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Rob Leurs - One of the best experts on this subject based on the ideXlab platform.
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homologs of histamine as histamine h3 receptor antagonists a new potent and selective h3 antagonist 4 5 5 aminopentyl 1h imidazole
Journal of Medicinal Chemistry, 1995Co-Authors: R C Vollinga, Wiro M.b.p. Menge, Rob LeursAbstract:The influence of alkyl chain length variation on the histamine H 3 receptor activity of histamine homologs 1 was investigated. A series of 4(5)-(ω-aminoalkyl)-1H-Imidazoles 1 was prepared with an alkyl chain length varying from one methylene group to 10 methylene groups. Besides the Hg activity, the affinities of these compounds for the H 1 and H 2 receptors were determined. The ethylene chain of histamine is optimal for agonistic activity on all three histamine receptor subtypes. For the H 3 receptor, elongation of the alkyl chain from three methylene groups on leads to compounds with antagonistic properties. 4(5)-(5-Aminopentyl)-1H-Imidazole (impentamine, 1e) is the most potent and selective H 3 antagonist from this series of 4(5)-(ω-aminoalkyl)-1H-Imidazoles 1, with a pA 2 value of 8.4 (on guinea pig jejunum). A specific antagonistic binding site for this compound is proposed
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homologs of histamine as histamine h3 receptor antagonists a new potent and selective h3 antagonist 4 5 5 aminopentyl 1h imidazole
Journal of Medicinal Chemistry, 1995Co-Authors: R C Vollinga, Rob Leurs, Wiro M.b.p. Menge, Hendrik TimmermanAbstract:The influence of alkyl chain length variation on the histamine H3 receptor activity of histamine homologs 1 was investigated. A series of 4(5)-(omega-aminoalkyl)-1H-Imidazoles 1 was prepared with an alkyl chain length varying from one methylene group to 10 methylene groups. Besides the H3 activity, the affinities of these compounds for the H1 and H2 receptors were determined. The ethylene chain of histamine is optimal for agonistic activity on all three histamine receptor subtypes. For the H3 receptor, elongation of the alkyl chain from three methylene groups on leads to compounds with antagonistic properties. 4(5)-(5-Aminopentyl)-1H-Imidazole (impentamine, 1e) is the most potent and selective H3 antagonist from this series of 4(5)-(omega-aminoalkyl)-1H-Imidazoles 1, with a pA2 value of 8.4 (on guinea pig jejunum). A specific antagonistic binding site for this compound is proposed.
R C Vollinga - One of the best experts on this subject based on the ideXlab platform.
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homologs of histamine as histamine h3 receptor antagonists a new potent and selective h3 antagonist 4 5 5 aminopentyl 1h imidazole
Journal of Medicinal Chemistry, 1995Co-Authors: R C Vollinga, Wiro M.b.p. Menge, Rob LeursAbstract:The influence of alkyl chain length variation on the histamine H 3 receptor activity of histamine homologs 1 was investigated. A series of 4(5)-(ω-aminoalkyl)-1H-Imidazoles 1 was prepared with an alkyl chain length varying from one methylene group to 10 methylene groups. Besides the Hg activity, the affinities of these compounds for the H 1 and H 2 receptors were determined. The ethylene chain of histamine is optimal for agonistic activity on all three histamine receptor subtypes. For the H 3 receptor, elongation of the alkyl chain from three methylene groups on leads to compounds with antagonistic properties. 4(5)-(5-Aminopentyl)-1H-Imidazole (impentamine, 1e) is the most potent and selective H 3 antagonist from this series of 4(5)-(ω-aminoalkyl)-1H-Imidazoles 1, with a pA 2 value of 8.4 (on guinea pig jejunum). A specific antagonistic binding site for this compound is proposed
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homologs of histamine as histamine h3 receptor antagonists a new potent and selective h3 antagonist 4 5 5 aminopentyl 1h imidazole
Journal of Medicinal Chemistry, 1995Co-Authors: R C Vollinga, Rob Leurs, Wiro M.b.p. Menge, Hendrik TimmermanAbstract:The influence of alkyl chain length variation on the histamine H3 receptor activity of histamine homologs 1 was investigated. A series of 4(5)-(omega-aminoalkyl)-1H-Imidazoles 1 was prepared with an alkyl chain length varying from one methylene group to 10 methylene groups. Besides the H3 activity, the affinities of these compounds for the H1 and H2 receptors were determined. The ethylene chain of histamine is optimal for agonistic activity on all three histamine receptor subtypes. For the H3 receptor, elongation of the alkyl chain from three methylene groups on leads to compounds with antagonistic properties. 4(5)-(5-Aminopentyl)-1H-Imidazole (impentamine, 1e) is the most potent and selective H3 antagonist from this series of 4(5)-(omega-aminoalkyl)-1H-Imidazoles 1, with a pA2 value of 8.4 (on guinea pig jejunum). A specific antagonistic binding site for this compound is proposed.
Panayiotis A. Koutentis - One of the best experts on this subject based on the ideXlab platform.
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Reactions of Tetracyanoethylene with N′‑Arylbenzamidines: A Route to 2‑Phenyl‑3H‑imidazo[4,5‑b]quinoline-9-carbonitriles
2016Co-Authors: Styliana I. Mirallai, Maria Manoli, Panayiotis A. KoutentisAbstract:Eight 2-phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitriles 15 are prepared in four steps from N′-arylbenzamidines 11 and tetracyanoethylene (TCNE) in ∼70–90% yields. The transformation involves the initial formation of N-aryl-N′-(1,2,2-tricyanovinyl)benzamidines 12 in 87–99% yields, which in MeCN undergo a 5-exodig cyclization to give the 2-[1-aryl-5-imino-2-phenyl-1H-imidazol-4(5H)-ylidene]malononitriles 13 in 84–92% yields, while in MeOH the (Z)-2-[2-phenyl-4-(arylimino)-1H-imidazol-5(4H)-ylidene]malononitriles 14 are formed in 85–94% yields. The imidazoles 14 can also be prepared directly from imidazoles 13 via a Dimroth rearrangement in either neat MeOH or in DCM with DBU. Subsequent thermolysis of imidazoles 14 in diphenyl ether affords 2-phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitriles 15 in near quantitative yields. Mechanistic rationale is provided for all transformations
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reactions of tetracyanoethylene with n arylbenzamidines a route to 2 phenyl 3h imidazo 4 5 b quinoline 9 carbonitriles
Journal of Organic Chemistry, 2013Co-Authors: Styliana I. Mirallai, Maria Manoli, Panayiotis A. KoutentisAbstract:Eight 2-phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitriles 15 are prepared in four steps from N′-arylbenzamidines 11 and tetracyanoethylene (TCNE) in ∼70–90% yields. The transformation involves the initial formation of N-aryl-N′-(1,2,2-tricyanovinyl)benzamidines 12 in 87–99% yields, which in MeCN undergo a 5-exodig cyclization to give the 2-[1-aryl-5-imino-2-phenyl-1H-imidazol-4(5H)-ylidene]malononitriles 13 in 84–92% yields, while in MeOH the (Z)-2-[2-phenyl-4-(arylimino)-1H-imidazol-5(4H)-ylidene]malononitriles 14 are formed in 85–94% yields. The imidazoles 14 can also be prepared directly from imidazoles 13 via a Dimroth rearrangement in either neat MeOH or in DCM with DBU. Subsequent thermolysis of imidazoles 14 in diphenyl ether affords 2-phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitriles 15 in near quantitative yields. Mechanistic rationale is provided for all transformations.
Hendrik Timmerman - One of the best experts on this subject based on the ideXlab platform.
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homologs of histamine as histamine h3 receptor antagonists a new potent and selective h3 antagonist 4 5 5 aminopentyl 1h imidazole
Journal of Medicinal Chemistry, 1995Co-Authors: R C Vollinga, Rob Leurs, Wiro M.b.p. Menge, Hendrik TimmermanAbstract:The influence of alkyl chain length variation on the histamine H3 receptor activity of histamine homologs 1 was investigated. A series of 4(5)-(omega-aminoalkyl)-1H-Imidazoles 1 was prepared with an alkyl chain length varying from one methylene group to 10 methylene groups. Besides the H3 activity, the affinities of these compounds for the H1 and H2 receptors were determined. The ethylene chain of histamine is optimal for agonistic activity on all three histamine receptor subtypes. For the H3 receptor, elongation of the alkyl chain from three methylene groups on leads to compounds with antagonistic properties. 4(5)-(5-Aminopentyl)-1H-Imidazole (impentamine, 1e) is the most potent and selective H3 antagonist from this series of 4(5)-(omega-aminoalkyl)-1H-Imidazoles 1, with a pA2 value of 8.4 (on guinea pig jejunum). A specific antagonistic binding site for this compound is proposed.
Wiro M.b.p. Menge - One of the best experts on this subject based on the ideXlab platform.
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homologs of histamine as histamine h3 receptor antagonists a new potent and selective h3 antagonist 4 5 5 aminopentyl 1h imidazole
Journal of Medicinal Chemistry, 1995Co-Authors: R C Vollinga, Wiro M.b.p. Menge, Rob LeursAbstract:The influence of alkyl chain length variation on the histamine H 3 receptor activity of histamine homologs 1 was investigated. A series of 4(5)-(ω-aminoalkyl)-1H-Imidazoles 1 was prepared with an alkyl chain length varying from one methylene group to 10 methylene groups. Besides the Hg activity, the affinities of these compounds for the H 1 and H 2 receptors were determined. The ethylene chain of histamine is optimal for agonistic activity on all three histamine receptor subtypes. For the H 3 receptor, elongation of the alkyl chain from three methylene groups on leads to compounds with antagonistic properties. 4(5)-(5-Aminopentyl)-1H-Imidazole (impentamine, 1e) is the most potent and selective H 3 antagonist from this series of 4(5)-(ω-aminoalkyl)-1H-Imidazoles 1, with a pA 2 value of 8.4 (on guinea pig jejunum). A specific antagonistic binding site for this compound is proposed
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homologs of histamine as histamine h3 receptor antagonists a new potent and selective h3 antagonist 4 5 5 aminopentyl 1h imidazole
Journal of Medicinal Chemistry, 1995Co-Authors: R C Vollinga, Rob Leurs, Wiro M.b.p. Menge, Hendrik TimmermanAbstract:The influence of alkyl chain length variation on the histamine H3 receptor activity of histamine homologs 1 was investigated. A series of 4(5)-(omega-aminoalkyl)-1H-Imidazoles 1 was prepared with an alkyl chain length varying from one methylene group to 10 methylene groups. Besides the H3 activity, the affinities of these compounds for the H1 and H2 receptors were determined. The ethylene chain of histamine is optimal for agonistic activity on all three histamine receptor subtypes. For the H3 receptor, elongation of the alkyl chain from three methylene groups on leads to compounds with antagonistic properties. 4(5)-(5-Aminopentyl)-1H-Imidazole (impentamine, 1e) is the most potent and selective H3 antagonist from this series of 4(5)-(omega-aminoalkyl)-1H-Imidazoles 1, with a pA2 value of 8.4 (on guinea pig jejunum). A specific antagonistic binding site for this compound is proposed.