Novel 5-aryl-1,3-dihydro-indole-2-thiones: Potent, orally active progesterone receptor agonists

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 7, 2003, Pages 1317-1320

  Fensome, Andrew ^a   Koko, Marci ^a   Wrobel, Jay ^b   Zhang, Puwen ^a   Zhang, Zhiming ^a   Cohen, Jeffrey ^a   Lundeen, Scott ^a   Rudnick, Kelly ^a   Zhu, Yuan ^a   Winneker, Richard ^a  

^a PFIZER INC   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; INDOLE DERIVATIVE; PROGESTERONE RECEPTOR MODULATOR; THIOAMIDE;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

EID: 0037424718     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00129-X     Document Type: Article

References (14)

1. Mangelsdorf D.J., Thummel C., Beato M., Herrlich P., Schütz G., Umesono K., Blumberg B., Kastner P., Mark M., Chambon P., Evans R.M. Cell. 83:1995;835.
2. (a) Jeppsson S. Acta Obstet. Gynecol. Scand., Suppl. 101:1981;7
3. (b) O'Connell B.J. Current Opinion In Pediatrics. 7:1995;371.
4. (a) Zhang P., Terefenko E.A., Fensome A., Zhang Z., Zhu Y., Cohen J., Winneker R., Wrobel J., Yardley J. Bioorg. Med. Chem. Lett. 12:2002;787
5. (b) Zhi L., Tegley C.M., Marschke K.B., Mais D.E., Jones T.K. J. Med. Chem. 42:1999;1466
6. (c) Palmer S., Campen C.A., Allan G.F., Rybczynski P., Haynes-Johnson D., Hutchins A., Kraft P., Kiddoe M., Lai M.-T., Lombardi E., Pedersen P., Hodgen G., Combs D.W.J. Steroid Biochem. Mol. Bio. 5:2001;33.
7. (a) Fensome, A.; Bender, R.; Cohen, J.; Collins, M. A.; Mackner, V. A.; Miller, L. L.; John, W.; Ullrich, J. W.; Winneker, R. C.; Wrobel, J.; Zhang, P.; Zhang, Z; Zhu, Y.; Bioorg. Med. Chem. Lett., submitted for publication.
8. (b) Fensome, A.; Bender, R.; Collins, M.; Fletcher, H., III; Mackner, V.; Miller, L. L.; Ullrich, J.; Wrobel, J.; Zhang, P.; Zhang, Z.; Zhu, Y.; Cohen, J.; Winneker, R.: Abstracts of Papers, 223rd ACS National Meeting, Orlando, FL, USA, 7-11 April, 2002 (2002), MEDI-068.
9. (a) Zhang Z., Lundeen S.G., Zhu Y., Carver J.M., Winneker R.C. Steroids. 65:2000;637
10. (b) Beck C.A., Weigel N.L., Moyer M.L., Nordeen S.K., Edwards D. Proc. Natl. Acad. Sci. U.S.A. 90:1993;4441.
11. Lundeen S.G., Zhang Z., Zhu Y., Carver J.M., Winneker R.C. J. Steroid Biochem. Mol. Bio. 78:2001;137.
12. 3) δ 10.05 (s, 1H), 7.85 (d, 1H, J=1 Hz), 7.65 (s, 1H), 7.46-7.52 (m, 2H), 7.33-7.36 (m, 1H), 7.16 (d, 1H, J=8.1 Hz), 1.86-2,18 (m, 7H) and 1.54-1.66 (m, 3H); MS ((+)-APCI) m/z 337 [M+H]+.
13. 6) δ 12.82 (s, 1H), 8.0-7.98 (m, 2H), 7.73 (d, 1H, J=4 Hz), 7.69 (dd, 1H, J=8.2 and 1.5 Hz), 7.10 (d, 1H, J=8.2 Hz), 1.98-1.77 (m, 7H), 1.43-1.33 (m, 3H); MS (EI) M+ @ m/z 324.
14. Zhi L., Tegley C.M., Kallel E.A., Marschke K.B., Mais D.E., Gottardis M., Jones T.K. J. Med. Chem. 41:1998;291.