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Pyrrolidine-substituted nicotine analogs: Synthesis and ..

T1 - Hydroxylated pyrrolidines. Enantiospecific synthesis of all-cis 2,3,4,5-substituted pyrrolidine derivatives from serine

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pyrrolidine substituted—synthesis;

N2 - We report the enantiospecific synthesis of the sterically congested all-cis 2,3,4,5-substituted pyrrolidines 4, 5, and 6, from either D- or L-serine. Hemiaminal intermediate 13 is converted to the fully substituted pyrrolidine 15 by way of a tandem Wittig-Michael reaction. The endo stereochemistry of the C-3 methyl group of compound 15 is set by stereoselective reduction of the double bond in 11, driven by a preference for hydrogenation from the rear side of the molecule. The all-cis configuration of these fully substituted pyrrolidines has been established by X-ray analysis of compound 6. Removal of the benzenesulfonyl group from the highly substituted and functionalized intermediate 15 is successfully accomplished by sodium naphthalenide reduction.

Synthesis and biological evaluation of nojirimycin- and pyrrolidine-based trehalase inhibitors
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AB - We report the enantiospecific synthesis of the sterically congested all-cis 2,3,4,5-substituted pyrrolidines 4, 5, and 6, from either D- or L-serine. Hemiaminal intermediate 13 is converted to the fully substituted pyrrolidine 15 by way of a tandem Wittig-Michael reaction. The endo stereochemistry of the C-3 methyl group of compound 15 is set by stereoselective reduction of the double bond in 11, driven by a preference for hydrogenation from the rear side of the molecule. The all-cis configuration of these fully substituted pyrrolidines has been established by X-ray analysis of compound 6. Removal of the benzenesulfonyl group from the highly substituted and functionalized intermediate 15 is successfully accomplished by sodium naphthalenide reduction.

Overman pyrrolidine synthesis essay - Pro Anima

T1 - Improved synthesis of chiral pyrrolidine inhibitors and their binding properties to neuronal nitric oxide synthase
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The carboxamide N-(substituted phenyl) pyrrolidine-2-carboxamide (3a-i) and 1-acetyl-N-(4-chlorophenyl) pyrrolidine-2-carboxamide (4a-f) were prepared according to the previously reported procedures [5]. Pyrrolidine-2-carbonyl chloride 2 was synthesized from pyrrolidine-2-carboxylic acid (L-proline), which was then treated with appropriate substituted aromatic amines in dry acetone to obtain the resulting carboxamide derivatives (3a-i). The synthetic route for the resulting carboxamides derivatives (3a-i) is outlined in Scheme 1.

We report the enantiospecific synthesis of the sterically congested all-cis 2,3,4,5-substituted pyrrolidines 4, 5, and 6, from either D- or L-serine. Hemiaminal intermediate 13 is converted to the fully substituted pyrrolidine 15 by way of a tandem Wittig-Michael reaction. The endo stereochemistry of the C-3 methyl group of compound 15 is set by stereoselective reduction of the double bond in 11, driven by a preference for hydrogenation from the rear side of the molecule. The all-cis configuration of these fully substituted pyrrolidines has been established by X-ray analysis of compound 6. Removal of the benzenesulfonyl group from the highly substituted and functionalized intermediate 15 is successfully accomplished by sodium naphthalenide reduction.

Synthesis of Pyrrolidine Derivatives by the ..

Chiral Synthesis of Pyrrolidine Core Compounds en …
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AB - We report an efficient synthetic route to chiral pyrrolidine inhibitors of neuronal nitric oxide synthase (nNOS) and crystal structures of the inhibitors bound to nNOS and to endothelial NOS. The new route enables versatile structure-activity relationship studies on the pyrrolidine-based scaffold, which can be beneficial for further development of nNOS inhibitors. The X-ray crystal structures of five new fluorine-containing inhibitors bound to nNOS provide insights into the effect of the fluorine atoms on binding.

N2 - We report an efficient synthetic route to chiral pyrrolidine inhibitors of neuronal nitric oxide synthase (nNOS) and crystal structures of the inhibitors bound to nNOS and to endothelial NOS. The new route enables versatile structure-activity relationship studies on the pyrrolidine-based scaffold, which can be beneficial for further development of nNOS inhibitors. The X-ray crystal structures of five new fluorine-containing inhibitors bound to nNOS provide insights into the effect of the fluorine atoms on binding.

Patent EP2074087A2 - Synthesis of pyrrolidine …
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    Pyrrolidine synthesis essay

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SNU Chemistry builiding located at Gwanak Campus, Seoul, Kor.

In present investigation a series of N-(substituted phenyl) pyrrolidine-2-carboxamide derivatives were synthesized and were evaluated for activity by using maximal electroshock seizure (MES) test in mice. The structures of the synthesized compounds were confirmed on the basis of their spectral data and elemental analysis. Most of the compounds were found to be active in MES tests without any . Compounds 3a and 3d were found the most active of the series without any neurotoxicity and less CNS depressant effect as compared to standard drug .

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We report an efficient synthetic route to chiral pyrrolidine inhibitors of neuronal nitric oxide synthase (nNOS) and crystal structures of the inhibitors bound to nNOS and to endothelial NOS. The new route enables versatile structure-activity relationship studies on the pyrrolidine-based scaffold, which can be beneficial for further development of nNOS inhibitors. The X-ray crystal structures of five new fluorine-containing inhibitors bound to nNOS provide insights into the effect of the fluorine atoms on binding.

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