본문 바로가기
HOME> 논문 > 논문 검색상세

논문 상세정보

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

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  );
  • 초록

    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 ${\alpha}$ -cyano cinnamide to afford 13. On the other hand, double Michael cycloaddition of ethylcyanoacetate or tetrachlorophthalic anhydride to the suitable divinylketone were synthesized to produce 15-17. Selected compounds (13 and 6) were screened for muscle relaxant, anticonvulsant, and sedative activities using established pharmacological models. Their activities were compared with that of phenobarbital sodium taken as standard. Compound 6 was the most potent muscle relaxant while compounds 13a and 13c offered the highest anticonvulsant activity. Meanwhile compound 13c showed the highest potentiation of phenobarbital induced sleep in mice.


  • 주제어

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

  • 참고문헌 (20)

    1. 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) 
    2. 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) 
    3. 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) 
    4. Vollhardt, K. P. C., Organic Chemistry., W .H. Freeman and Company New York 3rd Edition, 1048 (1999) 
    5. Reddy, T. I. and Varma, R. S., Rare-earth (RE) exchanged nay zeolite promoted Knoevenagel condensation. Tetrahedron Lett., 38, 1721 (1997) 
    6. Sykes, P., A quidebook to Mechanism in Organic Chemistry Long mon London and New York, New York, 5th Edition, 198 (1985) 
    7. Carrol, F. A., Prespectives on structure and Mechanism. In Organic Chernistry. Brooks/Cole Publishing Company 3rd Edition 645 (1988) 
    8. 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) 
    9. 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) 
    10. 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) 
    11. 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) 
    12. 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). 
    13. 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) 
    14. Meyers, F. H. Jawetz, E., and GoldFien, A., Review of Medicinal Pharmaacology., Lange Medical Publications, Los Atlos, California; 5th Edition, 222 (1976) 
    15. Vogel, A. G. and Vogel, W. H., Drug Discovery and Evaluation, Pharmacological Assay, Spring, Berlin 260 (1997) 
    16. 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) 
    17. 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). 
    18. 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) 
    19. March, J., Advanced Organic Chemistry. John Willey and Sons, 4th Edition,741 (2000) 
    20. De, A. U. and Pal, D., Possible Antineoplastic Agents 11., J. Pharm. Sci., 66, 232 (1977) 
  • 이 논문을 인용한 문헌 (1)

    1. 2013. "" Fisheries and aquatic sciences, 16(1): 1~5     

 활용도 분석

  • 상세보기

    amChart 영역
  • 원문보기

    amChart 영역

원문보기

무료다운로드
유료다운로드

유료 다운로드의 경우 해당 사이트의 정책에 따라 신규 회원가입, 로그인, 유료 구매 등이 필요할 수 있습니다. 해당 사이트에서 발생하는 귀하의 모든 정보활동은 NDSL의 서비스 정책과 무관합니다.

원문복사신청을 하시면, 일부 해외 인쇄학술지의 경우 외국학술지지원센터(FRIC)에서
무료 원문복사 서비스를 제공합니다.

NDSL에서는 해당 원문을 복사서비스하고 있습니다. 위의 원문복사신청 또는 장바구니 담기를 통하여 원문복사서비스 이용이 가능합니다.

이 논문과 함께 출판된 논문 + 더보기