A full conformational characterization of 13-ethylprogestogens through theoretical calculations and nuclear magnetic resonance spectroscopy

Journal of Steroid Biochemistry and Molecular Biology

Volumn 103, Issue 2, 2007, Pages 163-169

  Colombo, Diego ^a   Ferraboschi, Patrizia ^a   Legnani, Laura ^b   Prestileo, Paolo ^a   Toma, Lucio ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF PAVIA   (Italy)

Author keywords

DFT calculations; Molecular modeling; NMR; Progestins

Indexed keywords

13 ETHYLPROGESTOGEN; ESTRANE DERIVATIVE; ETHISTERONE; ETONOGESTREL; GESTAGEN; GESTODENE; LEVONORGESTREL; METHYL GROUP; NORETHISTERONE; STEROID; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATIONAL TRANSITION; GEOMETRY; HORMONE STRUCTURE; MATHEMATICAL ANALYSIS; METABOLITE; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ANALYSIS; TRANS ISOMER;

MAGNETIC RESONANCE SPECTROSCOPY; MODELS, BIOLOGICAL; MODELS, MOLECULAR; MODELS, THEORETICAL; MOLECULAR CONFORMATION; PROGESTERONE CONGENERS;

EID: 33846434871     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2006.09.036     Document Type: Article

References (19)

1. Pasqualini J.R. Progestins: present and future. J. Steroid Biochem. Mol. Biol. 59 5-6 (1996) 357-365
2. Schindler A.E., Campagnoli C., Druckmann R., Huber J., Pasqualini J.R., Schweppe K.W., and Thijssen J.H.H. Classification and pharmacology of progestins. Maturitas 46S1 (2003) S7-S16
3. Bursi R., and Groen M.B. Application of (quantitative) structure-activity relationships to progestagens: from serendipidity to structure-based design. Eur. J. Med. Chem. 35 9 (2000) 787-796
4. Vendrame R., Ferreira M.M.C., Collins C.H., and Takahata Y. Structure-activity relationships (SAR) of contraceptive progestogens studied with four different methods using calculated physicochemical parameters. J. Mol. Graph. Model. 20 4 (2002) 345-358
5. Kiralj R., Takahata Y., and Ferreira M.M.C. QSAR of progestogens: use of a priori and computed molecular descriptors and molecular graphics. QSAR Comb. Sci. 22 4 (2003) 430-448
6. Galdecki Z., Grochulski P., Wawrzak Z., Galdecka E., Duax W.L., and Strong P.D. Crystal structure of 4,11-pregnadiene-3,20-dione and 21-methyl-20-oxa-4-pregnene-3,20-dione. J. Chem. Crystallogr. 26 7 (1996) 497-502
7. Raynaud J.P., Ojasoo T., Bouton M.M., and Philibert D. In: Ariens E.J. (Ed). Drug Design (1979), Academic Press, New York 169-214
8. Broess A.I.A., Groen M.B., and Hamersma H. Synthesis of conformationally restricted progestational 13-ethylsteroids. Bioorg. Med. Chem. Lett. 7 23 (1997) 2929-2934
9. Szyczewsky A., Holderna-Natkaniec K., and Natkaniec I. Progesterone and testosterone studies by neutron scattering and nuclear magnetic resonance methods and quantum chemistry calculations. J. Mol. Struct. 693 1-3 (2004) 49-71
10. Colombo D., Ferraboschi P., Prestileo P., and Toma L. A comparative molecular modeling study of dydrogesterone with other progestational agents through theoretical calculations and nuclear magnetic resonance spectroscopy. J. Steroid Biochem. Mol. Biol. 98 1 (2006) 56-62
11. Ferraboschi P., Grisenti P., Onofri A., and Prestileo P. A simple synthesis of gestodene from 18-methyl-4-estren-3,17-dione. Synlett 10 (2004) 1838-1840
12. Ferriño S., Lopez-Tapia F., and Salgano-Zamora H. An improved alternative norgestrel preparation. Synthetic Commun. 26 7 (1996) 1461-1465
13. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision B. 02 (2003), Gaussian Inc., Pittsburgh, PA
14. Cremer D., and Pople J.A. A general definition of ring puckering coordinates. J. Am. Chem. Soc. 97 6 (1975) 1354-1358
15. van Geerestein V.J., Duisenberg A.J.M., Duits M.H.G., Kanters J.A., and Kroon J. Structure of modifications (I) and (II) of 13-ethyl-17β-hydroxy-18,19-dinor-17α-pregna-4,15-dien-20-yn-3-one (gestodene). Acta Cryst. C 43 12 (1987) 2402-2405
16. DeAngelis N.J., Doyne T.H., and Grob L. The crystal and molecular structure of d-norgestrel, a progestational steroid. Acta Cryst. B 31 8 (1975) 2040-2043
17. van Geerestein V.J., Kanters J.A., and Kroon J. Structure of 13-ethyl-17β-hydroxy-11-methylene-18,19-dinor-17α-pregn-4-en-20-yn-3-one (3-ketodesogestrel). Acta Cryst. C 43 12 (1987) 2398-2401
18. Mornon J.P., Lepicard G., and Delettré J. Crystal structure of norethindrone (19-nor-17α-ethynyltestosterone). C.R. Acad. Sci. Paris C 282 8 (1976) 387-390
19. Haasnoot C.A.G., de Leeuw F.A.A.M., and Altona C. The relationship between proton-proton NMR coupling constants and substituent electronegativities. Part I. An empirical generalization of the Karplus equation. Tetrahedron 36 19 (1980) 2783-2792