Synthesis and biological evaluation of 16β-pyrrolidinosteroidal derivatives

Arzneimittel-Forschung/Drug Research

Volumn 53, Issue 2, 2003, Pages 73-79

  Jindal, Dharam Paul ^a   Piplani, Poonam ^a   Fajrak, Hassan ^b   Prior, Chris ^b   Marshall, Ian G ^b  

^a PANJAB UNIVERSITY   (India)

^b UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

16 Pyrrolidinosteroidal derivatives, biological evaluation, synthesis; Ammonium derivatives, bisquaternary, monoquaternary; CAS 57 94 3; d Tubocurarine

Indexed keywords

16BETA PYRROLIDINO 5 ANDROSTENE 23BETA,17BETA DIOL METHIODIDE; 16BETA PYRROLIDINO 5 ANDROSTENE 3BETA,17BETA DIOL; 16BETA PYRROLIDINO 5 ANDROSTENE 3BETA,17BETA DIOL DIACETATE METHIODIDE; 16BETA PYRROLIDINOSTEROID DERIVATIVE; 17 OXO 16BETA PYRROLIDINO 5 ANDROSTEN 3BETA OL METHIODIDE; 3BETA,16BETA DIPYRROLIDINO 5 ANDROSTEN 17BETA OL DIMETHIODIDE; 3BETA,16BETA DIPYRROLIDINO 5 ANDROSTEN 17BETA YL ACETATE DIMETHIODIDE; CARBACHOL; CHANDONIUM IODIDE; DPJ 500; DPJ 527; DPJ 529; NEUROMUSCULAR BLOCKING AGENT; PANCURONIUM BROMIDE; QUATERNARY AMMONIUM DERIVATIVE; STEROID; SUXAMETHONIUM; TUBOCURARINE CHLORIDE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CAT; CHICKEN; DOSE RESPONSE; DRUG POTENCY; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LC 50; NEUROMUSCULAR BLOCKING; NEWBORN; NONHUMAN; STRUCTURE ACTIVITY RELATION;

EID: 0037283263     PISSN: 00044172     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0031-1297075     Document Type: Article

References (23)

1. Stenlake, J. B., Molecular interaction at the cholinergic receptor in neuromuscular blockade. In: Progress in Medicinal Chemistry, Vol. 16, G. P. Ellis, G. B. West (eds.), pp. 257-286, Elsevier/North-Holland Biomedical Press, Amsterdam (1979)
2. th ed., pp. 177-197, McGraw-Hill, New York (1996)
3. Cavallito, C. J., Gray, A. P., Chemical nature and pharmacological actions of quaternary ammonium salts. In: Progress in Drug Research, Vol. 2, E. Jucker (ed.), pp. 135-225, Birkhäuser, Switzerland (1960)
4. Cavallito, C. J., Quaternary ammonium salts-advances in chemistry and pharmacology since 1960. In: Progress in Drug Research, Vol. 24, E. Jucker (ed.), pp. 267-358, Birkhäuser, Switzerland (1980)
5. Feldman, S., Neuromuscular blocking drugs. Drugs of today 32, 159 (1990)
6. Baird, W. L. M., Reid, A. M., The neuromuscular blocking properties of a new steroid compound, Pancuronium bromide. Br. J. Anaesth. 39, 775 (1967)
7. Speight, T. M., Avery, G. S., Pancuronium bromide: A review of its pharmacological properties and clinical application. Drugs 4, 163 (1972)
8. Singh, H., Paul, D., Chandonium iodide (17a-methyl-3β-pyrrolidino-17a-aza-D-homo-androst-5-ene dimethiodide) and other quaternary ammonium steroid analogues. J. Chem. Soc. Perkin Trans. 1, 1475 (1974)
9. Abraham, J. Jindal, D. P., Singh, H. et al., Certain new azasteroidal bisquaternary neuromuscular blockers. Eur. J. Med. Chem. 28, 231 (1993)
10. Verma, A. K., Lee, C. Y., Habtemariam, S. et al., Synthesis and biological activity of 17-azasteroidal neuromuscular blocking agents. Eur. J. Med. Chem. 29, 331 (1994)
11. Jindal, D. P., Piplani, P., Fajrak, H. et al., Synthesis and neuromuscular blocking activity of 16β-piperidinosteroidal derivatives. Eur. J. Med. Chem. 36, 195 (2001)
12. Gandiha, A., Marshall, I. G., Paul, D. et al., Neuromuscular and other blocking actions of a new series of mono and bisquaternary aza steroids. J. Pharm. Pharmacol. 26, 871 (1974)
13. Harvey, A. L., Paul, D., Rodger, I. W. et al., Actions of the muscle relaxant chandonium iodide on guinea-pig ileum and vas deferens preparations. J. Pharm. Pharmacol. 28, 617 (1976)
14. th ed., pp. 431-460, John Wiley & Sons, New York (1981)
15. Singh, H. Chaudhary, A. K., Bhardwaj, T. R. et al., Neuromuscular blocking agents. J. Sci. Ind. Res. 43, 306 (1984)
16. Singh, H., Jindal, D. P., Yadav, M. R. et al., Heterosteroids and drug research. In: Progress in Medicinal Chemistry, Vol. 28, G. E Ellis, G. B. West (eds.), pp. 233-315, Elsevier/North Holland Biomedical Press, Amsterdam (1991)
17. Palmer, R. A., Kalam, M. A., Singh, H. et al., Structure and function of synthetic bisquaternary azasteroidal neuromuscular blocking agents. J. Cryst. Mol. Str. 10, 31 (1980)
18. Savage, D. S., Cameron, A. F., Ferguson, G. et al., Molecular structure of Pancuronium Bromide, a neuromuscular blocking agent. Crystal and molecular structure of water: methylene chloride solvate. J. Chem. Soc. B 410 (1971)
19. Von Philipsborn, W., Schmid, H., Karrer, P., Über die Bruttoformeln der Curarae-Alkaloide aus Calebassen und Strychnos-Arten. Helv. Chim. Acta. 39, 913 (1956)
20. Glazier, E. R., Bromination with cupricbromide II. Bromination in the presence of an olefinic bond. J. Org. Chem. 27, 4397 (1962)
21. Hewett, C. L., Savage, D. S., Amino-steroids. Part I. 16-piperidino-and 16-morpholino-androstanes and oestra-1,3,5(10)-trienes. J. Chem. Soc. C 484 (1966)
22. Numazava, M., Nagaoka, M., Stereospecific synthesis of 16α-hydroxy 17-oxo steroids by controlled hydrolysis of corresponding 16-bromo-17-ketones and its reaction mechanism. J. Org. Chem. 47, 4024 (1982)
23. Arunlakshana, O., Schild, H. O., Some quantitative uses of drug antagonists. Br. J. Pharmacol. Chemother. 14, 48 (1959)