Stereospecific 7α-alkylation of 20-hydroxyecdysone in a lithium–ammonia solution
[Display omitted] •For the first time stereoselective 7α-alkylation of ecdysteroids was accomplished.•Efficient syntheses of novel 7α-alkylecdysteroids as potential pharmacologically active compounds.•The structures of novel compounds were confirmed by NMR (1H, 13C, COSY, NOESY, HSQC and HMBC) and X...
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| Veröffentlicht in: | Steroids 2015-06, Vol.98, p.122-125 |
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| creator | Galyautdinov, Ilgiz V. Khairullina, Zarema R. Zaripova, Elvira R. Sametov, Valery P. Mescheryakova, Ekaterina S. Muslimov, Zabir S. Mozgovoi, Oleg S. Khalilov, Leonard M. Odinokov, Victor N. |
| description | [Display omitted]
•For the first time stereoselective 7α-alkylation of ecdysteroids was accomplished.•Efficient syntheses of novel 7α-alkylecdysteroids as potential pharmacologically active compounds.•The structures of novel compounds were confirmed by NMR (1H, 13C, COSY, NOESY, HSQC and HMBC) and X-ray diffraction analysis.
The reaction of 20-hydroxyecdysone with methyl or ethyl iodide or allyl bromide in a lithium–ammonia solution results in stereospecific 7α-alkylation to give 7α-methyl-, 7α-ethyl-, and 7α-allyl-14-deoxy-Δ8(14)-20-hydroxyecdysones, respectively. By catalytic hydrogenation (Pd-C/MeOH), the 7α-allyl derivative was converted to 7α-n-propyl-14-deoxy-Δ8(14)-20-hydroxyecdysone. |
| doi_str_mv | 10.1016/j.steroids.2015.03.002 |
| format | Article |
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•For the first time stereoselective 7α-alkylation of ecdysteroids was accomplished.•Efficient syntheses of novel 7α-alkylecdysteroids as potential pharmacologically active compounds.•The structures of novel compounds were confirmed by NMR (1H, 13C, COSY, NOESY, HSQC and HMBC) and X-ray diffraction analysis.
The reaction of 20-hydroxyecdysone with methyl or ethyl iodide or allyl bromide in a lithium–ammonia solution results in stereospecific 7α-alkylation to give 7α-methyl-, 7α-ethyl-, and 7α-allyl-14-deoxy-Δ8(14)-20-hydroxyecdysones, respectively. By catalytic hydrogenation (Pd-C/MeOH), the 7α-allyl derivative was converted to 7α-n-propyl-14-deoxy-Δ8(14)-20-hydroxyecdysone.</description><identifier>ISSN: 0039-128X</identifier><identifier>EISSN: 1878-5867</identifier><identifier>DOI: 10.1016/j.steroids.2015.03.002</identifier><identifier>PMID: 25777947</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>20-Hydroxyecdysone ; 7α-Alkylation ; 7α-Methyl-, 7α-ethyl-, 7α-n-propyl-, 7α-allyl-14-deoxy-Δ8-20-hydroxyecdysone ; Alkylation ; Ammonia - chemistry ; Catalysis ; Ecdysterone - chemistry ; Lithium - chemistry ; Lithium–ammonia solution</subject><ispartof>Steroids, 2015-06, Vol.98, p.122-125</ispartof><rights>2015 Elsevier Inc.</rights><rights>Copyright © 2015 Elsevier Inc. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c368t-4756b5fb5234f672442a841bdca232e3fca1d681757e67007ffa154fb7c3ea823</citedby><cites>FETCH-LOGICAL-c368t-4756b5fb5234f672442a841bdca232e3fca1d681757e67007ffa154fb7c3ea823</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.steroids.2015.03.002$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,27923,27924,45994</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25777947$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Galyautdinov, Ilgiz V.</creatorcontrib><creatorcontrib>Khairullina, Zarema R.</creatorcontrib><creatorcontrib>Zaripova, Elvira R.</creatorcontrib><creatorcontrib>Sametov, Valery P.</creatorcontrib><creatorcontrib>Mescheryakova, Ekaterina S.</creatorcontrib><creatorcontrib>Muslimov, Zabir S.</creatorcontrib><creatorcontrib>Mozgovoi, Oleg S.</creatorcontrib><creatorcontrib>Khalilov, Leonard M.</creatorcontrib><creatorcontrib>Odinokov, Victor N.</creatorcontrib><title>Stereospecific 7α-alkylation of 20-hydroxyecdysone in a lithium–ammonia solution</title><title>Steroids</title><addtitle>Steroids</addtitle><description>[Display omitted]
•For the first time stereoselective 7α-alkylation of ecdysteroids was accomplished.•Efficient syntheses of novel 7α-alkylecdysteroids as potential pharmacologically active compounds.•The structures of novel compounds were confirmed by NMR (1H, 13C, COSY, NOESY, HSQC and HMBC) and X-ray diffraction analysis.
The reaction of 20-hydroxyecdysone with methyl or ethyl iodide or allyl bromide in a lithium–ammonia solution results in stereospecific 7α-alkylation to give 7α-methyl-, 7α-ethyl-, and 7α-allyl-14-deoxy-Δ8(14)-20-hydroxyecdysones, respectively. By catalytic hydrogenation (Pd-C/MeOH), the 7α-allyl derivative was converted to 7α-n-propyl-14-deoxy-Δ8(14)-20-hydroxyecdysone.</description><subject>20-Hydroxyecdysone</subject><subject>7α-Alkylation</subject><subject>7α-Methyl-, 7α-ethyl-, 7α-n-propyl-, 7α-allyl-14-deoxy-Δ8-20-hydroxyecdysone</subject><subject>Alkylation</subject><subject>Ammonia - chemistry</subject><subject>Catalysis</subject><subject>Ecdysterone - chemistry</subject><subject>Lithium - chemistry</subject><subject>Lithium–ammonia solution</subject><issn>0039-128X</issn><issn>1878-5867</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkM1O3DAUha2qqDP8vALKspsE_yS-ya5o1AISEosBiZ3lONfC0yQe7KRqdrwDT9IX6UPwJGQ0TLdd3c13ztH9CDlnNGOUyYtNFgcM3jUx45QVGRUZpfwTWbISyrQoJXwmS0pFlTJePi7IcYwbSqkUFf9CFrwAgCqHJVmv5xr0cYvGWWcS-Psn1e3PqdWD833ibcJp-jQ1wf-e0DRT9D0mrk900rrhyY3d28ur7jrfO51E34671Ck5srqNePZxT8jDj-_3q-v09u7qZnV5mxohyyHNoZB1YeuCi9xK4HnOdZmzujGaC47CGs0aWTIoACVQCtZqVuS2BiNQl1yckK_73m3wzyPGQXUuGmxb3aMfo2ISQEAuq2pG5R41wccY0KptcJ0Ok2JU7YSqjToIVTuhigo1C52D5x8bY91h8y92MDgD3_YAzp_-chhUNA57g40LaAbVePe_jXfkd403</recordid><startdate>201506</startdate><enddate>201506</enddate><creator>Galyautdinov, Ilgiz V.</creator><creator>Khairullina, Zarema R.</creator><creator>Zaripova, Elvira R.</creator><creator>Sametov, Valery P.</creator><creator>Mescheryakova, Ekaterina S.</creator><creator>Muslimov, Zabir S.</creator><creator>Mozgovoi, Oleg S.</creator><creator>Khalilov, Leonard M.</creator><creator>Odinokov, Victor N.</creator><general>Elsevier Inc</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></search><sort><creationdate>201506</creationdate><title>Stereospecific 7α-alkylation of 20-hydroxyecdysone in a lithium–ammonia solution</title><author>Galyautdinov, Ilgiz V. ; Khairullina, Zarema R. ; Zaripova, Elvira R. ; Sametov, Valery P. ; Mescheryakova, Ekaterina S. ; Muslimov, Zabir S. ; Mozgovoi, Oleg S. ; Khalilov, Leonard M. ; Odinokov, Victor N.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c368t-4756b5fb5234f672442a841bdca232e3fca1d681757e67007ffa154fb7c3ea823</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>20-Hydroxyecdysone</topic><topic>7α-Alkylation</topic><topic>7α-Methyl-, 7α-ethyl-, 7α-n-propyl-, 7α-allyl-14-deoxy-Δ8-20-hydroxyecdysone</topic><topic>Alkylation</topic><topic>Ammonia - chemistry</topic><topic>Catalysis</topic><topic>Ecdysterone - chemistry</topic><topic>Lithium - chemistry</topic><topic>Lithium–ammonia solution</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Galyautdinov, Ilgiz V.</creatorcontrib><creatorcontrib>Khairullina, Zarema R.</creatorcontrib><creatorcontrib>Zaripova, Elvira R.</creatorcontrib><creatorcontrib>Sametov, Valery P.</creatorcontrib><creatorcontrib>Mescheryakova, Ekaterina S.</creatorcontrib><creatorcontrib>Muslimov, Zabir S.</creatorcontrib><creatorcontrib>Mozgovoi, Oleg S.</creatorcontrib><creatorcontrib>Khalilov, Leonard M.</creatorcontrib><creatorcontrib>Odinokov, Victor N.</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><jtitle>Steroids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Galyautdinov, Ilgiz V.</au><au>Khairullina, Zarema R.</au><au>Zaripova, Elvira R.</au><au>Sametov, Valery P.</au><au>Mescheryakova, Ekaterina S.</au><au>Muslimov, Zabir S.</au><au>Mozgovoi, Oleg S.</au><au>Khalilov, Leonard M.</au><au>Odinokov, Victor N.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereospecific 7α-alkylation of 20-hydroxyecdysone in a lithium–ammonia solution</atitle><jtitle>Steroids</jtitle><addtitle>Steroids</addtitle><date>2015-06</date><risdate>2015</risdate><volume>98</volume><spage>122</spage><epage>125</epage><pages>122-125</pages><issn>0039-128X</issn><eissn>1878-5867</eissn><abstract>[Display omitted]
•For the first time stereoselective 7α-alkylation of ecdysteroids was accomplished.•Efficient syntheses of novel 7α-alkylecdysteroids as potential pharmacologically active compounds.•The structures of novel compounds were confirmed by NMR (1H, 13C, COSY, NOESY, HSQC and HMBC) and X-ray diffraction analysis.
The reaction of 20-hydroxyecdysone with methyl or ethyl iodide or allyl bromide in a lithium–ammonia solution results in stereospecific 7α-alkylation to give 7α-methyl-, 7α-ethyl-, and 7α-allyl-14-deoxy-Δ8(14)-20-hydroxyecdysones, respectively. By catalytic hydrogenation (Pd-C/MeOH), the 7α-allyl derivative was converted to 7α-n-propyl-14-deoxy-Δ8(14)-20-hydroxyecdysone.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>25777947</pmid><doi>10.1016/j.steroids.2015.03.002</doi><tpages>4</tpages></addata></record> |
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| subjects | 20-Hydroxyecdysone 7α-Alkylation 7α-Methyl-, 7α-ethyl-, 7α-n-propyl-, 7α-allyl-14-deoxy-Δ8-20-hydroxyecdysone Alkylation Ammonia - chemistry Catalysis Ecdysterone - chemistry Lithium - chemistry Lithium–ammonia solution |
| title | Stereospecific 7α-alkylation of 20-hydroxyecdysone in a lithium–ammonia solution |
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