The Experts below are selected from a list of 315 Experts worldwide ranked by ideXlab platform
Wouter De Looff - One of the best experts on this subject based on the ideXlab platform.
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bioisosteric replacements of the pyrazole moiety of rimonabant synthesis biological properties and molecular modeling investigations of Thiazoles triazoles and imidazoles as potent and selective cb1 cannabinoid receptor antagonists
Journal of Medicinal Chemistry, 2005Co-Authors: Josephus H M Lange, Herman H Van Stuivenberg, Hein K A C Coolen, Tiny J P Adolfs, Andrew C Mccreary, Hiskias G Keizer, Henri C Wals, Willem Veerman, Alice J M Borst, Wouter De LooffAbstract:Series of Thiazoles, triazoles, and imidazoles were designed as bioisosteres, based on the 1,5-diarylpyrazole motif that is present in the potent CB1 receptor antagonist rimonabant (SR141716A, 1). A number of target compounds was synthesized and evaluated in cannabinoid (hCB1 and hCB2) receptor assays. The Thiazoles, triazoles, and imidazoles elicited in vitroCB1 antagonistic activities and in general exhibited considerable CB1 vs CB2 receptor subtype selectivities, thereby demonstrating to be cannabinoid bioisosteres of the original diarylpyrazole class. Some key representatives in the imidazole series showed potent pharmacological in vivo activities after oral administration in both a CB agonist-induced hypotension model and a CB agonist-induced hypothermia model. Molecular modeling studies showed a close three-dimensional structural overlap between the key compound 62 and rimonabant. A structure−activity relationship (SAR) study revealed a close correlation between the biological results in the imidazo...
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bioisosteric replacements of the pyrazole moiety of rimonabant synthesis biological properties and molecular modeling investigations of Thiazoles triazoles and imidazoles as potent and selective cb1 cannabinoid receptor antagonists
Journal of Medicinal Chemistry, 2005Co-Authors: Josephus H M Lange, Herman H Van Stuivenberg, Hein K A C Coolen, Tiny J P Adolfs, Andrew C Mccreary, Hiskias G Keizer, Henri C Wals, Willem Veerman, Alice J M Borst, Wouter De LooffAbstract:Series of Thiazoles, triazoles, and imidazoles were designed as bioisosteres, based on the 1,5-diarylpyrazole motif that is present in the potent CB(1) receptor antagonist rimonabant (SR141716A, 1). A number of target compounds was synthesized and evaluated in cannabinoid (hCB(1) and hCB(2)) receptor assays. The Thiazoles, triazoles, and imidazoles elicited in vitro( )()CB(1) antagonistic activities and in general exhibited considerable CB(1) vs CB(2) receptor subtype selectivities, thereby demonstrating to be cannabinoid bioisosteres of the original diarylpyrazole class. Some key representatives in the imidazole series showed potent pharmacological in vivo activities after oral administration in both a CB agonist-induced hypotension model and a CB agonist-induced hypothermia model. Molecular modeling studies showed a close three-dimensional structural overlap between the key compound 62 and rimonabant. A structure-activity relationship (SAR) study revealed a close correlation between the biological results in the imidazole and pyrazole series.
Mirella Rambaldi - One of the best experts on this subject based on the ideXlab platform.
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Synthesis and antitubercular activity of imidazo[2,1-b]Thiazoles
European journal of medicinal chemistry, 2001Co-Authors: Aldo Andreani, Massimiliano Granaiola, Alberto Leoni, Alessandra Locatelli, Rita Morigi, Mirella RambaldiAbstract:A number of selected imidazo[2,1-b]Thiazoles entered the screening at the Tuberculosis Antimicrobial Acquisition and Coordinating Facility (TAACF) and one of these compounds, 2-chloro-6-phenylimidazo[2,1-b]thiazole, showed antitubercular activity. On this basis we planned the synthesis of new analogues bearing a substituted ring at the 6 position. For one compound only (2-chloro-6-p-chlorophenylimidazo[2,1-b]thiazole) the 5-nitroso derivative was also prepared. The antitubercular activity of these compounds was compared with the known analogues lacking the chlorine at the 2 position. 5-Nitroso-6-p-chlorophenylimidazo[2,1-b]thiazole showed potent antitubercular activity.
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Short communication Synthesis and antitubercular activity of imidazo(2,1-b)Thiazoles
2001Co-Authors: Aldo Andreani, Massimiliano Granaiola, Alberto Leoni, Alessandra Locatelli, Rita Morigi, Mirella RambaldiAbstract:A number of selected imidazo(2,1-b)Thiazoles entered the screening at the Tuberculosis Antimicrobial Acquisition and Coordinating Facility (TAACF) and one of these compounds, 2-chloro-6-phenylimidazo(2,1-b)thiazole, showed antitubercular activity. On this basis we planned the synthesis of new analogues bearing a substituted ring at the 6 position. For one compound only (2-chloro-6-p-chlorophenylimidazo(2,1-b)thiazole) the 5-nitroso derivative was also prepared. The antitubercular activity of these compounds was compared with the known analogues lacking the chlorine at the 2 position. 5-Nitroso-6-p-chlorophenylimi- dazo(2,1-b)thiazole showed potent antitubercular activity. © 2001 Editions scientifiques et medicales Elsevier SAS antitubercular activity / imidazo(2,1-b)Thiazoles / nitroso derivatives
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Synthesis of imidazo[2,1-b]Thiazoles as herbicides
Pharmaceutica Acta Helvetiae, 1996Co-Authors: Aldo Andreani, Alberto Leoni, Alessandra Locatelli, Mirella Rambaldi, Franco Andreani, Jean-claude GehretAbstract:Abstract A series of imidazo[2,1-b]Thiazoles bearing halogens or a sulfonylurea group or an imidazolidone group, were synthesized and subjected to pre- and post-emergence herbicidal tests. 5-Bromo-6-(3-pyridyl)-2,3-dihydroimidazo[2,1-b]thiazole (4e) and 6-(2,3,4-trichlorophenyl)-2,3-dihydroimidazo[2,1-b]thiazole-5-carboxylic acid (8b) showed moderate activity in the post-emergence herbicidal tests only.
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Thienylimidazo[2,1-b]Thiazoles as inhibitors of mitochondrial NADH dehydrogenase.
Journal of medicinal chemistry, 1995Co-Authors: Mirella Rambaldi, Alberto Leoni, Alessandra Locatelli, Anna Ghelli, Marina Ratta, Bruna Benelli, Mauro Degli EspostiAbstract:The synthesis of 6-substituted 5-(thienylvinyl)imidazo[2,1-b]Thiazoles and 6-thienylimidazo[2,1-b]Thiazoles is reported. These compounds were tested as specific inhibitors of the NADH: ubiquinone (UBQ) reductase activity of NADH dehydrogenase in mitochondrial membranes. The 6-thienylimidazo[2,1-b]Thiazoles were more potent in mammalian than in nematode mitochondria and had an average titer of 0.11 mM for 2-methyl-6-(2-thienyl)imidazo[2,1-b]thiazole (10). This compound is noncompetitive with the ubiquinone substrate and interacts with a site which is mutually exclusive with that of rotenone but nonexclusive with that of piericidin and several other inhibitors of NADH dehydrogenase. In the series of 5-(thienylvinyl)imidazoThiazoles, the hydrobromide of (E)-6-chloro-5-(2-thienylvinyl)imidazo[2,1-b]thiazole (E-5.HBr) was found to be more potent as an inhibitor of the NADH:UBQ activity (IC50 = 15-17 microM) than the 6-thienylimidazoles such as 10. The inhibitory action of E-5.HBr and its analogs is different from that of compound 10 as indicated by the mutual exclusivity with other inhibitors and the relative inhibition of the activity with various electron acceptors.
Jurgen Liebscher - One of the best experts on this subject based on the ideXlab platform.
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ring transformation of pyrimidine 4 1h thiones with cyclohexanespiro 3 oxaziridine synthesis of 5 2 amino 1 arylethenyl 1 2 4 thiadiazoles
Synthesis, 1993Co-Authors: Michael Patzel, Jurgen LiebscherAbstract:Pyrimidine-4(1H)-thiones 2 react with cyclohexanespiro-3'-oxaziridine (3) by S-amination and ring transformation to give 5-(2-amino-1-arylethenyl)-1,2,4-thiadiazoles 5. Reactions of the precursors of 2, i. e. N-(3-aminothioacryloyl)formamidines 1, with cyclohexanespiro-3'-oxaziridine (3) mostly gave complex reaction mixtures containing the expected thiadiazoles 6, isomeric 5-formamidino-1,2-Thiazoles 8, the 5-formylamino-1,2-thiazole 9 or 3-pyrrolidinocinnamonitrile 10
Josephus H M Lange - One of the best experts on this subject based on the ideXlab platform.
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bioisosteric replacements of the pyrazole moiety of rimonabant synthesis biological properties and molecular modeling investigations of Thiazoles triazoles and imidazoles as potent and selective cb1 cannabinoid receptor antagonists
Journal of Medicinal Chemistry, 2005Co-Authors: Josephus H M Lange, Herman H Van Stuivenberg, Hein K A C Coolen, Tiny J P Adolfs, Andrew C Mccreary, Hiskias G Keizer, Henri C Wals, Willem Veerman, Alice J M Borst, Wouter De LooffAbstract:Series of Thiazoles, triazoles, and imidazoles were designed as bioisosteres, based on the 1,5-diarylpyrazole motif that is present in the potent CB1 receptor antagonist rimonabant (SR141716A, 1). A number of target compounds was synthesized and evaluated in cannabinoid (hCB1 and hCB2) receptor assays. The Thiazoles, triazoles, and imidazoles elicited in vitroCB1 antagonistic activities and in general exhibited considerable CB1 vs CB2 receptor subtype selectivities, thereby demonstrating to be cannabinoid bioisosteres of the original diarylpyrazole class. Some key representatives in the imidazole series showed potent pharmacological in vivo activities after oral administration in both a CB agonist-induced hypotension model and a CB agonist-induced hypothermia model. Molecular modeling studies showed a close three-dimensional structural overlap between the key compound 62 and rimonabant. A structure−activity relationship (SAR) study revealed a close correlation between the biological results in the imidazo...
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bioisosteric replacements of the pyrazole moiety of rimonabant synthesis biological properties and molecular modeling investigations of Thiazoles triazoles and imidazoles as potent and selective cb1 cannabinoid receptor antagonists
Journal of Medicinal Chemistry, 2005Co-Authors: Josephus H M Lange, Herman H Van Stuivenberg, Hein K A C Coolen, Tiny J P Adolfs, Andrew C Mccreary, Hiskias G Keizer, Henri C Wals, Willem Veerman, Alice J M Borst, Wouter De LooffAbstract:Series of Thiazoles, triazoles, and imidazoles were designed as bioisosteres, based on the 1,5-diarylpyrazole motif that is present in the potent CB(1) receptor antagonist rimonabant (SR141716A, 1). A number of target compounds was synthesized and evaluated in cannabinoid (hCB(1) and hCB(2)) receptor assays. The Thiazoles, triazoles, and imidazoles elicited in vitro( )()CB(1) antagonistic activities and in general exhibited considerable CB(1) vs CB(2) receptor subtype selectivities, thereby demonstrating to be cannabinoid bioisosteres of the original diarylpyrazole class. Some key representatives in the imidazole series showed potent pharmacological in vivo activities after oral administration in both a CB agonist-induced hypotension model and a CB agonist-induced hypothermia model. Molecular modeling studies showed a close three-dimensional structural overlap between the key compound 62 and rimonabant. A structure-activity relationship (SAR) study revealed a close correlation between the biological results in the imidazole and pyrazole series.
Henri Doucet - One of the best experts on this subject based on the ideXlab platform.
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Palladium-catalyzed direct arylation of heteroarenes using 1-(bromophenyl)-1,2,3-triazoles as aryl source
Catalysis Communications, 2017Co-Authors: Halima Hadj Mokhtar, Nouria Laidaoui, Douniazad El Abed, Jean-françois Soulé, Henri DoucetAbstract:A variety of 1-aryl-1,2,3-triazoles contg. heteroarenes at C2-, C3- or C4-positions on the aryl ring I [Ar = 2-(2-ethyl-4-methyl-1,3-thiazol-5-yl)phenyl, 3-(5-methylthiophen-2-yl)phenyl, 4-(5-formyl-1-methylpyrrol-2-yl)phenyl, etc.; R = Me, Et, Ph] was successfully prepd. via palladium-catalyzed direct arylation. These couplings were performed by employing 1 mol% of phosphine-free Pd(OAc)2 catalyst with 1-(bromophenyl)-1,2,3-triazoles II (X = 2-Br, 3-Br, 4-Br) and heteroarenes such as 2-acetylthiophene, Me 2-methylfuran-3-carboxylate, 3,5-dimethylisoxazole, etc. as coupling partners. A wide variety of heteroarenes such as Thiazoles, thiophenes, furans, pyrroles or isoxazoles was tolerated.
