111924-49-3Relevant articles and documents
The thioacetate approach to the synthesis of the side chain of vitamin D metabolites and analogues
Fall, Yagamare,Diouf, Ousmane,Gómez, Generosa,Bola?o, Tamara
, p. 6069 - 6072 (2003)
We describe an efficient synthesis of thia analogues of the vitamin D side chain that is based on the in situ generation of a thiolate anion and its alkylation with electrophiles.
Carborane-based design of a potent Vitamin D receptor agonist
Otero, Rocio,Seoane, Samuel,Sigüeiro, Rita,Belorusova, Anna Y.,Maestro, Miguel A.,Pérez-Fernández, Roman,Rochel, Natacha,Mouri?o, Antonio
, p. 1033 - 1037 (2016)
The vitamin D nuclear receptor (VDR) is a potential target for cancer therapy. It is expressed in many tumors and its ligand shows anticancer actions. To combine these properties with the application of boron neutron capture therapy (BNCT), we design and
A protecting group-free synthesis of (-)-hortonones A-C from the Inhoffen-Lythgoe diol
Stambulyan, Hovsep,Minehan, Thomas G.
, p. 8728 - 8731 (2016)
A synthesis of hortonones A-C has been accomplished from vitamin D2via the Inhoffen-Lythgoe diol without the use of protective groups. Key steps in the syntheses include a TMS-diazomethane mediated regioselective homologation of the cyclohexano
Synthesis and biological evaluation of calcioic acid
Arnold, Leggy A.,Di Milo, Elliot S.,Mutchie, Tania R.,Yu, Olivia B.
, (2019/11/25)
Herein, we describe the synthesis of calcioic acid following a recently developed synthetic strategy for calcitroic acid. Several improvements to reaction conditions were made, which resulted in higher yields. The improved workup and isolation procedures
Design, synthesis, and evaluation of hybrid vitamin D3 side chain analogues as hedgehog pathway inhibitors
Banerjee, Upasana,Deberardinis, Albert M.,Hadden, M. Kyle
, p. 548 - 555 (2015/01/30)
Vitamin D3 (VD3) is a moderately potent and non-selective inhibitor of the Hedgehog (Hh) signaling cascade. Previous studies have established that the CD-ring region of VD3 serves as the Hh inhibitory pharmacophore. Subsequently, compound 3, an ester link
Synthesis and preliminary biological evaluation of new antiproliferative aromatic analogues of 1α,25-dihydroxyvitamin D3
Thomas, Emmanuel,Brion, Jean-Daniel,Peyrat, Jean-Fran?ois
, p. 381 - 393 (2014/11/07)
In an effort to develop novel vitamin D3 analogues, a series of aromatic compounds was synthetized, using efficient Negishi cross coupling between alkenylzinc reagents of the C,D-ring moiety of vitamin D3, and various substituted aromatic halides as A-ring mimics. The study aimed at exploring the influence of the replacement of the original vitamin D3 diene by a styrene unit on the biological activities. Potency in the induction of the differentiation of HL-60 cells for the lead compound 36 was 12 fold less important than calcitriol correlating with a weaker binding affinity for VDR.
Efficient and scalable total synthesis of calcitroic acid and its 13C-labeled derivative
Meyer, Daniel,Rentsch, Lara,Marti, Roger
, p. 32327 - 32334 (2014/08/18)
Calcitroic acid, the deactivated form of the physiological active vitamin D3 metabolite calcitrol, and its 13C labeled derivative has been synthesized starting from the commercially available Inhoffen-Lythgoe diol in 11 steps with an
26- and 27-Methyl groups of 2-substituted, 19-nor-1α,25- dihydroxylated vitamin D compounds are essential for calcium mobilization in vivo
Grzywacz, Pawel,Plum, Lori A.,Clagett-Dame, Margaret,Deluca, Hector F.
, p. 9 - 16 (2013/05/09)
Twelve new analogs of 19-nor-1α,25-dihydroxyvitamin D3 6-17, were prepared by a multi-step procedure from known alcohols 18 and 19. We have examined the influence of removing two methyl groups located at C-25, as well as the 25-hydroxy group, o
Analogues of the Inhoffen-Lythgoe diol with anti-proliferative activity
Deberardinis, Albert M.,Lemieux, Steven,Hadden, M. Kyle
supporting information, p. 5367 - 5370 (2013/09/23)
The anti-proliferative activity of a series of ester- and amide-linked Inhoffen-Lythgoe side chain analogues is reported. Whereas the Inhoffen-Lythgoe diol was inactive in these studies, a number of aromatic and aliphatic ester-linked side chains demonstr
Synthesis and biological activities of vitamin D-like inhibitors of CYP24 hydroxylase
Chiellini, Grazia,Rapposelli, Simona,Zhu, Jinge,Massarelli, Ilaria,Saraceno, Marilena,Bianucci, Anna Maria,Plum, Lori A.,Clagett-Dame, Margaret,Deluca, Hector F.
experimental part, p. 212 - 223 (2012/04/04)
Selective inhibitors of CYP24A1 represent an important synthetic target in a search for novel vitamin D compounds of therapeutic value. In the present work, we show the synthesis and biological properties of two novel side chain modified 2-methylene-19-no
