Synthesis and in vitro evaluation of side chain-unsaturated analogs of 24a,24b-dihomo-1,25-dihydroxycholecalciferol
A synthesis and an in vitro evaluation of side chain-unsaturated analogs 3 and 4 of 24a,24b-dihomo-1,25-dihydroxycholecalciferol ( 1) are described. Novel C 23a,24-vitamin D synthons (sulfone 10 and aldehyde 11) were used for the synthesis of analog 4 and for the efficient preparation of the parent...
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| Veröffentlicht in: | Steroids 1997-07, Vol.62 (7), p.546-553 |
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| creator | Chodyński, Michał Wojciechowska, Wanda Halkes, Sebastian J. van de Velde, Jan-Paul Kutner, Andrzej |
| description | A synthesis and an in vitro evaluation of side chain-unsaturated analogs
3 and
4 of 24a,24b-dihomo-1,25-dihydroxycholecalciferol (
1) are described. Novel C
23a,24-vitamin D synthons (sulfone
10 and aldehyde
11) were used for the synthesis of analog
4 and for the efficient preparation of the parent compound
1. The synthetic approach developed allows the use of easily available side chain fragments, such as oxirane
12 or Witting reagent
15 for the preparation of compound
1 and analog
4, respectively. Introduction of a 4a
E double bond results in a selective, 1000-fold increase in the binding affinity of analog
4 for the vitamin D receptor, compared to the affinity of
1, whereas the affinity of
4 for the vitamin D-binding protein and the activity in stimulating the differentiation of human promyelocytic leukemia HL-60 cells remained largely unchanged. |
| doi_str_mv | 10.1016/S0039-128X(97)00040-8 |
| format | Article |
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3 and
4 of 24a,24b-dihomo-1,25-dihydroxycholecalciferol (
1) are described. Novel C
23a,24-vitamin D synthons (sulfone
10 and aldehyde
11) were used for the synthesis of analog
4 and for the efficient preparation of the parent compound
1. The synthetic approach developed allows the use of easily available side chain fragments, such as oxirane
12 or Witting reagent
15 for the preparation of compound
1 and analog
4, respectively. Introduction of a 4a
E double bond results in a selective, 1000-fold increase in the binding affinity of analog
4 for the vitamin D receptor, compared to the affinity of
1, whereas the affinity of
4 for the vitamin D-binding protein and the activity in stimulating the differentiation of human promyelocytic leukemia HL-60 cells remained largely unchanged.</description><identifier>ISSN: 0039-128X</identifier><identifier>EISSN: 1878-5867</identifier><identifier>DOI: 10.1016/S0039-128X(97)00040-8</identifier><identifier>PMID: 9253795</identifier><identifier>CODEN: STEDAM</identifier><language>eng</language><publisher>New York, NY: Elsevier Inc</publisher><subject>Biological and medical sciences ; Calcitriol - analogs & derivatives ; Calcitriol - chemical synthesis ; Calcitriol - metabolism ; Calcitriol - pharmacology ; Calcium - metabolism ; calcium activity ; cell differentiation ; Cell Differentiation - drug effects ; Drug Evaluation, Preclinical ; Enzymes. Coenzymes. Vitamins. Pigments ; Fundamental and applied biological sciences. Psychology ; HL-60 Cells - drug effects ; Humans ; Intestinal Mucosa - metabolism ; Intestines - drug effects ; Isomerism ; Kidney - drug effects ; Kidney - metabolism ; Metabolisms and neurohumoral controls ; Receptors, Calcitriol - drug effects ; Receptors, Calcitriol - metabolism ; Structure-Activity Relationship ; Vertebrates: anatomy and physiology, studies on body, several organs or systems ; vitamin D analogs ; vitamin D receptor ; vitamin D-binding protein ; Vitamin D-Binding Protein - blood ; Vitamin D-Binding Protein - drug effects ; Vitamin D-Binding Protein - metabolism</subject><ispartof>Steroids, 1997-07, Vol.62 (7), p.546-553</ispartof><rights>1997</rights><rights>1997 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c389t-516f44bcec6cbd9aacc3a340a7716a8a45af6e115f84ab46e0722dcfcbdf06a13</citedby><cites>FETCH-LOGICAL-c389t-516f44bcec6cbd9aacc3a340a7716a8a45af6e115f84ab46e0722dcfcbdf06a13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/S0039-128X(97)00040-8$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,778,782,3539,27911,27912,45982</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2772029$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9253795$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chodyński, Michał</creatorcontrib><creatorcontrib>Wojciechowska, Wanda</creatorcontrib><creatorcontrib>Halkes, Sebastian J.</creatorcontrib><creatorcontrib>van de Velde, Jan-Paul</creatorcontrib><creatorcontrib>Kutner, Andrzej</creatorcontrib><title>Synthesis and in vitro evaluation of side chain-unsaturated analogs of 24a,24b-dihomo-1,25-dihydroxycholecalciferol</title><title>Steroids</title><addtitle>Steroids</addtitle><description>A synthesis and an in vitro evaluation of side chain-unsaturated analogs
3 and
4 of 24a,24b-dihomo-1,25-dihydroxycholecalciferol (
1) are described. Novel C
23a,24-vitamin D synthons (sulfone
10 and aldehyde
11) were used for the synthesis of analog
4 and for the efficient preparation of the parent compound
1. The synthetic approach developed allows the use of easily available side chain fragments, such as oxirane
12 or Witting reagent
15 for the preparation of compound
1 and analog
4, respectively. Introduction of a 4a
E double bond results in a selective, 1000-fold increase in the binding affinity of analog
4 for the vitamin D receptor, compared to the affinity of
1, whereas the affinity of
4 for the vitamin D-binding protein and the activity in stimulating the differentiation of human promyelocytic leukemia HL-60 cells remained largely unchanged.</description><subject>Biological and medical sciences</subject><subject>Calcitriol - analogs & derivatives</subject><subject>Calcitriol - chemical synthesis</subject><subject>Calcitriol - metabolism</subject><subject>Calcitriol - pharmacology</subject><subject>Calcium - metabolism</subject><subject>calcium activity</subject><subject>cell differentiation</subject><subject>Cell Differentiation - drug effects</subject><subject>Drug Evaluation, Preclinical</subject><subject>Enzymes. Coenzymes. Vitamins. Pigments</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>HL-60 Cells - drug effects</subject><subject>Humans</subject><subject>Intestinal Mucosa - metabolism</subject><subject>Intestines - drug effects</subject><subject>Isomerism</subject><subject>Kidney - drug effects</subject><subject>Kidney - metabolism</subject><subject>Metabolisms and neurohumoral controls</subject><subject>Receptors, Calcitriol - drug effects</subject><subject>Receptors, Calcitriol - metabolism</subject><subject>Structure-Activity Relationship</subject><subject>Vertebrates: anatomy and physiology, studies on body, several organs or systems</subject><subject>vitamin D analogs</subject><subject>vitamin D receptor</subject><subject>vitamin D-binding protein</subject><subject>Vitamin D-Binding Protein - blood</subject><subject>Vitamin D-Binding Protein - drug effects</subject><subject>Vitamin D-Binding Protein - metabolism</subject><issn>0039-128X</issn><issn>1878-5867</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1997</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkFFrFDEQx4Mo9Xr6EQr7IFKhqUk2u0meRIpVoeBDFXwLs8nEi-xtarJ79L59d3vHvfoQEpjfPzPzI-SCs2vOePvxnrHaUC7070ujPjDGJKP6BVlxrTRtdKtektUJeU3OS_k7Q21txBk5M6KplWlWpNzvh3GDJZYKBl_FodrFMacKd9BPMMY0VClUJXqs3AbiQKehwDhlGNHPCejTn7IQQsKVkB31cZO2ifIr0Szvvc_pce82qUcHvYsBc-rfkFcB-oJvj_ea_Lr98vPmG7378fX7zec76mptRtrwNkjZOXSt67wBcK6GWjJQiregQTYQWuS8CVpCJ1tkSgjvwgwH1gKv1-T94d-HnP5NWEa7jcVh38OAaSpWGa5rPZ81aQ6gy6mUjME-5LiFvLec2UW2fZZtF5PWKPss2y65i2ODqduiP6WOduf6u2Mdyrx-yDC4WE6YUEowYWbs0wHDWcYuYrbFRRwc-pjRjdan-J9BngD5tp2t</recordid><startdate>19970701</startdate><enddate>19970701</enddate><creator>Chodyński, Michał</creator><creator>Wojciechowska, Wanda</creator><creator>Halkes, Sebastian J.</creator><creator>van de Velde, Jan-Paul</creator><creator>Kutner, Andrzej</creator><general>Elsevier Inc</general><general>Elsevier Science</general><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><scope>7X8</scope></search><sort><creationdate>19970701</creationdate><title>Synthesis and in vitro evaluation of side chain-unsaturated analogs of 24a,24b-dihomo-1,25-dihydroxycholecalciferol</title><author>Chodyński, Michał ; Wojciechowska, Wanda ; Halkes, Sebastian J. ; van de Velde, Jan-Paul ; Kutner, Andrzej</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c389t-516f44bcec6cbd9aacc3a340a7716a8a45af6e115f84ab46e0722dcfcbdf06a13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1997</creationdate><topic>Biological and medical sciences</topic><topic>Calcitriol - analogs & derivatives</topic><topic>Calcitriol - chemical synthesis</topic><topic>Calcitriol - metabolism</topic><topic>Calcitriol - pharmacology</topic><topic>Calcium - metabolism</topic><topic>calcium activity</topic><topic>cell differentiation</topic><topic>Cell Differentiation - drug effects</topic><topic>Drug Evaluation, Preclinical</topic><topic>Enzymes. Coenzymes. Vitamins. Pigments</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>HL-60 Cells - drug effects</topic><topic>Humans</topic><topic>Intestinal Mucosa - metabolism</topic><topic>Intestines - drug effects</topic><topic>Isomerism</topic><topic>Kidney - drug effects</topic><topic>Kidney - metabolism</topic><topic>Metabolisms and neurohumoral controls</topic><topic>Receptors, Calcitriol - drug effects</topic><topic>Receptors, Calcitriol - metabolism</topic><topic>Structure-Activity Relationship</topic><topic>Vertebrates: anatomy and physiology, studies on body, several organs or systems</topic><topic>vitamin D analogs</topic><topic>vitamin D receptor</topic><topic>vitamin D-binding protein</topic><topic>Vitamin D-Binding Protein - blood</topic><topic>Vitamin D-Binding Protein - drug effects</topic><topic>Vitamin D-Binding Protein - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chodyński, Michał</creatorcontrib><creatorcontrib>Wojciechowska, Wanda</creatorcontrib><creatorcontrib>Halkes, Sebastian J.</creatorcontrib><creatorcontrib>van de Velde, Jan-Paul</creatorcontrib><creatorcontrib>Kutner, Andrzej</creatorcontrib><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><collection>MEDLINE - Academic</collection><jtitle>Steroids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chodyński, Michał</au><au>Wojciechowska, Wanda</au><au>Halkes, Sebastian J.</au><au>van de Velde, Jan-Paul</au><au>Kutner, Andrzej</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and in vitro evaluation of side chain-unsaturated analogs of 24a,24b-dihomo-1,25-dihydroxycholecalciferol</atitle><jtitle>Steroids</jtitle><addtitle>Steroids</addtitle><date>1997-07-01</date><risdate>1997</risdate><volume>62</volume><issue>7</issue><spage>546</spage><epage>553</epage><pages>546-553</pages><issn>0039-128X</issn><eissn>1878-5867</eissn><coden>STEDAM</coden><abstract>A synthesis and an in vitro evaluation of side chain-unsaturated analogs
3 and
4 of 24a,24b-dihomo-1,25-dihydroxycholecalciferol (
1) are described. Novel C
23a,24-vitamin D synthons (sulfone
10 and aldehyde
11) were used for the synthesis of analog
4 and for the efficient preparation of the parent compound
1. The synthetic approach developed allows the use of easily available side chain fragments, such as oxirane
12 or Witting reagent
15 for the preparation of compound
1 and analog
4, respectively. Introduction of a 4a
E double bond results in a selective, 1000-fold increase in the binding affinity of analog
4 for the vitamin D receptor, compared to the affinity of
1, whereas the affinity of
4 for the vitamin D-binding protein and the activity in stimulating the differentiation of human promyelocytic leukemia HL-60 cells remained largely unchanged.</abstract><cop>New York, NY</cop><pub>Elsevier Inc</pub><pmid>9253795</pmid><doi>10.1016/S0039-128X(97)00040-8</doi><tpages>8</tpages></addata></record> |
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| ispartof | Steroids, 1997-07, Vol.62 (7), p.546-553 |
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| language | eng |
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| source | Elsevier ScienceDirect Journals Complete - AutoHoldings; MEDLINE |
| subjects | Biological and medical sciences Calcitriol - analogs & derivatives Calcitriol - chemical synthesis Calcitriol - metabolism Calcitriol - pharmacology Calcium - metabolism calcium activity cell differentiation Cell Differentiation - drug effects Drug Evaluation, Preclinical Enzymes. Coenzymes. Vitamins. Pigments Fundamental and applied biological sciences. Psychology HL-60 Cells - drug effects Humans Intestinal Mucosa - metabolism Intestines - drug effects Isomerism Kidney - drug effects Kidney - metabolism Metabolisms and neurohumoral controls Receptors, Calcitriol - drug effects Receptors, Calcitriol - metabolism Structure-Activity Relationship Vertebrates: anatomy and physiology, studies on body, several organs or systems vitamin D analogs vitamin D receptor vitamin D-binding protein Vitamin D-Binding Protein - blood Vitamin D-Binding Protein - drug effects Vitamin D-Binding Protein - metabolism |
| title | Synthesis and in vitro evaluation of side chain-unsaturated analogs of 24a,24b-dihomo-1,25-dihydroxycholecalciferol |
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