- NMR Spectra and Stereochemistry of 1,5- and 1,6-Disubstituted Perhydrooxazolo pyridines
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13C and 1H NMR spectroscopy showed that with the exception of r-1,t-6,t-8a-1-alkyl-6-ethylperhydrooxazolo pyridines (alkyl= ethyl, isopropyl) which adopt the O-inside cis-fused conformation, all the other 1-alkyl-6-ethyl- and 1-alkyl-cis(H-5,H-8a)-5-methyl-perhydrooxazolo pyridines adopt trans-fused conformations (CDCl3, 298 K). KEY WORDS Perhydrooxazolo pyridines Conformation 1H and 13C NMR
- Crabb, Trevor A.,Trethewey, Andrew N.
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- Discovery of potent and simplified piperidinone-based inhibitors of the MDM2-p53 interaction
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Continued optimization of the N-substituent in the piperidinone series provided potent piperidinone-pyridine inhibitors 6, 7, 14, and 15 with improved pharmacokinetic properties in rats. Reducing structure complexity of the N-alkyl substituent led to the discovery of 23, a potent and simplified inhibitor of MDM2. Compound 23 exhibits excellent pharmacokinetic properties and substantial in vivo antitumor activity in the SJSA-1 osteosarcoma xenograft mouse model.
- Yu, Ming,Wang, Yingcai,Zhu, Jiang,Bartberger, Michael D.,Canon, Jude,Chen, Ada,Chow, David,Eksterowicz, John,Fox, Brian,Fu, Jiasheng,Gribble, Michael,Huang, Xin,Li, Zhihong,Liu, Jiwen,Lo, Mei-Chu,McMinn, Dustin,Oliner, Jonathan D.,Osgood, Tao,Rew, Yosup,Saiki, Anne Y.,Shaffer, Paul,Yan, Xuelei,Ye, Qiuping,Yu, Dongyin,Zhao, Xiaoning,Zhou, Jing,Olson, Steven H.,Medina, Julio C.,Sun, Daqing
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supporting information
p. 894 - 899
(2014/09/17)
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- N-alkylation of lactams with secondary heterobenzylic bromides
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We herein report a general N-alkylation reaction of lactams with secondary heterobenzylic bromides. This methodology features mild reaction condition, moderate to high product isolation yield, and broad substrate scope. Good chemical and structural tolerance has also been demonstrated by both the secondary heterobenzylic bromides and lactam substrates.
- Yu, Ming,Stevenson, Karis,Zhou, Gene
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supporting information
p. 5591 - 5594
(2014/12/11)
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- New Alkaloids from Ants: Identification and Synthesis of (3R,5S,9R)-3-Butyl-5-(1-oxopropyl)indolizidine and (3R,5R,9R)-3-Butyl-5-(1-oxopropyl)indolizidine Constituents of the Poison Gland Secretion in Myrmicaria eumenoides (Hymenoptera Formicidae)
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The (3R,5S,9R) and (3R,5R,9R) stereoisomers of 3-butyl-5-(1-oxopropyl)indolizidine (9) were identified as major constituents of the poison gland secretion of the African ant, Myrmicaria eumenoides.Racemates of the four diastereomers of 9 were synthesized via the corresponding ethyl 5-(5-butylpyrrolidin-2-yl)pentanoates (6).Enantiomerically pure samples of the (3R)-stereoisomers of 9 were obtained by starting from (2R)-2,3-O-isopropylideneglyceric aldehyde (21) and 6-methylpyridine-2-carboxaldehyde (20).In addition, the enantiomeric separation by chiral gas chromatography and unambiguous structure assignment of the target compounds are described. - Key Words: Ants/ Alkaloids/ Myrmicaria eumenoides/ 3-Butyl-5-(1-oxopropyl)indolizidine, (3R,5S,9R)-, (3R,5R,9R)-
- Francke, Wittko,Schroeder, Frank,Walter, Felix,Sinnwell, Volker,Baumann, Horst,Kaib, Manfred
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p. 965 - 978
(2007/10/02)
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