- Synthesis and biological evaluation of novel isoxazole derivatives from acridone
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The present study was carried out in an?attempt to synthesize a new class of potential antibacterial agents. In this context, novel isoxazoles were synthesized and evaluated for their potential antibacterial behavior against four pathogenic bacterial strains. The synthesized compounds exhibited moderate-to-good antibacterial activity against these strains. The highest antibacterial activity was observed against the Escherichia coli strains, particularly for compounds 4a and 4e with phenyl and para-nitrophenyl groups on the isoxazole–acridone skeleton;?they showed promising minimum inhibitory concentration values of 16.88 and 19.01 μg/ml, respectively, compared with the standard drug chloramphenicol (22.41 μg/ml). The synthesized compounds were subjected to in silico docking studies to understand the mode of their interactions with the DNA topoisomerase complex (PDB ID: 3FV5) of E. coli. The molecular docking results showed that compounds 4a–l occupy the active site of DNA topoisomerase (PDB ID: 3FV5), stabilized via hydrogen bonding and hydrophobic interactions, which may be the reason behind their interesting in vitro antibacterial activity.
- Aarjane, Mohammed,Slassi, Siham,Tazi, Bouchra,Amine, Amina
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- Vanillin isoxazole compound and preparation method and application thereof
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The invention relates to the technical field of bactericides, in particular to a vanillin isoxazole compound and a preparation method and application thereof. The vanillin isoxazole compound has a structural general formula as shown in a formula A, wherei
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Paragraph 0104-0108
(2021/07/24)
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- Potassium Poly(Heptazine Imide): Transition Metal-Free Solid-State Triplet Sensitizer in Cascade Energy Transfer and [3+2]-cycloadditions
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Polymeric carbon nitride materials have been used in numerous light-to-energy conversion applications ranging from photocatalysis to optoelectronics. For a new application and modelling, we first refined the crystal structure of potassium poly(heptazine imide) (K-PHI)—a benchmark carbon nitride material in photocatalysis—by means of X-ray powder diffraction and transmission electron microscopy. Using the crystal structure of K-PHI, periodic DFT calculations were performed to calculate the density-of-states (DOS) and localize intra band states (IBS). IBS were found to be responsible for the enhanced K-PHI absorption in the near IR region, to serve as electron traps, and to be useful in energy transfer reactions. Once excited with visible light, carbon nitrides, in addition to the direct recombination, can also undergo singlet–triplet intersystem crossing. We utilized the K-PHI centered triplet excited states to trigger a cascade of energy transfer reactions and, in turn, to sensitize, for example, singlet oxygen (1O2) as a starting point to synthesis up to 25 different N-rich heterocycles.
- Antonietti, Markus,Guldi, Dirk M.,Hussain, Tanveer,Karton, Amir,Markushyna, Yevheniia,Mazzanti, Stefano,Oschatz, Martin,Sánchez Vadillo, José Manuel,Savateev, Aleksandr,Strauss, Volker,Tarakina, Nadezda V.,Tyutyunnik, Alexander P.,Walczak, Ralf,ten Brummelhuis, Katharina
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supporting information
p. 15061 - 15068
(2020/06/17)
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- Synthesis and in vitro evaluation of neutral aryloximes as reactivators of Electrophorus eel acetylcholinesterase inhibited by NEMP, a VX surrogate
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Casualties caused by nerve agents, potent acetylcholinesterase inhibitors, have attracted attention from media recently. Poisoning with these chemicals may be fatal if not correctly addressed. Therefore, research on novel antidotes is clearly warranted. Pyridinium oximes are the only clinically available compounds, but poor penetration into the blood-brain barrier hampers efficient enzyme reactivation at the central nervous system. In searching for structural factors that may be explored in SAR studies, we synthesized and evaluated neutral aryloximes as reactivators for acetylcholinesterase inhibited by NEMP, a VX surrogate. Although few tested compounds reached comparable reactivation results with clinical standards, they may be considered as leads for further optimization.
- Cavalcante, Samir F. de A.,Kitagawa, Daniel A.S.,Rodrigues, Rafael B.,Bernardo, Leandro B.,da Silva, Thiago N.,dos Santos, Wellington V.,Correa, Ana Beatriz de A.,de Almeida, Joyce S.F.D.,Fran?a, Tanos C.C.,Ku?a, Kamil,Simas, Alessandro B.C.
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- Synthesis of nitrogenated lignin-derived compounds and reactivity with laccases. Study of their application in mild chemoenzymatic oxidative processes
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The chemical synthesis of a series of lignin-derived nitrogenated compounds was performed in high yields (73-99%) through simple conventional chemical transformations starting from natural monomers such as vanillin, syringaldehyde or 3,4-dihydroxybenzaldehyde. The study of the vanillin-derived compounds as substrates for commercially available laccases from Trametes versicolor and Myceliophthora thermophila in oxidative transformations, generally led to the isolation of several dimeric species in high to excellent conversions (>70%), while for hydrazone derivatives a more rapidly oxidative coupling was evidenced by the formation of oligomers and/or polymers. Remarkably, vanillin was obtained due to the hydrolysis of some of the nitrogenated functional groups, such as the hydrazone or the hydrazono tetrazole. The three families of lignin-derived compounds can provide a great source of new laccase-mediator systems (LMS), the possibility of employing them for lignin modification being particularly attractive. Preliminary experiments showed promising levels of activity towards the oxidation of a monomer (veratryl alcohol, up to 70% conversion) and a dimer (adlerol, up to 22% conversion) lignin models, higher than those achieved with the natural vanillin and syringaldehyde (up to 7% conversion with veratryl alcohol and almost negligible conversion with adlerol), these processes being also highly influenced by the pH of the reaction medium.
- Albarrán-Velo, Jesús,López-Iglesias, María,Gotor, Vicente,Gotor-Fernández, Vicente,Lavandera, Iván
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p. 50459 - 50471
(2017/11/10)
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- Constructing novel dihydrofuran and dihydroisoxazole analogues of isocombretastatin-4 as tubulin polymerization inhibitors through [3+2] reactions
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[3+2] reactions play a key role in constructing various pharmaceutical moleculars. In this study, using Mn(OAc)3 mediated and 1,3-dipolar [3+2] cyclization reactions, 38 novel dihydrofuran and dihydroisoxazole analogues of isoCA-4 were synthesized as inhibitors of tubulin polymerization. Among them, compound 6g was found to be the most potent cytotoxic agents against PC-3 cells with IC50 value of 0.47 μM, and compound 5p exhibted highest activity on HeLa cells with IC50 vaule of 2.32 μM. Tubulin polymerization assay revealed that 6g was a dose-dependent and effective inhibitor of tubulin assembly. Immunohistochemistry studies and cell cycle distribution analysis indicated that 6g severely disrupted microtubule network and significantly arrested most cells in the G2/M phase of the cell cycle in PC-3 cells. In addition, molecular docking studies showed that two chiral isomers of 6g can bind efficiently and similarly at colchicine binding site of tubulin.
- Song, Ming-Yu,Cao, Chen-Yu,He, Qiu-Rui,Dong, Qing-Miao,Li, Ding,Tang, Jiang-Jiang,Gao, Jin-Ming
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p. 5290 - 5302
(2017/10/06)
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- APPLICATIONS OF N6-SUBSTITUTED ADENOSINE DERIVATIVE AND N6-SUBSTITUTED ADENINE DERIVATIVE TO CALMING, HYPNOSES, CONVULSION RESISTANCE, EPILEPTIC RESISTANCE, PARKINSON DISEASE RESISTANCE, AND DEMENTIA PREVENTION AND TREATMENT
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PROBLEM TO BE SOLVED: To prepare analgesics, hypnotic agents, anticonvulsant agents, antiepileptics, antiparkinson drugs, dementia prophylactics, and health care food. SOLUTION: The present invention relates to an N6-substituted adenosine derivative and an N6-substituted adenine derivative selected from the group consisting of specific compounds. The present invention also relates to a pharmaceutical composition at least comprising a therapeutically effective amount of the compounds and a pharmaceutically acceptable carrier. The invention further relates to the compounds used in preparation of analgesics, hypnotic agents, anticonvulsant agents, antiepileptics, antiparkinson drugs, dementia prophylactics, and health care food. COPYRIGHT: (C)2016,JPO&INPIT
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Paragraph 0115
(2018/10/27)
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- Green and highly selective protocol for the synthesis of oximes
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A green and efficient protocol has been developed for the synthesis of either exclusively a monoxime or exclusively a dioxime from a host of 1,2-dicarbonyl compounds on silica.
- Ghosh, Pranab,Subba, Raju
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p. 529 - 532
(2013/11/06)
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- N6-SUBSTITUTED ADENOSINE DERIVATIVES AND N6-SUBSTITUTED ADENINE DERIVATIVES AND USES THEREOF
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The present invention provides N6-substituted adenosine derivatives and N6-substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.
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Paragraph 0161
(2013/03/26)
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- Oximation of carbonyl compounds by basic alumina supported amberlite IRA 400 under microwave energy and pestle/mortar
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An efficient and novel method for the preparation of oximes from carbonyl compounds under solventless conditions.
- Singh, Sanjeev Pratap,Singh
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experimental part
p. 1354 - 1356
(2012/09/21)
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- N6-SUBSTITUTED ADENOSINE DERIVATIVES, N6-SUBSTITUTED ADENINE DERIVATIVES AND USES THEREOF
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The present invention provides N6-substituted adenosine derivatives and N6-substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.
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Page/Page column 49
(2012/11/06)
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- Facile synthesis and promising antibacterial properties of a new guaiacol-based polymer
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A new acrylamide-type monomer (N-(4-hydroxy-3-methoxy-benzyl)-acrylamide) derived from guaiacol was successfully synthesized. Polymers containing guaiacol moiety were obtained via conventional radical polymerization of this monomer with AIBN as initiator. The influence of reaction time, initiator concentration and temperature on polymers characteristics was studied. Evaluation of the termination mode in free-radical polymerization was performed by MALDI-TOF mass spectrometry. Termination occurs mainly by disproportionation reaction. Additional peaks in the spectrum were attributed to side chain reactions implying phenoxy radicals. This new polymer exhibits a potential antibacterial activity against Bacillus subtilis by using anti-adhesion and anti-biofilm tests. After an adhesion time of 3 h, compared to a non-coated glass slide, there was a decrease of bacteria of 99% on the polymer coated glass slide. After three days of culture in a bacterial suspension, no biofilm was observed on the polymer coated surface.
- Liu, Hefang,Lepoittevin, Bénédicte,Roddier, Céline,Guerineau, Vincent,Bech, Lo?c,Herry, Jean-Marie,Bellon-Fontaine, Marie-Noelle,Roger, Philippe
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experimental part
p. 1908 - 1916
(2011/12/02)
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- Synthesis and bio-evaluation of human macrophage migration inhibitory factor inhibitor to develop anti-inflammatory agent
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Macrophage migration inhibitory factor (MIF), a pro-inflammatory cytokine, is involved in the development of an array of inflammatory disorders including rheumatoid arthritis, inflammatory bowel disease, psoriasis, multiple sclerosis and sepsis. The synthesis of MIF-inhibitor is a rationale approach to develop novel anti-inflammatory agent to treat multitude of inflammatory diseases. In this work, we have synthesized and evaluated MIF-inhibitory activity of a series of small molecules containing isoxazoline skeleton. Mode of binding of this inhibitor to human MIF (huMIF) was determined by docking studies. The synthesized molecules inhibit tautomerase activity of huMIF. The anti-inflammatory activity of the most active inhibitor, 4-((3-(4-hydroxy-3- methoxyphenyl)-4, 5-dihydroisoxazol-5-yl) methoxy) benzaldehyde (4b) was evaluated against huMIF-induced inflammation in a cellular model (RAW 264.7 cell). Compound 4b significantly inhibits huMIF-mediated NF-κB translocation to the nucleus, up-regulation of inducible nitric oxide synthase and nitric oxide production in RAW 264.7 cell which are the markers for inflammation. The compound 4b is not cytotoxic as evident from cell viability assay. Hence, the compound 4b has potential to be a novel anti-inflammatory agent.
- Alam, Athar,Pal, Chinmay,Goyal, Manish,Kundu, Milan Kumar,Kumar, Rahul,Iqbal, Mohd Shameel,Dey, Sumanta,Bindu, Samik,Sarkar, Souvik,Pal, Uttam,Maiti, Nakul C.,Adhikari, Susanta,Bandyopadhyay, Uday
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experimental part
p. 7365 - 7373
(2012/01/06)
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- Solvent free, microwave assisted conversion of aldehydes into nitriles and oximes in the presence of NH2OH · HCl and TiO2
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Aromatic aldehydes bearing electron-donating groups are easily converted into their respective nitriles using NH2OH · HCl and TiO 2 under microwave irradiation, while those bearing an electron-withdrawing group give the corresponding oximes.
- Hoelz, Lucas Villas-Boas,Goncalves, Biank Tomaz,Barros, Jose Celestino,Silva, Joaquim Fernando Mendes Da
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experimental part
p. 94 - 99
(2010/05/18)
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- Design and synthesis of low molecular weight compounds with complement inhibition activity
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An attempt was made to synthesize a series of non-cytotoxic low molecular weight compounds of varying substitutions and functionalities having pharmacophore activity like carbonyl compounds, carboxylic acid and bioisosteres like tetrazole and phenyl acrylic acid. The in vitro assay of these analogues for the inhibition of complement activity revealed significant inhibitory activity for varying substituents and, particularly, for bioisosteres, that is, tetrazole and phenyl acrylic acid derivatives.
- Master, Hoshang E.,Khan, Shabana I.,Poojari, Krishna A.
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p. 4891 - 4899
(2007/10/03)
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- Method for producing vanillylamine hydrochloride
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The invention relates to a method for producing vanillylamine or one of the salts thereof, whereby a) vanillin is reacted with hydroxylamine or the salts of the same in the presence of an organic salt which can optionally be produced in situ; and b) the vanillyloxime produced is then hydrogenated with hydrogen in the presence of a suitable catalyst and an organic and/or inorganic acid. Said method is characterised in that step a) is carried out in an inorganic or organic acid used as a diluent.
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Page/Page column 4
(2008/06/13)
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- An efficient method for the preparation of nitriles via the dehydration of aldoximes with phthalic anhydride
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A new and highly efficient method for the conversion of aldoximes to nitriles was established. By fusing with phthalic anhydride, aldoximes were efficiently and smoothly converted into nitriles, in high yields (over 85%) and in a short time (within 5 minutes). The mixture of phthalic anhydride, a cyclic anhydride, and aldoximes in fusing state set up an ideal transition state for a selective [3.3]-sigmatropic rearrangement of the acylated aldoximes to nitriles.
- Wang, Eng-Chi,Huang, Keng-Shiang,Chen, Hsing-Ming,Wu, Chung-Chin,Lin, Gwo-Jiun
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p. 619 - 627
(2007/10/03)
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- Discovery of 3-amino-4-chlorophenyl P1 as a novel and potent benzamidine mimic via solid-phase synthesis of an isoxazoline library
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In an effort to identify orally bioavailable factor Xa inhibitors, two isoxazolines libraries were prepared to scan for novel P1 ligands. From this work, 4-chloro-3-aniline was identified as a novel and potent benzamidine mimic.
- Lam, Patrick Y. S.,Adams, Jessica J.,Clark, Charles G.,Calhoun, W. Jason,Luettgen, Joseph M.,Knabb, Robert M.,Wexler, Ruth R.
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p. 1795 - 1799
(2007/10/03)
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- bis(trichloromethyl)carbonate, an efficient activator for the one-pot conversion of aldehydes into nitriles under mild conditions
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A single step conversion of aldehydes into the corresponding nitriles has been achieved in high yields using stoichiometric amounts of NH2OH·HCl, Et3N and bis(trichloromethyl)-carbonate at room temperature.
- Bose, D. Subhas,Goud, P. Ravinder
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p. 3621 - 3624
(2007/10/03)
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- Facile and selective deprotection of aryl acetates using sodium perborate under mild and neutral conditions
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A variety of aryl acetates are cleaved to the corresponding phenols using sodium perborate in methanol under mild conditions (25°C). The effectiveness of this protocol is manifested in its tolerance of different functional groups and selectivity of deprotection towards aryl acetates whereas alkyl acetates are found to be unreactive under these reaction conditions.
- Bandgar, Babasaheb P.,Uppalla, Lavkumar S.,Sadavarte, Vaibhav S.,Patil, Suresh V.
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p. 1273 - 1276
(2007/10/03)
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- Hydroxy- or methoxy-substituted benzaldoximes and benzaldehyde-O-alkyloximes as tyrosinase inhibitors
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Several benzaldoximes, benzaldehyde-O-ethyloximes, and acetophenone-oximes were synthesized and evaluated as tyrosinase inhibitors by an assay based on tyrosinase catalyzed L-DOPA oxidation. Whereas benzaldoxime itself is only a weak inhibitor, its deriva
- Ley, Jakob P,Bertram, Heinz-Jürgen
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p. 1879 - 1885
(2007/10/03)
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- Chemoselective preparation of oximes, semicarbazones, and tosylhydrazones without catalyst and solvent
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A simple and versatile method for the synthesis of oximes, semicarbazones, and tosylhydrazones of aldehydes in the presence of ketones without catalyst and solvent is presented.
- Bandgar, Babasaheb P.,Sadavarte, Vaibhav S.,Uppalla, Lav S.,Govande, Rahul
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p. 403 - 406
(2007/10/03)
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- An efficient one-pot synthesis of aromatic nitriles from aldehydes using Fe modified K10
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Aromatic aldehydes were converted to the corresponding aromatic nitriles in one step using hydroxylamine hydrochloride and FeCl3 modified Montmorillonite K10.
- Bajpai, Anu R.,Deshpande, Abhay B.,Samant, Shriniwas D.
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p. 2785 - 2791
(2007/10/03)
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- The Capsaicinoids: Their Separation, Synthesis, and Mutagenicity
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Capsaicin (1b), the pungent ingredient in many varietes of Capsicums has recently been implicated as a possible carcinogen.When obtained from natural sources 1b is always accompanied by a number of related homologues.We have isolated seven of these homologues, characterized them, and synthesized them by a general and unique route developed in our laboratories.Also reported are mutagenicity data for 1b and an extract of red pepper as measured by the Ames assay and the V-79 mammalian cell assay.
- Gannett, Peter M.,Nagel, Donald L.,Reilly, Pam J.,Lawson, Terence,Sharpe, Jody,Toth, Bela
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p. 1064 - 1071
(2007/10/02)
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