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Information Journal Paper

Title

SYNTHESIS OF CERTAIN 1,7,7-TRIMETHYL-BICYCLO[2.2.1]HEPTANE DERIVATIVES WITHANTICONVULSANT, HYPOGLYCEMIC AND ANTI-INFLAMMATORY POTENTIAL

Pages

  191-208

Keywords

1 
7 
7-TRIMETHLYL-BICYCLO[2.2.1]HEPTANE AMINOALCOHOLS 

Abstract

 Starting from (1,7,7-trimethyl-bicyclo[2.2.1]hept-2-ylideneamino)-acetic acid methyl esters 6a, 6b, the aryl esters of exo-2-[methyl-(1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-amino]-ethanol (10a-f) and exo-2-[methyl-(1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-amino-2-phenyl-ethanol (10g-n) are prepared. Also, from the reaction of 1,7,7-trimethyl-bicyclo[2.2.1]heptan nitramine 4 with either 2-amino-1-(4-nitrophenyl)-propane-1,3-diol (17) or 1-aminomethyl-cyclohexanol (18), the alcohol exo-1-[(1,7,7-trimethyl-bicylo[2.2.1]hept-2-ylamino)-methyl]-cyclohexanol (13), exo-1-(4-aminophenyl)-2-(1,7,7-trimethyl-bicyclo[2.2.1]hept-2-ylamino)-propane-1,3-diol (14) and 1-(4-aminophenyl)-2-[methyl-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]-amino]-propane-1,3-diol (16) are synthesized. At a dose level of 12.5 mg/kg, compounds 16 and 14 show a significant anticonvulsant protection against pentylenetetrazole seizures (100% and 83% protection, respectively) compared with diphenylhydantoin sodium (50 mg/kg, 100%) and deramciclane fumarate (25 mg/kg, 83%), used as reference drugs. Compound 10b at dose level of 50 mg/kg displayed 41%, hypoglycemic activity, compared with gliclazide (10 mg/kg, 23%) as reference drug.  Furthermore, the prepared compounds are screened for their anti-inflammatory potential at a dose level of 50 mg/kg.  Compounds 10i, 10g, 14 and 10m exhibited 92%, 90%, 88% and 80% inhibition in rat paw weight, respectively, with no sign of ulcerogenicity, compared with indomethecin (5 mg/kg, 81%).

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    APA: Copy

    ABOUL-ENEIN, M.N., EL-AZZOUNY, A.A., MAKLAD, Y.A., SOKEIRIK, Y.S., & SAFWAT, H.. (2006). SYNTHESIS OF CERTAIN 1,7,7-TRIMETHYL-BICYCLO[2.2.1]HEPTANE DERIVATIVES WITHANTICONVULSANT, HYPOGLYCEMIC AND ANTI-INFLAMMATORY POTENTIAL. JOURNAL OF THE IRANIAN CHEMICAL SOCIETY(JICS), 3(2), 191-208. SID. https://sid.ir/paper/282077/en

    Vancouver: Copy

    ABOUL-ENEIN M.N., EL-AZZOUNY A.A., MAKLAD Y.A., SOKEIRIK Y.S., SAFWAT H.. SYNTHESIS OF CERTAIN 1,7,7-TRIMETHYL-BICYCLO[2.2.1]HEPTANE DERIVATIVES WITHANTICONVULSANT, HYPOGLYCEMIC AND ANTI-INFLAMMATORY POTENTIAL. JOURNAL OF THE IRANIAN CHEMICAL SOCIETY(JICS)[Internet]. 2006;3(2):191-208. Available from: https://sid.ir/paper/282077/en

    IEEE: Copy

    M.N. ABOUL-ENEIN, A.A. EL-AZZOUNY, Y.A. MAKLAD, Y.S. SOKEIRIK, and H. SAFWAT, “SYNTHESIS OF CERTAIN 1,7,7-TRIMETHYL-BICYCLO[2.2.1]HEPTANE DERIVATIVES WITHANTICONVULSANT, HYPOGLYCEMIC AND ANTI-INFLAMMATORY POTENTIAL,” JOURNAL OF THE IRANIAN CHEMICAL SOCIETY(JICS), vol. 3, no. 2, pp. 191–208, 2006, [Online]. Available: https://sid.ir/paper/282077/en

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