Synthesis of certain unsubstituted, 9-exo-(dialkylaminomethyl)-, and 9- endo-(aralkyl)-tricyclo [5.2.1.02,6 decane-8-ketoxime esters and ethers with local anesthetic and analgesic activities

Farmaco

Volumn 53, Issue 3, 1998, Pages 197-208

  Aboul Enein M, Nabil ^a   El Azzouny, Aida ^a   Abdallah, Nevine A ^a   Maklad, Yousreya A ^a   Saleh, Ola A ^a   Ebeid, M Y ^b  

^a NATIONAL RESEARCH CENTRE   (Egypt)

^b CAIRO UNIVERSITY   (Egypt)

Author keywords

Analgesic activity; Local anesthetic activity; Stereochemistry; Structure activity relationship; Tricyclo 5.2.1.02,6 decane 8 ketoxime esters and ethers

Indexed keywords

9 (ARALKYL)TRICYCLODECANE 8 KETOXIME; 9 (DIALKYLAMINOMETHYL)TRICYCLODECANE 8 KETOXIME; ACETYLSALICYLIC ACID; ANALGESIC AGENT; ANESTHETIC AGENT; MORPHINE; UNCLASSIFIED DRUG;

ANALGESIA; ANESTHESIA; ARTICLE; DRUG ACTIVITY; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; LIPOPHILICITY; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0032029529     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-827X(98)00008-1     Document Type: Article

References (22)

1. [1] M. Nógrádi, Drugs of the Future 9 (1984) 34-35 and references cited therein.
2. [2] A. Ranise, F. Bondavalli, O. Bruno, P. Schenone, ω-Dialkylaminoalkyl ethers of 3-exo-dialkylamino-(Z)-camphoroximes with antiarrythmic and local anesthetic activities, Farmaco Ed. Sci. 45 (1990) 187-202.
3. [3] M. Dàmico, C. Vacca, M. Falciani, A. Filippelli, O-[ω-(Dialkylamino)alkyl] oximes of (+)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one with hypotensive, antiinflammatory, analgesic, local anesthetic and other activities, Farmaco Ed. Sci. 49 (1994) 545-550.
4. [4] S. Schenone, O. Bruno, A. Ranise, F. Bondavalli, N-substituted O-(3-amíno-2-hydroxypropyl) oximes of 1,3,3-trimethyl-5-endo-(1-piperidinyl or 4-morpholinyl)-2-oxabicyclo[2.2.2]octan-6-ones with platelet antiaggregating and local anesthetic activities, Farmaco Ed. Sci. 47 (1992) 1249-1262.
5. [5] E. Mariani, A. Bargagna, M. Longobardi, P. Schenone, O-(2-Dialkylaminoethyl) oximes of 5-(aralkylmethylene)-1,3,3-trimethyl-2-oxabicyclo[2.2.2|octan-6-ones with hypotensive, antiarrythmic and other activities, Farmaco Ed. Sci. 49 (1994) 267-270.
6. [6] M.N. Aboul-Enein, A.A. Makhlouf, A.A. El-Azzouny, N.A. Abdallah, Synthesis of some basic ethers of 6-arylidenehexahydro-4,7-methanoindan-5-one oximes and their salts as local anesthetics, Sci. Pharm. 60 (1992) 57-64.
7. [7] M.N. Aboul-Enein, A.M. Maklouf, A.A. El-Azzouny, Synthesis of certain spirohexahydro-4,7-methanoindanpiperazine derivatives as analgesics. Sci. Pharm. 58 (1990) 263-271.
8. [8] J. Büchi, Grundlagen der Arzneimittel Forschung und der synthetischen Arzneimittel, Birkhäuser. Basel, 1963, pp. 369-379.
9. [9] W.H. Oldendorf, Blood-brain barrier permeability to drugs, Ann. Rev. Pharmacol. 14 (1974) 239-248.
10. [10] F. Bondavalli, S. Lanteri, M. Longobardi, P. Schenone, Synthesis and pharmacological activity of derivatives of exo-trimethylenenorbornane, Farmaco Ed. Sci. 34 (1979) 945-951.
11. [11] F.C. Uhle, Methylaminomethylsuccinic acid, J. Org. Chem. 27 (1962) 4081-4083.
12. [12] J.C. Sheehan, M. Goodman, G.P. Hess, Peptide derivatives containing hydroxyamino acids, J. Am. Chem. Soc. 78 (1995) 1367-1369.
13. [13] R.A. Boissonnas, Une nouvelle méthode de synthèse peptidique, Helv. Chim. Acta 34 (1951) 874-879.
14. [14] M. Nabil Aboul-Enein, A.A. El-Azzouny, N.A. Abdallah, S.M. Moharam, W. Werner, A. Eid, A.A. Makhluf, Synthesis of some 6-(alkylamino)methylhexahydro-5-aryl-and aralkyl-4,7-methanoindan-5-ols and certain of their propionate esters as analgesics, J. Islamic Acad. Sci. 6 (1993) 99-107.
15. [15] F.F. Blicke, in: R. Adams (ed.), Organic Reactions, vol. 1, Wiley, New York, 1947, pp. 303-341.
16. [16] J. Hine, W.S. Li, Synthesis of some cis-and Trans-2-dimethylaminomethyl cyclic amines and related diamines, J. Org. Chem. 40 (1975) 289-292 and references cited therein.
17. [17] B.J. Nicholaus, G. Pagáni, E. Testa, Synthese und Eigenschaften der O-(Phenylalkyl)hydroxylamine, Helv. Chim. Acta 45 (1962) 1381-1395.
18. [18] Vogel's Textbook of Practical Organic Chemistry, 5th ed., Longman, Singapore, 1991, pp. 609-610.
19. [19] E. Pretsch, Th. Clerc, J. Seibl, W. Simon, Tabellen zur Strukturaufklärung Organischer Verbindungen mit Spektroskopischen Methoden, Springer, Berlin, 1976.
20. [20] G. Buchbauer, H. Spreitzer, C. Puringer, Zur Synthese von Fungizid wirksamen Norbornanderivaten, Arch. Pharm. (Weinheim) 323 (1990) 367-373.
21. [21] L.J. McLeod, Pharmacological Experiments on Intact Preparation, E. and S. Livingstone, Edinburgh, 1970, pp. 33-35.
22. [22] P.A. Janssen, A. Jageneau, Potent analgesics d-1-(2,2-diphenyl-3-methyl-4-morpholinobutyryl) pyrrolidine and related amides. (1) Structure and pharmacological activity, J Pharm. Pharmacol. 9 (1957) 381-386.