메뉴 건너뛰기




Volumn 32, Issue 1 PART 2, 2012, Pages 311-317

C15-functionalized 16-Ene-1α,25-dihydroxyvitamin D 3 is a new vitamin D analog with unique biological properties

Author keywords

15 substituted vitamin D 3; 16 ene vitamin D 3; S N2 reaction

Indexed keywords

9,10 SECOCHOLESTA 5,7,10(19),16 TETRAEN 23 YNE 1,3,25 TRIOL; OSTEOCALCIN; VITAMIN D DERIVATIVE;

EID: 84862955879     PISSN: 02507005     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Conference Paper
Times cited : (5)

References (36)
  • 2
    • 0013367459 scopus 로고
    • Stereocontrolled synthesis of steroidal side chains
    • Dauben WG and Brookhart T: Stereocontrolled synthesis of steroidal side chains. J Am Chem Soc 103: 237-238, 1981.
    • (1981) J Am Chem Soc , vol.103 , pp. 237-238
    • Dauben, W.G.1    Brookhart, T.2
  • 5
    • 0642305926 scopus 로고    scopus 로고
    • A low-calcemic vitamin D analog (Ro 25-4020) inhibits the growth of LNCaP human prostate cancer cells with increased potency by producing an active 24-oxo metabolite (Ro 29-9970)
    • Reichrath J, Friedrich M and Tilgen W (eds.). Springer-Verlag, Berlin
    • Swami S, Zhao XY, Sarabia S, Siu-Caldera ML, Uskokovic M, Reddy SG, Feldman D: A low-calcemic vitamin D analog (Ro 25-4020) inhibits the growth of LNCaP human prostate cancer cells with increased potency by producing an active 24-oxo metabolite (Ro 29-9970). In: Vitamin D analogs in cancer prevention and therapy. Recent results in cancer research 164. Reichrath J, Friedrich M and Tilgen W (eds.). Springer-Verlag, Berlin, pp. 349-352, 2003.
    • (2003) Vitamin D Analogs in Cancer Prevention and Therapy. Recent Results in Cancer Research , vol.164 , pp. 349-352
    • Swami, S.1    Zhao, X.Y.2    Sarabia, S.3    Siu-Caldera, M.L.4    Uskokovic, M.5    Reddy, S.G.6    Feldman, D.7
  • 7
    • 0013373329 scopus 로고    scopus 로고
    • Synthesis and biological activity of new side chain analogues of 16-dehydrocalcitriol and its 20-epimer
    • Norman AW, Bouillon R, and Thomasset M (eds.). Vitamin D Workshop, Inc, Riverside, CA
    • von Daehne W, Hansen CM, Hansen D and Mathiasen IS: Synthesis and biological activity of new side chain analogues of 16-dehydrocalcitriol and its 20-epimer. In: Vitamin D: Chemistry, Biology and Clinical Applications of the Steroid Hormone. Norman AW, Bouillon R, and Thomasset M (eds.). Vitamin D Workshop, Inc, Riverside, CA, pp. 81-82, 1997.
    • (1997) Vitamin D: Chemistry, Biology and Clinical Applications of the Steroid Hormone , pp. 81-82
    • Von Daehne, W.1    Hansen, C.M.2    Hansen, D.3    Mathiasen, I.S.4
  • 9
    • 15144345623 scopus 로고    scopus 로고
    • 3. Synthesis and preliminary biological evaluation
    • DOI 10.1021/jm980031t
    • Posner GH, Lee JK, Wang Q, Peleg S, Burke M, Brem H, Dolan P and Kensler TW: Noncalcemic, antiproliferative, transcriptionally active, 24-fluorinated hybrid analogues of the hormone 1α,25-dihydroxyvitamin D3. Synthesis and preliminary biological evaluation. J Med Chem 41: 3008-3014, 1998. (Pubitemid 28359936)
    • (1998) Journal of Medicinal Chemistry , vol.41 , Issue.16 , pp. 3008-3014
    • Posner, G.H.1    Lee, J.K.2    Wang, Q.3    Peleg, S.4    Burke, M.5    Brem, H.6    Dolan, P.7    Kensler, T.W.8
  • 11
    • 0000487759 scopus 로고    scopus 로고
    • The 16-ene vitamin D analogs
    • Feldman D, Glorieux FH and Pike JW (eds.). Academic Press, New York, Chapter 62
    • Uskoković MR, Studzinski GP and Reddy GS: The 16-ene vitamin D analogs. In: Vitamin D. Feldman D, Glorieux FH and Pike JW (eds.). Academic Press, New York, Chapter 62, pp. 1045-1070, 1997.
    • (1997) Vitamin D , pp. 1045-1070
    • Uskoković, M.R.1    Studzinski, G.P.2    Reddy, G.S.3
  • 12
    • 0027196446 scopus 로고
    • 3 analogues on the proliferation and differentiation of cultured human keratinocytes, calcium metabolism and the differentiation of human HL-60 cells
    • 3 analogues on the proliferation and differentiation of cultured human keratinocytes, calcium metabolism and the differentiation of human HL-60 cells. J Nutr Biochem 4: 49-57, 1993.
    • (1993) J Nutr Biochem , vol.4 , pp. 49-57
    • Chen, T.C.1    Persons, K.2    Uskokovic, M.R.3    Horst, R.L.4    Holick, M.F.5
  • 19
    • 0027991818 scopus 로고
    • Design and synthesis of seco-oxysterol analogs as potential inhibitors of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase gene transcription
    • DOI 10.1021/jm00041a013
    • Larsen SD, Spilman CH, Yagi Y, Dinh DM, Hart KL and Hess GF: Design and synthesis of seco-oxysterol analogs as potential inhibitors of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase gene transcription. J Med Chem 37: 2343-2351, 1994. (Pubitemid 24262323)
    • (1994) Journal of Medicinal Chemistry , vol.37 , Issue.15 , pp. 2343-2351
    • Larsen, S.D.1    Spilman, C.H.2    Yagi, Y.3    Dinh, D.M.4    Hart, K.L.5    Hess, G.F.6
  • 20
    • 0027067026 scopus 로고
    • New strategies for the synthesis of vitamin D metabolites via Pd-catalyzed reactions
    • DOI 10.1021/ja00051a016
    • Trost BM, Dumas J and Villa M: New strategies for the synthesis of vitamin D metabolites via Pd-catalyzed reactions. J Am Chem Soc 114: 9836-9845, 1992. (Pubitemid 23021941)
    • (1992) Journal of the American Chemical Society , vol.114 , Issue.25 , pp. 9836-9845
    • Trost, B.M.1    Dumas, J.2    Villa, M.3
  • 23
    • 0346392102 scopus 로고    scopus 로고
    • 3 analogues utilizing Grignard reaction towards methyl 2,3-anhydro-4,6-o- benzylidene-α-D-mannopyranoside
    • 3 analogues utilizing Grignard reaction towards methyl 2,3-anhydro-4,6-o-benzylidene- α-D-mannopyranoside. Heterocycles 67: 327-228, 2003.
    • (2003) Heterocycles , vol.67 , pp. 327-1228
    • Honzawa, S.1    Yamamoto, Y.2    Hirasaka, K.3    Takayama, H.4    Kittaka, A.5
  • 24
    • 0025678705 scopus 로고
    • The vitamin D-responsive element in the human osteocalcin promoter
    • Ozono K, Liao J, Kerner SA, Scott RA and Pike JW: The vitamin D-responsive element in the human osteocalcin promoter. J Biol Chem 265: 21881-21888, 1990.
    • (1990) J Biol Chem , vol.265 , pp. 21881-21888
    • Ozono, K.1    Liao, J.2    Kerner, S.A.3    Scott, R.A.4    Pike, J.W.5
  • 25
    • 0009551015 scopus 로고
    • Synthesen von Alkyliden-Steroiden durch Wittig-Reaktion
    • Drefahl G, Ponsolt K and Schick H: Synthesen von Alkyliden-Steroiden durch Wittig-Reaktion. Chem Ber 98: 604-612, 1965.
    • (1965) Chem Ber , vol.98 , pp. 604-612
    • Drefahl, G.1    Ponsolt, K.2    Schick, H.3
  • 26
    • 0000973586 scopus 로고
    • A new stereospecific approach to steroid side chains: Conversion of dehydroepiandrosterone to cholesterol, isocholesterol, and their 15β-hydroxy derivatives
    • Marino JP and Abe H: A new stereospecific approach to steroid side chains: conversion of dehydroepiandrosterone to cholesterol, isocholesterol, and their 15β-hydroxy derivatives. J Am Chem Soc 103: 2907-2909, 1981.
    • (1981) J Am Chem Soc , vol.103 , pp. 2907-2909
    • Marino, J.P.1    Abe, H.2
  • 27
    • 33751189079 scopus 로고
    • Regio- and stereoselective 15β-hydroxy group and side chains to steroids by the palladium-catalysed reaction of 1,3-diene monoepoxides with carbonucleophiles
    • Takahashi T, Ootake A, Tsuji J and Tachibana K: Regio- and stereoselective 15β-hydroxy group and side chains to steroids by the palladium-catalysed reaction of 1,3-diene monoepoxides with carbonucleophiles. Tetrahedron 41: 5747-5754, 1985.
    • (1985) Tetrahedron , vol.41 , pp. 5747-5754
    • Takahashi, T.1    Ootake, A.2    Tsuji, J.3    Tachibana, K.4
  • 28
    • 0012379370 scopus 로고
    • Synthesis of dehydro-oogoniol and oogoniol: The adrenosterone route
    • Moon S, Stuhmiller LM, Chadha RK and McMorris TC: Synthesis of dehydro-oogoniol and oogoniol: the adrenosterone route. Tetrahedron 46: 2287-2306, 1990.
    • (1990) Tetrahedron , vol.46 , pp. 2287-2306
    • Moon, S.1    Stuhmiller, L.M.2    Chadha, R.K.3    McMorris, T.C.4
  • 29
    • 0018616981 scopus 로고
    • Stereospecific synthesis of the side chain of the steroidal plant sex hormone oogoniol
    • DOI 10.1021/jo01333a021
    • Wiersig JR, Waespe-Sarcevic N and Djerassi C: Stereospecific synthesis of the side chain of the steroidal plant sex hormone oogoniol. J Org Chem 44: 3374-3382, 1979. (Pubitemid 10192370)
    • (1979) Journal of Organic Chemistry , vol.44 , Issue.19 , pp. 3374-3382
    • Wiersig, J.R.1    Waespe-Sarcevic, N.2    Djerassi, C.3
  • 30
    • 0021717207 scopus 로고
    • Pavoninins: Shark-repelling ichthyotoxins from the defense secretion of the Pacific sole
    • Tachibana K, Sakaitanai M and Nakanishi K: Pavoninins: shark-repelling ichthyotoxins from the defense secretion of the pacific sole. Science 226: 703-705, 1984. (Pubitemid 15202151)
    • (1984) Science , vol.226 , Issue.4675 , pp. 703-705
    • Tachibana, K.1    Sakaitanai, M.2    Nakanishi, K.3
  • 31
    • 33745711831 scopus 로고    scopus 로고
    • Synthesis of the aglycone of the shark repellent pavoninin-4 using remote functionalization
    • DOI 10.1021/ol060079y
    • Gong H and Williams JR: Synthesis of the aglycone of the shark repellent pavoninin-4 using remote functionalization. Org Lett 8: 2253-2255, 2006. (Pubitemid 43998230)
    • (2006) Organic Letters , vol.8 , Issue.11 , pp. 2253-2255
    • Gong, H.1    Williams, J.R.2
  • 32
    • 0346677148 scopus 로고
    • N2′ displacements by organocuprate reagents
    • N2′ displacements by organocuprate reagents. Tetrahedron Lett 25: 3063-3066, 1984.
    • (1984) Tetrahedron Lett , vol.25 , pp. 3063-3066
    • Corey, E.J.1    Boaz, N.W.2
  • 35
    • 79955451040 scopus 로고    scopus 로고
    • Synthesis of C-2 substituted vitamin D derivatives having ringed side chains and biological evaluation, especially biological effect on bone by modification at C-2 position
    • Saitoh H, Chida T, Takagi K, Horie K, Sawai Y, Nakamura Y, Harada Y, Takenouchi K and Kittaka A: Synthesis of C-2 substituted vitamin D derivatives having ringed side chains and biological evaluation, especially biological effect on bone by modification at C-2 position. Org Biomol Chem 9: 3954-3964, 2011.
    • (2011) Org Biomol Chem , vol.9 , pp. 3954-3964
    • Saitoh, H.1    Chida, T.2    Takagi, K.3    Horie, K.4    Sawai, Y.5    Nakamura, Y.6    Harada, Y.7    Takenouchi, K.8    Kittaka, A.9


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.