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      3β-치환 5-Androstene-17-Carboxamides 합성과 5α-Reductase 저해 활성 = Synthesis and 5α-Reductase Inhibitory Activity of 3β-Substituted 5-Androstene-17-Carboxamides

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      https://www.riss.kr/link?id=A100412935

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      다국어 초록 (Multilingual Abstract)

      A series of 3β-substituted 5-androstene-17β-carboxamides were synthesized from analogs of 3β-hydroxy-5-androstene-17β-carboxylic acid (1) with tert-butylamine, N,N-diethylamine and 3-aminopyridine and some compounds were epoxidized with mCPBA. A rat prostate testosterone 5α-reductase inhibitory activity of synthesized compounds was assessed by radioimmunoassay using [1,2,6,7-3H]-testosterone as substrate. All synthesized compounds showed lower activity than finasteride and the N-(3-pyridino)-3β-carboxycarbonyloxy-5-androstene-17β-carboxamide (12) showed weak inhibitory activity (IC50: 2.4×10-7 M).
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      A series of 3β-substituted 5-androstene-17β-carboxamides were synthesized from analogs of 3β-hydroxy-5-androstene-17β-carboxylic acid (1) with tert-butylamine, N,N-diethylamine and 3-aminopyridine and some compounds were epoxidized with mCPBA. A r...

      A series of 3β-substituted 5-androstene-17β-carboxamides were synthesized from analogs of 3β-hydroxy-5-androstene-17β-carboxylic acid (1) with tert-butylamine, N,N-diethylamine and 3-aminopyridine and some compounds were epoxidized with mCPBA. A rat prostate testosterone 5α-reductase inhibitory activity of synthesized compounds was assessed by radioimmunoassay using [1,2,6,7-3H]-testosterone as substrate. All synthesized compounds showed lower activity than finasteride and the N-(3-pyridino)-3β-carboxycarbonyloxy-5-androstene-17β-carboxamide (12) showed weak inhibitory activity (IC50: 2.4×10-7 M).

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      참고문헌 (Reference)

      1 Kim, Y.-U, "Testosterone 5α-reductase inhibitors,menaquinone 7 produced by a Bacillus and Phenazine methosulfate" 22 (22): 1396-, 1999

      2 Ramirez, E, "Synthesis and pharmacological evaluation of new progesterone esters as 5α-reductase inhibitors" 53 (53): 1515-, 2005

      3 Li, J. S, "Synthesis and evaluation of pregnane derivatives as inhibitors of human testicular 17α-hydroxylase/C17,20-lyase" 39 : 4335-, 1996

      4 Andersson, S, "Structural and biochemical properties of cloned expressed human and rat steroid 5α-reductase" 87 : 3640-, 1990

      5 Carroll King, L, "Preparation of 21-pyridinium-3β-hydroxy-5-pregnene-20-one halides and 3β-hydroxy-5-androstene-17-carboxylic acid" 66 (66): 1612-, 1944

      6 Jones, C. D, "Nonsteroidal inhibitors of human type I steroid 5α-reductase" 36 : 421-, 1993

      7 Cabeza, M, "New progesterone esters as 5α-reductase inhibitors" 49 (49): 1081-, 2001

      8 Bratoeff, E, "Molecular interactions of new pregnenedione derivatives" 51 (51): 1132-, 2003

      9 McConnell, J. D, "Finasteride,and inhibitor of 5α-reductase, suppresses prostatic dihydrotestosterone in men with benign prostatic hyperplasia" 74 (74): 505-, 1992

      10 Nnane, I. P, "Effects of some novel inhibitors of C17,20-lyase and 5α-reductase in vitro and in vivo and their potential role in the treatment of prostste cancer" 38 : 3826-, 1998

      1 Kim, Y.-U, "Testosterone 5α-reductase inhibitors,menaquinone 7 produced by a Bacillus and Phenazine methosulfate" 22 (22): 1396-, 1999

      2 Ramirez, E, "Synthesis and pharmacological evaluation of new progesterone esters as 5α-reductase inhibitors" 53 (53): 1515-, 2005

      3 Li, J. S, "Synthesis and evaluation of pregnane derivatives as inhibitors of human testicular 17α-hydroxylase/C17,20-lyase" 39 : 4335-, 1996

      4 Andersson, S, "Structural and biochemical properties of cloned expressed human and rat steroid 5α-reductase" 87 : 3640-, 1990

      5 Carroll King, L, "Preparation of 21-pyridinium-3β-hydroxy-5-pregnene-20-one halides and 3β-hydroxy-5-androstene-17-carboxylic acid" 66 (66): 1612-, 1944

      6 Jones, C. D, "Nonsteroidal inhibitors of human type I steroid 5α-reductase" 36 : 421-, 1993

      7 Cabeza, M, "New progesterone esters as 5α-reductase inhibitors" 49 (49): 1081-, 2001

      8 Bratoeff, E, "Molecular interactions of new pregnenedione derivatives" 51 (51): 1132-, 2003

      9 McConnell, J. D, "Finasteride,and inhibitor of 5α-reductase, suppresses prostatic dihydrotestosterone in men with benign prostatic hyperplasia" 74 (74): 505-, 1992

      10 Nnane, I. P, "Effects of some novel inhibitors of C17,20-lyase and 5α-reductase in vitro and in vivo and their potential role in the treatment of prostste cancer" 38 : 3826-, 1998

      11 Lazier, C. B, "Dutasteride, the dual 5α-reductase inhibitor,inhibits androgen action and promates cell death in the LNCaP prostate cancer cell line" 58 : 130-, 2004

      12 Andersson, S, "Deletion of steroid 2 gene in male pseudohermaphroditism" 354 : 159-, 1991

      13 Geller, J, "Comparison of androgen metabolites in benign prostatic hypertrophy (BPH) and normal prostate" 43 : 486-, 1976

      14 Ekman, P, "BPH epidemiology and risk factors" 2 : 23-, 1989

      15 Labrie, F, "A combination therapy for prostate cancer" 71 : 1059-, 1993

      16 Cabeza, M, "5α-Reductase inhibitory and antiandrogenic activities of novel steroids in hamster seminal vesicles" 50 (50): 1447-, 2002

      17 Staunton, J, "3β-Acetoxyetienic acid" 5 : 8-, 1973

      18 Guarna, A, "19-Nor-10-azasterides: A noval class of inhibitors for human steroid 5α-reductase 1 and 2" 40 : 1112-, 1997

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      학술지 이력

      학술지 이력
      연월일 이력구분 이력상세 등재구분
      2027 평가예정 재인증평가 신청대상 (재인증)
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      2015-01-01 평가 등재학술지 유지 (등재유지) KCI등재
      2011-01-01 평가 등재학술지 유지 (등재유지) KCI등재
      2009-01-01 평가 등재학술지 유지 (등재유지) KCI등재
      2007-01-01 평가 등재학술지 유지 (등재유지) KCI등재
      2004-01-01 평가 등재학술지 선정 (등재후보2차) KCI등재
      2003-01-01 평가 등재후보 1차 PASS (등재후보1차) KCI등재후보
      2002-01-01 평가 등재후보학술지 유지 (등재후보1차) KCI등재후보
      1999-07-01 평가 등재후보학술지 선정 (신규평가) KCI등재후보
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      학술지 인용정보

      학술지 인용정보
      기준연도 WOS-KCI 통합IF(2년) KCIF(2년) KCIF(3년)
      2016 0.2 0.2 0.22
      KCIF(4년) KCIF(5년) 중심성지수(3년) 즉시성지수
      0.23 0.18 0.403 0.02
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