Microwave accelerated synthesis of isoxazole hydrazide inhibitors of the system xc-rter: Initial homology model

Afnan A. Matti; Joseph Mirzaei; John Rudolph; Stephen A. Smith; Jayme L. Newell; Sarjubhai A. Patel; Michael R. Braden; Richard J. Bridges; Nicholas R. Natale

doi:10.1016/j.bmcl.2013.08.080

Microwave accelerated synthesis of isoxazole hydrazide inhibitors of the system x_c^-rter: Initial homology model

Afnan A. Matti, Joseph Mirzaei, John Rudolph, Stephen A. Smith, Jayme L. Newell, Sarjubhai A. Patel, Michael R. Braden, Richard J. Bridges, Nicholas R. Natale

University of Montana

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

Abstract

Microwave accelerated reaction system (MARS) technology provided a good method to obtain selective and open isoxazole ligands that bind to and inhibit the Sxc^- antiporter. The MARS provided numerous advantages, including: shorter time, better yield and higher purity of the product. Of the newly synthesized series of isoxazoles the salicyl hydrazide 6 exhibited the highest level of inhibitory activity in the transport assay. A homology model has been developed to summarize the SAR results to date, and provide a working hypothesis for future studies.

Original language	English
Pages (from-to)	5931-5935
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	23
Issue number	21
DOIs	https://doi.org/10.1016/j.bmcl.2013.08.080
State	Published - Nov 1 2013

Funding

This work was supported in part by NIH NINDS Grants R21NS067466 (R.B. and N.N.) and P30-NS055022 (J.M. and N.N.). Modeling was carried out in the COBRE supported Molecular Computational Core facility with support from P20RR015583 and NIGMS P20GM103546 (M.B.). L.M. thanks Professor Sandy Ross of the University of Montana Graduate School for a graduate teaching assistantship. J.R. and S.A.S. acknowledge the support of the Neuroscience NSF REU at the University of Idaho .

Funders	Funder number
R21NS067466, P30-NS055022
P20RR015583
University of Idaho

Keywords

Cystine
Glutamate
Isoxazole
Microwave
Transporter

Access to Document

10.1016/j.bmcl.2013.08.080

Cite this

@article{de761170b2f2494d8c8f432999989ced,

title = "Microwave accelerated synthesis of isoxazole hydrazide inhibitors of the system xc-rter: Initial homology model",

abstract = "Microwave accelerated reaction system (MARS) technology provided a good method to obtain selective and open isoxazole ligands that bind to and inhibit the Sxc- antiporter. The MARS provided numerous advantages, including: shorter time, better yield and higher purity of the product. Of the newly synthesized series of isoxazoles the salicyl hydrazide 6 exhibited the highest level of inhibitory activity in the transport assay. A homology model has been developed to summarize the SAR results to date, and provide a working hypothesis for future studies.",

keywords = "Cystine, Glutamate, Isoxazole, Microwave, Transporter",

author = "Matti, \{Afnan A.\} and Joseph Mirzaei and John Rudolph and Smith, \{Stephen A.\} and Newell, \{Jayme L.\} and Patel, \{Sarjubhai A.\} and Braden, \{Michael R.\} and Bridges, \{Richard J.\} and Natale, \{Nicholas R.\}",

note = "Funding Information: This work was supported in part by NIH NINDS Grants R21NS067466 (R.B. and N.N.) and P30-NS055022 (J.M. and N.N.). Modeling was carried out in the COBRE supported Molecular Computational Core facility with support from P20RR015583 and NIGMS P20GM103546 (M.B.). L.M. thanks Professor Sandy Ross of the University of Montana Graduate School for a graduate teaching assistantship. J.R. and S.A.S. acknowledge the support of the Neuroscience NSF REU at the University of Idaho . ",

year = "2013",

month = nov,

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doi = "10.1016/j.bmcl.2013.08.080",

language = "English",

volume = "23",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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TY - JOUR

T1 - Microwave accelerated synthesis of isoxazole hydrazide inhibitors of the system xc-rter

T2 - Initial homology model

AU - Matti, Afnan A.

AU - Mirzaei, Joseph

AU - Rudolph, John

AU - Smith, Stephen A.

AU - Newell, Jayme L.

AU - Patel, Sarjubhai A.

AU - Braden, Michael R.

AU - Bridges, Richard J.

AU - Natale, Nicholas R.

N1 - Funding Information: This work was supported in part by NIH NINDS Grants R21NS067466 (R.B. and N.N.) and P30-NS055022 (J.M. and N.N.). Modeling was carried out in the COBRE supported Molecular Computational Core facility with support from P20RR015583 and NIGMS P20GM103546 (M.B.). L.M. thanks Professor Sandy Ross of the University of Montana Graduate School for a graduate teaching assistantship. J.R. and S.A.S. acknowledge the support of the Neuroscience NSF REU at the University of Idaho .

PY - 2013/11/1

Y1 - 2013/11/1

N2 - Microwave accelerated reaction system (MARS) technology provided a good method to obtain selective and open isoxazole ligands that bind to and inhibit the Sxc- antiporter. The MARS provided numerous advantages, including: shorter time, better yield and higher purity of the product. Of the newly synthesized series of isoxazoles the salicyl hydrazide 6 exhibited the highest level of inhibitory activity in the transport assay. A homology model has been developed to summarize the SAR results to date, and provide a working hypothesis for future studies.

AB - Microwave accelerated reaction system (MARS) technology provided a good method to obtain selective and open isoxazole ligands that bind to and inhibit the Sxc- antiporter. The MARS provided numerous advantages, including: shorter time, better yield and higher purity of the product. Of the newly synthesized series of isoxazoles the salicyl hydrazide 6 exhibited the highest level of inhibitory activity in the transport assay. A homology model has been developed to summarize the SAR results to date, and provide a working hypothesis for future studies.

KW - Cystine

KW - Glutamate

KW - Isoxazole

KW - Microwave

KW - Transporter

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DO - 10.1016/j.bmcl.2013.08.080

M3 - Article

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