Constrained TRPV1 agonists synthesized via silver-mediated intramolecular azo-methine ylide cycloaddition of α-iminoamides
dc.contributor.author | Painter, Thomas O. | |
dc.contributor.author | Kaszas, Krisztian | |
dc.contributor.author | Gross, Jacklyn | |
dc.contributor.author | Douglas, Justin T. | |
dc.contributor.author | Day, Victor W. | |
dc.contributor.author | Iadarola, Michael J. | |
dc.contributor.author | Santini, Conrad | |
dc.date.accessioned | 2017-05-31T18:06:42Z | |
dc.date.available | 2017-05-31T18:06:42Z | |
dc.date.issued | 2014-02-01 | |
dc.identifier.citation | Painter, T. O., Kaszas, K., Gross, J., Douglas, J. T., Day, V. W., Iadarola, M. J., & Santini, C. (2014). Constrained TRPV1 agonists synthesized via silver-mediated intramolecular azo-methine ylide cycloaddition of α-iminoamides. Bioorganic & Medicinal Chemistry Letters, 24(3), 963–968. http://doi.org/10.1016/j.bmcl.2013.12.061 | en_US |
dc.identifier.uri | http://hdl.handle.net/1808/24318 | |
dc.description.abstract | As part of an effort to identify agonists of TRPV1, a peripheral sensory nerve ion channel, high throughput screening of the NIH Small Molecule Repository (SMR) collection identified MLS002174161, a pentacyclic benzodiazepine. A synthesis effort was initiated that ultimately afforded racemic seco analogs 12 of the SMR compound via a silver mediated intramolecular [3+2] cycloaddition of an azo-methine ylide generated from α-iminoamides 11. The cycloaddition set four contiguous stereocenters and, in some cases, also spontaneously afforded imides 13 from 12. The synthesis of compounds 12, the features that facilitated the conversion of 12–13, and their partial agonist activity against TRPV1 are discussed. | en_US |
dc.publisher | Elsevier | en_US |
dc.rights | This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License 4.0 (CC BY-NC-ND 4.0), which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made. | en_US |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ | en_US |
dc.subject | Chronic pain | en_US |
dc.subject | Peripheral nerve ion channels | en_US |
dc.subject | Intramolecular cycloaddition | en_US |
dc.subject | TRPV1 agonists | en_US |
dc.title | Constrained TRPV1 agonists synthesized via silver-mediated intramolecular azo-methine ylide cycloaddition of α-iminoamides | en_US |
dc.type | Article | en_US |
kusw.kuauthor | Painter, Thomas O. | |
kusw.kuauthor | Douglas, Justin T. | |
kusw.kuauthor | Day, Victor W. | |
kusw.kuauthor | Santini, Conrad | |
kusw.kudepartment | Molecular Structures Group | en_US |
kusw.kudepartment | Center for Chemical Methodologies and Library Development | en_US |
dc.identifier.doi | 10.1016/j.bmcl.2013.12.061 | en_US |
kusw.oaversion | Scholarly/refereed, author accepted manuscript | en_US |
kusw.oapolicy | This item meets KU Open Access policy criteria. | en_US |
dc.identifier.pmid | PMC4568941 | en_US |
dc.rights.accessrights | openAccess |
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Except where otherwise noted, this item's license is described as: This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License 4.0 (CC BY-NC-ND 4.0), which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.