2955-65-9Relevant academic research and scientific papers
Discovery and structure-activity relationships of pyrrolone antimalarials
Murugesan, Dinakaran,Mital, Alka,Kaiser, Marcel,Shackleford, David M.,Morizzi, Julia,Katneni, Kasiram,Campbell, Michael,Hudson, Alan,Charman, Susan A.,Yeates, Clive,Gilbert, Ian H.
supporting information, p. 2975 - 2990 (2013/05/23)
In the pursuit of new antimalarial leads, a phenotypic screening of various commercially sourced compound libraries was undertaken by the World Health Organisation Programme for Research and Training in Tropical Diseases (WHO-TDR). We report here the detailed characterization of one of the hits from this process, TDR32750 (8a), which showed potent activity against Plasmodium falciparum K1 (EC50 ～ 9 nM), good selectivity (>2000-fold) compared to a mammalian cell line (L6), and significant activity against a rodent model of malaria when administered intraperitoneally. Structure-activity relationship studies have indicated ways in which the molecule could be optimized. This compound represents an exciting start point for a drug discovery program for the development of a novel antimalarial.
1-Aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamide: An effective scaffold for the design of either CB1 or CB2 receptor ligands
Piscitelli, Francesco,Ligresti, Alessia,La Regina, Giuseppe,Gatti, Valerio,Brizzi, Antonella,Pasquini, Serena,Allar, Marco,Carai, Mauro Antonio Maria,Novellino, Ettore,Colombo, Giancarlo,Di Marzo, Vincenzo,Corelli, Federico,Silvestri, Romano
experimental part, p. 5641 - 5653 (2012/01/02)
New 1-aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamides were synthesized as cannabinoid (CB) receptor ligands. Compound 11 (CB1 Ki = 2.3 nM, CB1 SI = 163.6) showed CB1 receptor affinity and selectivity superior to Rimonabant and AM251. Acute administration of 2 mg/kg 11 reduced sucrose, but not regular food, intake in rats. On the other hand, compound 23 (CB2 Ki = 0.51 nM, CB2 SI = 30.0) showed significant affinity and selectivity for the CB2 receptor. The results presented here show that the 1-aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3- carboxamide may serve as an effective scaffold for the design of either CB 1 or CB2 receptor ligands.
Zinc-mediated chain extension reaction of 1,3-diketones to 1,4-diketones and diastereoselective synthesis of trans-1,2-disubstituted cyclopropanols
Xue, Song,Li, Le-Zhen,Liu, Yong-Kang,Guo, Qing-Xiang
, p. 215 - 218 (2007/10/03)
A variety of 1,3-diketones can be efficiently converted into the corresponding 1,4-diketones and trans-1,2-disubstituted cyclopropanols by using organozinc species in one-pot reactions. It was found that 2.3 equiv of CF 3CO2ZnCH2I was effective to give the corresponding chain-extended products in 44-85% yields, while a mixture of organozinc species formed from 4.0 equiv of Et2Zn, 2.0 equiv of CF3CO2H, and 4.0 equiv of CH2I2 resulted in the formation of trans-1,2-disubstituted cyclopropanols with quite good yields and diastereoselectivity.
Nitroalkanes in Aqueous Medium as an Efficient and Eco-Friendly Source for the One-Pot Synthesis of 1,4-Diketones, 1,4-Diols, δ-Nitroalkanols, and Hydroxytetrahydrofurans
Ballini, Roberto,Barboni, Luciano,Giarlo, Guido
, p. 9173 - 9176 (2007/10/03)
The Michael addition of primary aliphatic nitro compounds to α,β-unsaturated enones, performed in aqueous media, provides the one-pot synthesis of 1,4-diketones, 1,4-diols, δ-nitroalkanols, and hydroxytetrahydrofurans, respectively, by the appropriate cho
Methoxycarbonylation versus Hydroacylation of Ethene; Dramatic Influence of the Ligand in Cationic Palladium Catalysis
Pugh, Robert I.,Drent, Eite
, p. 837 - 840 (2007/10/03)
The palladium-catalysed carbonylation of ethene in methanol shows acute sensitivity towards the diphosphine ligand used. Systems based on 1,3-bis(di-t-butylphosphino)propane afford catalysts for fast, selective methoxycarbonylation to methyl propionate; t
Oxazaborolidine-catalysed reduction of alk-2-ene-1,4-diones. A convenient access to chiral 1,4-diols
Bach, Jordi,Berenguer, Ramon,Garcia, Jordi,Lopez, Marta,Manzanal, Judith,Vilarrasa, Jaume
, p. 14947 - 14962 (2007/10/03)
An efficient method for the preparation of C2-symmetric, chiral alk-2- ene-1,4-diols (4) has been achieved, based on the borane-mediated reduction of symmetric alk-2-ene-1,4-diones (2) in the presence of oxazaborolidine (R)- 1. In general, the presence of the double bond in 2 has been beneficial (compared with the related saturated 1,4-diketones 3) not only as far as the stereoselectivity in the reduction step is concerned, but also because it allowed us to remove meso-4 by chomatography and/or to improve the stereochemical purity of several resulting mixtures of diols 4 by Sharpless' epoxidation. Enantioenricbed compounds 4 have been readily reduced to saturated diols with negligible loss of optical purity.
Stereoselective reduction of unsaturated 1,4-diketones. A practical route to chiral 1,4-diols
Bach, Jordi,Berenguer, Ramon,Garcia, Jordi,Loscertales, Teresa,Manzanal, Judith,Vilarrasa, Jaume
, p. 1091 - 1094 (2007/10/03)
A new synthetic route to C2-symmetric chiral 1,4-diols based on the borane-mediated oxazaborolidine-catalysed reduction of 2-ene-1,4-diones (2), of 2-yne-1,4-diones (3), and/or of Co-complexed diketones 4 is described. Good to excellent enantio- and diastereoselectivities have been obtained in the reduction of diketones 3 and 4, catalysed by oxazaborolidines 6 and 5, respectively.
The synthesis of diketones from bis-benzimidazole methiodide salts
Shi, Zhen,Gu, Huan,Hue, Li-Li
, p. 3174 - 3178 (2007/10/03)
The conversion of readily available bis-benzimidazole methiodide salts to symmetrical diketones is reported.The scope and limitations of this synthesis are discussed.
Reinvestigation on the Catalytic Isomerisation of Carbon-Carbon Triple Bonds
Guo, Cheng,Lu, Xiyan
, p. 1921 - 1924 (2007/10/02)
Based on the discovery that phosphines could catalyse the isomerisation of triple bonds, the isomerisation of acetylenic derivatives was differentiated into two types: phosphine-catalysed and transition metal-catalysed.
Efficient palladium catalysts for the copolymerization of carbon monoxide with olefins to produce perfectly alternating polyketones
Drent, E.,Broekhoven, J.A.M. van,Doyle, M.J.
, p. 235 - 251 (2007/10/02)
A class of highly efficient homogeneous palladium catalyst systems has been developed for the production of perfectly alternating copolymers of carbon monoxide with ethylene.Mixtures of carbon monoxide, ethylene and propene are converted into the correspo
