58343-42-3Relevant academic research and scientific papers
Design, synthesis and biological evaluation of imidazole and oxazole fragments as HIV-1 integrase-LEDGF/p75 disruptors and inhibitors of microbial pathogens
Rashamuse, Thompho J.,Harrison, Angela T.,Mosebi, Salerwe,van Vuuren, Sandy,Coyanis, E. Mabel,Bode, Moira L.
, (2019/11/26)
We describe here the synthesis of libraries of novel 1-subtituted-5-aryl-1H-imidazole, 5-aryl-4-tosyl-4,5-dihydro-1,3-oxazole and 5-aryl-1,3-oxazole fragments via microwave (MW)-assisted cycloaddition of para-toluenesulfonylmethyl isocyanide (TosMIC) to imines and aldehydes. The compounds obtained were biologically evaluated in an AlphaScreen HIV-1 IN-LEDGF/p75 inhibition assay with six imidazole-based compounds (16c, 16f, 17c, 17f, 20a and 20d) displaying more than 50% inhibition at 10 μM, with IC50 values ranging from 7.0 to 30.4 μM. Additionally the hypothesis model developed predicts all active scaffolds except 20d to occupy similar areas as the N-heterocyclic (A) moiety and two aromatic rings (B and C) of previously identified inhibitor 5. These results indicate that the identified compounds represent a viable starting point for their use as templates in the design of next generation inhibitors targeting the HIV-1 IN and LEDGF/p75 protein-protein interaction. In addition, the in vitro antimicrobial properties of these fragments were tested by minimum inhibitory concentration (MIC) assays showing that compound 16f exhibited a MIC value of 15.6 μg/ml against S. aureus, while 17f displayed a similar MIC value against B. cereus, suggesting that these compounds could be further developed to specifically target those microbial pathogens.
Preparation of new schiff base derived from cyclohexylamine with piperonaldehyde and its Cu+2, Co+2 and Rh+3 metal complexes
Shamkhy, Emanturky,Al-Karkhi, Isam Hussain T.
experimental part, p. 1403 - 1408 (2012/06/16)
A new ligand N-[(E)-1,3-benzodioxol-5-ylmethylidene]cyclohexanamine (L A) having nitrogen and oxygen atoms was synthesized from cyclohexylamine with piperonaldehyde the yield was 75.8%. Metal complexes were synthesized were prepared by reaction
Eco-friendly synthesis of imines by ultrasound irradiation
Guzen, Karla P.,Guarezemini, Alexandre S.,órf?o, Aline T.G.,Cella, Rodrigo,Pereira, Claudio M.P.,Stefani, Hélio A.
, p. 1845 - 1848 (2008/02/05)
A series of imines was synthesized by an ultrasound-assisted reaction of aldehydes and primary amines using silica as the promoter. Products were obtained in high yields even in large scale synthesis.
Influence of phenyl ring substituents in the cyclometallation of Schiff base ligands: Crystal and molecular structures of [Pd-{3,4-(OCH2O)C6H 2C(H)=N(Cy)-C2,N}(μ-O2CMe)]2 and [Pd-{3,4-(OCH2
Teijido, Berta,Fernández, Alberto,López-Torres, Margarita,Castro-Juiz, Samuel,Suárez, Antonio,Ortigueira, Juan M.,Vila, José M.,Fernández, Jesús J.
, p. 71 - 79 (2007/10/03)
Reaction of Pd(OAc)2 with the Schiff base ligands 3,4-{O(CH2)nO}C6H3C(H)=NR (n=1, 2; R=Cy, 3,4-(OCH2O)C6H3CH2-) leads to dinuclear cyclometallated products
The structure of two optically active products formed in reaction of piperonal with (-)-Menthyl chloroformate
Ratajczak-Sitarz,Naruszewicz,Kosturkiewicz,Jozkowiak,Rozwadowska
, p. 310 - 319 (2007/10/03)
Two new compounds, C22H30O4S2, (-)-2-(2-menthyloxycarbonyl-3,4-methylenedioxyphenyl)-1,3-dithiane (1) (space group P41212 with a = 9.566(1) A, c = 48.55(1) A, Z = 8 and R = 0.052), and Csu
Directed Metalation of Aromatic Aldimines with Lithium 2,2,6,6-Tetramethylpiperidide
Flippin, Lee A.,Muchowski, Joseph M.,Carter, David S.
, p. 2463 - 2467 (2007/10/02)
N-Cyclohexyl aromatic aldimines are ortho-lithiated or o-methyl-lithiated with 2 equiv of lithium 2,2,6,6-tetramethylpiperidide (LTMP) in THF solution at -15 deg C.The lithiated intermediates generally reacted with alkyl halides or CO2 to provide ortho-functionalized aldimine products which could be readily converted to the corresponding aldehydes by hydrolysis with aqueous 4 M HCl.Aromatic aldimines derived from (+/-)-trans-2-methylcyclohexylamine or 3-amino-2,4-dimethylpentane are resistant toward C=N addition with 1 equiv of n-BuLi at 0 deg C in THF solution; however, they are also surprisingly resistant toward directed metalation reactions with either LTMP or n-BuLi.Exceptions to the ortho-directing and o-methyl-directing effects of the aldimine group were observed in a reaction of 3-methylthiophene-2-carboxaldehyde cyclohexylimine (7) with LTMP, followed by CH3I, which gave a 9:1 mixture of 3,5-dimethylthiophene-2-carboxaldehyde cyclohexylimine (22) and 5-ethyl-3-methylthiophene-2-carboxaldehyde cyclohexylimine (23), and a reaction of p-tolualdehyde 2,4-dimethylpent-3-ylimine (11) with either n-BuLi or LTMP, followed by CH3I, which gave p-ethylbenzaldehyde 2,4-dimethylpent-3-ylimine (25).
Biphenyl derivatives, process for preparing the same and intermediates therefor
-
, (2008/06/13)
Novel biphenyl derivatives of the formula: wherein R1 is a substituted or unsubstituted aminocarbonyl group, aminothiocarbonyl group, a substituted or unsubstituted lower alkoxycarbonyl group, cyano group, or a group of the formula: STR1 one or
The Ambient Temperature Ullmann Reaction and Its Application to the Total Synthesis of (+/-)-Steganacin
Ziegler, Frederick E.,Chliwner, Irene,Fowler, Kerry W.,Kanfer, Sheldon J.,Kuo, Stephen J.,Sinha, Nanda D.
, p. 790 - 798 (2007/10/02)
The details of a new method for preparing unsymmetrical biphenyls at room temperature by a modification of the classical Ullmann reaction are discussed.An intramolecularly coordinated organocopper reagent is treated with an aryl iodide bearing a potential coordinating ligand to form the biphenyl.Nitrogen and sulfur have been utilized as ligands and as protecting groups for carbonyls.The application of this methodology to the synthesis of the antileukemic steganacin is detailed.
Total Synthesis of (+/-)-Chelidonine
Cushman, Mark,Choong, Tung-Chung,Valko, Joseph T.,Koleck, Mary P.
, p. 5067 - 5073 (2007/10/02)
Condensation of the Schiff base 8 with 3,4-(methylenedioxy)homophthalic anhydride (13) was exploited as the key step in a total synthesis of the benzophenanthridine alkaloid (+/-)-chelidonine (1).A variety of reaction conditions were investigated in order to maximize the production of the desired thermodynamically less stable cis diastereomer.A method was devised for the conversion of 24 to its acid chloride without production of the indenoisoquinoline 30.The migration of an aromatic ring was observed on treatment of the diazo ketone 26 with acid.This reaction is reminiscent of the Hayashi rearrangement.
