Loading…
Molecular design and an attempt to synthesize a conjugate of 2-methoxyestradiol with adamantane
Based on molecular modeling data, 2-adamantyl 8-[(2-methoxyestra-1,3,5(10)-triene-3,17β-diol-6α-yl)amino]octanoate 2d is proposed as a structural analogue of highly cytotoxic N -(8-(adamant-2-yloxi)-8-oxooctanoyl)- N -deacetylcolchycine. Three-step synthesis of adamant-2-yl 8-aminooctanoate 5 is des...
Saved in:
| Published in: | Moscow University chemistry bulletin 2015-03, Vol.70 (2), p.69-73 |
|---|---|
| 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-c288t-176d8252dc7aed80bd214eafe8230a4d8356120dc806fc6201c5402575c24c7c3 |
|---|---|
| cites | cdi_FETCH-LOGICAL-c288t-176d8252dc7aed80bd214eafe8230a4d8356120dc806fc6201c5402575c24c7c3 |
| container_end_page | 73 |
| container_issue | 2 |
| container_start_page | 69 |
| container_title | Moscow University chemistry bulletin |
| container_volume | 70 |
| creator | Zefirov, N. A. Glazkova, Ya. S. Kuznetsova, I. V. Nurieva, E. V. Zefirova, O. N. |
| description | Based on molecular modeling data, 2-adamantyl 8-[(2-methoxyestra-1,3,5(10)-triene-3,17β-diol-6α-yl)amino]octanoate
2d
is proposed as a structural analogue of highly cytotoxic
N
-(8-(adamant-2-yloxi)-8-oxooctanoyl)-
N
-deacetylcolchycine. Three-step synthesis of adamant-2-yl 8-aminooctanoate
5
is described. Reductive amination of 2-methoxy-6-oxo-17β-estradiol in weakly acidic medium in the presence of compound
5
and NaBH
3
CN or Na(OAc)
3
BH results in the product of elimination at the C
6
–C
7
bond of steroid
7
rather than the formation of conjugate
2d
. |
| doi_str_mv | 10.3103/S0027131415020108 |
| format | article |
| fullrecord | <record><control><sourceid>crossref_sprin</sourceid><recordid>TN_cdi_crossref_primary_10_3103_S0027131415020108</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>10_3103_S0027131415020108</sourcerecordid><originalsourceid>FETCH-LOGICAL-c288t-176d8252dc7aed80bd214eafe8230a4d8356120dc806fc6201c5402575c24c7c3</originalsourceid><addsrcrecordid>eNp9kM9OwzAMhyMEEmPwANzyAgUnadpwRBP_pCEOwLkyibt1apMpSQXj6ek0bkgcLB8-f5b9Y-xSwJUSoK5fAWQtlCiFBgkCzBGbiRulC5AVHLPZHhd7fsrOUtoA6Eqqesaa59CTHXuM3FHqVp6jd1NxzJmGbeY58LTzeT3Bb-LIbfCbcYWZeGi5LAbK6_C1o5Qjui70_LPLa44OB_QZPZ2zkxb7RBe_fc7e7-_eFo_F8uXhaXG7LKw0JheirpyRWjpbIzkDH06KkrAlIxVg6YzSlZDgrIGqtdX0odUlSF1rK0tbWzVn4rDXxpBSpLbZxm7AuGsENPuEmj8JTY48OGma9SuKzSaM0U9n_iP9AJzqaG0</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Molecular design and an attempt to synthesize a conjugate of 2-methoxyestradiol with adamantane</title><source>Springer Nature</source><creator>Zefirov, N. A. ; Glazkova, Ya. S. ; Kuznetsova, I. V. ; Nurieva, E. V. ; Zefirova, O. N.</creator><creatorcontrib>Zefirov, N. A. ; Glazkova, Ya. S. ; Kuznetsova, I. V. ; Nurieva, E. V. ; Zefirova, O. N.</creatorcontrib><description>Based on molecular modeling data, 2-adamantyl 8-[(2-methoxyestra-1,3,5(10)-triene-3,17β-diol-6α-yl)amino]octanoate
2d
is proposed as a structural analogue of highly cytotoxic
N
-(8-(adamant-2-yloxi)-8-oxooctanoyl)-
N
-deacetylcolchycine. Three-step synthesis of adamant-2-yl 8-aminooctanoate
5
is described. Reductive amination of 2-methoxy-6-oxo-17β-estradiol in weakly acidic medium in the presence of compound
5
and NaBH
3
CN or Na(OAc)
3
BH results in the product of elimination at the C
6
–C
7
bond of steroid
7
rather than the formation of conjugate
2d
.</description><identifier>ISSN: 0027-1314</identifier><identifier>EISSN: 1935-0260</identifier><identifier>DOI: 10.3103/S0027131415020108</identifier><language>eng</language><publisher>New York: Allerton Press</publisher><subject>Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science</subject><ispartof>Moscow University chemistry bulletin, 2015-03, Vol.70 (2), p.69-73</ispartof><rights>Allerton Press, Inc. 2015</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c288t-176d8252dc7aed80bd214eafe8230a4d8356120dc806fc6201c5402575c24c7c3</citedby><cites>FETCH-LOGICAL-c288t-176d8252dc7aed80bd214eafe8230a4d8356120dc806fc6201c5402575c24c7c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids></links><search><creatorcontrib>Zefirov, N. A.</creatorcontrib><creatorcontrib>Glazkova, Ya. S.</creatorcontrib><creatorcontrib>Kuznetsova, I. V.</creatorcontrib><creatorcontrib>Nurieva, E. V.</creatorcontrib><creatorcontrib>Zefirova, O. N.</creatorcontrib><title>Molecular design and an attempt to synthesize a conjugate of 2-methoxyestradiol with adamantane</title><title>Moscow University chemistry bulletin</title><addtitle>Moscow Univ. Chem. Bull</addtitle><description>Based on molecular modeling data, 2-adamantyl 8-[(2-methoxyestra-1,3,5(10)-triene-3,17β-diol-6α-yl)amino]octanoate
2d
is proposed as a structural analogue of highly cytotoxic
N
-(8-(adamant-2-yloxi)-8-oxooctanoyl)-
N
-deacetylcolchycine. Three-step synthesis of adamant-2-yl 8-aminooctanoate
5
is described. Reductive amination of 2-methoxy-6-oxo-17β-estradiol in weakly acidic medium in the presence of compound
5
and NaBH
3
CN or Na(OAc)
3
BH results in the product of elimination at the C
6
–C
7
bond of steroid
7
rather than the formation of conjugate
2d
.</description><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><issn>0027-1314</issn><issn>1935-0260</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNp9kM9OwzAMhyMEEmPwANzyAgUnadpwRBP_pCEOwLkyibt1apMpSQXj6ek0bkgcLB8-f5b9Y-xSwJUSoK5fAWQtlCiFBgkCzBGbiRulC5AVHLPZHhd7fsrOUtoA6Eqqesaa59CTHXuM3FHqVp6jd1NxzJmGbeY58LTzeT3Bb-LIbfCbcYWZeGi5LAbK6_C1o5Qjui70_LPLa44OB_QZPZ2zkxb7RBe_fc7e7-_eFo_F8uXhaXG7LKw0JheirpyRWjpbIzkDH06KkrAlIxVg6YzSlZDgrIGqtdX0odUlSF1rK0tbWzVn4rDXxpBSpLbZxm7AuGsENPuEmj8JTY48OGma9SuKzSaM0U9n_iP9AJzqaG0</recordid><startdate>20150301</startdate><enddate>20150301</enddate><creator>Zefirov, N. A.</creator><creator>Glazkova, Ya. S.</creator><creator>Kuznetsova, I. V.</creator><creator>Nurieva, E. V.</creator><creator>Zefirova, O. N.</creator><general>Allerton Press</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20150301</creationdate><title>Molecular design and an attempt to synthesize a conjugate of 2-methoxyestradiol with adamantane</title><author>Zefirov, N. A. ; Glazkova, Ya. S. ; Kuznetsova, I. V. ; Nurieva, E. V. ; Zefirova, O. N.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c288t-176d8252dc7aed80bd214eafe8230a4d8356120dc806fc6201c5402575c24c7c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zefirov, N. A.</creatorcontrib><creatorcontrib>Glazkova, Ya. S.</creatorcontrib><creatorcontrib>Kuznetsova, I. V.</creatorcontrib><creatorcontrib>Nurieva, E. V.</creatorcontrib><creatorcontrib>Zefirova, O. N.</creatorcontrib><collection>CrossRef</collection><jtitle>Moscow University chemistry bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zefirov, N. A.</au><au>Glazkova, Ya. S.</au><au>Kuznetsova, I. V.</au><au>Nurieva, E. V.</au><au>Zefirova, O. N.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Molecular design and an attempt to synthesize a conjugate of 2-methoxyestradiol with adamantane</atitle><jtitle>Moscow University chemistry bulletin</jtitle><stitle>Moscow Univ. Chem. Bull</stitle><date>2015-03-01</date><risdate>2015</risdate><volume>70</volume><issue>2</issue><spage>69</spage><epage>73</epage><pages>69-73</pages><issn>0027-1314</issn><eissn>1935-0260</eissn><abstract>Based on molecular modeling data, 2-adamantyl 8-[(2-methoxyestra-1,3,5(10)-triene-3,17β-diol-6α-yl)amino]octanoate
2d
is proposed as a structural analogue of highly cytotoxic
N
-(8-(adamant-2-yloxi)-8-oxooctanoyl)-
N
-deacetylcolchycine. Three-step synthesis of adamant-2-yl 8-aminooctanoate
5
is described. Reductive amination of 2-methoxy-6-oxo-17β-estradiol in weakly acidic medium in the presence of compound
5
and NaBH
3
CN or Na(OAc)
3
BH results in the product of elimination at the C
6
–C
7
bond of steroid
7
rather than the formation of conjugate
2d
.</abstract><cop>New York</cop><pub>Allerton Press</pub><doi>10.3103/S0027131415020108</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0027-1314 |
| ispartof | Moscow University chemistry bulletin, 2015-03, Vol.70 (2), p.69-73 |
| issn | 0027-1314 1935-0260 |
| language | eng |
| recordid | cdi_crossref_primary_10_3103_S0027131415020108 |
| source | Springer Nature |
| subjects | Chemistry Chemistry and Materials Science Chemistry/Food Science |
| title | Molecular design and an attempt to synthesize a conjugate of 2-methoxyestradiol with adamantane |
| url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-11T12%3A23%3A12IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-crossref_sprin&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Molecular%20design%20and%20an%20attempt%20to%20synthesize%20a%20conjugate%20of%202-methoxyestradiol%20with%20adamantane&rft.jtitle=Moscow%20University%20chemistry%20bulletin&rft.au=Zefirov,%20N.%20A.&rft.date=2015-03-01&rft.volume=70&rft.issue=2&rft.spage=69&rft.epage=73&rft.pages=69-73&rft.issn=0027-1314&rft.eissn=1935-0260&rft_id=info:doi/10.3103/S0027131415020108&rft_dat=%3Ccrossref_sprin%3E10_3103_S0027131415020108%3C/crossref_sprin%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c288t-176d8252dc7aed80bd214eafe8230a4d8356120dc806fc6201c5402575c24c7c3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |