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.
Pleuromutilin derivative with 1, 3, 4-oxadiazole side chain and preparation and application thereof
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Paragraph 0055-0056; 0070; 0090; 0092; 0095; 0103, (2021/07/24)
The invention belongs to the field of medicinal chemistry, and particularly relates to a pleuromutilin derivative with a 1, 3, 4-oxadiazole side chain and preparation and application thereof The pleuromutilin derivative with the 1, 3, 4-oxadiazole side chain is a compound shown in a formula 2 or a pharmaceutically acceptable salt thereof, and a solvent compound, an enantiomer, a diastereoisomer and a tautomer of the compound shown in the formula 2 or the pharmaceutically acceptable salt thereof or a mixture of the solvent compound, the enantiomer, the diastereoisomer and the tautomer in any proportion, including a racemic mixture. The pleuromutilin derivative has good antibacterial activity, is especially suitable for being used as a novel antibacterial agent for systemic system infection of animals or human beings, and has good water solubility.
Design, synthesis, and biological evaluation of new raloxifene analogues of improved antagonist activity and endometrial safety
Lambrinidis, George,Gouedard, Cedric,Stasinopoulou, Sotiria,Angelopoulou, Angeliki,Ganou, Vassiliki,Meligova, Aggeliki K.,Mitsiou, Dimitra J.,Marakos, Panagiotis,Pouli, Nicole,Mikros, Emmanuel,Alexis, Michael N.
supporting information, (2020/12/07)
Raloxifene agonism of estrogen receptor (ER) in post-menopausal endometrium is not negligible. Based on a rational drug design workflow, we synthesized 14 analogues of raloxifene bearing a polar group in the aromatic ring of the basic side chain (BSC) and/or changes in the bulkiness of the BSC amino group. Analogues with a polar BSC aromatic ring and amino group substituents of increasing volume displayed increasing ER antagonism in Ishikawa cells. Analogues with cyclohexylaminoethoxy (13a) or adamantylaminoethoxy BSC (13b) lacking a polar aromatic ring displayed high ER-binding affinity and ER antagonism in Ishikawa cells higher than raloxifene and similar to fulvestrant (ICI182,780). The endometrial surface epithelium of immature female CD1 mice injected with 13b was comparable to that of vehicle-treated mice, while that of mice treated with estradiol, raloxifene or 13b in combination with estradiol was hyperplastic. These findings indicate that raloxifene analogues with a bulky BSC amino group could provide for higher endometrial safety treatment of the menopausal syndrome.
Design, synthesis, in vitro and in vivo evaluation against MRSA and molecular docking studies of novel pleuromutilin derivatives bearing 1, 3, 4-oxadiazole linker
Liu, Jie,Zhang, Guang-Yu,Zhang, Zhe,Li, Bo,Chai, Fei,Wang, Qi,Zhou, Zi-Dan,Xu, Ling-Ling,Wang, Shou-Kai,Jin, Zhen,Tang, You-Zhi
, (2021/05/17)
A class of pleuromutilin derivatives containing 1, 3, 4-oxadiazole were designed and synthesized as potential antibacterial agents against Methicillin-resistant staphylococcus aureus (MRSA). The ultrasound-assisted reaction was proposed as a green chemistry method to synthesize 1, 3, 4-oxadiazole derivatives (intermediates 85–110). Among these pleuromutilin derivatives, compound 133 was found to be the strongest antibacterial derivative against MRSA (MIC = 0.125 μg/mL). Furthermore, the result of the time-kill curves displayed that compound 133 could inhibit the growth of MRSA in vitro quickly (- 4.36 log10 CFU/mL reduction). Then, compound 133 (- 1.82 log10 CFU/mL) displayed superior in vivo antibacterial efficacy than tiamulin (- 0.82 log10 CFU/mL) in reducing MRSA load in mice thigh model. Besides, compound 133 exhibited low cytotoxicity to RAW 264.7 cells. Molecular docking studies revealed that compound 133 was successfully localized in the binding pocket of 50S ribosomal subunit (ΔGb = -10.50 kcal/mol). The results indicated that these pleuromutilin derivatives containing 1, 3, 4-oxadiazole might be further developed into novel antibiotics against MRSA.
