2002
DOI: 10.1039/b209147j
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Synthesis, biological activity, and conformational analysis of CD-ring modified trans-decalin 1α,25-dihydroxyvitamin D analogsElectronic supplementary information (ESI) available: Further experimental details. See http://www.rsc.org/suppdata/ob/b2/b209147j/

Abstract: A novel series of analogs of 1,25-dihydroxyvitamin D3, the hormonally active metabolite of vitamin D3, characterised by the presence of a trans-fused decalin CD-ring system, possesses surprising biological activities in combination with specific structural modifications in the flexible parts of the molecule, when compared with the natural hydrindane derivatives. (1) A large difference in biological activity is observed between the 20-epimeric trans-decalin analogs that follows a pattern opposite to what is usu… Show more

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Cited by 39 publications
(11 citation statements)
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“…The trans-decalin analog CY10012 is at least 10 times as potent in antiproliferative action as 1,25-(OH) 2 D 3 but also twice as calcemic. Its 19-nor counterpart CY10010 has similar antiproliferative action but is as calcemic as 1,25-(OH) 2 D 3 [115].…”
Section: -(M-hydroxyphenyl)-125-(oh)2d3mentioning
confidence: 99%
“…The trans-decalin analog CY10012 is at least 10 times as potent in antiproliferative action as 1,25-(OH) 2 D 3 but also twice as calcemic. Its 19-nor counterpart CY10010 has similar antiproliferative action but is as calcemic as 1,25-(OH) 2 D 3 [115].…”
Section: -(M-hydroxyphenyl)-125-(oh)2d3mentioning
confidence: 99%
“…4a , 4b ) [ 10 ]; (iii) unsaturation at C8,C9 (e.g. 5a , 5b ) [ 11 ]; and (iv) analogues featuring an enlarged six-membered D-ring [ 12 ].…”
Section: Resultsmentioning
confidence: 99%
“…The same research group [65] also reported the synthesis of four D-ring-modified, natural side chain 19-nor-1α,25-(OH) 2 -D 3 derivatives 173 lacking C15 and diastereomeric at C17 and C20. Vandewalle's group [66,67] presented the synthesis of analogs 179 from a decalin-type CD-ring moiety (Scheme 35). In addition to the fundamental change of the natural hydrindane CD-ring fragment into a decalin system, they also combined this with other modifications as 20-epi and/or 14-epi, the latter being as consequence of the formation of transor cis-fused decalin.…”
Section: Synthesis Of D-ring-and Side-chain-modified Analogsmentioning
confidence: 99%
“…Vandewalle’s group [ 66 , 67 ] presented the synthesis of analogs 179 from a decalin-type CD-ring moiety ( Scheme 35 ). In addition to the fundamental change of the natural hydrindane CD-ring fragment into a decalin system, they also combined this with other modifications as 20- epi and/or 14- epi , the latter being as consequence of the formation of trans - or cis -fused decalin.…”
Section: Synthesis Of Cd-ring-modified 1α25-(oh) 2 mentioning
confidence: 99%