THE SYNTHESIS OF (-)-4-METHYL-8-CHLORO-TRANS-1,2,3,4,4A,5,6,10B-OCTAHYDROBENZO-[F]-QUINOLIN-3-ONE-[3-C-14] (LY300502-C-14]) VIA A CIRCUITOUS ROUTE

被引:2
作者
KUO, FJ [1 ]
WHEELER, WJ [1 ]
机构
[1] ELI LILLY & CO,LILLY CORP CTR,LILLY RES LABS,INDIANAPOLIS,IN 46285
关键词
SELECTIVE TYPE I 5-ALPHA-REDUCTASE INHIBITOR; LY300502; CARBON; 14;
D O I
10.1002/jlcr.2580341004
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
The synthesis of the C-14 labeled isotopomer of LY300502, a potent 5 alpha-reductase inhibitor has been accomplished in four radiochemical steps. The route involves the synthesis of LY300502-[C-14] from LY300502 via a circuitous route; the label was introduced with ethyl chloroformate-[carbonyl-C-14]
引用
收藏
页码:915 / 920
页数:6
相关论文
共 10 条
  • [1] STRUCTURAL AND BIOCHEMICAL-PROPERTIES OF CLONED AND EXPRESSED HUMAN AND RAT STEROID 5-ALPHA-REDUCTASES
    ANDERSSON, S
    RUSSELL, DW
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1990, 87 (10) : 3640 - 3644
  • [2] ASTLEFORD BA, 1993, UNPUB J ORG CHEM
  • [3] TREATMENT OF HIRSUTISM WITH 5-ALPHA-REDUCTASE INHIBITORS
    BROOKS, JR
    [J]. CLINICS IN ENDOCRINOLOGY AND METABOLISM, 1986, 15 (02): : 391 - 405
  • [4] HAIR-GROWTH EFFECTS OF ORAL-ADMINISTRATION OF FINASTERIDE, A STEROID 5-ALPHA-REDUCTASE INHIBITOR, ALONE AND IN COMBINATION WITH TOPICAL MINOXIDIL IN THE BALDING STUMPTAIL MACAQUE
    DIANI, AR
    MULHOLLAND, MJ
    SHULL, KL
    KUBICEK, MF
    JOHNSON, GA
    SCHOSTAREZ, HJ
    BRUNDEN, MN
    BUHL, AE
    [J]. JOURNAL OF CLINICAL ENDOCRINOLOGY & METABOLISM, 1992, 74 (02) : 345 - 350
  • [5] INHIBITION OF STEROID 5-ALPHA-REDUCTASE BY UNSATURATED 3-CARBOXYSTEROIDS
    HOLT, DA
    LEVY, MA
    OH, HJ
    ERB, JM
    HEASLIP, JI
    BRANDT, M
    LANHARGEST, HY
    METCALF, BW
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (03) : 943 - 950
  • [6] NONSTEROIDAL INHIBITORS OF HUMAN TYPE-I STEROID 5-ALPHA-REDUCTASE
    JONES, CD
    AUDIA, JE
    LAWHORN, DE
    MCQUAID, LA
    NEUBAUER, BL
    PIKE, AJ
    PENNINGTON, PA
    STAMM, NB
    TOOMEY, RE
    HIRSCH, KS
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (03) : 421 - 423
  • [7] AZASTEROIDS - STRUCTURE-ACTIVITY-RELATIONSHIPS FOR INHIBITION OF 5-ALPHA-REDUCTASE AND OF ANDROGEN RECEPTOR-BINDING
    RASMUSSON, GH
    REYNOLDS, GF
    STEINBERG, NG
    WALTON, E
    PATEL, GF
    LIANG, TM
    CASCIERI, MA
    CHEUNG, AH
    BROOKS, JR
    BERMAN, C
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (11) : 2298 - 2315
  • [8] DIFFERENTIAL RATES OF CONVERSION OF TESTOSTERONE TO DIHYDROTESTOSTERONE IN ACNE AND IN NORMAL HUMAN SKIN - POSSIBLE PATHOGENIC FACTOR IN ACNE
    SANSONE, G
    REISNER, RM
    [J]. JOURNAL OF INVESTIGATIVE DERMATOLOGY, 1971, 56 (05) : 366 - &
  • [9] RAPID CHROMATOGRAPHIC TECHNIQUE FOR PREPARATIVE SEPARATIONS WITH MODERATE RESOLUTION
    STILL, WC
    KAHN, M
    MITRA, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (14) : 2923 - 2925
  • [10] TISSUE CONTENT OF DIHYDROTESTOSTERONE IN HUMAN PROSTATIC HYPERPLASIA IS NOT SUPRANORMAL
    WALSH, PC
    HUTCHINS, GM
    EWING, LL
    [J]. JOURNAL OF CLINICAL INVESTIGATION, 1983, 72 (05) : 1772 - 1777