- Arene Trifunctionalization with Highly Fused Ring Systems through a Domino Aryne Nucleophilic and Diels–Alder Cascade
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A convenient and efficient domino aryne process was developed under transition-metal-free conditions to generate a range of tetra- and pentacyclic ring systems. This transformation was realized via a 1,2-benzdiyne through a nucleophilic and Diels–Alder reaction cascade using styrene as the diene moiety. Three new chemical bonds, namely one C?N and two C?C bonds, and two benzofused rings could be constructed concomitantly, which was made possible by distinct chemoselective control at both the 1,2-aryne and 2,3-aryne stages. Moreover, in-depth studies were carried out on the domino aryne precursors and controlling the diastereoselectivity.
- He, Jia,Jia, Zizi,Tan, Hongcheng,Luo, Xiaohua,Qiu, Dachuan,Shi, Jiarong,Xu, Hai,Li, Yang
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p. 18513 - 18518
(2019/11/19)
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- 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine Analogues. Inactivation of Monoamine Oxidase by Conformationally Rigid Analogues of N,N-Dimethylcinnamylamine
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1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) is potent neurotoxin and also an inactivator of monoamine oxidase (MAO).Since MPTP is a conformationally rigid analogue of N,N-dimethylcinnamylamine, other conformationally rigid analogues of N,N-dimethylcinnamylamine were synthesized and tested as inhibitors and inactivators of MAO. (E)-2-(Phenylmethylene)cyclohexanamine (5a), (E)-N,N-dimethyl-2-(phenylmethylene)cyclohexanamine (5b), 3-phenyl-2-cyclohexen-1-amine (6a), N,N-dimethyl-3-phenyl-2-cyclohexen-1-amine (6b), and (E)- and (Z)-N-methyl-3-(phenylmethylene)piperidine (7 and 8) are all inhibitors and time-dependent inactivators of MAO B, but none is as potent as MPTP. α-Methylation and methylation of the amino group in all cases increases the Ki value relative to that for the parent compound.Compounds 5a, 5b, 6a, and 6b are highly cytotoxic, but cytotoxicity is not prevented by pretreatment of the cells with pargyline.There does not appear to be a correlation between the configuration of the N,N-dimethylcinnamylamine analogue and its potency as a MAO inactivator.
- Hiebert, Charles K.,Silverman, Richard B.
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p. 1566 - 1570
(2007/10/02)
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