37850-75-2Relevant articles and documents
A non-calcemic sulfone version of the vitamin D3 analogue seocalcitol (EB 1089): chemical synthesis, biological evaluation and potency enhancement of the anticancer drug adriamycin
Posner, Gary H.,Crawford, Kenneth R.,Peleg, Sara,Welsh, Jo-Ellen,Romu, Saara,Gewirtz, David A.,Gupta, Mona S.,Dolan, Patrick,Kensler, Thomas W.
, p. 2365 - 2371 (2001)
Novel side-chain diene sulfones 5, analogues of the natural hormone 1α 25-dihydroxyvitamin D3 (calcitriol, 1), were designed to incorporate some of the therapeutically most favorable structural features of the Leo Pharmaceutical Companys drug candidate diene EB 1089 (seocalcitol, 4) and of the Hopkins' non-calcemic side-chain sulfone analogues 2 and 3. Synthesis of diene sulfones 5 features selective Swern oxidation of a primary silyl ether in the presence of a secondary silyl ether (9→10) and Horner Wadsworth Emmons aldehyde addition by a 1-phosphonyl-3-sulfonyl stabilized carbanion regiospecifically at the 1-position to form E,E-diene sulfone 11. Sulfone diene analogue 5a with natural 1α,3b-diol functionality, but not its diastereomer 5b with unnatural A-ring stereochemistry, is antiproliferative in vitro toward murine keratinocytes and malignant melanoma cells, as well as toward MCF-7 human breast cancer cells. Combining diene sulfone 5a with the currently used anticancer drug adriamycin (ADR) caused a noteworthy 3-fold enhancement of ADR antiproliferative potency in MCF-7 cells. Sulfone diene analogue 5a is weakly active transcriptionally in MCF-7 and ROS 17/2.8 cells, binds poorly but measurably to the vitamin D receptor (VDR), and desirably is non-calcemic in vivo at a daily dose (7 days) of 10 mg/kg of rat body weight. Copyright
Intermolecular Aminoallylation of Alkenes Using Allyl-Oxyphthalimide Derivatives: A Case Study in Radical Polarity Effects
Lardy, Samuel W.,Schmidt, Valerie A.
supporting information, p. 6796 - 6799 (2019/11/03)
A case study on the polarity effects of radical mediated intermolecular alkene aminoallylation is presented herein. This radical group transfer method pairs vinyl ethers with electronically deficient allyl-oxyphthalimide derivatives to give difunctionalized products while illustrating the guiding effects of polarity on this radical reactivity.
Synthesis and use of amino acid fluorides as peptide coupling reagents
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, (2008/06/13)
The present invention is directed to the process of preparing a peptide comprising reacting a first amino acid or peptide with an amino acid fluoride of the formula: STR1 or the acid fluoride salts thereof wherein BLK is an N-amino protecting group AA is an amino acid residue and X is H or a protecting group useful, and the first amino and peptide have a free amino group and a blocked carboxy end.