317355-80-9Relevant academic research and scientific papers
Interrupted Curtius Rearrangements of Quaternary Proline Derivatives: A Flow Route to Acyclic Ketones and Unsaturated Pyrrolidines
Baumann, Marcus,Moody, Thomas S.,Smyth, Megan,Wharry, Scott
, p. 14199 - 14206 (2021/07/20)
Conversion of N-Boc-protected quaternary proline derivatives under thermal Curtius rearrangement conditions was found to afford a series of ring-opened ketone and unsaturated pyrrolidine products instead of the expected carbamate species. The nature of the substituent on the quaternary carbon thereby governs the product outcome due to the stability of a postulated N-acyliminium species. A continuous flow process with in-line scavenging was furthermore developed to streamline this transformation and safely create products on a gram scale.
Design and Synthesis of 56 Shape-Diverse 3D Fragments
Atobe, Masakazu,Blakemore, David C.,Bond, Paul S.,Chan, Ngai S.,De Fusco, Claudia,Downes, Thomas D.,Firth, James D.,Hubbard, Roderick E.,Jones, S. Paul,Klein, Hanna F.,O'Brien, Peter,Roughley, Stephen D.,Vidler, Lewis R.,Waddelove, Laura,Whatton, Maria Ann,Wheldon, Mary C.,Woolford, Alison J.-A.,Wrigley, Gail L.
supporting information, (2020/07/13)
Fragment-based drug discovery is now widely adopted for lead generation in the pharmaceutical industry. However, fragment screening collections are often predominantly populated with flat, 2D molecules. Herein, we describe a workflow for the design and synthesis of 56 3D disubstituted pyrrolidine and piperidine fragments that occupy under-represented areas of fragment space (as demonstrated by a principal moments of inertia (PMI) analysis). A key, and unique, underpinning design feature of this fragment collection is that assessment of fragment shape and conformational diversity (by considering conformations up to 1.5 kcal mol?1 above the energy of the global minimum energy conformer) is carried out prior to synthesis and is also used to select targets for synthesis. The 3D fragments were designed to contain suitable synthetic handles for future fragment elaboration. Finally, by comparing our 3D fragments with six commercial libraries, it is clear that our collection has high three-dimensionality and shape diversity.
2-PYRROLIDINE PHENYLHYDRAZIDES ANTIBACTERIAL AGENTS
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Page/Page column 58, (2018/02/28)
2-Pyrrolidine phenylhydrazides antibacterial agents The present invention relates to 2-pyrrolidine phenylhydrazide compounds of formula (I), which are selective antibacterials specifically agalnstAcineto barter baumannii.The invention also relates to their therapeutic use as antibacterials, to a process for their preparation and to pharmaceutical compositions containing them.
COMPOUNDS FOR TREATING DISORDERS MEDIATED BY METABOTROPIC GLUTAMATE RECEPTOR 5, AND METHODS OF USE THEREOF
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Page/Page column 177, (2011/07/07)
Provided herein are compounds and methods of synthesis thereof. The compounds set forth herein are useful for the treatment, prevention, and/or management of various disorders, such as neurological disorders, neurodegenerative disorders, neuropsychiatric disorders, disorders of cognition, learning or memory, gastrointestinal disorders, lower urinary tract disorder, and cancer. Compounds set forth herein modulate the activity of metabotropic glutamate receptor 5 (mGluR5) in the central nervous system or the periphery. Pharmaceutical formulations containing the compounds and their methods of use are also provided herein.
Structure-reactivity relationships of l-proline derived spirolactams and α-methyl prolinamide organocatalysts in the asymmetric Michael addition reaction of aldehydes to nitroolefins
Kelleher, Fintan,Kelly, Sinead,Watts, John,McKee, Vickie
experimental part, p. 3525 - 3536 (2010/06/17)
l-Proline derived spirolactams and α-methyl prolinamides act as organocatalysts for the asymmetric conjugate addition of aldehydes to nitroolefins in excellent yields, with good diastereoselectivity and enantioselectivity. Furthermore, low catalyst loadings (5 mol %) and a low aldehyde molar excess (1.5 M equiv) were achieved.
Intramolecular conjugate displacement: A general route to hexahydroquinolizines, hexahydroindolizines, and related [m,n,0]-bicyclic structures with nitrogen at a bridgehead
Clive, Derrick L. J.,Li, Zhiyong,Yu, Maolin
, p. 5608 - 5617 (2008/02/09)
(Chemical Equation Presented) N-Protected amino aldehydes can be converted into allylic alcohols by the classical Morita-Baylis-Hillman reaction (cf. 2 → 3) or by condensation with selenium-stabilized carbanions, followed by oxidation (cf. 2 → 8 → 3). The
Novel antibacterial class: A series of tetracyclic derivatives
Hinman, Mira M.,Rosenberg, Teresa A.,Balli, Darlene,Black-Schaefer, Candace,Chovan, Linda E.,Kalvin, Douglas,Merta, Philip J.,Nilius, Angela M.,Pratt, Steve D.,Soni, Niru B.,Wagenaar, Frank L.,Weitzberg, Moshe,Wagner, Rolf,Beutel, Bruce A.
, p. 4842 - 4856 (2007/10/03)
We describe the synthesis and antibacterial activity of a series of tetracyclic naphthyridones. The members of this series act primarily via inhibition of bacterial translation and belong to the class of novel ribosome inhibitors (NRIs). In this paper we
