- Synthesis and biological evaluation of calcioic acid
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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
- Arnold, Leggy A.,Di Milo, Elliot S.,Mutchie, Tania R.,Yu, Olivia B.
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Read Online
- A new approach to the synthesis of the 25-hydroxy-22-oxa-vitamin D3 side chain
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An efficient new method is described for the construction of the 25-hydroxy-22-oxavitamin D3 side-chain, which is present in several analogues of calcitriol with antitumour activity.
- Fall, Yagamare
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Read Online
- Efficient and scalable total synthesis of calcitroic acid and its 13C-labeled derivative
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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
- Meyer, Daniel,Rentsch, Lara,Marti, Roger
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p. 32327 - 32334
(2014/08/18)
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- Synthesis of 20-epi-eldecalcitol [20-epi-1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3: 20-epi-ED-71]
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A convergent synthesis of biologically interesting 20-epi-eldecalcitol which possesses an inverted C-21 methyl substituent at the 20-position of the side chain of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (eldecalcitol) is described.
- Yoshino, Madoka,Eto, Kohei,Takahashi, Keisuke,Ishihara, Jun,Hatakeyama, Susumi,Ono, Yoshiyuki,Saito, Hitoshi,Kubodera, Noboru
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experimental part
p. 381 - 394
(2010/09/05)
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- Synthesis and preliminary biological evaluation of 20-epi-eldecalcitol [20-epi-1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3: 20-epi-ED-71]
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Eldecalcitol [1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3, developing code: ED-71] is an analog of active vitamin D3, 1α,25-dihydroxyvitamin D3 [1,25(OH)2D3] that possesses a hydroxypropoxy substituent at the 2β-position of 1,25(OH)2D3. Eldecalcitol has potent biological effects on bone and is now in preparation for approval as a promising medicine for the treatment of osteoporosis in Japan. To explore chemical structure-biological activity relationships between eldecalcitol and related analogs, we have already synthesized 1-epi-eldecalcitol, 3-epi-eldecalcitol, and 1,3-diepi-eldecalcitol with inherent biological interests of each targeted analog and evaluated their biological responses. It has been reported that 20-epi-1,25(OH)2D3, a diastereomer of 1,25(OH)2D3 that possesses an inverted methyl substituent at the 20-position of the side chain, shows remarkably enhanced biological activities compared to parental compound, 1,25(OH)2D3. As a continuation of our modification studies on eldecalcitol, we took great interest in 20-epi-eldecalcitol and its biological responses. In this paper, the synthesis of 20-epi-eldecalcitol by the Trost coupling reaction between the A-ring fragment and the C/D-ring fragment as well as in vitro preliminary biological evaluation of 20-epi-eldecalcitol are described. In the induction of human myeloid leukemia cell (HL-60) differentiation, inhibition of the human histiocytic lymphoma cell (U937) proliferation, and increase in osteocalcin concentration in the human osteosarcoma cell (MG-63), 20-epi-eldecalcitol showed significantly enhanced activity compared to eldecalcitol.
- Hatakeyama, Susumi,Yoshino, Madoka,Eto, Kohei,Takahashi, Keisuke,Ishihara, Jun,Ono, Yoshiyuki,Saito, Hitoshi,Kubodera, Noboru
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scheme or table
p. 25 - 28
(2011/12/01)
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- 2-Methylene-(20E)-20(22)-Dehydro-19-Nor-Vitamin D Analogs
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This invention discloses 2-methylene-(20E)-20(22)-dehydro-19-nor-vitamin D analogs, and specifically 2-methylene-(20E)-20(22)-dehydro-19-nor-1α,25-dihydroxyvitamin D3, and pharmaceutical uses therefor. This compound exhibits relatively high tra
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Page/Page column 4; 6
(2010/02/17)
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- 2-Methylene-20(21)-Dehydro-19-Nor-Vitamin D Analogs
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This invention discloses 2-methylene-20(21)-dehydro-19-nor-vitamin D analogs, and specifically 2-methylene-20(21)-dehydro-19-nor-1α,25-dihydroxyvitamin D3, and pharmaceutical uses therefor. This compound exhibits relatively high transcription a
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Page/Page column 4
(2010/02/17)
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- Vitamin D and click chemistry. Part 1: A stereoselective route to vitamin D analogues with triazole rings in their side chains
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Efficient preparation of vitamin D CD ring system synthons with triazole rings in their side chains is based on the formation of the triazole ring from a [3+2]-cycloaddition of a vitamin D side chain terminal azide with a terminal acetylene.
- Suarez, Pedro Lois,Gándara, Zoila,Gómez, Generosa,Fall, Yagamare
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p. 4619 - 4621
(2007/10/03)
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- Synthesis of 1alpha,25-dihydroxyvitamin D3-26,23-lactams (DLAMs), a novel series of 1 alpha,25-dihydroxyvitamin D3 antagonist.
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Novel vitamin D(3) analogs having a lactam structure in their side chains, 1 alpha,25-dihydroxyvitamin D(3)-26,23-lactams (DLAMs), were designed based on the principle of regulation of the folding of helix-12 in the vitamin D nuclear receptor (VDR). The n
- Kato, Yuko,Nakano, Yusuke,Sano, Hiroko,Tanatani, Aya,Kobayashi, Hisayoshi,Shimazawa, Rumiko,Koshino, Hiroyuki,Hashimoto, Yuichi,Nagasawa, Kazuo
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p. 2579 - 2583
(2007/10/03)
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- Novel heteroatom-containing vitamin D3 analogs: Efficient synthesis of 1α,25-dihydroxyvitamin D3-26,23-lactam
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Vitamin D3 and its synthetic analogs are promising compounds for controlling various types of cell differentiation. In this article, we describe the synthesis of novel vitamin D3 analogs containing heteroatoms in their side chains - so-called vitamin D3 lactam analogs - via 1,3-dipolar cycloaddition reaction as a key step.
- Kato, Yuko,Hashimoto, Yuichi,Nagasawa, Kazuo
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p. 488 - 499
(2007/10/03)
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- Vitamin D heterocyclic analogues. Part 1: A stereoselective route to CD systems with pyrazole rings in their side chains
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Efficient preparation of two vitamin D CD ring system synthons with pyrazole rings in their side chains is based on the formation of the pyrazole ring from an α-acetylenic ketone.
- Fall, Yagamare,Barreiro, Candida,Fernández, Carlos,Mouri?o, Antonio
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p. 1433 - 1436
(2007/10/03)
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- Stereoselective synthesis and structural establishment of (25S)-24,24- difluoro-1α,25,26-trihydroxyvitamin D3, a major metabolite of 24,24- difluoro-1α,25-dihydroxyvitamin D3
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(25S)-24,24-Difluoro-1α,25,26-trihydroxyvitamin D3 (3a) and its (25R)- epimer (3b), either of which is expected to be a major metabolite of 24,24- difluoro-1α,25-dihydroxyvitamin D3 (2), were synthesized. Asymmetric addition to β-ket
- Iwasaki, Hiroshi,Hosotani, Ryuzo,Miyamoto, Yoichi,Nakano, Yoshio,Yamamoto, Keiko,Yamada, Sachiko,Shinki, Toshimasa,Suda, Tatsuo,Yamaguchi, Kentaro,Konno, Katsuhiro,Takayama, Hiroaki
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p. 14705 - 14724
(2007/10/03)
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- Studies on the Synthesis of Side-Chain Hydroxylated Metabolites of Vitamin D. 3. Synthesis of 25-Ketovitamin D3 and 25-Hydroxyvitamin D3
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A general method for the synthesis of the principal vitamin D3 metabolites whether unlabeled or with radiolabeled side chains is described.The synthesis of the key de-A,B-(ethylenedioxy)cholestanone derivative 7d is based on the coupling between the iodid
- Mascarenas, J. L.,Mourino, A.,Castedo, L.
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p. 1269 - 1272
(2007/10/02)
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- Stereocontrolled Total Synthesis of 1α,25-Dihydroxycholecalciferol and 1α,25-Dihydroxyergocalciferol
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1α,25-dihydroxycholecalciferol (4) and 1α,25-dihydroxyergocalciferol (7), the hormonally active forms of vitamin D3 (1) and vitamin D2 (5), were synthesized by a Horner-Wittig reaction of the phosphine oxide 11 with the ketones 10 and 12, respectively.The synthon 11 was obtained by a sequence that involves the stereospecific opening of epoxide 15, with sodium acetate in acetic acid, followed by oxidative degradation of the isopropenyl side chain and dehydration of the intermediate 22.Photoisomerisation of the resulting 23 gave 24, which was finally converted to 11.The hydroxylated ketone 10 was obtained from the known intermediate 28.The introduction of the 25-hydroxy side chain was achieved by reaction of the lithium derivative of 30 with the tosylate 29 to give 31, which was catalytically hydrogenated to 32 and then converted to 10.The ketone 12 was prepared by a stereocontrolled route that involves as the key step, the dipolar cycloaddition of nitrone 35 with methyl 3,3-dimethylacrylate (36) to give a 1:1 mixture of isoxazolidines 37 and 38.Stereochemical control was achieved by taking advantage of the thermal reversibility of the cycloaddition, which allows the reequilibration of undesired 37.Isoxazolidine 38 was readily transformed to 43 by reduction, followed by elimination of the nitrogen function, and finally oxidation to 12.
- Baggiolini, Enrico G.,Iacobelli, Jerome A.,Hennessy, Bernard M.,Batcho, Andrew D.,Sereno, John F.,Uskokovic, Milan R.
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p. 3098 - 3108
(2007/10/02)
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