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Flavonoids. 8. Synthesis and antifertility and estrogen receptor binding activities of coumarins and delta3-isoflavenes.

Publication ,  Journal Article
Wani, MC; Rector, DH; Christensen, HD; Kimmel, GL; Cook, CE
Published in: J Med Chem
October 1975

A series of coumarins and delta3-isoflavenes was prepared. Although antifertility activity was shown by all of these compounds, the required dosage in mice varied from 13.5 mug/kg/day to 50 mg/kg/day. The most potent compounds were the 2-methyl-4-ethylisoflavenes, two of which (2a and 2b) were about equipotent with DES on a molar basis. They were followed by the 2,2-dimethylisoflavenes, the 2-unsubstituted isoflavene, and the coumarins. The most active compounds possessed an acetoxy group at C-7 and an oxygen function at C-4'. Presence of fluorine at C-4' or diethylaminoethoxy at C-M decreased the antifertility activity. The uterotropic activity followed the same trends as the antifertility activity with some evidence for the separation of the two effects in the 2,2-dimethylisoflavene series. Based on a limited study it appears that two phenolic hydroxyl groups are required for the presence of good estrogen receptor binding activity. An apparent lack of correlation between the estrogen binding activity and uterotropic or antifertility effects is probably explained by in vivo metabolism.

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Published In

J Med Chem

DOI

ISSN

0022-2623

Publication Date

October 1975

Volume

18

Issue

10

Start / End Page

982 / 985

Location

United States

Related Subject Headings

  • Uterus
  • Receptors, Cell Surface
  • Rats
  • Organ Size
  • Mice
  • Medicinal & Biomolecular Chemistry
  • Flavonoids
  • Fertility
  • Female
  • Estrogens, Non-Steroidal
 

Citation

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Wani, M. C., Rector, D. H., Christensen, H. D., Kimmel, G. L., & Cook, C. E. (1975). Flavonoids. 8. Synthesis and antifertility and estrogen receptor binding activities of coumarins and delta3-isoflavenes. J Med Chem, 18(10), 982–985. https://doi.org/10.1021/jm00244a006
Wani, M. C., D. H. Rector, H. D. Christensen, G. L. Kimmel, and C. E. Cook. “Flavonoids. 8. Synthesis and antifertility and estrogen receptor binding activities of coumarins and delta3-isoflavenes.J Med Chem 18, no. 10 (October 1975): 982–85. https://doi.org/10.1021/jm00244a006.
Wani MC, Rector DH, Christensen HD, Kimmel GL, Cook CE. Flavonoids. 8. Synthesis and antifertility and estrogen receptor binding activities of coumarins and delta3-isoflavenes. J Med Chem. 1975 Oct;18(10):982–5.
Wani, M. C., et al. “Flavonoids. 8. Synthesis and antifertility and estrogen receptor binding activities of coumarins and delta3-isoflavenes.J Med Chem, vol. 18, no. 10, Oct. 1975, pp. 982–85. Pubmed, doi:10.1021/jm00244a006.
Wani MC, Rector DH, Christensen HD, Kimmel GL, Cook CE. Flavonoids. 8. Synthesis and antifertility and estrogen receptor binding activities of coumarins and delta3-isoflavenes. J Med Chem. 1975 Oct;18(10):982–985.
Journal cover image

Published In

J Med Chem

DOI

ISSN

0022-2623

Publication Date

October 1975

Volume

18

Issue

10

Start / End Page

982 / 985

Location

United States

Related Subject Headings

  • Uterus
  • Receptors, Cell Surface
  • Rats
  • Organ Size
  • Mice
  • Medicinal & Biomolecular Chemistry
  • Flavonoids
  • Fertility
  • Female
  • Estrogens, Non-Steroidal