Synthesis of N-Glyoxyl Prolyl and Pipecolyl Amides and Thioesters and Evaluation of Their In Vitro and In Vivo Nerve Regenerative Effects
The recent discovery that small molecule ligands for the peptidyl−prolyl isomerase (PPIase) FKBP12 possess powerful neuroprotective and neuroregenerative properties in vitro and in vivo suggests therapeutic utility for such compounds in neurodegenerative disease. The neurotrophic effects of these co...
Gespeichert in:
| Veröffentlicht in: | Journal of medicinal chemistry 2002-08, Vol.45 (16), p.3549-3557 |
|---|---|
| Hauptverfasser: | , , , , , , , , , , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3557 |
|---|---|
| container_issue | 16 |
| container_start_page | 3549 |
| container_title | Journal of medicinal chemistry |
| container_volume | 45 |
| creator | Hamilton, Gregory S Wu, Yong-Qian Limburg, David C Wilkinson, Douglas E Vaal, Mark J Li, Jia-He Thomas, Christine Huang, Wei Sauer, Hansjorg Ross, Douglas T Soni, Raj Chen, Yi Guo, Hongshi Howorth, Pamela Valentine, Heather Liang, Shi Spicer, Dawn Fuller, Mike Steiner, Joseph P |
| description | The recent discovery that small molecule ligands for the peptidyl−prolyl isomerase (PPIase) FKBP12 possess powerful neuroprotective and neuroregenerative properties in vitro and in vivo suggests therapeutic utility for such compounds in neurodegenerative disease. The neurotrophic effects of these compounds are independent of the immunosuppressive pathways by which drugs such as FK506 and rapamycin operate. Previous work by ourselves and other groups exploring the structure−activity relationships (SAR) of small molecules that mimic only the FKBP binding domain portion of FK506 has focused on esters of proline and pipecolic acid. We have explored amide and thioester analogues of these earlier structures and found that they too are extremely potent in promoting recovery of lesioned dopaminergic pathways in a mouse model of Parkinson's disease. Several compounds were shown to be highly effective upon oral administration after lesioning of the dopaminergic pathway, providing further evidence of the potential clinical utility of a variety of structural classes of FKBP12 ligands. |
| doi_str_mv | 10.1021/jm010556c |
| format | Article |
| fullrecord | <record><control><sourceid>acs_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_jm010556c</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>a858266127</sourcerecordid><originalsourceid>FETCH-LOGICAL-a379t-c3e6626f9233090c996aafc4e70662062f61ccf0c3803ed44ea0c420aa744213</originalsourceid><addsrcrecordid>eNptkMtOIzEQRS0EGjIwC34A9YYFix7Kj7jTS0AhIDEQJq3ZWsYpE4dOO7I7EfmE-Wuch8iGVemWj6_sQ8gZhd8UGL2azoBCtyvNAenQLoNc9EAckg4AYzmTjB-TnzFOAYBTxn-QY8ooL4WUHfJ_tGraCUYXM2-zp3xQr_zHqs6Gwddp6GacDd0czSZdz9wY42ZZTZzH2GLYxv5S1wvdOt-sa6oJupA9NNk_1wa_ATZh6bMnDEvM_uIbNhjShRT61qJp4yk5srqO-Gs3T0h1169u7_PH58HD7fVjrnlRtrnhKCWTtmScQwmmLKXW1ggsIO1BMiupMRYM7wHHsRCowQgGWhdCpG-fkMttrQk-xoBWzYOb6bBSFNTapvqymdjzLTtfvM5wvCd3-hJwsQN0NLq2QTfGxT3He4wztubyLeeSso-vcx3elSx40VXVcKRGfxjQl8GNutn3ahPV1C9Ck4x888BPJiGXzA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Synthesis of N-Glyoxyl Prolyl and Pipecolyl Amides and Thioesters and Evaluation of Their In Vitro and In Vivo Nerve Regenerative Effects</title><source>ACS Publications</source><source>MEDLINE</source><creator>Hamilton, Gregory S ; Wu, Yong-Qian ; Limburg, David C ; Wilkinson, Douglas E ; Vaal, Mark J ; Li, Jia-He ; Thomas, Christine ; Huang, Wei ; Sauer, Hansjorg ; Ross, Douglas T ; Soni, Raj ; Chen, Yi ; Guo, Hongshi ; Howorth, Pamela ; Valentine, Heather ; Liang, Shi ; Spicer, Dawn ; Fuller, Mike ; Steiner, Joseph P</creator><creatorcontrib>Hamilton, Gregory S ; Wu, Yong-Qian ; Limburg, David C ; Wilkinson, Douglas E ; Vaal, Mark J ; Li, Jia-He ; Thomas, Christine ; Huang, Wei ; Sauer, Hansjorg ; Ross, Douglas T ; Soni, Raj ; Chen, Yi ; Guo, Hongshi ; Howorth, Pamela ; Valentine, Heather ; Liang, Shi ; Spicer, Dawn ; Fuller, Mike ; Steiner, Joseph P</creatorcontrib><description>The recent discovery that small molecule ligands for the peptidyl−prolyl isomerase (PPIase) FKBP12 possess powerful neuroprotective and neuroregenerative properties in vitro and in vivo suggests therapeutic utility for such compounds in neurodegenerative disease. The neurotrophic effects of these compounds are independent of the immunosuppressive pathways by which drugs such as FK506 and rapamycin operate. Previous work by ourselves and other groups exploring the structure−activity relationships (SAR) of small molecules that mimic only the FKBP binding domain portion of FK506 has focused on esters of proline and pipecolic acid. We have explored amide and thioester analogues of these earlier structures and found that they too are extremely potent in promoting recovery of lesioned dopaminergic pathways in a mouse model of Parkinson's disease. Several compounds were shown to be highly effective upon oral administration after lesioning of the dopaminergic pathway, providing further evidence of the potential clinical utility of a variety of structural classes of FKBP12 ligands.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm010556c</identifier><identifier>PMID: 12139466</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine ; Administration, Oral ; Amides - chemical synthesis ; Amides - chemistry ; Amides - pharmacology ; Animals ; Biological and medical sciences ; Corpus Striatum - enzymology ; Corpus Striatum - pathology ; Corpus Striatum - ultrastructure ; Degenerative and inherited degenerative diseases of the nervous system. Leukodystrophies. Prion diseases ; Dopamine Agents ; Immunohistochemistry ; Ligands ; Medical sciences ; Mice ; Molecular Mimicry ; Nerve Regeneration - drug effects ; Neurites - drug effects ; Neurology ; Neuroprotective Agents - chemical synthesis ; Neuroprotective Agents - chemistry ; Neuroprotective Agents - pharmacology ; Parkinson Disease, Secondary - chemically induced ; Parkinson Disease, Secondary - drug therapy ; Parkinson Disease, Secondary - pathology ; Pipecolic Acids - chemical synthesis ; Pipecolic Acids - chemistry ; Pipecolic Acids - pharmacology ; Proline - analogs & derivatives ; Proline - chemical synthesis ; Proline - chemistry ; Proline - pharmacology ; Structure-Activity Relationship ; Substantia Nigra - enzymology ; Substantia Nigra - pathology ; Substantia Nigra - ultrastructure ; Sulfhydryl Compounds - chemical synthesis ; Sulfhydryl Compounds - chemistry ; Sulfhydryl Compounds - pharmacology ; Tacrolimus Binding Protein 1A - antagonists & inhibitors ; Tacrolimus Binding Protein 1A - chemistry ; Tyrosine 3-Monooxygenase - metabolism</subject><ispartof>Journal of medicinal chemistry, 2002-08, Vol.45 (16), p.3549-3557</ispartof><rights>Copyright © 2002 American Chemical Society</rights><rights>2002 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-c3e6626f9233090c996aafc4e70662062f61ccf0c3803ed44ea0c420aa744213</citedby><cites>FETCH-LOGICAL-a379t-c3e6626f9233090c996aafc4e70662062f61ccf0c3803ed44ea0c420aa744213</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm010556c$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm010556c$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=13823226$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12139466$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hamilton, Gregory S</creatorcontrib><creatorcontrib>Wu, Yong-Qian</creatorcontrib><creatorcontrib>Limburg, David C</creatorcontrib><creatorcontrib>Wilkinson, Douglas E</creatorcontrib><creatorcontrib>Vaal, Mark J</creatorcontrib><creatorcontrib>Li, Jia-He</creatorcontrib><creatorcontrib>Thomas, Christine</creatorcontrib><creatorcontrib>Huang, Wei</creatorcontrib><creatorcontrib>Sauer, Hansjorg</creatorcontrib><creatorcontrib>Ross, Douglas T</creatorcontrib><creatorcontrib>Soni, Raj</creatorcontrib><creatorcontrib>Chen, Yi</creatorcontrib><creatorcontrib>Guo, Hongshi</creatorcontrib><creatorcontrib>Howorth, Pamela</creatorcontrib><creatorcontrib>Valentine, Heather</creatorcontrib><creatorcontrib>Liang, Shi</creatorcontrib><creatorcontrib>Spicer, Dawn</creatorcontrib><creatorcontrib>Fuller, Mike</creatorcontrib><creatorcontrib>Steiner, Joseph P</creatorcontrib><title>Synthesis of N-Glyoxyl Prolyl and Pipecolyl Amides and Thioesters and Evaluation of Their In Vitro and In Vivo Nerve Regenerative Effects</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>The recent discovery that small molecule ligands for the peptidyl−prolyl isomerase (PPIase) FKBP12 possess powerful neuroprotective and neuroregenerative properties in vitro and in vivo suggests therapeutic utility for such compounds in neurodegenerative disease. The neurotrophic effects of these compounds are independent of the immunosuppressive pathways by which drugs such as FK506 and rapamycin operate. Previous work by ourselves and other groups exploring the structure−activity relationships (SAR) of small molecules that mimic only the FKBP binding domain portion of FK506 has focused on esters of proline and pipecolic acid. We have explored amide and thioester analogues of these earlier structures and found that they too are extremely potent in promoting recovery of lesioned dopaminergic pathways in a mouse model of Parkinson's disease. Several compounds were shown to be highly effective upon oral administration after lesioning of the dopaminergic pathway, providing further evidence of the potential clinical utility of a variety of structural classes of FKBP12 ligands.</description><subject>1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine</subject><subject>Administration, Oral</subject><subject>Amides - chemical synthesis</subject><subject>Amides - chemistry</subject><subject>Amides - pharmacology</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Corpus Striatum - enzymology</subject><subject>Corpus Striatum - pathology</subject><subject>Corpus Striatum - ultrastructure</subject><subject>Degenerative and inherited degenerative diseases of the nervous system. Leukodystrophies. Prion diseases</subject><subject>Dopamine Agents</subject><subject>Immunohistochemistry</subject><subject>Ligands</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Molecular Mimicry</subject><subject>Nerve Regeneration - drug effects</subject><subject>Neurites - drug effects</subject><subject>Neurology</subject><subject>Neuroprotective Agents - chemical synthesis</subject><subject>Neuroprotective Agents - chemistry</subject><subject>Neuroprotective Agents - pharmacology</subject><subject>Parkinson Disease, Secondary - chemically induced</subject><subject>Parkinson Disease, Secondary - drug therapy</subject><subject>Parkinson Disease, Secondary - pathology</subject><subject>Pipecolic Acids - chemical synthesis</subject><subject>Pipecolic Acids - chemistry</subject><subject>Pipecolic Acids - pharmacology</subject><subject>Proline - analogs & derivatives</subject><subject>Proline - chemical synthesis</subject><subject>Proline - chemistry</subject><subject>Proline - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>Substantia Nigra - enzymology</subject><subject>Substantia Nigra - pathology</subject><subject>Substantia Nigra - ultrastructure</subject><subject>Sulfhydryl Compounds - chemical synthesis</subject><subject>Sulfhydryl Compounds - chemistry</subject><subject>Sulfhydryl Compounds - pharmacology</subject><subject>Tacrolimus Binding Protein 1A - antagonists & inhibitors</subject><subject>Tacrolimus Binding Protein 1A - chemistry</subject><subject>Tyrosine 3-Monooxygenase - metabolism</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtOIzEQRS0EGjIwC34A9YYFix7Kj7jTS0AhIDEQJq3ZWsYpE4dOO7I7EfmE-Wuch8iGVemWj6_sQ8gZhd8UGL2azoBCtyvNAenQLoNc9EAckg4AYzmTjB-TnzFOAYBTxn-QY8ooL4WUHfJ_tGraCUYXM2-zp3xQr_zHqs6Gwddp6GacDd0czSZdz9wY42ZZTZzH2GLYxv5S1wvdOt-sa6oJupA9NNk_1wa_ATZh6bMnDEvM_uIbNhjShRT61qJp4yk5srqO-Gs3T0h1169u7_PH58HD7fVjrnlRtrnhKCWTtmScQwmmLKXW1ggsIO1BMiupMRYM7wHHsRCowQgGWhdCpG-fkMttrQk-xoBWzYOb6bBSFNTapvqymdjzLTtfvM5wvCd3-hJwsQN0NLq2QTfGxT3He4wztubyLeeSso-vcx3elSx40VXVcKRGfxjQl8GNutn3ahPV1C9Ck4x888BPJiGXzA</recordid><startdate>20020801</startdate><enddate>20020801</enddate><creator>Hamilton, Gregory S</creator><creator>Wu, Yong-Qian</creator><creator>Limburg, David C</creator><creator>Wilkinson, Douglas E</creator><creator>Vaal, Mark J</creator><creator>Li, Jia-He</creator><creator>Thomas, Christine</creator><creator>Huang, Wei</creator><creator>Sauer, Hansjorg</creator><creator>Ross, Douglas T</creator><creator>Soni, Raj</creator><creator>Chen, Yi</creator><creator>Guo, Hongshi</creator><creator>Howorth, Pamela</creator><creator>Valentine, Heather</creator><creator>Liang, Shi</creator><creator>Spicer, Dawn</creator><creator>Fuller, Mike</creator><creator>Steiner, Joseph P</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20020801</creationdate><title>Synthesis of N-Glyoxyl Prolyl and Pipecolyl Amides and Thioesters and Evaluation of Their In Vitro and In Vivo Nerve Regenerative Effects</title><author>Hamilton, Gregory S ; Wu, Yong-Qian ; Limburg, David C ; Wilkinson, Douglas E ; Vaal, Mark J ; Li, Jia-He ; Thomas, Christine ; Huang, Wei ; Sauer, Hansjorg ; Ross, Douglas T ; Soni, Raj ; Chen, Yi ; Guo, Hongshi ; Howorth, Pamela ; Valentine, Heather ; Liang, Shi ; Spicer, Dawn ; Fuller, Mike ; Steiner, Joseph P</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-c3e6626f9233090c996aafc4e70662062f61ccf0c3803ed44ea0c420aa744213</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine</topic><topic>Administration, Oral</topic><topic>Amides - chemical synthesis</topic><topic>Amides - chemistry</topic><topic>Amides - pharmacology</topic><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Corpus Striatum - enzymology</topic><topic>Corpus Striatum - pathology</topic><topic>Corpus Striatum - ultrastructure</topic><topic>Degenerative and inherited degenerative diseases of the nervous system. Leukodystrophies. Prion diseases</topic><topic>Dopamine Agents</topic><topic>Immunohistochemistry</topic><topic>Ligands</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Molecular Mimicry</topic><topic>Nerve Regeneration - drug effects</topic><topic>Neurites - drug effects</topic><topic>Neurology</topic><topic>Neuroprotective Agents - chemical synthesis</topic><topic>Neuroprotective Agents - chemistry</topic><topic>Neuroprotective Agents - pharmacology</topic><topic>Parkinson Disease, Secondary - chemically induced</topic><topic>Parkinson Disease, Secondary - drug therapy</topic><topic>Parkinson Disease, Secondary - pathology</topic><topic>Pipecolic Acids - chemical synthesis</topic><topic>Pipecolic Acids - chemistry</topic><topic>Pipecolic Acids - pharmacology</topic><topic>Proline - analogs & derivatives</topic><topic>Proline - chemical synthesis</topic><topic>Proline - chemistry</topic><topic>Proline - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>Substantia Nigra - enzymology</topic><topic>Substantia Nigra - pathology</topic><topic>Substantia Nigra - ultrastructure</topic><topic>Sulfhydryl Compounds - chemical synthesis</topic><topic>Sulfhydryl Compounds - chemistry</topic><topic>Sulfhydryl Compounds - pharmacology</topic><topic>Tacrolimus Binding Protein 1A - antagonists & inhibitors</topic><topic>Tacrolimus Binding Protein 1A - chemistry</topic><topic>Tyrosine 3-Monooxygenase - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hamilton, Gregory S</creatorcontrib><creatorcontrib>Wu, Yong-Qian</creatorcontrib><creatorcontrib>Limburg, David C</creatorcontrib><creatorcontrib>Wilkinson, Douglas E</creatorcontrib><creatorcontrib>Vaal, Mark J</creatorcontrib><creatorcontrib>Li, Jia-He</creatorcontrib><creatorcontrib>Thomas, Christine</creatorcontrib><creatorcontrib>Huang, Wei</creatorcontrib><creatorcontrib>Sauer, Hansjorg</creatorcontrib><creatorcontrib>Ross, Douglas T</creatorcontrib><creatorcontrib>Soni, Raj</creatorcontrib><creatorcontrib>Chen, Yi</creatorcontrib><creatorcontrib>Guo, Hongshi</creatorcontrib><creatorcontrib>Howorth, Pamela</creatorcontrib><creatorcontrib>Valentine, Heather</creatorcontrib><creatorcontrib>Liang, Shi</creatorcontrib><creatorcontrib>Spicer, Dawn</creatorcontrib><creatorcontrib>Fuller, Mike</creatorcontrib><creatorcontrib>Steiner, Joseph P</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hamilton, Gregory S</au><au>Wu, Yong-Qian</au><au>Limburg, David C</au><au>Wilkinson, Douglas E</au><au>Vaal, Mark J</au><au>Li, Jia-He</au><au>Thomas, Christine</au><au>Huang, Wei</au><au>Sauer, Hansjorg</au><au>Ross, Douglas T</au><au>Soni, Raj</au><au>Chen, Yi</au><au>Guo, Hongshi</au><au>Howorth, Pamela</au><au>Valentine, Heather</au><au>Liang, Shi</au><au>Spicer, Dawn</au><au>Fuller, Mike</au><au>Steiner, Joseph P</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of N-Glyoxyl Prolyl and Pipecolyl Amides and Thioesters and Evaluation of Their In Vitro and In Vivo Nerve Regenerative Effects</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2002-08-01</date><risdate>2002</risdate><volume>45</volume><issue>16</issue><spage>3549</spage><epage>3557</epage><pages>3549-3557</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>The recent discovery that small molecule ligands for the peptidyl−prolyl isomerase (PPIase) FKBP12 possess powerful neuroprotective and neuroregenerative properties in vitro and in vivo suggests therapeutic utility for such compounds in neurodegenerative disease. The neurotrophic effects of these compounds are independent of the immunosuppressive pathways by which drugs such as FK506 and rapamycin operate. Previous work by ourselves and other groups exploring the structure−activity relationships (SAR) of small molecules that mimic only the FKBP binding domain portion of FK506 has focused on esters of proline and pipecolic acid. We have explored amide and thioester analogues of these earlier structures and found that they too are extremely potent in promoting recovery of lesioned dopaminergic pathways in a mouse model of Parkinson's disease. Several compounds were shown to be highly effective upon oral administration after lesioning of the dopaminergic pathway, providing further evidence of the potential clinical utility of a variety of structural classes of FKBP12 ligands.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12139466</pmid><doi>10.1021/jm010556c</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 2002-08, Vol.45 (16), p.3549-3557 |
| issn | 0022-2623 1520-4804 |
| language | eng |
| recordid | cdi_crossref_primary_10_1021_jm010556c |
| source | ACS Publications; MEDLINE |
| subjects | 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine Administration, Oral Amides - chemical synthesis Amides - chemistry Amides - pharmacology Animals Biological and medical sciences Corpus Striatum - enzymology Corpus Striatum - pathology Corpus Striatum - ultrastructure Degenerative and inherited degenerative diseases of the nervous system. Leukodystrophies. Prion diseases Dopamine Agents Immunohistochemistry Ligands Medical sciences Mice Molecular Mimicry Nerve Regeneration - drug effects Neurites - drug effects Neurology Neuroprotective Agents - chemical synthesis Neuroprotective Agents - chemistry Neuroprotective Agents - pharmacology Parkinson Disease, Secondary - chemically induced Parkinson Disease, Secondary - drug therapy Parkinson Disease, Secondary - pathology Pipecolic Acids - chemical synthesis Pipecolic Acids - chemistry Pipecolic Acids - pharmacology Proline - analogs & derivatives Proline - chemical synthesis Proline - chemistry Proline - pharmacology Structure-Activity Relationship Substantia Nigra - enzymology Substantia Nigra - pathology Substantia Nigra - ultrastructure Sulfhydryl Compounds - chemical synthesis Sulfhydryl Compounds - chemistry Sulfhydryl Compounds - pharmacology Tacrolimus Binding Protein 1A - antagonists & inhibitors Tacrolimus Binding Protein 1A - chemistry Tyrosine 3-Monooxygenase - metabolism |
| title | Synthesis of N-Glyoxyl Prolyl and Pipecolyl Amides and Thioesters and Evaluation of Their In Vitro and In Vivo Nerve Regenerative Effects |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-09T16%3A35%3A24IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%20N-Glyoxyl%20Prolyl%20and%20Pipecolyl%20Amides%20and%20Thioesters%20and%20Evaluation%20of%20Their%20In%20Vitro%20and%20In%20Vivo%20Nerve%20Regenerative%20Effects&rft.jtitle=Journal%20of%20medicinal%20chemistry&rft.au=Hamilton,%20Gregory%20S&rft.date=2002-08-01&rft.volume=45&rft.issue=16&rft.spage=3549&rft.epage=3557&rft.pages=3549-3557&rft.issn=0022-2623&rft.eissn=1520-4804&rft.coden=JMCMAR&rft_id=info:doi/10.1021/jm010556c&rft_dat=%3Cacs_cross%3Ea858266127%3C/acs_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/12139466&rfr_iscdi=true |