SYNTHESIS AND EVALUATION OF THE ANTI-OVULATORY ACTIVITY OF A VARIETY OF MELATONIN ANALOGS

被引:66
作者
FLAUGH, ME
CROWELL, TA
CLEMENS, JA
SAWYER, BD
机构
[1] The Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana
关键词
D O I
10.1021/jm00187a015
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of melatonin analogues was synthesized and examined for ovulation-blocking activity. Deviation from the 5-methoxy group or substitution of the 1 position prevented activity. Activity was not particularly sensitive to minor variations in the N-acyl group nor was it significantly altered by methylation of position 2 or the α-methylene; however, a pronounced enhancement resulted from halogenation of the 6 position. © 1979, American Chemical Society. All rights reserved.
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页码:63 / 69
页数:7
相关论文
共 30 条
[1]   ALKALOIDS OF SHEPHERDIA-ARGENTEA AND SHEPHERDIA-CANADENSIS [J].
AYER, WA ;
BROWNE, LM .
CANADIAN JOURNAL OF CHEMISTRY, 1970, 48 (13) :1980-&
[2]  
Batcho A. D., 1973, U.S. Pat., Patent No. [US3732245, 3732245]
[3]   HYDROXYLATION-INDUCED MIGRATION - NIH SHIFT [J].
GUROFF, G ;
DALY, JW ;
JERINA, DM ;
RENSON, J ;
WITKOP, B ;
UDENFRIE.S .
SCIENCE, 1967, 157 (3796) :1524-&
[4]   THE SYNTHESIS OF ALPHA-METHYLTRYPTOPHANS AND ALPHA-ALKYLTRYPTAMINES [J].
HEINZELMAN, RV ;
ANTHONY, WC ;
LYTTLE, DA ;
SZMUSZKOVICZ, J .
JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (09) :1548-1558
[5]   ISOLATION OF A NEW PLANT-GROWTH HORMONE, 3-INDOLYLACETONITRILE [J].
HENBEST, HB ;
JONES, ERH ;
SMITH, GF .
JOURNAL OF THE CHEMICAL SOCIETY, 1953, (DEC) :3796-3801
[6]  
HIRATA F, 1974, J BIOL CHEM, V249, P1311
[7]   The nitrosation of phenols Part VII Resorcinol monomethyl ether and m-cresol [J].
Hodgson, HH ;
Clay, H .
JOURNAL OF THE CHEMICAL SOCIETY, 1929, :2775-2778
[8]  
KAMBERI IA, 1970, ENDOCRINOLOGY, V87, P1
[9]   SYNTHESIS OF RING-FLUORINATED SEROTONINS AND MELATONINS [J].
KIRK, KL .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1976, 13 (06) :1253-1256
[10]  
KOPIN IJ, 1961, J BIOL CHEM, V236, P3072