메뉴 건너뛰기




Volumn 14, Issue 11, 2009, Pages 4655-4668

Synthesis of pregnane derivatives, their cytotoxicity on LNCaP and PC-3 cells, and screening on 5α-reductase inhibitory activity

Author keywords

20 oxime pregnanes; 5 reductase inhibitor; Epoxypregnanes; LNCaP; PC 3

Indexed keywords

PREGNANE DERIVATIVE; STEROID 5ALPHA REDUCTASE;

EID: 73349088133     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14114655     Document Type: Article
Times cited : (21)

References (22)
  • 1
    • 0015402161 scopus 로고
    • 4-5β-reductase
    • 4-5β-reductase. Steroids 1972, 20, 215-222.
    • (1972) Steroids , vol.20 , pp. 215-222
    • Abul-Hajj, Y.J.1
  • 2
    • 16544385945 scopus 로고    scopus 로고
    • Novel 17-substituted pregnadiene derivatives as 5α-reductase inhibitors and their binding affinity for the androgen receptor
    • Cabeza, M.; Flores, E.; Heuze, I.; Sanchez, M.; Bratoeff, E.; Ramirez, E.; Francolugo, V. A. Novel 17-substituted pregnadiene derivatives as 5α-reductase inhibitors and their binding affinity for the androgen receptor. Chem. Pharm. Bull. 2004, 52, 535-539.
    • (2004) Chem. Pharm. Bull , vol.52 , pp. 535-539
    • Cabeza, M.1    Flores, E.2    Heuze, I.3    Sanchez, M.4    Bratoeff, E.5    Ramirez, E.6    Francolugo, V.A.7
  • 3
    • 0024446655 scopus 로고
    • Expression cloning and regulation of steroid 5α-reductase, an enzyme essential for male sexual differentiation
    • Andersson, S. R.; Bishop, R. W.; Russell, D. W. Expression cloning and regulation of steroid 5α-reductase, an enzyme essential for male sexual differentiation. J. Biol. Chem. 1989, 264, 16249-16255.
    • (1989) J. Biol. Chem , vol.264 , pp. 16249-16255
    • Andersson, S.R.1    Bishop, R.W.2    Russell, D.W.3
  • 4
    • 0025303307 scopus 로고
    • Structural and biochemical properties of cloned expressed human and rat steroid 5α-reductase
    • Andersson, S.; Russell, D. W. Structural and biochemical properties of cloned expressed human and rat steroid 5α-reductase. Proc. Natl. Acad. Sci. USA 1990, 87, 3640-3644.
    • (1990) Proc. Natl. Acad. Sci. USA , vol.87 , pp. 3640-3644
    • Andersson, S.1    Russell, D.W.2
  • 5
    • 0028173882 scopus 로고
    • Steroid 5alpha-reductase: Two genes/two enzymes
    • Russell, D. W.; Wilson, J. D. Steroid 5alpha-reductase: Two genes/two enzymes. Ann. Rev. Biochem. 1994, 63, 25-61.
    • (1994) Ann. Rev. Biochem , vol.63 , pp. 25-61
    • Russell, D.W.1    Wilson, J.D.2
  • 7
    • 0034597612 scopus 로고    scopus 로고
    • Synthesis and evaluation of novel steroidal oxime inhibitors of P450 17 (17α-hydroxylase/C17, 20-lyase) and 5α-reductase types 1 and 2
    • Hartmann, R. W.; Hector, M.; Haidar, S.; Ehmer, P. B.; Reichert, W.; Jose, J. Synthesis and evaluation of novel steroidal oxime inhibitors of P450 17 (17α-hydroxylase/C17, 20-lyase) and 5α-reductase types 1 and 2. J. Med. Chem. 2000, 43, 4266-4277.
    • (2000) J. Med. Chem , vol.43 , pp. 4266-4277
    • Hartmann, R.W.1    Hector, M.2    Haidar, S.3    Ehmer, P.B.4    Reichert, W.5    Jose, J.6
  • 9
    • 0027494989 scopus 로고
    • Synthesis of the individual enantiomers of the benzoquinolinone human type 1 steroid 5α-reductase inhibitors LY191704 and LY266111
    • Audia, J. E.; Lawhorn, D. E.; Deeter, J. B. Synthesis of the individual enantiomers of the benzoquinolinone human type 1 steroid 5α-reductase inhibitors LY191704 and LY266111. Tetrahedron Lett. 1993, 34, 7001-7004.
    • (1993) Tetrahedron Lett , vol.34 , pp. 7001-7004
    • Audia, J.E.1    Lawhorn, D.E.2    Deeter, J.B.3
  • 10
    • 0026653910 scopus 로고
    • Antiandrons and 5alphareductaseinhibition of the proliferation rate in PC 3 and DU 145 human prostatic cancer cell lines
    • Bologna, M.; Muzi, P.; Biordi, L.; Festuccia, C.; Vicentini, C. Antiandrons and 5alphareductaseinhibition of the proliferation rate in PC 3 and DU 145 human prostatic cancer cell lines. Curr. Ther. Res. 1991, 51, 799-813.
    • (1991) Curr. Ther. Res , vol.51 , pp. 799-813
    • Bologna, M.1    Muzi, P.2    Biordi, L.3    Festuccia, C.4    Vicentini, C.5
  • 12
    • 0029240370 scopus 로고
    • Finasteride dose-dependently reduces the proliferation rate of the LNCaP human prostatic cancer cell line in vitro
    • Bologna, M.; Muzi, P.; Biordi, L.; Festuccia, C.; Vicentini, C. Finasteride dose-dependently reduces the proliferation rate of the LNCaP human prostatic cancer cell line in vitro. Urology 1995, 45, 282-290.
    • (1995) Urology , vol.45 , pp. 282-290
    • Bologna, M.1    Muzi, P.2    Biordi, L.3    Festuccia, C.4    Vicentini, C.5
  • 13
    • 0001760102 scopus 로고    scopus 로고
    • Comparative QSAR analysis of 5α-reductase inhibitors
    • Kurup, A.; Garg, R.; Hansch, C. Comparative QSAR analysis of 5α-reductase inhibitors. Chem. Rev. 2000, 100, 909-924.
    • (2000) Chem. Rev , vol.100 , pp. 909-924
    • Kurup, A.1    Garg, R.2    Hansch, C.3
  • 14
    • 0027323620 scopus 로고
    • Finasteride The first 5 alpha-reductase inhibitor
    • Sudduth, S. L.; Koronkowski, M. J. Finasteride The first 5 alpha-reductase inhibitor. Pharmacotherapy 1993, 309-325.
    • (1993) Pharmacotherapy , pp. 309-325
    • Sudduth, S.L.1    Koronkowski, M.J.2
  • 15
    • 0742287752 scopus 로고    scopus 로고
    • Dutasteride, the dual 5 α-reductase inhibitor, inhibits androgen action and promotes cell death in the LNCaP prostate cancer cell line
    • Lazier, C. B.; Thomas, L. N.; Douglas, R. C.; Vessey, J. P.; Rittmaster, R. S. Dutasteride, the dual 5 α-reductase inhibitor, inhibits androgen action and promotes cell death in the LNCaP prostate cancer cell line. Prostate 2004, 58, 130-144.
    • (2004) Prostate , vol.58 , pp. 130-144
    • Lazier, C.B.1    Thomas, L.N.2    Douglas, R.C.3    Vessey, J.P.4    Rittmaster, R.S.5
  • 16
    • 33745184934 scopus 로고    scopus 로고
    • Effects of the dual 5 α-reductase inhibitor dutasteride on apoptosis in primary cultures of prostate cancer epithelial cells and cell lines
    • McCrohan, A. M.; Morrissey, C.; O'Keane, C.; Mulligan, N.; Watson, C.; Smith, J.; Fitzpatrick, J. M.; Watson, R. W. Effects of the dual 5 α-reductase inhibitor dutasteride on apoptosis in primary cultures of prostate cancer epithelial cells and cell lines. Cancer 2006, 106, 2743-2752.
    • (2006) Cancer , vol.106 , pp. 2743-2752
    • McCrohan, A.M.1    Morrissey, C.2    O'Keane, C.3    Mulligan, N.4    Watson, C.5    Smith, J.6    Fitzpatrick, J.M.7    Watson, R.W.8
  • 17
    • 0031759097 scopus 로고    scopus 로고
    • Synthesis and in vivo acting of some epimeric 20α-hydroxy, 20-oxime and aziridine pregnene derivatives as inhibitors of human 17α-hydroxylase/C17, 20-lyase and 5α-reductase
    • Ling, Y.; Li, J.; Liu, Y.; Wang, X.; Klus, G. T.; Marat, K.; Nnane, I. P.; Brodie, A. M. H. Synthesis and in vivo acting of some epimeric 20α-hydroxy, 20-oxime and aziridine pregnene derivatives as inhibitors of human 17α-hydroxylase/C17, 20-lyase and 5α-reductase. Bioorg. Med. Chem. 1998, 6, 1683-1693.
    • (1998) Bioorg. Med. Chem , vol.6 , pp. 1683-1693
    • Ling, Y.1    Li, J.2    Liu, Y.3    Wang, X.4    Klus, G.T.5    Marat, K.6    Nnane, I.P.7    Brodie, A.M.H.8
  • 19
    • 1642634574 scopus 로고    scopus 로고
    • Highly selective lipase-mediated diastereomeric 5, 6-epoxysteroids
    • Cruz-Silva, M. M.; Riva, S.; Sáe-Melo, M. L. Highly selective lipase-mediated diastereomeric 5, 6-epoxysteroids. Tetrahedron Asymmetry 2004, 15, 1173-1179.
    • (2004) Tetrahedron Asymmetry , vol.15 , pp. 1173-1179
    • Cruz-Silva, M.M.1    Riva, S.2    Sáe-Melo, M.L.3
  • 20
    • 33947432702 scopus 로고    scopus 로고
    • Epoxidation and reduction of DHEA, 1, 4, 6-androstatrien-3-one and 4, 6-androstadiene-3β, 17β-diol
    • Ma, E.; Kim, E. Epoxidation and reduction of DHEA, 1, 4, 6-androstatrien-3-one and 4, 6-androstadiene-3β, 17β-diol. Molecules 2005, 10, 572-582.
    • (2005) Molecules , vol.10 , pp. 572-582
    • Ma, E.1    Kim, E.2
  • 22
    • 0016216094 scopus 로고    scopus 로고
    • Binding of steroids to progesterone receptor proteins in chick oviduct and human uterus
    • ©
    • Smith, H. E.; Smith, R. G.; Toft, D. O.; Neergaaed, J. R.; Burrows, E. P.; O'Malley, B. W. Binding of steroids to progesterone receptor proteins in chick oviduct and human uterus. J. Biol. Chem. 1974, 249, 5924-5932. © 2009
    • (2009) J. Biol. Chem , vol.1974 , Issue.249 , pp. 5924-5932
    • Smith, H.E.1    Smith, R.G.2    Toft, D.O.3    Neergaaed, J.R.4    Burrows, E.P.5    O'Malley, B.W.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.