentanos
2.
Eur J Pharm Sci ; 200: 106826, 2024 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-38866112

RESUMO

The separation and purification of plant-based Active Pharmaceutical Ingredients (API) from extracts is a crucial part in pharmaceutical process development. For the purification of the antimalarial drug component artemisinin (ARTE) from an Artemisia anna L. toluene extract, antisolvent crystallization is considered. Solubilities of ARTE in binary solvent mixtures of toluene and two potential antisolvents, n-heptane and ethanol, were determined at temperatures from 278.15 K to 313.15 K. The experimental work was supported by the application of various models, utilizing varying amounts of experimental input data. The goal was the identification of models that are able to predict solubilities in binary solvent mixtures sufficiently accurate and, thus, can help to reduce the experimental effort for future solvent screenings. In this study, we applied the PC-SAFT model both with and without fitting the binary interaction parameter kij between ARTE and the respective solvent, as well as the empirical Jouyban-Acree model. From the experiments, n-heptane demonstrated to be a promising antisolvent, while ethanol acted more as a cosolvent. All models tested were capable of distinguishing between effective and ineffective antisolvents. The purely predictive PC-SAFT model applied with kij = 0 exhibited the largest deviation from the experimental data. This was followed by the PC-SAFT model including fitted kij values, based on at least four experimental data points. The Jouyban-Acree model fitted the data most accurately. Its parametrization required a minimum of ten experimental data points.


Assuntos
Antimaláricos , Artemisininas , Solubilidade , Solventes , Artemisininas/química , Solventes/química , Antimaláricos/química , Etanol/química , Heptanos/química , Tolueno/química , Modelos Químicos , Artemisia annua/química , Cristalização
3.
J Chromatogr A ; 1721: 464850, 2024 Apr 26.
Artigo em Inglês | MEDLINE | ID: mdl-38564932

RESUMO

The solvation parameter model uses five system independent descriptors to characterize compound properties defined as excess molar refraction, E, dipolarity/polarizability, S, hydrogen-bond acidity, A, hydrogen-bond basicity, B, and McGowan's characteristic volume, V, to model transfer properties between condensed phases. The V descriptor is assigned from structure. For compounds liquid at 20 °C the E descriptor can be assigned from the characteristic volume and its refractive index. The E descriptor for compounds solid at 20 °C and the S, A, and B descriptors are experimental properties traditionally assigned from chromatographic, liquid-liquid partition, and solubility measurements. In this report liquid-liquid partition constants in totally organic and aqueous biphasic systems are evaluated as a standalone technique for descriptor assignments. Using six totally organic biphasic systems the S, A, and B descriptors were assigned with an average absolute deviation (AAD) of about 0.04, 0.03, and 0.04, respectively, compared with the best estimate of the true descriptor values for 65 compounds. The E descriptor for compounds solid at 20 °C can only be estimated with an AAD of approximately 0.1. For six aqueous biphasic systems the B descriptor is assigned with a lower AAD of 0.028 and higher AAD of 0.08 and 0.05 for the S and A descriptors, respectively, than for the totally organic biphasic systems for compounds with a reliable value for the E descriptor. The preferred system for descriptor assignments utilizes both totally organic biphasic systems (heptane-1,1,1-trifluoroethanol, isopentyl ether-propylene carbonate, isopentyl ether-ethanolamine, heptane-ethylene glycol, heptane-formamide, and 1,2-dichloroethane-ethylene glycol) and aqueous biphasic systems (octanol-water, cyclohexane-water) with the possible substitution of some systems with alternative systems of similar selectivity. For 55 varied compounds this combination of eight organic and aqueous biphasic systems resulted in an AAD of approximately 0.03, 0.02, and 0.02 for the S, A, and B descriptors compared to the best estimate of the true descriptor value. For 30 compounds solid at 20 °C the AAD for the E descriptor of 0.11 is poorly assigned. The relative average absolute deviation in percent (RAAD) corresponds to 9.7 %, 3.1 %. 4.0 % and 8.3 % for E, S, A, and B, respectively, for the eight biphasic systems. Liquid-liquid partition is compared to reversed-phase liquid and gas chromatography as a standalone technique for descriptor assignments.


Assuntos
Éteres , Água , Etilenoglicóis , Heptanos/química , Hidrogênio , Água/química , Cicloexanos/química , Octanóis/química
4.
Chemosphere ; 355: 141820, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38561158

RESUMO

Organic solvent nanofiltration (OSN) is an incipient technology in the field of organic liquid-liquid separation. The incomplete separations and complexity involved in these, forces many organic liquids to be released as effluents and the adverse effects of these on environment is enormous and irreparable. The work prominences on the complete separation of industrially significant cyclohexanone: cyclohexanol (keto-alcohol oil) and heptane: toluene mixtures. The separations of these above-mentioned organic liquid mixtures were carried out using the fabricated Lewis acid modified graphitic carbon nitride (Cu2O@g-C3N4) incorporated polyvinylidene difluoride (PVDF) composite membranes. These fabricated membranes showed a separation factor of 18.16 and flux of 1.62 Lm-2h-1 for cyclohexanone: cyclohexanol mixture and separation of heptane and toluene mixture (with heptane flux of 1.52 Lm-2h-1) showed a separation factor of 9.9. The selectivity and productivity are based on the polarity and size of the organic liquids. The role of Cu2O@g-C3N4 is influencing the pore size distribution, increased divergence from solubility parameters, polarity, solvent uptake and porosity of the composite membranes. The developed composite membranes are thus envisioned to be apt for a wide range of liquid-liquid separations due to its implicit nature.


Assuntos
Cicloexanóis , Cicloexanonas , Heptanos , Solventes , Tolueno
5.
Artigo em Inglês | MEDLINE | ID: mdl-38520897

RESUMO

Extraction of vitamin D, including its hydroxylated and esterified metabolites, from soft tissues such as the liver is challenging due to the lipophilic character of matrix and analytes that are expected in very low concentration levels. In this study, we aimed at the optimization of two-step extraction using solid-liquid extraction as the first step, followed by solid-phase extraction. Various solvents, including ethanol, acetonitrile, methanol, acetone, heptane, and heptane with isopropanol, were investigated to isolate vitamin D compounds from liver tissue in the first step. Acetone was finally selected as the most suitable solvent for the solid-liquid extraction, with the highest recovery in the range of 67 - 98% for polar hydroxylated forms and 3 - 28% for lipophilic vitamin D and esters. Two solid phase extraction (SPE) based on the (i) "bind and elute strategy" and (ii) "removal strategy" using hydrophilic-lipophilic balanced SPE sorbent were optimized as a proceeding step for acetone extracts to increase the method selectivity. Finally, two optimized methods, combining solid-liquid extraction and individual SPE strategy, were examined in terms of sensitivity, recovery, matrix effect, accuracy, and precision. The limits of quantification were in the range of 1 - 10 ng/mL and 3 - 20 ng/mL analyzed by ultra-high performance supercritical fluid chromatography and ultra-high performance liquid chromatography hyphenated a with tandem mass spectrometer, respectively. The absolute recovery determined for the "bind and elute strategy" protocol was in the range of 3 - 24 %. Nevertheless, this method was free of matrix effects, which were determined to be in the 73 - 120 % range. On the contrary, the "removal strategy" approach provided higher recovery values for all compounds (47 - 123 %), but the results for nonpolar vitamin D and esters were strongly affected by signal suppression (matrix effects 3 - 51 %). Both methods fulfilled the criteria for accuracy and precision requested by the European Medicine Agency Guideline on Bioanalysis. "Removal strategy" SPE with decreased manual intervention and lower solvent consumption was finally applied to mouse liver tissue to determine vitamin D and its hydroxylated and esterified metabolites for the first time. The results, i.e., vitamin D esters detected in liver tissue, supported the notion that esters of vitamin D can be stored in lipophilic tissues to release vitamin D.


Assuntos
Espectrometria de Massas em Tandem , Vitamina D , Animais , Camundongos , Espectrometria de Massas em Tandem/métodos , Acetona , Cromatografia Líquida de Alta Pressão/métodos , Solventes , Vitaminas , Fígado , Heptanos , Extração em Fase Sólida/métodos
6.
Curr Protoc ; 4(3): e1013, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38483118

RESUMO

Universal solid supports are widely used in solid-phase oligonucleotide (ON) synthesis based on phosphoramidite chemistry. Herein, we describe the synthesis of hydrophobic universal linkers, namely phenanthrene ring-fused 7-oxabicyclo[2.2.1]heptane-2,3-diol derivatives (PT linkers), their coupling to solid supports [e.g., controlled pore glass (CPG) and polystyrene (PS)], and the use of the resulting PT-linker-modified solid supports in ON synthesis. PT linkers were synthesized in four steps from commercial materials and subsequently attached to CPG and PS resins through succinyl and diethylene glycol-containing spacers, respectively. Cleavage of the desired ON from the resins was accomplished under standard basic conditions, indicating that the reactivity of the PT linkers was comparable to that of conventional universal linkers. Furthermore, owing to their high hydrophobicity, the desired ON could be readily separated from impurities originating from the PT linker by reversed phase HPLC. © 2024 Wiley Periodicals LLC. Basic Protocol 1: Synthesis of phenanthrene ring-fused 7-oxabicyclo[2.2.1]heptane-2,3-diol (PT linker) derivatives Basic Protocol 2: Preparation of PT-linker-modified CPG and PS resins Basic Protocol 3: Solid-phase ON synthesis using PT-linker-modified solid supports and cleavage of ONs from resins.


Assuntos
Heptanos , Oligonucleotídeos , Oligonucleotídeos/química , Interações Hidrofóbicas e Hidrofílicas
7.
Int J Prosthodont ; 37(7): 71-77, 2024 Feb 21.
Artigo em Inglês | MEDLINE | ID: mdl-38498859

RESUMO

PURPOSE: To evaluate the effect of food-simulating liquids (FSLs) on the mechanical properties of provisional restoration materials fabricated by 3D printing, milling, and traditional fabricating methods. MATERIALS AND METHODS: The bar specimens were fabricated with traditional, milling, and 3D-printing methods according to ISO 10477 specifications. Each group of specimens was randomly subdivided into four groups to be immersed in various FSLs: distilled water (control group), n-heptane, 50% ethyl alcohol, and 0.02 mol/L citric acid for 7 days at room temperature (n = 19 per group). The Knoop hardness (KHN) was evaluated, and the specimens were subjected to a three-point bending (3PB) test to evaluate flexural strength (FS) and flexural modulus (FM). One-way ANOVA and Tukey tests were used to analyze the data. RESULTS: Fabrication methods had a significant effect on the mechanical properties of the materials being tested. FSLs had no effect on the FS and FM of materials being tested. The 50% ethyl alcohol solution significantly decreased the hardness of traditional group specimens, and the n-heptane and 50% ethyl alcohol solutions increased the hardness of the 3D-printed specimens significantly (P ≤ .05). Scanning electron microscopy (SEM) revealed that while traditional and milling group specimens showed a ductile fracture type, 3D-printed specimens showed a brittle fracture type. CONCLUSIONS: Production methods affected the mechanical properties of provisional restoration materials. Immersion in 50% ethyl alcohol solution decreased the KHN of the traditional specimens. FSLs had no negative effect on the mechanical properties of the milled and 3D-printed specimens.


Assuntos
Materiais Dentários , Heptanos , Impressão Tridimensional , Teste de Materiais , Estresse Mecânico , Etanol , Propriedades de Superfície
8.
Angew Chem Int Ed Engl ; 63(9): e202316557, 2024 02 26.
Artigo em Inglês | MEDLINE | ID: mdl-38251921

RESUMO

The spiro[3.3]heptane core, with the non-coplanar exit vectors, was shown to be a saturated benzene bioisostere. This scaffold was incorporated into the anticancer drug sonidegib (instead of the meta-benzene), the anticancer drug vorinostat (instead of the phenyl ring), and the anesthetic drug benzocaine (instead of the para-benzene). The patent-free saturated analogs obtained showed a high potency in the corresponding biological assays.


Assuntos
Antineoplásicos , Benzeno , Heptanos , Fenômenos Químicos , Antineoplásicos/farmacologia
9.
Environ Sci Pollut Res Int ; 31(6): 8608-8632, 2024 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-38180670

RESUMO

Recent global challenges encompass profound environmental pollution and the depletion of finite fuel resources. In this study, the biodiesel used in the mixture was derived from Azolla pinnata microalgae oil through a trans-esterification reaction chosen for its high oil concentration. During the initial phase of the experiment, varying volumes of biodiesel (5%, 10%, and 15%) and n-heptane (5%, 10%, and 15%) were introduced to diesel to form a ternary fuel blend. The experimental outcome shows that an n-heptane and biodiesel mixture of 10% by volume would produce the best results. Next, experiments were carried out by incorporating 10, 40, and 80 ppm titanium oxide (TiO2) nanoparticles (NPs) in a recommended ternary fuel blend. The experimental investigation showed that D80A10H10TNP40 (diesel 80% + biodiesel 10% + n-heptane 10% + TiO2 40 ppm) caused a 7.21% increase in brake thermal efficiency (BTE) with a decrease in brake specific fuel consumption (BSFC) and brake specific energy consumption (BSEC) by 9.58% and 10%, respectively, compared to (diesel 80% + biodiesel 20%) D80A20. D80A10H10TNP40 exhibits lower emissions, with a significant reduction of 11.29% and 20.96% in carbon monoxide (CO) and unburnt hydrocarbons (UBHC), respectively. Nitrogen oxide (NOX) and smoke emissions were reduced by 3.3% and 11.13%, respectively, compared to D80A10H10. Furthermore, D80A10H10TNP40 demonstrated enhanced combustion properties, comprising a significant rise of 4.39% in-cylinder pressure (CP), 35.29% in heat release rate (HRR), and 25.05% in the rate of pressure rise (RPR). The findings of this investigation indicate that D80A10H10TNP40 exhibits enhanced efficiency, emission, and combustion properties compared to the D80A20 fuel.


Assuntos
Heptanos , Microalgas , Nanopartículas , Gasolina , Biocombustíveis , Emissões de Veículos , Óxido Nítrico , Monóxido de Carbono/análise
10.
Arch Pharm (Weinheim) ; 357(3): e2300549, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38036303

RESUMO

A new series of heterocyclic derivatives with a 1,7,7-trimethylbicyclo[2.2.1]heptane fragment was designed, synthesised and biologically evaluated. Synthesis of the target compounds was performed using the Cu(I) catalysed cycloaddition reaction. The key starting substances in the click reaction were an alkyne containing a 1,7,7-trimethylbicyclo[2.2.1]heptane fragment and a series of azides with saturated nitrogen-containing heterocycles. Some of the derivatives were found to exhibit strong antiviral activity against Marburg and Ebola pseudotype viruses. Lysosomal trapping assays revealed the derivatives to possess lysosomotropic properties. The molecular modelling study demonstrated the binding affinity between the compounds investigated and the possible active site to be mainly due to hydrophobic interactions. Thus, combining a natural hydrophobic structural fragment and a lysosome-targetable heterocycle may be an effective strategy for designing antiviral agents.


Assuntos
Heptanos , Triazóis , Relação Estrutura-Atividade , Catálise , Triazóis/farmacologia , Antivirais/farmacologia
11.
Shokuhin Eiseigaku Zasshi ; 64(4): 154-160, 2023.
Artigo em Japonês | MEDLINE | ID: mdl-37673605

RESUMO

An inter-laboratory study involving 24 laboratories was conducted to validate the modified analytical method for the migration solution of heptane for the determination of bisphenol A migrating from polycarbonate food processing materials. In this study, two concentrations of samples were blindly coded. Each laboratory determined the analyte (bisphenol A, phenol and p-tert-butylphenol) concentration in each sample according to the established protocol. The obtained values were analyzed statistically using internationally accepted guidelines. Horwitz ratios were calculated based on the reproducibility relative standard deviation (RSDR), which was estimated from the inter-laboratory study, and predicted RSDR, which was calculated using the Horwitz/Thompson equation. Horwitz ratios of the two samples ranged from 0.15 to 0.37 for the three compounds, meeting the performance criteria of less than 2 set by the Codex Alimentarius for analytical method approval. These results showed that this modified analytical method shows good performance as an analytical method for the migration solution of heptane.


Assuntos
Heptanos , Fenóis , Reprodutibilidade dos Testes
12.
Cannabis Cannabinoid Res ; 8(S1): S1-S10, 2023 09.
Artigo em Inglês | MEDLINE | ID: mdl-37721987

RESUMO

Introduction: The psychoactive properties of Δ10-THC isomers (trans- and cis-Δ10-THC) are poorly understood. To shed more light on the biological effects of these compounds, we studied in vitro receptor binding of Δ10-THC isomers at cannabinoid CB1 and CB2 receptors. Materials and Methods: We first optimized and simplified catalytic synthesis of trans- and cis-Δ10-THC to allow their safe and cheap large-scale synthesis. In our synthesis, BuLi was replaced with KOtBu, and DMSO/anisole or NEt3/heptane solvent systems were used instead of HMPA/toluene. Single crystal X-ray analysis confirmed the structure of both isomers and the configuration of their chiral centers. Results: In the radioligand replacement assay, both isomers showed strong affinity toward the CB1 receptor, with IC50=29.1 nM for the trans isomer and IC50=294.2 nM for the cis counterpart. However, the IC50 values were significantly higher than that of Δ9-THC (2.1 nM), a naturally occurring psychoactive component of cannabis sativa, suggesting a lower affinity of Δ10-THCs toward this receptor. In function assays, in contrast to Δ9-THC, both isomers failed to show any agonist properties at concentrations up to 10 µM suggesting a lack of THC-like psychoactivity for trans- and cis-Δ10-THC. Conclusions: Our results established Δ10-THC isomers among antagonists of the CB1 receptor as both cis and trans isomers antagonized CP55,490 with IC50=460 nM for trans and IC50=1040 nM for cis. This functional property has not been previously observed for any other THC isomers.


Assuntos
Bioensaio , Receptor CB1 de Canabinoide , Ensaio Radioligante , Catálise , Heptanos
13.
Chem Commun (Camb) ; 59(73): 10964-10967, 2023 Sep 12.
Artigo em Inglês | MEDLINE | ID: mdl-37608736

RESUMO

Azaspiro[3.3]heptanes are valuable synthetic targets for drug discovery programs. The challenges associated with the preparation and diversification of this moiety as compared to other small, saturated rings have led to limited applications of compounds containing this spirocycle. In this regard, important advances in the field of synthetic photochemistry have exploited the biradical nature of the triplet excited state of 2-isoxazoline-3-carboxylates, engaging these species in intermolecular coupling reactions under visible light irradiation. As a continuation of our program preparing F(sp3)-rich, structurally complex molecules for DNA-encoded library technology (DELT) applications via photocatalysis, we disclose herein the incorporation of unique and densely functionalized 2-oxa-1-azabicyclo[3.2.0]heptanes via [2+2] cycloaddition energy transfer sensitization, providing access to an unexplored library of azaspiro compounds, many of which include additional synthetic handles important for further functionalization of the DNA-conjugated products and for library production.


Assuntos
Heptanos , Luz , Transferência de Energia , Catálise , DNA
14.
Eur J Med Chem ; 260: 115731, 2023 Nov 15.
Artigo em Inglês | MEDLINE | ID: mdl-37643546

RESUMO

Ulcerative colitis is a chronic inflammatory disease with a remitting-relapsing clinical course, it has evolved into a global burden given its high incidence worldwide. Cantharidin (CTD) derivatives are a class of compounds whose structures characterized with a 7-oxabicyclo [2.2.1]heptane core. Though potent cytotoxicity CTD and its derivatives showed, their clinical usage as anti-cancer drugs was limited by the toxicity in organs. In order to find new CTD analogues with good activity and lower toxicity, 21 CTD analogues with or without alkynyl substitution at C5 position of 7-oxabicyclo [2.2.1]heptane core were synthesized, some compounds showed better in vitro anti-inflammatory activity compared to CTD and norcantharidin (NCTD). Based on the structure-activity relationship results of in vitro experiment, analogue 3i was chosen for further study. Results from the acute toxicity in mice showed that 3i was hypotoxic with the single-dose MTD (maximum tolerated dose) for oral administration is over 1852 mg/kg, at least 35-fold lower than that of NCTD. Mechanism study indicated that 3i could potently inhibit TNF-α induced activation of NF-κB signaling by down-regulation the expression levels of phosphor- IKK, IκBα, and NF-κB p65, and alleviated dextran sulfate sodium-induced colitis in mice. This study indicated that CTD analogues with alkynyl substitution at C5 position of 7-oxabicyclo [2.2.1]heptane core is a kind of new compounds with good anti-inflammatory activity and lower toxicity in vivo, and might be used as therapeutic agents for inflammatory diseases.


Assuntos
Colite , NF-kappa B , Animais , Camundongos , Cantaridina/farmacologia , Cantaridina/uso terapêutico , Sulfato de Dextrana , Colite/induzido quimicamente , Colite/tratamento farmacológico , Heptanos
15.
Shokuhin Eiseigaku Zasshi ; 64(3): 111-115, 2023.
Artigo em Japonês | MEDLINE | ID: mdl-37380481

RESUMO

A validation study was performed on the modified analytical method for the migration solution of heptane, 20% ethanol and 4% acetic acid for the determination of bisphenol A migrating from polycarbonate food apparatuses, containers, and packaging. The analytes for the method were bisphenol A, phenol and p-tert-butylphenol. The repeatability, within-laboratory reproducibility and trueness of the method was estimated in the range of 0.2-1.8%, 0.4-2.6% and 95-102% respectively. These results showed that the method is useful as an analytical method for the migration solution of heptane, 20% ethanol and 4% acetic acid. Furthermore, the applicability of the determination methods with a fluorescence detector was verified. As a result of the validation study, the repeatability, within-laboratory reproducibility and trueness of the method was estimated in the range of 0.1-2.9%, 0.2-3.1% and 94-101% respectively. It was confirmed that the measurement with a fluorescence detector is also available.


Assuntos
Ácido Acético , Fenóis , Reprodutibilidade dos Testes , Etanol , Heptanos
16.
Food Chem ; 400: 133988, 2023 Jan 30.
Artigo em Inglês | MEDLINE | ID: mdl-36088888

RESUMO

The present study was designed to study the effect of green solvent processing in two folds, (i) to extract valuable protein from dairy and non-dairy expired milk products and (ii) to compare extraction efficiency and quality of extracted protein using conventional (CS) and green solvents (GS). Ethyl acetate, ethanol, isopropanol, n-heptane and cyclopentyl methyl ether (CPME) were selected as the GS for the possible substitution of hexane and ethyl ether. For each respective solvent, protein recovery, structural and functional modifications were studied. Protein yield was extracted most effectively by GS n-heptane in dairy milk (5.33 ± 0.01%) with a protein purity of 39.73 ± 0.90%. Non-dairy milk and product had similar protein yield when treated with CS and GS. Total mean of extraction efficiency, structural and functional modifications across all samples showed GS solvents were statistically more effective than CS.


Assuntos
Éteres Metílicos , Leite , 2-Propanol , Animais , Etanol , Etil-Éteres , Heptanos , Hexanos/química , Éteres Metílicos/química , Solventes/química
17.
J Am Chem Soc ; 144(51): 23685-23690, 2022 12 28.
Artigo em Inglês | MEDLINE | ID: mdl-36523116

RESUMO

The development of synthetic strategies for the preparation of bioisosteric compounds is a demanding undertaking in medicinal chemistry. Numerous strategies have been developed for the synthesis of bicyclo[1.1.1]pentanes (BCPs), bridge-substituted BCPs, and bicyclo[2.1.1]hexanes. However, progress on the synthesis of bicyclo[3.1.1]heptanes, which serve as meta-substituted arene bioisosteres, has not been previously explored. Herein, we disclose the first photoinduced [3σ + 2σ] cycloaddition for the synthesis of trisubstituted bicyclo[3.1.1]heptanes using bicyclo[1.1.0]butanes and cyclopropylamines. This transformation not only uses mild and operationally simple conditions but also provides unique meta-substituted arene bioisosteres. The applicability of this method is showcased by simple derivatization reactions.


Assuntos
Compostos Bicíclicos com Pontes , Heptanos , Compostos Bicíclicos com Pontes/química , Heptanos/química , Reação de Cicloadição , Hexanos/química , Butanos
18.
Nat Commun ; 13(1): 7176, 2022 11 23.
Artigo em Inglês | MEDLINE | ID: mdl-36418900

RESUMO

In recent years, the flourishing of synthetic methodology studies has provided concise access to numerous molecules with new chemical space. These compounds form a large library with unique scaffolds, but their application in hit discovery is not systematically evaluated. In this work, we establish a synthetic methodology-based compound library (SMBL), integrated with compounds obtained from our synthetic researches, as well as their virtual derivatives in significantly larger scale. We screen the library and identify small-molecule inhibitors to interrupt the protein-protein interaction (PPI) of GIT1/ß-Pix complex, an unrevealed target involved in gastric cancer metastasis. The inhibitor 14-5-18 with a spiro[bicyclo[2.2.1]heptane-2,3'-indolin]-2'-one scaffold, considerably retards gastric cancer metastasis in vitro and in vivo. Since the PPI targets are considered undruggable as they are hard to target, the successful application illustrates the structural specificity of SMBL, demonstrating its potential to be utilized as compound source for more challenging targets.


Assuntos
Neoplasias Gástricas , Humanos , Biblioteca Gênica , Heptanos , Restrição Física , Fatores de Troca de Nucleotídeo Guanina Rho , Mapeamento de Interação de Proteínas
19.
Phys Chem Chem Phys ; 24(46): 28403-28410, 2022 Nov 30.
Artigo em Inglês | MEDLINE | ID: mdl-36398692

RESUMO

Alternation in various properties of n-alkanes (CnH2n+2) as a function of carbon content (n) is termed 'odd-even effect'. Here, we report a comprehensive molecular dynamics simulation study on n-alkane systems carried out with n ranging between 3 (propane) and 8 (octane), examining the odd-even effect in melting point, density, intramolecular conformational ordering, translational and rotational motion. We observe an odd-even alternation in these properties, but with heptane (n = 7) exhibiting anomalous behavior for all except conformational ordering. Our simulations also show the presence of odd-even behavior in rotational and translational dynamics, below and above the melting point, respectively. The results highlight the role of both molecular shape and the variation in density and their interplay in the origins of the odd-even effect.


Assuntos
Alcanos , Simulação de Dinâmica Molecular , Propano , Heptanos , Carbono
20.
J Am Chem Soc ; 144(48): 21848-21852, 2022 12 07.
Artigo em Inglês | MEDLINE | ID: mdl-36342862

RESUMO

There is increasing interest in replacement of the planar aromatic rings of drug candidates with three-dimensional caged scaffolds in order to improve the physical properties, but bioisosteres of meta-substituted benzenes have remained elusive. We focused on the bicyclo[3.1.1]heptane (BCH) scaffold as a novel bioisostere of meta-substituted benzenes, anticipating that [3.1.1]propellane (2) would be a versatile precursor of diversely functionalized BCHs. Here, we describe a practical preparative method for [3.1.1]propellane from newly developed 1,5-diiodobicyclo[3.1.1]heptane (1), as well as difunctionalization reactions of 2 leading to functionalized BCHs. We also report postfunctionalization reactions of these products.


Assuntos
Heptanos
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