메뉴 건너뛰기




Volumn 68, Issue 7-8, 2003, Pages 659-666

Synthetic approaches for the synthesis of a cytostatic steroidal B-D bilactam

Author keywords

B,D bilactam; Beckmann rearrangement; Homo aza steroids; N Benzoyl protection; Steroidal synthesis

Indexed keywords

3BETA ACETOXY 17ALPHA AZA DEXTRO HOMO 5 ANDROSTEN 17 ONE; 3BETA ACETOXY 5 ANDROSTEN 17 ONE; 3BETA HYDROXY 7ALPHA,17ALPHA DIAZADIHOMO 5 ANDROSTEN 7,17 DIONE; 7 KETONE; ALLYL COMPOUND; AMIDE; CYTOSTATIC AGENT; KETONE DERIVATIVE; LACTAM DERIVATIVE; NITROGEN; STEROID; UNCLASSIFIED DRUG;

EID: 0042236776     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(03)00095-3     Document Type: Article
Times cited : (30)

References (26)
  • 1
    • 85031084327 scopus 로고    scopus 로고
    • Erlichman C, Loprinzi CL. Hormonal therapies. In: CANCER principles and practice of oncology. 5th ed. Philadelphia: Lippincott-Raven Publication; 1997. p. 395.
    • Erlichman C, Loprinzi CL. Hormonal therapies. In: CANCER principles and practice of oncology. 5th ed. Philadelphia: Lippincott-Raven Publication; 1997. p. 395.
  • 2
    • 0029802704 scopus 로고    scopus 로고
    • Hormones, vitamins and growth factors in cancer treatment and prevention
    • Lupulescu A.P. Hormones, vitamins and growth factors in cancer treatment and prevention. Cancer. 78:1996;2264-2280.
    • (1996) Cancer , vol.78 , pp. 2264-2280
    • Lupulescu, A.P.1
  • 3
    • 85031082880 scopus 로고    scopus 로고
    • Wasan H, Waxman J. In: Pusztai LL, Lewis CE, Yap E, editors. Cell proliferation cancer. Oxford: Oxford University Press; 1996. p. 260-81.
    • Wasan H, Waxman J. In: Pusztai LL, Lewis CE, Yap E, editors. Cell proliferation cancer. Oxford: Oxford University Press; 1996. p. 260-81.
  • 5
    • 0014575950 scopus 로고
    • The effect of some steroidal alkylating agents on experimental animal mammary tumor and leukaemia systems
    • Wall M.E., Abernethy G.S. Jr., Caroll F.J., Taylor D.J. The effect of some steroidal alkylating agents on experimental animal mammary tumor and leukaemia systems. J. Med. Chem. 12:1969;810-818.
    • (1969) J. Med. Chem. , vol.12 , pp. 810-818
    • Wall, M.E.1    Abernethy G.S., Jr.2    Caroll, F.J.3    Taylor, D.J.4
  • 6
    • 0018652237 scopus 로고
    • A new steroidal alkylating agent with improved activity in advanced murine leukaemias
    • Catsoulacos P., Politis D., Wampler G.L. A new steroidal alkylating agent with improved activity in advanced murine leukaemias. Cancer Chemother. Pharmacol. 3:1979;67-70.
    • (1979) Cancer Chemother. Pharmacol. , vol.3 , pp. 67-70
    • Catsoulacos, P.1    Politis, D.2    Wampler, G.L.3
  • 7
    • 0020058519 scopus 로고
    • Activity of 3β-hydroxy-13α-amino-13,17-seco-5α -androstan-17-oic-13,17-lactam-p-bis(2-chloroethyl)aminophenylacetate
    • Catsoulacos P., Wampler G.L. Activity of 3β-hydroxy-13α -amino-13,17-seco-5α-androstan-17-oic-13,17-lactam-p-bis(2-chloroethyl) aminophenylacetate. Oncology. 39:1982;109-112.
    • (1982) Oncology , vol.39 , pp. 109-112
    • Catsoulacos, P.1    Wampler, G.L.2
  • 8
    • 0020961408 scopus 로고
    • Chromosome damage and SCE induced by the cytostatic factor homo-aza-steroidal ester of p-bis(2-chloroethyl)amino phenyl acetic acid in CHO cells in culture
    • Athanasiou K., Demopoulos N., Catsoulacos P. Chromosome damage and SCE induced by the cytostatic factor homo-aza-steroidal ester of p-bis(2-chloroethyl)amino phenyl acetic acid in CHO cells in culture. Environ. Mutagen. 5:1983;279-283.
    • (1983) Environ. Mutagen. , vol.5 , pp. 279-283
    • Athanasiou, K.1    Demopoulos, N.2    Catsoulacos, P.3
  • 9
    • 0033860902 scopus 로고    scopus 로고
    • Synergistic antineoplastic and cytogenetic effects by the combined action of two homo-aza-steroidal esters of nitrogen mustards on P388 and L1210 leukemias in vivo and in vitro
    • Nikolaropoulos S.S., Tsavdaridis D., Arsenou E.S., Papageorgiou A., Karaberis E., Mourelatos D. Synergistic antineoplastic and cytogenetic effects by the combined action of two homo-aza-steroidal esters of nitrogen mustards on P388 and L1210 leukemias in vivo and in vitro. Anticancer Res. 20:2000;2745-2752.
    • (2000) Anticancer Res. , vol.20 , pp. 2745-2752
    • Nikolaropoulos, S.S.1    Tsavdaridis, D.2    Arsenou, E.S.3    Papageorgiou, A.4    Karaberis, E.5    Mourelatos, D.6
  • 10
    • 0023612270 scopus 로고
    • Response of transplantable tumors in mice of macromolecular synthesis to 17β-acetamido-3-aza-A-homo-4α-androsten-4-one
    • Athanasiou C., Catsoulacos P., Papageorgiou A., Athanasiou K. Response of transplantable tumors in mice of macromolecular synthesis to 17β-acetamido-3-aza-A-homo-4α-androsten-4-one. Cancer Invest. 5:1987;301-307.
    • (1987) Cancer Invest. , vol.5 , pp. 301-307
    • Athanasiou, C.1    Catsoulacos, P.2    Papageorgiou, A.3    Athanasiou, K.4
  • 11
    • 0038737974 scopus 로고
    • Steroids and related studies. Part XXXVI. 7α-17α -Diaza-7,17-dioxo-B,D-dihomo-5-androsten-3β-yl acetate
    • Singh H., Gupta S.K., Padmanablan D.P., Bhardwaj T.R. Steroids and related studies. Part XXXVI. 7α-17α -Diaza-7,17-dioxo-B,D-dihomo-5-androsten-3β-yl acetate. Indian J. Chem. 15B:1977;101-102.
    • (1977) Indian J. Chem. , vol.15 B , pp. 101-102
    • Singh, H.1    Gupta, S.K.2    Padmanablan, D.P.3    Bhardwaj, T.R.4
  • 12
    • 85031083140 scopus 로고    scopus 로고
    • Shoppee CW, Akhtar MI, Lack RE. Aza-steroids. Part VIII. 7α-Aza-B-homo-5α-cholestane and 7α-aza-B-homocholest-5-ene. J Chem Soc 1964:3392-5.
    • Shoppee CW, Akhtar MI, Lack RE. Aza-steroids. Part VIII. 7α-Aza-B-homo-5α-cholestane and 7α-aza-B-homocholest-5-ene. J Chem Soc 1964:3392-5.
  • 13
    • 0041824403 scopus 로고
    • 3,7α-Diaza-A,B-bishomocholest-4α-ene-4,7-dione
    • Singh H., Padmanabhan S. 3,7α-Diaza-A,B-bishomocholest-4α -ene-4,7-dione. Tetrahedron Lett. 38:1967;3689-3692.
    • (1967) Tetrahedron Lett. , vol.38 , pp. 3689-3692
    • Singh, H.1    Padmanabhan, S.2
  • 14
    • 0001657356 scopus 로고
    • 17 and 17α-aza-D-homo-steroids
    • Regan B.M., Hayes F.N. 17 and 17α-aza-D-homo-steroids. J. Am. Chem. Soc. 78:1956;634-643.
    • (1956) J. Am. Chem. Soc. , vol.78 , pp. 634-643
    • Regan, B.M.1    Hayes, F.N.2
  • 16
    • 8644290293 scopus 로고
    • Preparation of ethylenethioketals
    • Fieser L. Preparation of ethylenethioketals. J. Am. Chem. Soc. 76:1954;1945-1947.
    • (1954) J. Am. Chem. Soc. , vol.76 , pp. 1945-1947
    • Fieser, L.1
  • 18
    • 0000708263 scopus 로고
    • Synthesis of unsaturated carbonyl compounds via a chromium-mediated allylic oxidation by 70% tert-butyl hydroperoxide
    • Muzart J. Synthesis of unsaturated carbonyl compounds via a chromium-mediated allylic oxidation by 70% tert-butyl hydroperoxide. Tetrahedron Lett. 28:1987;4665-4668.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 4665-4668
    • Muzart, J.1
  • 19
    • 0030220720 scopus 로고    scopus 로고
    • Steroidal allylic fluorination using diethylaminosulfur trifluoride: A convenient method for the synthesis of 3β-acetoxy-7α- and 7β-fluoroandrost-5-en-17-one
    • Padma M., Thoden J.B., Powell D.R., Lardy H.A. Steroidal allylic fluorination using diethylaminosulfur trifluoride: a convenient method for the synthesis of 3β-acetoxy-7α- and 7β-fluoroandrost-5-en-17-one. Steroids. 61:1996;453-460.
    • (1996) Steroids , vol.61 , pp. 453-460
    • Padma, M.1    Thoden, J.B.2    Powell, D.R.3    Lardy, H.A.4
  • 20
    • 0018412879 scopus 로고
    • A general methology for pseudoguaiane synthesis: Total synthesis of (±)-damsinic acid and (±)-confertin
    • Wender P.A., Eissenstat M.A., Filosa M.P. A general methology for pseudoguaiane synthesis: total synthesis of (±)-damsinic acid and (±)-confertin. JACS. 101(8):1979;2196-2198.
    • (1979) JACS , vol.101 , Issue.8 , pp. 2196-2198
    • Wender, P.A.1    Eissenstat, M.A.2    Filosa, M.P.3
  • 22
    • 0035400867 scopus 로고    scopus 로고
    • Ergosteroids IV: Synthesis and biological activity of steroid glucuronosides, ethers and alkylcarbonates
    • Marwah P., Marwah A., Kneer N., Lardy H. Ergosteroids IV: synthesis and biological activity of steroid glucuronosides, ethers and alkylcarbonates. Steroids. 66:2001;581-595.
    • (2001) Steroids , vol.66 , pp. 581-595
    • Marwah, P.1    Marwah, A.2    Kneer, N.3    Lardy, H.4
  • 23
    • 0344193633 scopus 로고    scopus 로고
    • Synthesis of (19E)-3β,7α -dihydroxy-17-oxoandrost-5-en-19-al-19-(O-carboxymethyl)oxime, a new hapten for 7α-hydroxydehydroepiandrosterone (3β,7α -dihydroxy-androst-5-en-17-one)
    • Pouzar V., Slavíkovà T., Èerný I. Synthesis of (19E)-3β,7α -dihydroxy-17-oxoandrost-5-en-19-al-19-(O-carboxymethyl)oxime, a new hapten for 7α-hydroxydehydroepiandrosterone (3β,7α -dihydroxy-androst-5-en-17-one). Steroids. 63:1998;454-458.
    • (1998) Steroids , vol.63 , pp. 454-458
    • Pouzar, V.1    Slavíkovà, T.2    Èerný, I.3
  • 25
    • 0042325261 scopus 로고
    • Steroids. Part X. Some 5-en-7-ones and 7α-aza-B-homo-5-en-7-ones in spirostan, androstan and pregnane series
    • Singh H., Padmanabhan S. Steroids. Part X. Some 5-en-7-ones and 7α-aza-B-homo-5-en-7-ones in spirostan, androstan and pregnane series. Indian J. Chem. 7:1969;1084-1087.
    • (1969) Indian J. Chem. , vol.7 , pp. 1084-1087
    • Singh, H.1    Padmanabhan, S.2
  • 26
    • 0002725547 scopus 로고
    • The Beckmann reactions: Rearrangements, elimination-additions, fragmentations and rearrangement-cyclizations
    • Gawley R.E. The Beckmann reactions: rearrangements, elimination-additions, fragmentations and rearrangement-cyclizations. Org. React. 35:1988;1-420.
    • (1988) Org. React. , vol.35 , pp. 1-420
    • Gawley, R.E.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.