(S)-spiro[1,3-diazacyclopent-1-ene)-5,2'-(7'-methyl-1',2',3',4'- tetrahydronaphthalene)]: Resolution, stereospecific synthesis, and preliminary pharmacological characterization as a partial α-adrenergic agonist

Journal of Medicinal Chemistry

Volumn 40, Issue 18, 1997, Pages 2931-2935

  Cordi, Alex A ^a   Lacoste, Jean Michel ^a   Le Borgne, Fabrice ^b   Herve, Yolande ^b   Vaysse Ludot, Lucile ^b   Descombes, Jean Jacques ^a   Courchay, Christine ^a   Laubie, Michel ^a   Verbeuren, Tony J ^a  

^a INSTITUT DE RECHERCHES SERVIER   (France)

^b ORIL   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA ADRENERGIC RECEPTOR STIMULATING AGENT; IMIDAZOLINE DERIVATIVE; SPIRO[(1,3 DIAZACYCLOPENT 1 ENE) 5,2' (7' METHYL 1',2',3',4' TETRAHYDRONAPHTHALENE)]; SPIROIMIDAZOLINE; UNCLASSIFIED DRUG;

ARTERY CONSTRICTION; ARTICLE; BLOOD VESSEL TONE; CHIRALITY; DRUG DESIGN; DRUG SYNTHESIS; FEMORAL ARTERY; MEAN ARTERIAL PRESSURE; PRESSOR RESPONSE; SAPHENOUS VEIN; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; VENOCONSTRICTION; X RAY DIFFRACTION;

ADRENERGIC ALPHA-AGONISTS; ANIMALS; BLOOD PRESSURE; CRYSTALLOGRAPHY, X-RAY; FEMORAL ARTERY; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; MUSCLE CONTRACTION; MUSCLE, SMOOTH, VASCULAR; PHENYLEPHRINE; PRAZOSIN; RATS; SAPHENOUS VEIN; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAHYDRONAPHTHALENES; YOHIMBINE;

EID: 0030868652     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970282m     Document Type: Article

References (20)

1. Cordi, A. A.; Lacoste, J.-M.; Descombes, J.-J.; Courchay, C.; Vanhoutte, P. M.; Laubie, M.; Verbeuren, T. J. Design, Synthesis and Structure-Activity Relationships of a New Series of Alpha Adrenergic Agonists: the Spiro[(1,3-diazacyclopent-1-ene)-5:2′-(1′,2′,3′, 4′-tetrahydronaphthalene)]. J. Med. Chem. 1995, 38, 4056-4069.
2. Seiler, J. P. Chiral Drugs-The View of the Swiss Intercantonal Office for the Control of Medecines. Drug Inf. J. 1993, 27, 485-489.
3. Smith, R. L.; Caldwell, J. Racemates: Towards a New Year Resolution? Trends Pharmacol. Sci. 1988, 9, 75-79.
4. Weinges, K.; Gries, K.; Stemmle, B.; Schrank, W. Über die Asymmetrische Strecker-Synthese mit (S)-(-)-1-Phenylethylamine als Chiralem Hilfsreagens. Chem. Ber. 1977, 110, 2098-2105.
5. Harada, K. Asymmetric Synthesis of α-Amino-acids by the Strecker Synthesis. Nature 1963, 200, 1201. Harada, K.; Fox, S. W. Stereospecific Synthesis of an Optically Active α-Amino Acid. Naturwiss. 1964, 51, 106-107.
6. Harada, K. Asymmetric Synthesis of α-Amino-acids by the Strecker Synthesis. Nature 1963, 200, 1201. Harada, K.; Fox, S. W. Stereospecific Synthesis of an Optically Active α-Amino Acid. Naturwiss. 1964, 51, 106-107.
7. Mai, K.; Patil, G. Asymmetric Synthesis of α-Aminonitriles. Synth. Commun. 1984, 14, 1299-1304.
8. Weinges, K.; Brachmann, H.; Stahnecker, P.; Rodewald, H.; Nixdorf, M.; Irngartinger, H. Synthese der Enantiomerenreinen 2-(2-Thienyl)-und 2-(3-Thienyl)-glycine - Molekulstruktur der als Zwischenprodukte Auftretenden Schiffschen Basen. Liebigs Ann. Chem. 1985, 566-578.
9. Kunz, H.; Sager, W. Diastereoselective Strecker Synthesis of α-Aminonitriles on Carbohydrate Templates. Angew. Chem., Int. Ed. Engl. 1987, 26, 557-559.
10. Kunz, H.; Pfrengle, W.; Rück, K.; Sager, W. Stereoselective Synthesis of L-Amino Acids via Strecker and Ugi Reactions on Carbohydrate Templates. Synthesis 1991, 26, 1039-1042.
11. Bousquet, C.; Tadros, Z.; Tonnel, J.; Mion, L.; Taillades, J. Auxiliaires Cétoniques Chiraux dans la Synthese Asymëtrique des α-Aminoacides selon Strecker. Bull. Soc. Chim. Fr. 1993, 130, 513-520.
12. Davis, F. A.; Portonova, P. S.; Reddy, R. E.; Chiu, Y. Asymmetric Strecker Synthesis Using Enantiopure Sulfinimines and Diethylaluminium Cyanide: The Alcohol Effect. J. Org. Chem. 1996, 61, 440-441.
13. Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. Asymmetric Catalysis of the Strecker Amino Acid Synthesis by a Cyclic Dipeptide. J. Am. Chem. Soc. 1996, 118, 4910-4911.
14. For a recent review on this subject, see: Kunz H. Stereoselective Synthesis: Formation of C-C bond by Addition to Imino Group via Strecker and Ugi Reactions. In Houben-Weyl Methoden der Organischen Chemie Band E21b; Müller, E., Ed.; Georg Thieme Verlag: Stuttgart, New York, 1995; pp 1933-1945.
15. Weinges, K.; Graab, G., Nagel, D.; Stemmle, B. Die Externe Asymmetrische Strecker-Synthese von α-Methyl-aminosäuren. Chem. Ber. 1971, 104, 3594-3606.
16. Subralanian, P. K.; Woodard, R. W. An Asymmetric Strecker Synthesis of (R)-(+)-2-Methyl-3-Phenylalanine: An Efficient Preparation, Synth. Commun. 1986, 16, 337-342.
17. 1-Adrenoceptor Agonist Based on Hexahydronapht[2,3-b]-1,4-oxazines and Octahydrobenzo[g]quinolines. J. Med. Chem. 1992, 35, 480-489.
18. 1-Adrenoceptors. J. Med Chem. 1983, 26, 1215-1218.
19. Verbeuren, T. J.; Vayssettes-Courchay, C.; Descombes, J.-J.; Simonet, S.; Lacoste, J.-M.; Cordi, A. A.; Laubie, M. S 18149 is a Partial Agonist at α-Adrenoceptors: Studies in Pithed Rats and isolated Canine and Human Blood Vessels. Br. J. Pharmacol. 1996, 117, 277P.
20. Vayssettes-Courchay, C.; Lacoste, J.-M.; Cordi, A. A.; Laubie, M.; Verbeuren, T. J. In vivo Cardiovascular Effects of the α-Adrenoceptor Agonist S 18149 in the Anaesthetized Dog. Br. J. Pharmacol. 1996, 117, 255P.