ChemInform Abstract: The 16‐Ene Vitamin D Analogues

Abstract

The 16-Ene Vitamin D Analogues -(synthesis and application against prostate cancer; 41 refs.). -(USKOKOVIC, M. R.; STUDZINSKI, G. P.; GARDNER, J. P.; REDDY, S. G.; CAMPBELL, M. J.; KOEFFLER, H. P.; Curr.

Vitamin D analogues targeting CYP24 in chronic kidney disease

“…Moreover, we also prepared a series of side chain sulfone analogues capable of acting as side chain hydrogen-bond acceptors [15]. Inspired by seminal Hoffman-LaRoche studies [16], we incorporated a 16,23-diene unit into our designer sulfones. We identified two promising analogues: the sulfoximine MK-24(S)-S(O)(NH)-Ph-1 (CTA091), which is a potent, selective and non-calcemic inhibitor of CYP24 [17] (Fig.…”

The development of a bone- and parathyroid-specific analog of vitamin D: 2-methylene-19-Nor-(20S)-1α,25-dihydroxyvitamin D3

“…Following the isolation, identification and demonstration of the importance of 1a,25-dihydroxyvitamin D 3 (1,25-(OH) 2 D 3 ) as the hormonal form of vitamin D, syntheses not only of the 1,25-(OH) 2 D 3 but also of variations in that structure were carried out in an attempt to reduce the undesirable hypercalcemic effect of the native hormone. 1,2 Many of these analogs have not been thoroughly tested to determine whether they have selective activity. Further, the assays in laboratories differ, and thus a comparison of their biological activities is difficult.…”

The Synthesis and Biological Evaluation of D-Ring-Modified Vitamin D Analogues

“…Next, 17 was converted to iodide (18), followed by the Zn/Ni-promoted Michael addition of iodide (18) to ethyl acrylate to produce ethyl ester (19). The ethyl ester (19) was treated with methyl magnesium bromide or ethyl magnesium bromide to give alcohol (20,21). After oxidation of 20 and 21, protection of the C25-hydroxy group afforded 8-keto-CD-ring (22) and (23).…”

“…The ethyl ester (19) was treated with methyl magnesium bromide or ethyl magnesium bromide to give alcohol (20,21). After oxidation of 20 and 21, protection of the C25-hydroxy group afforded 8-keto-CD-ring (22) and (23). Each ketone (22,23) and the racemic A-ring moiety (24) were coupled using PhLi, and then protecting groups of the coupling products were removed in the presence of TBAF to afford 16-ene analogues (9-12) (Scheme 3).…”

“…The 26,27-fluorinated-16-ene ( 63 , 64 , 66 , 69 , 71 , 73 , 80–83 , 85 , 87 , 90 , 92 – 95 ) and non-fluorinated ( 3 , 65 , 67 , 68 , 70 , 72 , 74–79 , 84 , 86 , 88 , 89 , 91 ) analogues have been synthesized to date ( Figure 1 ). Uskoković et al published a comprehensive review article in this field, including synthetic routes and biological activities [ 21 ].…”