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Synthesis and Pharmacological Screening for Muscle Relaxant, Anticonvulsant, and Sedative Activities of Certain Organic Compounds Produced by Michael Addition 원문보기

Archives of pharmacal research : a publication of the Pharmaceutical Society of Korea, v.27 no.12, 2004년, pp.1194 - 1201  

Said , Makarem M. (Organic chemistry Department , Faculty of Pharmacy, Cairo University) ,  Ahmed, Amany A. E. (Pharmacology Department, Faculty of Pharmacy, King Saud University) ,  El-Alfy, Abir T. (Pharmacology Department, Faculty of Pharmacy, King Saud University)

Abstract ▼ AI-Helper 아이콘AI-Helper

Michael addition of certain nucleophiles on ${\alpha}$ , ${\beta}$-unsaturated ketones 1 led to the formation of adducts 2-7 as well as the reaction of arylidene derivatives with secondary amines afforded the amino compounds 9 and 11. Also, dialkylmalonates were treated with

주제어

#Michael addition   #2-Pyridone   #Muscle relaxant   #Anticonvulsant   #Sedative activities  

AI 본문요약
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제안 방법

  • Accordingly, the present study focused on the application of Michael reaction to produce novel heterocyclic compounds. The study also screened synthesized compounds for their potential muscle relaxant, anticonvulsant, and sedative activities.

대상 데이터

  • Adult male Swiss Albino mice, 20-25 g, were obtained from the animal house facility at King Saud University. The animals were housed in cages with 12/12 h light/dark cycle at 21±2℃.
  • The mice were divided into five groups of eleven animals each. One group received 90 ㎎/㎏ phenobarbital sodium i.
  • , 1992). The test was conducted in groups of ten previously screened animals, 15 minutes after the injection of either saline phenobarbital (90 ㎎/㎏, i.p.) or the test compounds (13a-13c and 6) (50 ㎎/㎏, i.p.).

데이터처리

  • * Statistically significant difference compared to the strychnine treated group {P<0.05) using Students t-test.
  • 05). The comparison among the different test groups(compounds 13a-13c and 6) was done using one way analysis of variance (ANOVA) followed by the multiple comparison tests of Tukey-Kramer (p<0.05).
  • The data were expressed as mean±SEM and drug potency compared to control was tested using the Student t-test (p<0.05). The comparison among the different test groups(compounds 13a-13c and 6) was done using one way analysis of variance (ANOVA) followed by the multiple comparison tests of Tukey-Kramer (p<0.
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참고문헌 (20)

  1. Aboal-Enein, M. N. and El-Azzouny, A. A., A Facile Synthesis of 2',3',7',8'-Tetrahydro-7'-Aryl and Aralkylspiro[cycloalkyl 1,6'(5'H)-imidazo[1,2-a] pyrazin]-5'-ones. A Heterocycle of Potential Analgesic Profile. Egypt. J. Chem., 31, 141 (1988). 

  2. Allen, L. E., Ferguson. H. C., and Kissel, J. W., Psychosedative Agents2,8-(4-substituted-1-piperazinylalkyl)-8-azaspiro-[4.5]decane- 7,9-diones. J. Med. Chem., 15, 477 (1972) 

    상세보기 crossref

  3. Bloom, F., Neurotransmission and the Centralnervoussystem. In the Pharmacological basis of therapeutics. Hardman J, Limbird L, Goodman A (eds). 10th Edition McGraw Hill Companies Jne. New York, USA(2001). 

  4. Bose, M., Dutta, D., Pathak, B., and Patra, B., Synthesis of some spiro[5.5] undecanes as possible Analgesic agents. J. Indian Chem. Soc., 62, 69 (1985) 

  5. Braulio, I, Alfredo, P., John, V., and Jairo, Q., Synthesis of 2,3dihydropyrido and 2,3-dihydropyrimido[1,4] diazepines from triamino pyridine and triamino pyrimidine. J. Heterocyclic Chem., 34, 1555 (1997) 

    상세보기 crossref

  6. Carrol, F. A., Prespectives on structure and Mechanism. In Organic Chernistry. Brooks/Cole Publishing Company 3rd Edition 645 (1988) 

  7. Collins, I., Moyes, C., Davey, W., Rowley, M., Bromidge, F., Quirk, K., Atack, J., McKernan, R., Thompson, S. A., Wafford, K., Dawson, G., Pike, A., Sohal, B., Tsou, N., Bull, R., and Castro, J., 3-Heteroaryl-2-pyridones: Benzodiazepine site ligands with functional selectivity for $\alpha$ 2/ $\alpha$ 3-subtypes of human GABAA receptor-ion channels. J. Med. Chem., 45, 1887-1900 (2002) 

    상세보기 crossref

  8. De, A. U. and Pal, D., Possible Antineoplastic Agents 11., J. Pharm. Sci., 66, 232 (1977) 

    상세보기 crossref

  9. Goehring, R. R, Greenwood, T. D., Nwokogus, G. C., Pisipati, J. S., Rogers, T. G., Wolfe, J. F. (Harvey W. Peters Res Cent. Study Parkinsons Dis. Disord. Cent. Nerv. Syst. Virginia Polytechnic Inst. And state Univ. Blacksburg. VA 24061 USA), Synthesis and anticonvulsant activity of 2-benzylglutarimides. J. Med. Chem., 33 (3), 926 (Eng) (1990). T.C.A 112, 118615p (1990) 

    상세보기 crossref

  10. James, A. R., Gordon, D. J., Witold, F. K., Teanby, H. S., and John, W. P. (wellcome Foundation Ltd.), PCT Int. Appl. WO 9501326 (CI. Co7 C233/25), 12 Jan 1995, GB Appl. 93/13, 459, 30 Jun 1993; 60pp., Preparation of antiatheroscierotic diaryl compounds; T.C.A. 123, 143447V. (1995) 

  11. March, J., Advanced Organic Chemistry. John Willey and Sons, 4th Edition,741 (2000) 

  12. Meyers, F. H. Jawetz, E., and GoldFien, A., Review of Medicinal Pharmaacology., Lange Medical Publications, Los Atlos, California; 5th Edition, 222 (1976) 

  13. Osman, A. N., Kandeel, M. M., Said, M. M., and Ahmed, E. M., Synthesis and anticonvulsant activity of some spiro compound derived from barbituric and thiobarbituric acids. Indian J. Chem., 35 B, 1073 (1996) 

  14. Reddy, D. B., Padmavathi, V., and Reddy, P. V. R., Cyclokexanone dicarboxylates as precursors for the synthesis of some spiropyrimidinetetrones and spiropyrazolidinetriones. Indian J. Chem., 31 B, 774 (1992) 

  15. Reddy, T. I. and Varma, R. S., Rare-earth (RE) exchanged nay zeolite promoted Knoevenagel condensation. Tetrahedron Lett., 38, 1721 (1997) 

    상세보기 crossref

  16. Sergio, M., Tiziane, B., Enzo, B., Metlide, B. (Farmitalia Carlo Erba S.R.I.) Eur. Pat. Appl. Ep 449, 346 (CI C07D 457/02), 02 Oct 1991. GB Appl. 9016, 722, 27 Mar 1990; 9 pp.; preparation of [(4.piperidinyl)akyl] ergolines as antiparkinson agents; T.C.A. 116, 21303e (1992) 

  17. Sykes, P., A quidebook to Mechanism in Organic Chemistry Long mon London and New York, New York, 5th Edition, 198 (1985) 

  18. Villar, R., Laguna, M. R., Calleja, J. M., and Cadavid, I., Effect of Kseletonema statum extracts on the central nervous system. Planta Med., 38, 398 (1992) 

  19. Vogel, A. G. and Vogel, W. H., Drug Discovery and Evaluation, Pharmacological Assay, Spring, Berlin 260 (1997) 

  20. Vollhardt, K. P. C., Organic Chemistry., W .H. Freeman and Company New York 3rd Edition, 1048 (1999) 

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