有机化学研究  >> Vol. 2 No. 1 (March 2014)

1α,25-二羟基维生素D3及其类似物的合成研究进展
Advances on Synthesis of 1α,25-Dihydroxyvitamin D3 and Related Analogues

DOI: 10.12677/JOCR.2014.21001, PDF, HTML, 下载: 2,569  浏览: 11,591 

作者: 刘重阳, 汪秋安:湖南大学化学化工学院,长沙;杨 辉:澧县中医院,湖南澧县

关键词: 25-二羟基维生素D3类似物合成进展α25-Dihydroxyvitamin D3; Analogues; Synthesis; Advances

摘要: 许多合成的维生素D类似物正在被应用当作新的治疗药物和灵敏的生物分子探针,本文综述了活性维生素D31α,25-二羟基维生素D3及其类似物的合成方法研究进展。
Abstract: An increasing number of synthetic Vitamin D analogues are now being used as new powerful drugs for treatment of various human diseases and also as sensitive molecular biology probes. This paper reviews the synthetic methods and advances in synthesis of 1α,25-dihydroxyvitamin D3 and related analogues.

文章引用: 刘重阳, 杨辉, 汪秋安. 1α,25-二羟基维生素D3及其类似物的 合成研究进展 [J]. 有机化学研究, 2014, 2(1): 1-12. http://dx.doi.org/10.12677/JOCR.2014.21001

参考文献

[1] Zhu, G.D. and Okamura, W.H. (1995) Synthesis of vitamin D (Calciferol). Chemical Reviews, 95, 1877-1952.
[2] Posner, G.H. and Kahraman, M. (2003) Organic chemistry of vitamin D analogues (Deltanoids). Eu-ropean Journal of Organic Chemistry, 2013, 3889-3895.
[3] Perlman, K.L., Sicinski, R.R., Schnoes, H.K. and Deluce, H.F. (1990) 1α,25-Dihydroxy-19-nor vitamin D3, a novel vitamin D-related compound with potential therapeutic activity. Tetrahedron Letters, 31, 1823-1824.
[4] 蔡祖恽 (2013) 近年来活性维生素D类似物的合成进展概述. 有机化学, 33, 2244-2258.
[5] Lythgoe, B., Moran, T.A., Nambudiry, M.E.N., Rustern, S., Tideswell, J. and Wright, P.W. (1975) A practical synthesis of 1α,25-dihydroxy-vitamin D3 by Wittig-Horner reaction. Tetrahedron Letters, 16, 3863-3867.
[6] Posner, G.H., Gouch, R.D. and Kinter, C. (1991) One-flask, regiospecific conversion of allylic alco-hols into two-casbon-extended, conjugated dienoate esters. Use of a new sulfinyl orthoester. The Journal of Organic Chemistry, 56, 6981-6986.
[7] Kabat, M.M., Lange, M., Wovkulich, P.M. and Uskokovic, M.R. (1992) Asymmetric synthesis of a key 1α, 25-dihydroxy-vitamin D3 ring A synthon. Tetrahedron Letters, 33, 7701-7705.
[8] Andrzej, R.D., Lisa, M.G., Stanley, D.H., Marek, M.K., Liu, W., Masami, O., Roumen, R. and George, P.Y. (2002) Efficient synthesis of the A-ring phosphine oxide building block useful for 1α,25-dihydroxy-vitamin D3 and analogues. The Journal of Organic Chemistry, 67, 1580-1587.
[9] Takahashi, T. and Nakazawa, M. (1993) Synthesis of 2-hydroxyl 1α,25-dihydroxy-vitamin D3 ring A synthon by Heck reaction. Synlett, 37-40.
[10] Kobayashi, S., Shibata, J., Shimada, M. and Ohno, M. (1990) An enantioselective synthesis of the A-ring synthon for Vitamin D3 metabolites by chemi-coenzymatic approach. Tetrahedron Letters, 31, 1577-1580.
[11] Kamikubo, T. and Ogasawara, K. (1995) Concise enantiocontrolled synthesis of the A-ring precursor of calcitriol from the chiral cyclohexadienone synthon. Journal of the Chemical Society, Chemical Communications, 19, 1951-1954.
[12] Sicinski, R.R., Perlman, K.L. and Deluca, H.F. (1994) Synthesis and biological activity of 2-hydroxy and 2-alkoxy analogs of 1,25-dihydroxy-19-norvitamin D3. Journal of Medicinal Chemistry, 37, 3730-3738.
[13] Sicinski, R.R., Prahl, J.M., Smith, C.M. and Deluca, H.F. (1998) New 1α, 25-dihydroxy-19-nor vitamin D3 compounds of high biological activity: Synthesis and biological evaluation of 2-hydroxymethyl, 2-methyl, and methylene analogues. Journal of Medicinal Chemistry, 41, 4662-4674.
[14] Yagamare, F., Carlos, F., Cristian, V. and Antonio, M. (2000) Stereoselective synthesis of vitamin D3 analogues with cyclic side chains. Tetrahedron Letters, 41, 7323-7326.
[15] Cornella, I., Sestelo, J.P., Mourino and Sarandeses, L.A. (2002) Synthesis of new 18-substituted analogues of calcitriol using a photochemical remote functionalization. The Journal of Organic Chemistry, 67, 4707-4714.
[16] Maehr, H., Rochel, N., Lee, H.J., Suh, N. and Uskokovic, M.R. (2013) Diastereotopic and deuterium effects in Gemini. Journal of Medicinal Chemistry, 56, 3878-3888.
[17] Lamblin, M., Spingarn, R., Wang, T.T., Burger, M.C., Dabbas, B., Moitessier, N., White, J.H. and Gleason, J.L. (2010) An o-aminoaniline analogue of 1α,25-dihydroxyvitamin D3 functions as a strong vitamin D receptor antagonist. Journal of Medicinal Chemistry, 53, 7461-7465.
[18] Sestelo, J.P., Mascarenas, J.L., Lastedo, L. and Mourino, A. (1993) Ultrasonically induced conjugate addition of iodides to electron-deficient olefins and its applicatin to the synthesis of side-chain analogs of the hormone 1α, 25-dihydroxylvitamin. Journal of Organic Chemistry, 58, 118-123.
[19] Desmaele, D. and Tanler, S. (1985) Nouvelle synthese du cycle A du 1s-hydroxycholeca licferol a partir DE Lacide quinque. Tetrahedron Letters, 26, 4941-4946.
[20] Castedo, L., Mascarenas, J.L. and Mourino, A. (1987) An improved synthesis of 1α,25-dihydroxy-vitamin D A synthons. Tetrahedron Letters, 28, 2099-2102.
[21] Stepanenko, W. and Wicha, J. (1998) Enantioselective synthesis of 24, 25-dihydroxy vitamin D3 nor-thernportion from (s)-3-hydroxy-2,2-dimethylcyclohexane-1-one. Remote asymmetric induction in an acid-catalysed conjugate addition. Tetrahedron Letters, 39, 885-889.
[22] Lu, Y., Barth, G., Kieslich, K., Strong, P.D., Duax, W.L. and Djerassi, C. (1983) Optical rotatory dispersion studies: Enzymatic reduction of 2-methyl-2-(trideuteriomethyl) cyclohexane-1,3-dione, unusual conformation of 2,2-dimethyl3-hydroxycyclohexanone. Journal of Organic Chemistry, 48, 4549-4552.
[23] Wu, Y., Zhao, Y., Tian, H., Clercq, P.D., Vandewalle, M., Berthier, M., Pellegrino, G., Maillos, P. and Pascal, J.-C. (2001) Apractical synthesis of A-ring precursors for 19-nor-1α,25-dihydroxy vitamin D3 analogues. European Journal of Organic Chemistry, 3779-3783.
[24] Huang, P.Q., Sabbe, K., Pottie, M. and Vandewalle, M. (1995) A novel synthesis of 19-nor 1α-,25-dihydroxyvitamin D3 and related analogues. Tetrahedron Letters, 36, 8299-8302.
[25] 吴勇 (1999) 19-失碳-1α, 25-二羟基维生素D3A环合成子的合成. 有机化学, 19, 374-378.
[26] Wang, Q.A. and Zhao, Y.R. (2003) Efficient synthesis of 2-ethyl-A-ring analogues of 19-nor-1α,25-dihydroxyvitamin D3. Chemical Research in Chinese Universities, 19, 165-173.
[27] 万阳, 文鹏, 张攀, 陆群 (2012) 化学与生物转化法合成帕立骨化醇. 有机化学, 10, 1988-1992.
[28] Trost, B.M., Dumas, J. and Villa, M. (1992) New strategies for the synthesis of vitamin D metabolites via Pd-catalyzed reactions. Journal of the American Chemical Society, 114, 9836-9845.
[29] Yoshitomo, S., Kenichi, N., Masaaki, K., Atsushi, K., Kentaro, Y., Toshie, F., Katsuhiro, K., Naoki, M. and Hiroaki, T. (2001) Efficient and versatile synthesis of novel 2α-substituted 1α,25-dihydroxyvitamin D3 analogues and their clocking to vitamin D receptors. The Journal of Organic Chemistry, 66, 8760-8771.
[30] Xu, W.M.; He, J., Yu, M.Q. and Shen, G.X. (2010) Site-selective modification of vitamin D analogue (Deltanoid) through a resin-based version of organoselenium 2,3-sigmatropic rearrangement. Organic Letters, 12, 4431-4433.