- Enantioselective Synthesis of Chiral Substituted 2,4-Diketoimidazolidines and 2,5-Diketopiperazines via Asymmetric Hydrogenation
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An enantioselective hydrogenation of 5-alkylidene-2,4-diketoimidazolidines (hydantoins) and 3-alkylidene-2,5-ketopiperazines catalyzed by the Rh/f-spiroPhos complex under mild conditions has been developed, which provides an efficient approach to the highly enantioselective synthesis of chiral hydantoins and 2,5-ketopiperazine derivatives with high enantioselectivities up to 99.9% ee.
- Xiao, Guiying,Xu, Shuang,Xie, Chaochao,Zi, Guofu,Ye, Weiping,Zhou, Zhangtao,Hou, Guohua,Zhang, Zhanbin
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supporting information
p. 5734 - 5738
(2021/08/01)
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- Ir-Catalyzed Double Asymmetric Hydrogenation of 3,6-Dialkylidene-2,5-diketopiperazines for Enantioselective Synthesis of Cyclic Dipeptides
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An Ir/spiro[4,4]-1,6-nonadiene-based phosphine-oxazoline ligand (SpinPHOX) complex-catalyzed double asymmetric hydrogenation of 3,6-dialkylidene-1,4-dimethylpiperazine-2,5-diones has been developed, providing efficient and practical access to a wide varie
- Ge, Yao,Han, Zhaobin,Wang, Zheng,Ding, Kuiling
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supporting information
p. 8981 - 8988
(2019/06/13)
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- Discovery of a class of diketopiperazines as antiprion compounds
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Prion diseases are fatal neurodegenerative and infectious disorders for which effective pharmacological tools are not yet available. This unmet challenge and the recently proposed interplay between prion diseases and Alzheimer's have led to a more urgent demand for new antiprion agents. Herein, we report the identification of a novel bifunctional diketopiperazine (DKP) derivative 1d, which exhibits activity in the low micromolar range against prion replication in ScGT1 cells, while showing low cytotoxicity. Supported by properly addressed molecular modeling studies, we hypothesized that a planar conformation is the major determinant for activity in this class of compounds. Moreover, studies aimed at assessing the mechanism-of-action at the molecular level showed that 1d might interact directly with recombinant prion protein (recPrP) to prevent its conversion to the pathogenic misfolded prion protein (PrPSc)-like form. This investigation suggests that DKP based antiprion compounds can serve as a promising lead scaffold in developing new drugs to combat prion diseases.
- Bolognesi, Maria Laura,Tran, Hoang Ngoc Ai,Staderini, Matteo,Monaco, Alessandra,Lopez-Cobeas, Alberto,Bongarzone, Salvatore,Biarnes, Xevi,Lopez-Alvarado, Pilar,Cabezas, Nieves,Caramelli, Maria,Carloni, Paolo,Menendez, J. Carlos,Legname, Giuseppe
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experimental part
p. 1324 - 1334
(2011/01/04)
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- Solution-phase combinatorial synthesis and evaluation of piperazine-2,5- dione derivatives
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An efficient one-pot synthesis of a 61-membered combinatorial chemistry library of piperazine-2,5-diones was accomplished. Results of combinatorial synthesis, purification, analysis, and biological evaluation are described.
- Loughlin, Wendy A.,Marshall, Raymond L.,Carreiro, Adelina,Elson, Kathryn E.
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- Pharmaceutical compounds
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Diketopiperazines of the formula: STR1 where each of R1 to R10, which may be the same or different, is independently selected from the group consisting of hydrogen, C1 -C6 alkyl unsubstituted or substituted by o
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- Potassium Fluoride on Alumina: Condensation of 1,4-Diacetylpiperazine-2,5-dione with Aldehydes. Dry Condensation under Microwave Irradiation. Synthesis of Albonursin and Analogues
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1,4-Diacetylpiperazine-2,5-dione (1) was condensated with aldehydes (2) with KF on alumina without solvent under microwaves or in at room temperature in the presence of DMF.The reaction was stereoselective and some natural products (4a-c) like albonursin (4c) were synthesized.
- Villemin, Didier,Alloum, Abdelkrim Ben
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p. 3325 - 3331
(2007/10/02)
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- Pyrazine Chemistry. II. Reduction of 3,6-Dibenzylidenepiperazine-2,5-diones
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A reinvestigation of the reduction of 3,6-dibenzylidenepiperazine-2,5-dione (1) with zinc and acetic acid established that this reaction gave (Z)-6-benzyl-3-benzylidenepiperazine-2,5-dione (10).When a mixture of acetic acid and hydrochloric acid was used
- Marcuccio, Sebastian M.,Elix, John A.
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p. 1791 - 1794
(2007/10/02)
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- α,β-Unsaturated Carboxylic Acid Derivatives. Part 18. Syntheses of Geometric Isomers of 3,6-Dibenzylidene- and 3-p-Anisylidene-6-benzylidene-2,5-piperazinediones
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Naturally occuring 3,6-dibenzylidene- and 3-p-anisylidene-6-benzylidene-2,5-piperazinediones and their geometric isomers were synthesized by the condensation of 1-acetyl or 1,4-diacetyl derivative of (E)- and (Z)-benzylidene- or p-anisylidene-2,5-piperazinediones with an appropriate aldehyde.The configuration of these compounds were assigned on the basis of the spectroscopic analyses, and those of natural products were determined to be (3Z,6Z).
- Shin, Chung-gi,Hayakawa, Masato,Kato, Haruo,Mikami, Kazutoshi,Yoshimura, Juji
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p. 419 - 421
(2007/10/02)
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