143965-32-6Relevant articles and documents
Synthesis and Anticancer Activity of Novel Actinonin Derivatives as HsPDF Inhibitors
Hu, Liu,Cai, Xing,Dong, Suzhen,Zhen, Yongjia,Hu, Jidi,Wang, Shenjun,Jiang, Jingwen,Huang, Jiawu,Han, Yuqiao,Qian, Yu,Yuan, Yanqiu,Hu, Wenhao
, p. 6959 - 6978 (2020/08/14)
Human mitochondrial peptide deformylase (HsPDF) is responsible for removing the formyl group from N-terminal formylmethionines of newly synthesized mitochondrial proteins and plays important roles in maintaining mitochondria function. It is overexpressed
Synthesis and Absolute Configuration of Natural 2-Pyrones
Burkhardt, Immo,Dickschat, Jeroen S.
supporting information, p. 3144 - 3157 (2018/07/06)
2-Pyrones are frequently produced by microorganisms and often exhibit interesting bioactivities. Therefore, a short and easy synthetic access to these natural products is desirable. Synthetic routes to nectriapyrone, gibepyrone A, racemic gulypyrone A, (+)-germicidin C, (ent)-desoxygermicidin C and (ent)-prolipyrone A via a modular approach are presented, allowing the assignment of the absolute configurations of the latter three chiral compounds. The method failed for the synthesis of (ent)-phomapyrone B that was thus synthesized via a different route, resulting in an assignment of the absolute configuration of natural phomapyrone B.
Peptide deformylase inhibitors
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Page/Page column, (2014/12/09)
The present invention relates to a compound of Formula (I): or a pharmaceutically acceptable salt thereof, corresponding pharmaceutical compositions, compound preparation and treatment methods directed to bacterial infections and inhibition of bacterial peptide deformylase (PDF) activity.
PEPTIDE DEFORMYLASE INHIBITORS
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Page/Page column, (2014/02/15)
The present invention relates to a compound of Formula (I): or a pharmaceutically acceptable salt thereof, corresponding pharmaceutical compositions, compound preparation and treatment methods directed to bacterial infections and inhi-bition of bacterial peptide deformylase (PDF) activity
A facile asymmetric synthesis of (S)-14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth
Zhang, Tao,Ma, Wei-Li,Li, Tian-Rui,Wu, Jia,Wang, Jun-Run,Du, Zhen-Ting
, p. 5201 - 5208 (2013/06/27)
An asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth has been achieved. The target molecule was synthesized in six linear steps and in 30.3% overall yield from commercially available hexanoyl chloride, (S)-4-benzyloxazolidin-2-one and 1,9-nonanediol. The hexanoyl chloride was connected with (S)-4-benzyloxazolidin-2-one, and with the induction of the chiral oxazolidinone auxiliary, after chiral methylation, LAH reduction and then tosylation gave the chiral key intermediate 5 in high stereoselectivity. 1,9-Nonanediol, was selectively brominated, THP protected and subjected to Li2CuCl4-mediated C-C coupling to afford a C12 intermediate. The target molecule, (S)-14-methyl-1-octadecene, was obtained after the two parts were subjected to a second Li 2CuCl4-mediated C-C coupling. Our synthetic approach represents the first time a substrate-control asymmetric synthesis of (S)-14-methyl-1-octadecene has been reported.
NOVEL COMPOUNDS, PHARMACEUTICAL COMPOSITION AND METHODS FOR USE IN TREATING METABOLIC DISORDERS
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Page/Page column 49, (2011/12/14)
The present invention is directed to novel compounds of formula (I) and their use in treating metabolic diseases.
The first enantioselective synthesis of cytotoxic marine natural product palau'imide and assignment of its C-20 stereochemistry
Lan, Hong-Qiao,Ruan, Yuan-Ping,Huang, Pei-Qiang
supporting information; scheme or table, p. 5319 - 5321 (2010/09/03)
Methyl tetramate derivative 6 has been developed as a new building block for the flexible and racemization-free synthesis of methyl 5-benzyl-3- methyltetramate via alkylation, and used in the first asymmetric synthesis of palau'imide (1). This allowed the establishment of the hitherto unknown stereochemistry at the C-20 of palau'imide as S.
Peptide deformylase inhibitors of Mycobacterium tuberculosis: Synthesis, structural investigations, and biological results
Pichota, Arkadius,Duraiswamy, Jeyaraj,Yin, Zheng,Keller, Thomas H.,Alam, Jenefer,Liung, Sarah,Lee, Gladys,Ding, Mei,Wang, Gang,Chan, Wai Ling,Schreiber, Mark,Ma, Ida,Beer, David,Ngew, Xinyi,Mukherjee, Kakoli,Nanjundappa, Mahesh,Teo, Jeanette W.P.,Thayalan, Pamela,Yap, Amelia,Dick, Thomas,Meng, Wuyi,Xu, Mei,Koehn, James,Pan, Shi-Hao,Clark, Kirk,Xie, Xiaoling,Shoen, Carolyn,Cynamon, Michael
scheme or table, p. 6568 - 6572 (2009/09/30)
Bacterial peptide deformylase (PDF) belongs to a subfamily of metalloproteases catalyzing the removal of the N-terminal formyl group from newly synthesized proteins. We report the synthesis and biological activity of highly potent inhibitors of Mycobacterium tuberculosis (Mtb) PDF enzyme as well as the first X-ray crystal structure of Mtb PDF. Structure-activity relationship and crystallographic data clarified the structural requirements for high enzyme potency and cell based potency. Activities against single and multi-drug-resistant Mtb strains are also reported.
Structure-activity relationships of the peptide deformylase inhibitor BB-3497: Modification of the methylene spacer and the P1′ side chain
Davies, Stephen J.,Ayscough, Andrew P.,Beckett, R. Paul,Bragg, Ryan A.,Clements, John M.,Doel, Sheila,Grew, Christine,Launchbury, Steven B.,Perkins, Gemma M.,Pratt, Lisa M.,Smith, Helen K.,Spavold, Zoe M.,Thomas, S. Wayne,Todd, Richard S.,Whittaker, Mark
, p. 2709 - 2713 (2007/10/03)
Structural modifications to the peptide deformylase inhibitor BB-3497 are described. In this paper, we describe the initial SAR around this lead for modifications to the methylene spacer and the P1′ side chain. Enzyme inhibition and antibacterial activity data revealed that the optimum distance between the N-formyl hydroxylamine metal binding group and the P1′ side chain is one unsubstituted methylene unit. Additionally, lipophilic P1′ side chains that closely mimic the methionine residue in the substrate provided compounds with the best microbiological profile.
α-substituted hydroxamic acids as novel bacterial deformylase inhibitor-based antibacterial agents
Jain,Sundram,Lopez,Neckermann,Wu,Hackbarth,Chen,Wang,Ryder,Weidmann,Patel,Trias,White,Yuan
, p. 4223 - 4228 (2007/10/03)
We report the synthesis and biological activity of analogues of VRC3375 (N-hydroxy-3-R-butyl-3-[(2-S-(tert-butoxycarbonyl)-pyrrolidin-1-ylcarbonyl] propionamide), an orally active peptide deformylase inhibitor. This study explores the structure-activity relationship of various chelator groups, alpha substituents, P2′ and P3′ substituents in order to achieve optimal antibacterial activity with minimal toxicity liability.