The Experts below are selected from a list of 23205 Experts worldwide ranked by ideXlab platform
Philip Thorne - One of the best experts on this subject based on the ideXlab platform.
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concise synthesis of novel 2 6 diazaspiro 3 3 heptan 1 ones and their conversion into 2 6 diazaspiro 3 3 Heptanes
Synlett, 2007Co-Authors: Michael J Stocks, Daniel Hamza, Jeffrey P Stonehouse, Garry Pairaudeau, Philip ThorneAbstract:A concise synthesis, amenable to library production of 2,6-diazaspiro[3.3]heptan-1-ones and their subsequent conversion into 2,6-diazaspiro[3.3]Heptanes is reported.
Erick M. Carreira - One of the best experts on this subject based on the ideXlab platform.
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2 6 diazaspiro 3 3 Heptanes synthesis and application in pd catalyzed aryl amination reactions
Organic Letters, 2008Co-Authors: Johannes A Burkhard, Erick M. CarreiraAbstract:A concise and scalable synthesis of a 2,6-diazaspiro[3.3]Heptane building block is reported. The usefulness of this structural surrogate of piperazine is shown in arene amination reactions yielding a variety of N-Boc-N′-aryl-2,6-diazaspiro[3.3]Heptanes.
Paola Viani - One of the best experts on this subject based on the ideXlab platform.
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novel n aryl nicotinamide derivatives taking stock on 3 6 diazabicyclo 3 1 1 Heptanes as ligands for neuronal acetylcholine receptors
European Journal of Medicinal Chemistry, 2019Co-Authors: Gabriele Murineddu, Katiuscia Martinello, Simona Plutino, Sergio Fucile, Veronika Temml, Milena Moretti, Battistina Asproni, Cecilia Gotti, Paola Corona, Paola VianiAbstract:Abstract We designed the synthesis of a small library of 3-substituted-3,6-diazabicyclo[3.1.1]Heptanes whose affinity on neuronal nicotinic receptors (nAChRs) was evaluated. Among the synthesized compounds, the 5-(3,6-diazabicyclo[3.1.1]Heptane-3-yl)- N -(2-fluorophenyl)nicotinamide 43 proved to be the most interesting compound with α 4 β 2 Ki value of 10 pM and a very high α 7 /α 4 β 2 selectivity. Furthermore, compounds 35 , 39 and 43 elicited a selective partial agonist activity for α 4 β 2 nAChR subtype. Finally, in this paper we also report the conclusions on the 3,6-diazabicyclo[3.1.1]Heptanes as ligands for nAChRs, resulting from our consolidated structure activity relationship (SAR) studies on this template.
Tomohiko Ohwada - One of the best experts on this subject based on the ideXlab platform.
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an evaluation of amide group planarity in 7 azabicyclo 2 2 1 Heptane amides low amide bond rotation barrier in solution
Journal of the American Chemical Society, 2003Co-Authors: Yuko Otani, Kentaro Yamaguchi, Satoshi Inagaki, Osamu Nagae, Yuji Naruse, Masashi Ohno, Gaku Yamamoto, Masanobu Uchiyama, Tomohiko OhwadaAbstract:Here we show that amides of bicyclic 7-azabicyclo[2.2.1]Heptane are intrinsically nitrogen-pyramidal. Single-crystal X-ray diffraction structures of some relevant bicyclic amides, including the prototype N-benzoyl-7-azabicyclo[2.2.1]Heptane, exhibited nitrogen-pyramidalization in the solid state. We evaluated the rotational barriers about the amide bonds of various N-benzoyl-7-azabicyclo[2.2.1]Heptanes in solution. The observed reduction of the rotational barriers of the bicyclic amides, as compared with those of the monocyclic pyrrolidine amides, is consistent with a nitrogen-pyramidal structure of 7-azabicyclo[2.2.1]Heptane amides in solution. A good correlation was found between the magnitudes of the rotational barrier of N-benzoyl-7-azabicyclo[2.2.1]Heptanes bearing para-substituents on the benzoyl group and the Hammett's σp+ constants, and this is consistent with the similarity of the solution structures. Calculations with the density functional theory reproduced the nitrogen-pyramidal structures of ...
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structural features of aliphatic n nitrosamines of 7 azabicyclo 2 2 1 Heptanes that facilitate n no bond cleavage
Journal of the American Chemical Society, 2001Co-Authors: Tomohiko Ohwada, Motoko Miura, Haruko Tanaka, Shigeru Sakamoto, Kentaro Yamaguchi, Hirotaka Ikeda, Satoshi InagakiAbstract:N-Nitrosamines can be considered as potential nitric oxide (NO)/nitrosonium ion (NO+) donors. However, the relation of the structures of N-nitrosamines, in particular of aliphatic N-nitrosamines, to the characteristics of release of NO or NO+ remains unclear. Here we show that aliphatic N-nitrosoamines of 7-azabicyclo[2.2.1]Heptanes can undergo heterolytic N−NO bond cleavage. On the basis of the observation of reduced rotational barriers of the N−NO bonds in solution and nitrogen-pyramidal structures of the N-nitroso group in the solid state, we postulate that N−NO bond cleavage of N-nitrosamines is enhanced by a reduction of the resonance in the N−NO group. Computational studies suggest that these structural features of the N-nitrosamines of 7-azabicyclo[2.2.1]Heptane are derived from angle strain imposed on the CNC angles.
Satoshi Inagaki - One of the best experts on this subject based on the ideXlab platform.
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an evaluation of amide group planarity in 7 azabicyclo 2 2 1 Heptane amides low amide bond rotation barrier in solution
Journal of the American Chemical Society, 2003Co-Authors: Yuko Otani, Kentaro Yamaguchi, Satoshi Inagaki, Osamu Nagae, Yuji Naruse, Masashi Ohno, Gaku Yamamoto, Masanobu Uchiyama, Tomohiko OhwadaAbstract:Here we show that amides of bicyclic 7-azabicyclo[2.2.1]Heptane are intrinsically nitrogen-pyramidal. Single-crystal X-ray diffraction structures of some relevant bicyclic amides, including the prototype N-benzoyl-7-azabicyclo[2.2.1]Heptane, exhibited nitrogen-pyramidalization in the solid state. We evaluated the rotational barriers about the amide bonds of various N-benzoyl-7-azabicyclo[2.2.1]Heptanes in solution. The observed reduction of the rotational barriers of the bicyclic amides, as compared with those of the monocyclic pyrrolidine amides, is consistent with a nitrogen-pyramidal structure of 7-azabicyclo[2.2.1]Heptane amides in solution. A good correlation was found between the magnitudes of the rotational barrier of N-benzoyl-7-azabicyclo[2.2.1]Heptanes bearing para-substituents on the benzoyl group and the Hammett's σp+ constants, and this is consistent with the similarity of the solution structures. Calculations with the density functional theory reproduced the nitrogen-pyramidal structures of ...
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structural features of aliphatic n nitrosamines of 7 azabicyclo 2 2 1 Heptanes that facilitate n no bond cleavage
Journal of the American Chemical Society, 2001Co-Authors: Tomohiko Ohwada, Motoko Miura, Haruko Tanaka, Shigeru Sakamoto, Kentaro Yamaguchi, Hirotaka Ikeda, Satoshi InagakiAbstract:N-Nitrosamines can be considered as potential nitric oxide (NO)/nitrosonium ion (NO+) donors. However, the relation of the structures of N-nitrosamines, in particular of aliphatic N-nitrosamines, to the characteristics of release of NO or NO+ remains unclear. Here we show that aliphatic N-nitrosoamines of 7-azabicyclo[2.2.1]Heptanes can undergo heterolytic N−NO bond cleavage. On the basis of the observation of reduced rotational barriers of the N−NO bonds in solution and nitrogen-pyramidal structures of the N-nitroso group in the solid state, we postulate that N−NO bond cleavage of N-nitrosamines is enhanced by a reduction of the resonance in the N−NO group. Computational studies suggest that these structural features of the N-nitrosamines of 7-azabicyclo[2.2.1]Heptane are derived from angle strain imposed on the CNC angles.
