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Volumn 16, Issue 12, 2011, Pages 9868-9885

Synthesis and screening of aromatase inhibitory activity of substituted C 19 steroidal 17-oxime analogs

Author keywords

4 substituted androstene 17 oxime; Aromatase inhibitor; Breast cancer; Conjugated androstadiene 17 oxime

Indexed keywords

AROMATASE; AROMATASE INHIBITOR; OXIME; STEROID;

EID: 84555189852     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16129868     Document Type: Article
Times cited : (17)

References (28)
  • 1
    • 0023180688 scopus 로고
    • Purification and characterization of human placental aromatase cytochrome P-450
    • Kellis, J., Jr.; Vickery, L.E. Purification and characterization of human placental aromatase cytochrome P-450. J. Biol. Chem. 1987, 262, 4413-4420. (Pubitemid 17102645)
    • (1987) Journal of Biological Chemistry , vol.262 , Issue.9 , pp. 4413-4420
    • Kellis Jr., J.T.1    Vickery, L.E.2
  • 4
    • 34249991719 scopus 로고    scopus 로고
    • Estradiol inhibits the estrone sulfatase activity in normal and cancerous human breast tissues
    • DOI 10.1016/j.jsbmb.2007.03.030, PII S0960076007000829, 17th International Symposium of the Journal of Steroid Biochemistry and Molecular Biology 'Recent Advances in Steroid Biochemistry and Molecular Biology'
    • Chetrite, G.S.; Prieto, J.C.C.; Philippe, J.C.; Pasqualini, J.R. Estradiol inhibits the estrone sulfatase activity in normal and cancerous human breast tissues. J. Steroid Biochem. Mol. Biol. 2007, 104, 289-292. (Pubitemid 46891831)
    • (2007) Journal of Steroid Biochemistry and Molecular Biology , vol.104 , Issue.3-5 , pp. 289-292
    • Chetrite, G.S.1    Cortes-Prieto, J.-C.2    Philippe, J.-C.3    Pasqualini, J.R.4
  • 5
    • 33846428861 scopus 로고    scopus 로고
    • Influences on circulating oestrogens in postmenopausal women: Relationship with breast cancer
    • DOI 10.1016/j.jsbmb.2006.07.011, PII S0960076006002780
    • Kendall, A.; Folkerd, E.J.; Dowsett, M. Influences on circulating oestrogens in postmenopausal women: Relationship with breast cancer. J. Steroid Biochem. Mol. Biol. 2007, 103, 99-109. (Pubitemid 46149297)
    • (2007) Journal of Steroid Biochemistry and Molecular Biology , vol.103 , Issue.2 , pp. 99-109
    • Kendall, A.1    Folkerd, E.J.2    Dowsett, M.3
  • 6
    • 18844443185 scopus 로고    scopus 로고
    • Aromatase inhibitors in the treatment of breast cancer
    • DOI 10.1210/er.2004-0015
    • Brueggemeier, R.W.; Hackett, J.C.; Diaz-Cruz, E.S. Aromatase inhibitors in the treatment of breast cancer. Endocr. Rev. 2005, 26, 331-345. (Pubitemid 40686647)
    • (2005) Endocrine Reviews , vol.26 , Issue.3 , pp. 331-345
    • Brueggemeier, R.W.1    Hackett, J.C.2    Diaz-Cruz, E.S.3
  • 7
    • 67349101669 scopus 로고    scopus 로고
    • The androgen metabolic 5-androstane-3,17-diol (3-Adiol) induces breast cancer growth via estrogen receptor; Implication for aromatase inhibitor resistance
    • Sikora, M.J.; Condero, K.E.; Larios, J.M.; Johnson, M.D.; Lippman, M.E.; Rae, J.M. The androgen metabolic 5-androstane-3,17-diol (3-Adiol) induces breast cancer growth via estrogen receptor; implication for aromatase inhibitor resistance. Breast Cancer Res. Treat. 2009, 115, 289-296.
    • (2009) Breast Cancer Res. Treat. , vol.115 , pp. 289-296
    • Sikora, M.J.1    Condero, K.E.2    Larios, J.M.3    Johnson, M.D.4    Lippman, M.E.5    Rae, J.M.6
  • 8
    • 0015594143 scopus 로고
    • Studies on the mechanism of estrogen biosynthesis. VII. The development of inhibitors of the enzyme system in human placenta
    • Schwarzel, W.C.; Kruggel, W.G.; Brodie, H.J. Studies on the mechanism of estrogen biosynthesis. VII. The development of inhibitors of the enzyme system in human placenta. Endocrinology 1973, 92, 866-880.
    • (1973) Endocrinology , vol.92 , pp. 866-880
    • Schwarzel, W.C.1    Kruggel, W.G.2    Brodie, H.J.3
  • 9
    • 0019800997 scopus 로고
    • Inactivation of aromatase activity in placental and ovarian microsomes by 4-hydroxyandrostene-3,17-dione and 4-acetoxyandrostenedione-3,17-dione
    • Brodie, A.M.H.; Garrett, W.M.; Hendrickson, J.R.; Marcotte, P.A.; Robinson, C.H. Inactivation of aromatase activity in placental and ovarian microsomes by 4-hydroxyandrostene-3,17-dione and 4-acetoxyandrostenedione-3,17- dione. Steroids 1981, 38, 693-702.
    • (1981) Steroids , vol.38 , pp. 693-702
    • Brodie, A.M.H.1    Garrett, W.M.2    Hendrickson, J.R.3    Marcotte, P.A.4    Robinson, C.H.5
  • 10
    • 0025648483 scopus 로고
    • 4-Aminoandrostenedione derivatives: A novel class of irreversible aromatase inhibitors. Comparison with FCE24304 and 4-hydroxyandrostenedione
    • Disalle, E.; Giudici, D.; Ornati, G.; Briatico, G.; D'Alessio, R.; Villa, V.; Lombardi, P. 4-Aminoandrostenedione derivatives: A novel class of irreversible aromatase inhibitors. Comparison with FCE24304 and 4-hydroxyandrostenedione. J. Steroid Biochem. Mol. Biol. 1990, 37, 369-374.
    • (1990) J. Steroid Biochem. Mol. Biol. , vol.37 , pp. 369-374
    • Disalle, E.1    Giudici, D.2    Ornati, G.3    Briatico, G.4    D'Alessio, R.5    Villa, V.6    Lombardi, P.7
  • 12
    • 0029148611 scopus 로고
    • Synthesis and evaluation of substituted-4-androstene-3,17- dione derivatives as aromatase inhibitors
    • Abul-Hajj, Y.J.; Liu, X.-P.; Hedge, M. Synthesis and evaluation of substituted-4-androstene-3,17- dione derivatives as aromatase inhibitors. J. Steroid Biochem. Mol. Chem. 1995, 54, 111-119.
    • (1995) J. Steroid Biochem. Mol. Chem. , vol.54 , pp. 111-119
    • Abul-Hajj, Y.J.1    Liu, X.-P.2    Hedge, M.3
  • 13
    • 0031562390 scopus 로고    scopus 로고
    • Isolation and synthesis of the first natural 6-hydroximino 4-en-3-one-steroids from the sponge Cinachyrella spp
    • DOI 10.1016/S0040-4039(97)00163-9, PII S0040403997001639
    • Rodríguez, J.; Nunez, L.; Peixinbo, S.; Jimenez, C. Isolation and synthesis of the first natural 6-hydroxyimino-4-en-3-one steroids from the sponges Cinachyrella spp. Tetrahedron Lett. 1997, 38, 1833-1836. (Pubitemid 27102342)
    • (1997) Tetrahedron Letters , vol.38 , Issue.10 , pp. 1833-1836
    • Rodriguez, J.1    Nunez, L.2    Peixinho, S.3    Jimenez, C.4
  • 14
    • 0035797355 scopus 로고    scopus 로고
    • Synthesis of cytotoxic 6E-hydroximino-4-ene steroids: Structure/activity studies
    • DOI 10.1021/jm010867n
    • Deive, N.; Rodriguez, J.; Jimenez, C. Synthesis of cytotoxic 6E-hydroxyimino-4-ene steroids: Structure/activity studies. J. Med. Chem. 2001, 44, 2612-2618. (Pubitemid 32852151)
    • (2001) Journal of Medicinal Chemistry , vol.44 , Issue.16 , pp. 2612-2618
    • Deive, N.1    Rodriguez, J.2    Jimenez, C.3
  • 15
    • 57249094264 scopus 로고    scopus 로고
    • Synthesis and evaluation of some steroid oximes as cytotoxic agents: Structure/activity studies (I)
    • Cui, J.G.; Fan, I.; Huang, L.I.; Liu, H.L.; Zhou, A.M. Synthesis and evaluation of some steroid oximes as cytotoxic agents: Structure/activity studies (I). Steroids 2009, 74, 62-72.
    • (2009) Steroids , vol.74 , pp. 62-72
    • Cui, J.G.1    Fan, I.2    Huang, L.I.3    Liu, H.L.4    Zhou, A.M.5
  • 17
    • 37049086433 scopus 로고
    • Synthesis of 6-hydroximino-3-oxo steroids, a new class of aromatase inhibitor
    • Hollands, H.L.; Kumaresan, S.; Tan, L.; Nzar, V.C.O. Synthesis of 6-hydroximino-3-oxo steroids, a new class of aromatase inhibitor. J. Chem. Soc. Perkin Trans. 1 1992, 13, 585-587.
    • (1992) J. Chem. Soc. Perkin Trans. 1 , vol.13 , pp. 585-587
    • Hollands, H.L.1    Kumaresan, S.2    Tan, L.3    Nzar, V.C.O.4
  • 18
    • 0345306221 scopus 로고    scopus 로고
    • Synthesis and antineoplastic activity of 2-alkylaminoethyl derivatives of various steroidal oximes
    • DOI 10.1016/j.ejmech.2003.09.002
    • Jindal, D.P.; Chattopadhaya, R.; Guleria, S.; Gupta, R. Synthesis and antineoplastic activity of 2-alkylaminoethyl derivatives of various steroidal oximes. Eur. J. Med. Chem. 2003, 38, 1025-1034. (Pubitemid 37452430)
    • (2003) European Journal of Medicinal Chemistry , vol.38 , Issue.11-12 , pp. 1025-1034
    • Jindal, D.P.1    Chattopadhaya, R.2    Guleria, S.3    Gupta, R.4
  • 19
    • 0019449456 scopus 로고
    • Enzyme-generated intermediates derived from 4-androstene-3,6,17- trione and 1,4,6-androstatriene-3,17-dione
    • Covey, D.F.; Hood, H.F. Enzyme-generated intermediates derived from 4-androstene-3,6,17- trione and 1,4,6-androstatriene-3,17-dione. Endocrinology 1981, 108, 1597-1599.
    • (1981) Endocrinology , vol.108 , pp. 1597-1599
    • Covey, D.F.1    Hood, H.F.2
  • 20
    • 37049110008 scopus 로고
    • Stereocontrolled synthesis of Withanolide D and related compounds
    • Gamoh, K.; Hirayama, M.; Ikekawa, N. Stereocontrolled synthesis of Withanolide D and related compounds. J. Chem. Soc. Perkin Trans. 1 1984, 440-454.
    • (1984) J. Chem. Soc. Perkin Trans. 1 , pp. 440-454
    • Gamoh, K.1    Hirayama, M.2    Ikekawa, N.3
  • 21
    • 0002464862 scopus 로고
    • Metal-catalysed highly selective oxygenations of olefins and acetylenes with tert-butyl hydroperoxide. Practical considerations and mechanisms
    • Sharpless, K.B.; Verhoeven, T.R. Metal-catalysed, highly selective oxygenations of olefins and acetylenes with tert-butyl hydroperoxide. Practical considerations and mechanisms. Aldrichim. Acta 1979, 12, 63-75.
    • (1979) Aldrichim. Acta , vol.12 , pp. 63-75
    • Sharpless, K.B.1    Verhoeven, T.R.2
  • 22
    • 0142216815 scopus 로고
    • Biological aromatization of steroids
    • Ryan, K.J. Biological aromatization of steroids. J. Biol. Chem. 1959, 234, 268-272.
    • (1959) J. Biol. Chem. , vol.234 , pp. 268-272
    • Ryan, K.J.1
  • 23
    • 0016272566 scopus 로고
    • The involvement of human microsomal cytochrome P-450 in aromatization
    • Thompson, A.E., Jr.; Siiteri, P.K. The involvement of human microsomal cytochrome P-450 in aromatization. J. Biol. Chem. 1975, 249, 5373-5378.
    • (1975) J. Biol. Chem. , vol.249 , pp. 5373-5378
    • Thompson Jr., A.E.1    Siiteri, P.K.2
  • 24
    • 0017231086 scopus 로고
    • Kinetic properties of human placental aromatase
    • Reed, K.C.; Ohno, S. Kinetic properties of human placental aromatase. J. Biol. Chem. 1976, 251, 1625-1631.
    • (1976) J. Biol. Chem. , vol.251 , pp. 1625-1631
    • Reed, K.C.1    Ohno, S.2
  • 25
    • 0028321927 scopus 로고
    • Synthesis of androst-5-en-7-ones and androsta-3,5-dien-7-ones and their related 7-deoxy analogs as conformational and catalytic probes for the active site of aromatase
    • DOI 10.1021/jm00040a012
    • Numazawa, M.; Mutsumi, A.; Tachibana, M.; Hoshi, K. Synthesis of androst-5-en-7-ones and androst-3,5-diene-7-ones and their related 7-deoxyanalogues as conformational and catalytic probes for the active site on aromatase. J. Med. Chem. 1994, 37, 2198-2205. (Pubitemid 24228448)
    • (1994) Journal of Medicinal Chemistry , vol.37 , Issue.14 , pp. 2198-2205
    • Numazawa, M.1    Mutsumi, A.2    Tachibana, M.3    Hoshi, K.4
  • 26
    • 0032979982 scopus 로고    scopus 로고
    • 19 steroids having a 1,4-diene, 4,6-diene, or 1,4,6-triene structure as aromatase inhibitors
    • DOI 10.1016/S0039-128X(98)00088-9, PII S0039128X98000889
    • Numazawa, M.; Yamaguchi, S. Synthesis and structure-activity relationships of 6-phenylaliphaticsubstituted C19 steroids having a 1,4-diene, 4,6-diene or 1,4,6-triene structure as aromatase inhibitors. Steroids 2001, 64, 187-196. (Pubitemid 29283671)
    • (1999) Steroids , vol.64 , Issue.3 , pp. 187-196
    • Numazawa, M.1    Yamaguchi, S.2
  • 27
    • 0025089852 scopus 로고
    • Aromatase inhibition by 4-thiosubstituted-4-androstene-3,17-dione derivatives
    • DOI 10.1016/0022-4731(90)90158-O
    • Abul-Hajj, Y.J. Aromatase inhibition by 4-thiosubstituted-4-androstene-3, 17-dione derivatives. J. Steroid Biochem. 1990, 35, 139-143. (Pubitemid 20075411)
    • (1990) Journal of Steroid Biochemistry , vol.35 , Issue.1 , pp. 139-143
    • Abul-Hajj, Y.J.1
  • 28
    • 33947432702 scopus 로고    scopus 로고
    • Epoxidation and reduction of DHEA, 1,4,6-androstatrien-3-one and 4,6-androstadien-3?,17?-diol
    • Ma, E.; Kim, E. Epoxidation and reduction of DHEA, 1,4,6-androstatrien-3- one and 4,6-androstadien-3?,17?-diol. Molecules 2005, 10, 572-582.
    • (2005) Molecules , vol.10 , pp. 572-582
    • Ma, E.1    Kim, E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.