120-47-8Relevant articles and documents
The dihydropyrone Diels-Alder reaction: Development and application to the synthesis of highly functionalized 1-oxa-4-decalones
Seth, Punit P.,Chen, Deqi,Wang, Junquan,Gao, Xiuchun,Totah, Nancy I.
, p. 10185 - 10195 (2000)
A facile method for the synthesis of highly functionalized 1-oxadecalone derivatives is described via the Diels-Alder reaction of 2,3-dihydro-4-pyrone dienophiles with electron rich dienes. By this process a variety of functional groups and substitution patterns can be incorporated into the oxadecalone framework. (C) 2000 Elsevier Science Ltd.
Conformational, structural, vibrational and quantum chemical analysis on 4-aminobenzohydrazide and 4-hydroxybenzohydrazide-A comparative study
Arjunan,Jayaprakash,Carthigayan,Periandy,Mohan
, p. 100 - 114 (2013)
Experimental and theoretical quantum chemical studies were carried out on 4-hydroxybenzohydrazide (4HBH) and 4-aminobenzohydrazide (4ABH) using FTIR and FT-Raman spectral data. The structural characteristics and vibrational spectroscopic analysis were carried performed by quantum chemical methods with the hybrid exchange-correlation functional B3LYP using 6-31G, 6-311++G and aug-cc-pVDZ basis sets. The most stable conformer of the title compounds have been determined from the analysis of potential energy surface. The stable molecular geometries, electronic and thermodynamic parameters, IR intensities, harmonic vibrational frequencies, depolarisation ratio and Raman intensities have been computed. Molecular electrostatic potential and frontier molecular orbitals were constructed to understand the electronic properties. The potential energy distributions (PEDs) were calculated to explain the mixing of fundamental modes. The theoretical geometrical parameters and the fundamental frequencies were compared with the experimental. The interactions of hydroxy and amino group substitutions on the characteristic vibrations of the ring and hydrazide group have been analysed.
Synthesis, characterization and antimicrobial evaluation of novel (E)-N′-(4-(1-((3,4-dimethoxypyridin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)benzylidene)benzohydrazide derivatives
Saidugari, Swamy,Vadali, Lakshmana Rao,Vidya,Ram
, p. 2155 - 2161 (2016)
The synthesis of novel 1,2,3-triazole-hydrazone derivatives embedded with 3,4-dimethoxy pyridine ring nucleus is described. These derivatives were prepared utilizing, 2-(chloromethyl)-3,4-dimethoxypyridine 1, 4-ethynylbenzaldehye 5 and various benzohydrazides7a-7j. The structures of the newly synthesized 1,2,3-triazole-hydrazones 8a-j was established on the basis of the spectroscopic techniques like 1H NMR, mass and IR data. They were evaluated against a panel of bacterial and fungal pathogens such as Staphylococcus. pyogens, Staphylococcus. Aureus (Gram positive bacteria), Escherichia.coli, Pseudomonas. aeruginosa (Gram negative bacteria) and Aspergillus niger and Candida albicans (Fungal stains). Compounds 8b, 8c, 8d, 8e and 8f with R = 4-OH, 4-OMe, 4-SO2Me, 3,45,-OMe and 3-NO2 respectively showed moderate antibacterial activity while compounds 8b, 8d, 8i and 8j with R = 4-OH, 4-SO2Me, 3,5-dichloro and 2,5-difluoro substitution exhibited very good fungal activity.
Novel Benzothiazole Ionic Liquids as Catalysts for the Synthesis of Parabens
Liu, B.,Liu, Y.,Sun, J.,Yin, D.
, p. 1476 - 1483 (2020)
Abstract: A simple and green approach to the esterification of p-hydroxybenzoic acid and aliphatic alcohols to obtain parabens was developed. First, two novel benzothiazole ionic liquids [HBth]H2PW12O40 (IL1) and [HBth]H4PMo12O41 (IL2) were synthesized with benzothiazole and heteropolyacids as starting materials. The synthesized ionic liquids were characterized by FTIR spectroscopy, TGA, PXRD analysis, and SEM. The application of IL1 and IL2 as catalysts for the synthesis of parabens was explored. The results showed that the ILs had a high catalytic activity in the synthesis of parabens, and, at the same time, they could be easily recovered and reused five times without loss of activity.
Construction of cis-azadecalone units via novel intermolecular Diels-Alder reaction
Dhimane, Hamid,Meunier, Stéphane,Vanucci-Bacqué, Corinne,Lhommet, Gérard
, p. 1645 - 1648 (2002)
N-Methoxycarbonyl-5-ethoxycarbonyl-2,3-dihydropyridin-4-one 1 reacts under thermal or Lewis acid-catalysed conditions with trimethylsilyloxybutadienes to give cis-azadecalones via a formal [4+2] cycloaddition.
Synthesis of Nipagin esters using acidic functional ionic liquids as catalysts
Wang, Guohua,Li, Lu,Xie, Congxia,Yu, Shitao,Liu, Fusheng,Ye, Xiaoling
, p. 945 - 952 (2011)
(Chemical Equation Presented) Several Bronsted acidic functional ionic liquids (FILs) with an alkane sulfonic acid group were synthesized. These FILs as dual solvent-catalysts for Nipagin esterification reactions were investigated. The results indicated that [HSO3-pMIM]HSO4 has the best catalytic activity and recyclability among the various kinds of FILs investigated, and its structure was characterized by infrared and NMR. The [HSO3-pMIM]HSO4 could be easily separated from the reaction mixture and reused without noticeably decreasing the catalytic activity. Copyright Taylor & Francis Group, LLC.
The influence of the thioalkyl terminal group on the mesomorphic behavior of some 6-alkoxy-2-naphthoates derived from 1,3,4-oxadiazole
Chothani,Akbari,Patel,Patel
, p. 31 - 46 (2016)
A new series of mesogenic compounds having a naphthalene moiety has been synthesized by esterification of 4-(5-(alkyllthio)-1,3,4-oxadiazol-2-yl)phenol and 6-alkoxy-2-naphthoic acid and their liquid crystalline properties have been studied. All the members of the series are enantiotropic and exhibit smectic as well as nematic mesophase. The plot of transition temperatures versus number of carbon atoms in the alkoxy chain exhibits no odd even effect and falling tendency for isotropic transition temperatures. High anisotropy, linearity confers rich mesomorphic properties on the system.
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Hewitt,Winmill
, p. 441 (1907)
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Development of hydrogel lenses with surface-immobilized PEG layers to reduce protein adsorption
Jee, Jun-Pil,Kim, Ho-Joong
, p. 2682 - 2687 (2015)
This paper describes the synthesis and characterization of a series of poly(2-hydroxyethyl methacrylate) (pHEMA)-based hydrogel lenses coated with poly(ethylene glycol) (PEG) chains. A novel tri-branched PEG-substituted hydrazide is synthesized, which imparts densely packed, covalently bound PEG layers on hydrogels, to determine whether branching provides improved coverage of the lens surface, thereby reducing protein adsorption. Surface modification of hydrogels with PEG was performed via amide-coupling reactions between PEG-substituted hydrazide and the pHEMA matrix. Protein adsorption, water content, optical transparency, and surface properties of the hydrogels were investigated. The hydrogels exhibited transmittance of >90% and improved surface hydrophilicity. Notably, the amount of lysozyme adsorbed on tri-branched PEGcoated hydrogels decreased significantly compared to the amount adsorbed onto the surface of control and linear PEG-coated hydrogels. These results provide insight into the mechanism by which PEGs reduce lysozyme adsorption and suggest that PEG coating may offer an intriguing potential for ophthalmic biomaterials as well as protein-resistant devices.
Using m icrowave and ultrasound to synthesis of substituted bis-acyl hydrazone derivatives
Mohammed, Salim J.,Sheat, Attallah M.,A.abood, Salih,Yahya, Omar M.
, p. 6423 - 6427 (2021/11/01)
In this paper, some new bis-acyl hydrazone derivatives (4a-f) were prepared through the reaction of carboxylic acid hydrazides with 1,4-diacetylbenzene using classical methods, microwave and ultrasound irradiation methods. These compounds are obtained through a series of reactions where some carboxylic acids react with ethanol first in the presence of concentrated sulfuric acid to give the corresponding esters (2a-f), which when treatment with aqueous hydrazine give carboxylic acid hydrazides (3a-f).thus, The results proved that the use of microwave and ultrasound techniques is much better than the classical methods, as it gave a higher yield, shorter reaction time, and the absence of the use of solvents. All newly synthesized compounds were confirmed by IR, (1H & 13C) NMR spectral analysis and the corresponding reactions were monitored by TLC using the reported eluent.
Novel arylcarbamate-N-acylhydrazones derivatives as promising BuChE inhibitors: Design, synthesis, molecular modeling and biological evaluation
Yamazaki, Diego A.S.,Rozada, Andrew M.F.,Baréa, Paula,Reis, Elaine C.,Basso, Ernani A.,Sarragiotto, Maria Helena,Seixas, Flávio A.V.,Gauze, Gisele F.
, (2021/01/18)
A novel series of arylcarbamate-N-acylhydrazones derivatives have been designed and synthesized as potential anti-cholinesterase agents. In vitro studies revealed that these compounds demonstrated selective for butyrylcholinesterase (BuChE) with potent inhibitory activity. The compounds 10a-d, 12b and 12d were the most potent BuChE inhibitors with IC50 values of 0.07–2.07 μM, highlighting the compound 10c (IC50 = 0.07 μM) which showed inhibitory activity 50 times greater than the reference drug donepezil (IC50 = 3.54 μM). The activity data indicates that the position of the carbamate group in the aromatic ring has a greater influence on the inhibitory activity of the derivatives. The enzyme kinetics studies indicate that the compound 10c has a non-competitive inhibition against BuChE with Ki value of 0.097 mM. Molecular modeling studies corroborated the in vitro inhibitory mode of interaction and show that compound 10c is stabilized into hBuChE by strong hydrogen bond interaction with Tyr128, π-π stacking interaction with Trp82 and CH?O interactions with His438, Gly121 and Glu197. Based on these data, compound 10c was identified as low-cost promising candidate for a drug prototype for AD treatment.
Synthesis and mesomorphic characterization of some novel steroidal mesogens: A structure–property correlation
Bhat S, Vanishree,Kumar, Sandeep,Raghunathan, V. A.
, (2021/08/25)
The steroidal derivatives are found to be extremely good mesogens since their inception. Because of their inherent chirality, they have the potential to induce a wide variety of liquid crystalline phases, including frustrated phases depending upon the structure of the steroidal skeleton and the substituents attached. In this report, a series of novel monoalkoxy and dialkoxy benzoate derivatives of ergosterol and a few monoalkoxy derivatives of stigmasterol have been synthesized and their mesomorphic property has been investigated. The derivatives exhibited various mesophases including SmA, SmC*, N*, TGB and blue phases. Also, the gelation ability of some of these derivatives with various organic solvents has been examined. Furthermore, the mesomorphism of these derivatives has been compared with the analogous cholesteryl counterparts.