Loading…
Synthesis and biological evaluation of longanlactone analogues as neurotrophic agents
Evaluation of neurotrophic activity of longanlactone along with its analogues has been achieved for the first time. A total of 12-analogues have been prepared including C4-epimers. [Display omitted] •Longanlactone, a natural pyrrole-lactone alkaloid, analogs were synthesized.•Neurotrophic effects of...
Saved in:
| Published in: | Bioorganic & medicinal chemistry letters 2018-02, Vol.28 (4), p.673-676 |
|---|---|
| Main Authors: | , , , , , , , , |
| Format: | Article |
| Language: | English |
| Subjects: | |
| Citations: | Items that this one cites Items that cite this one |
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| cited_by | cdi_FETCH-LOGICAL-c434t-3aba0084008caf6792613da84412606ac71abfcded1224a4422a75c857ef5d763 |
|---|---|
| cites | cdi_FETCH-LOGICAL-c434t-3aba0084008caf6792613da84412606ac71abfcded1224a4422a75c857ef5d763 |
| container_end_page | 676 |
| container_issue | 4 |
| container_start_page | 673 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 28 |
| creator | Reddy, Chada Raji Tukaram, Amol Gorgile Mohammed, Siddique Z. Dilipkumar, Uredi Babu, Bathini Nagendra Chakravarty, Sumana Bhattacharya, Dwaipayan Joshi, Pranav C. Grée, René |
| description | Evaluation of neurotrophic activity of longanlactone along with its analogues has been achieved for the first time. A total of 12-analogues have been prepared including C4-epimers.
[Display omitted]
•Longanlactone, a natural pyrrole-lactone alkaloid, analogs were synthesized.•Neurotrophic effects of Longanlactone analogs were studied for the first time.•mRNA Fold change was observed in BDNF gene expression study of Longanlactone.
Longanlactone analogues were synthesized using a route featuring Friedel-Crafts acylation, Sonogashira coupling and 1,3-dipolar cycloaddition reactions. Structure–activity relationships were investigated for neurotrophic activity. Compound 6 was found to have the most potent neurotrophic activity among all the synthesized analogues in Neuro2a cells as evidenced by a battery of in vitro/cell based assays for assessment of neurogenic and potential neurotrophic activity including neurite outgrowth assay and real time PCR for popular markers of augmented neurotrophic activity. Compound 6 might serve as a template for further development of highly effective neurotrophic molecules. |
| doi_str_mv | 10.1016/j.bmcl.2018.01.020 |
| format | article |
| fullrecord | <record><control><sourceid>proquest_hal_p</sourceid><recordid>TN_cdi_hal_primary_oai_HAL_hal_01737386v1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0960894X18300301</els_id><sourcerecordid>1995151322</sourcerecordid><originalsourceid>FETCH-LOGICAL-c434t-3aba0084008caf6792613da84412606ac71abfcded1224a4422a75c857ef5d763</originalsourceid><addsrcrecordid>eNp9kMFq3DAQhkVpabZpX6CH4mN7sCPJY9mGXkJIm8JCD00gNzGWx7tatNJWshfy9tGyaY49iAHx_f8MH2OfBa8EF-pqVw174yrJRVdxUXHJ37CVAAVlDbx5y1a8V7zseni8YB9S2nEugAO8ZxeyBy5bgBV7-PPk5y0lmwr0YzHY4MLGGnQFHdEtONvgizAVLvgNeodmDp4yihlbKIdS4WmJYY7hsLWmwA35OX1k7yZ0iT69zEv28OP2_uauXP_--evmel0aqGEuaxyQ8w7yMziptpdK1CN2AEIqrtC0AofJjDQKKQEBpMS2MV3T0tSMraov2bdz7xadPkS7x_ikA1p9d73Wpz8u2rqtO3UUmf16Zg8x_M2nz3pvkyHn0FNYkhZ934hG1FJmVJ5RE0NKkabXbsH1Sb3e6ZN6fVKfd-isPoe-vPQvw57G18g_1xn4fgYoGzlaijoZS97QaCOZWY_B_q__GQASlM0</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1995151322</pqid></control><display><type>article</type><title>Synthesis and biological evaluation of longanlactone analogues as neurotrophic agents</title><source>ScienceDirect Freedom Collection 2022-2024</source><creator>Reddy, Chada Raji ; Tukaram, Amol Gorgile ; Mohammed, Siddique Z. ; Dilipkumar, Uredi ; Babu, Bathini Nagendra ; Chakravarty, Sumana ; Bhattacharya, Dwaipayan ; Joshi, Pranav C. ; Grée, René</creator><creatorcontrib>Reddy, Chada Raji ; Tukaram, Amol Gorgile ; Mohammed, Siddique Z. ; Dilipkumar, Uredi ; Babu, Bathini Nagendra ; Chakravarty, Sumana ; Bhattacharya, Dwaipayan ; Joshi, Pranav C. ; Grée, René</creatorcontrib><description>Evaluation of neurotrophic activity of longanlactone along with its analogues has been achieved for the first time. A total of 12-analogues have been prepared including C4-epimers.
[Display omitted]
•Longanlactone, a natural pyrrole-lactone alkaloid, analogs were synthesized.•Neurotrophic effects of Longanlactone analogs were studied for the first time.•mRNA Fold change was observed in BDNF gene expression study of Longanlactone.
Longanlactone analogues were synthesized using a route featuring Friedel-Crafts acylation, Sonogashira coupling and 1,3-dipolar cycloaddition reactions. Structure–activity relationships were investigated for neurotrophic activity. Compound 6 was found to have the most potent neurotrophic activity among all the synthesized analogues in Neuro2a cells as evidenced by a battery of in vitro/cell based assays for assessment of neurogenic and potential neurotrophic activity including neurite outgrowth assay and real time PCR for popular markers of augmented neurotrophic activity. Compound 6 might serve as a template for further development of highly effective neurotrophic molecules.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2018.01.020</identifier><identifier>PMID: 29402744</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Animals ; Brain-Derived Neurotrophic Factor - genetics ; Cell Line, Tumor ; Chemical Sciences ; Drug Design ; Lactones - chemical synthesis ; Lactones - pharmacology ; Lactones - toxicity ; Longanlactone ; Medicinal Chemistry ; Mice ; Molecular Structure ; Neuronal Outgrowth - drug effects ; Neurotrophic agent ; Organic chemistry ; Pyrrole alkaloid ; Pyrroles - chemical synthesis ; Pyrroles - pharmacology ; Pyrroles - toxicity ; RNA, Messenger - metabolism</subject><ispartof>Bioorganic & medicinal chemistry letters, 2018-02, Vol.28 (4), p.673-676</ispartof><rights>2018 Elsevier Ltd</rights><rights>Copyright © 2018 Elsevier Ltd. All rights reserved.</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c434t-3aba0084008caf6792613da84412606ac71abfcded1224a4422a75c857ef5d763</citedby><cites>FETCH-LOGICAL-c434t-3aba0084008caf6792613da84412606ac71abfcded1224a4422a75c857ef5d763</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29402744$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://univ-rennes.hal.science/hal-01737386$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Reddy, Chada Raji</creatorcontrib><creatorcontrib>Tukaram, Amol Gorgile</creatorcontrib><creatorcontrib>Mohammed, Siddique Z.</creatorcontrib><creatorcontrib>Dilipkumar, Uredi</creatorcontrib><creatorcontrib>Babu, Bathini Nagendra</creatorcontrib><creatorcontrib>Chakravarty, Sumana</creatorcontrib><creatorcontrib>Bhattacharya, Dwaipayan</creatorcontrib><creatorcontrib>Joshi, Pranav C.</creatorcontrib><creatorcontrib>Grée, René</creatorcontrib><title>Synthesis and biological evaluation of longanlactone analogues as neurotrophic agents</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Evaluation of neurotrophic activity of longanlactone along with its analogues has been achieved for the first time. A total of 12-analogues have been prepared including C4-epimers.
[Display omitted]
•Longanlactone, a natural pyrrole-lactone alkaloid, analogs were synthesized.•Neurotrophic effects of Longanlactone analogs were studied for the first time.•mRNA Fold change was observed in BDNF gene expression study of Longanlactone.
Longanlactone analogues were synthesized using a route featuring Friedel-Crafts acylation, Sonogashira coupling and 1,3-dipolar cycloaddition reactions. Structure–activity relationships were investigated for neurotrophic activity. Compound 6 was found to have the most potent neurotrophic activity among all the synthesized analogues in Neuro2a cells as evidenced by a battery of in vitro/cell based assays for assessment of neurogenic and potential neurotrophic activity including neurite outgrowth assay and real time PCR for popular markers of augmented neurotrophic activity. Compound 6 might serve as a template for further development of highly effective neurotrophic molecules.</description><subject>Animals</subject><subject>Brain-Derived Neurotrophic Factor - genetics</subject><subject>Cell Line, Tumor</subject><subject>Chemical Sciences</subject><subject>Drug Design</subject><subject>Lactones - chemical synthesis</subject><subject>Lactones - pharmacology</subject><subject>Lactones - toxicity</subject><subject>Longanlactone</subject><subject>Medicinal Chemistry</subject><subject>Mice</subject><subject>Molecular Structure</subject><subject>Neuronal Outgrowth - drug effects</subject><subject>Neurotrophic agent</subject><subject>Organic chemistry</subject><subject>Pyrrole alkaloid</subject><subject>Pyrroles - chemical synthesis</subject><subject>Pyrroles - pharmacology</subject><subject>Pyrroles - toxicity</subject><subject>RNA, Messenger - metabolism</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp9kMFq3DAQhkVpabZpX6CH4mN7sCPJY9mGXkJIm8JCD00gNzGWx7tatNJWshfy9tGyaY49iAHx_f8MH2OfBa8EF-pqVw174yrJRVdxUXHJ37CVAAVlDbx5y1a8V7zseni8YB9S2nEugAO8ZxeyBy5bgBV7-PPk5y0lmwr0YzHY4MLGGnQFHdEtONvgizAVLvgNeodmDp4yihlbKIdS4WmJYY7hsLWmwA35OX1k7yZ0iT69zEv28OP2_uauXP_--evmel0aqGEuaxyQ8w7yMziptpdK1CN2AEIqrtC0AofJjDQKKQEBpMS2MV3T0tSMraov2bdz7xadPkS7x_ikA1p9d73Wpz8u2rqtO3UUmf16Zg8x_M2nz3pvkyHn0FNYkhZ934hG1FJmVJ5RE0NKkabXbsH1Sb3e6ZN6fVKfd-isPoe-vPQvw57G18g_1xn4fgYoGzlaijoZS97QaCOZWY_B_q__GQASlM0</recordid><startdate>20180215</startdate><enddate>20180215</enddate><creator>Reddy, Chada Raji</creator><creator>Tukaram, Amol Gorgile</creator><creator>Mohammed, Siddique Z.</creator><creator>Dilipkumar, Uredi</creator><creator>Babu, Bathini Nagendra</creator><creator>Chakravarty, Sumana</creator><creator>Bhattacharya, Dwaipayan</creator><creator>Joshi, Pranav C.</creator><creator>Grée, René</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>1XC</scope><scope>VOOES</scope></search><sort><creationdate>20180215</creationdate><title>Synthesis and biological evaluation of longanlactone analogues as neurotrophic agents</title><author>Reddy, Chada Raji ; Tukaram, Amol Gorgile ; Mohammed, Siddique Z. ; Dilipkumar, Uredi ; Babu, Bathini Nagendra ; Chakravarty, Sumana ; Bhattacharya, Dwaipayan ; Joshi, Pranav C. ; Grée, René</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c434t-3aba0084008caf6792613da84412606ac71abfcded1224a4422a75c857ef5d763</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Animals</topic><topic>Brain-Derived Neurotrophic Factor - genetics</topic><topic>Cell Line, Tumor</topic><topic>Chemical Sciences</topic><topic>Drug Design</topic><topic>Lactones - chemical synthesis</topic><topic>Lactones - pharmacology</topic><topic>Lactones - toxicity</topic><topic>Longanlactone</topic><topic>Medicinal Chemistry</topic><topic>Mice</topic><topic>Molecular Structure</topic><topic>Neuronal Outgrowth - drug effects</topic><topic>Neurotrophic agent</topic><topic>Organic chemistry</topic><topic>Pyrrole alkaloid</topic><topic>Pyrroles - chemical synthesis</topic><topic>Pyrroles - pharmacology</topic><topic>Pyrroles - toxicity</topic><topic>RNA, Messenger - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Reddy, Chada Raji</creatorcontrib><creatorcontrib>Tukaram, Amol Gorgile</creatorcontrib><creatorcontrib>Mohammed, Siddique Z.</creatorcontrib><creatorcontrib>Dilipkumar, Uredi</creatorcontrib><creatorcontrib>Babu, Bathini Nagendra</creatorcontrib><creatorcontrib>Chakravarty, Sumana</creatorcontrib><creatorcontrib>Bhattacharya, Dwaipayan</creatorcontrib><creatorcontrib>Joshi, Pranav C.</creatorcontrib><creatorcontrib>Grée, René</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Reddy, Chada Raji</au><au>Tukaram, Amol Gorgile</au><au>Mohammed, Siddique Z.</au><au>Dilipkumar, Uredi</au><au>Babu, Bathini Nagendra</au><au>Chakravarty, Sumana</au><au>Bhattacharya, Dwaipayan</au><au>Joshi, Pranav C.</au><au>Grée, René</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and biological evaluation of longanlactone analogues as neurotrophic agents</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2018-02-15</date><risdate>2018</risdate><volume>28</volume><issue>4</issue><spage>673</spage><epage>676</epage><pages>673-676</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Evaluation of neurotrophic activity of longanlactone along with its analogues has been achieved for the first time. A total of 12-analogues have been prepared including C4-epimers.
[Display omitted]
•Longanlactone, a natural pyrrole-lactone alkaloid, analogs were synthesized.•Neurotrophic effects of Longanlactone analogs were studied for the first time.•mRNA Fold change was observed in BDNF gene expression study of Longanlactone.
Longanlactone analogues were synthesized using a route featuring Friedel-Crafts acylation, Sonogashira coupling and 1,3-dipolar cycloaddition reactions. Structure–activity relationships were investigated for neurotrophic activity. Compound 6 was found to have the most potent neurotrophic activity among all the synthesized analogues in Neuro2a cells as evidenced by a battery of in vitro/cell based assays for assessment of neurogenic and potential neurotrophic activity including neurite outgrowth assay and real time PCR for popular markers of augmented neurotrophic activity. Compound 6 might serve as a template for further development of highly effective neurotrophic molecules.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>29402744</pmid><doi>10.1016/j.bmcl.2018.01.020</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2018-02, Vol.28 (4), p.673-676 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_hal_primary_oai_HAL_hal_01737386v1 |
| source | ScienceDirect Freedom Collection 2022-2024 |
| subjects | Animals Brain-Derived Neurotrophic Factor - genetics Cell Line, Tumor Chemical Sciences Drug Design Lactones - chemical synthesis Lactones - pharmacology Lactones - toxicity Longanlactone Medicinal Chemistry Mice Molecular Structure Neuronal Outgrowth - drug effects Neurotrophic agent Organic chemistry Pyrrole alkaloid Pyrroles - chemical synthesis Pyrroles - pharmacology Pyrroles - toxicity RNA, Messenger - metabolism |
| title | Synthesis and biological evaluation of longanlactone analogues as neurotrophic agents |
| url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-04T05%3A51%3A51IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_hal_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20and%20biological%20evaluation%20of%20longanlactone%20analogues%20as%20neurotrophic%20agents&rft.jtitle=Bioorganic%20&%20medicinal%20chemistry%20letters&rft.au=Reddy,%20Chada%20Raji&rft.date=2018-02-15&rft.volume=28&rft.issue=4&rft.spage=673&rft.epage=676&rft.pages=673-676&rft.issn=0960-894X&rft.eissn=1464-3405&rft_id=info:doi/10.1016/j.bmcl.2018.01.020&rft_dat=%3Cproquest_hal_p%3E1995151322%3C/proquest_hal_p%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c434t-3aba0084008caf6792613da84412606ac71abfcded1224a4422a75c857ef5d763%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1995151322&rft_id=info:pmid/29402744&rfr_iscdi=true |