The investigation of the reactions of some pyrazole-3-carboxylic acids with various diamines and diols
Yıl 2012,
Cilt: 16 Sayı: 1, 47 - 52, 01.06.2012
Rahmi Kasımoğulları
Makbule Maden
Samet Mert
Kaynakça
- inflammatory activities of cannabinoid receptor ligands in mouse peritonitis models, Pharmacology, 432 (1), 107–119, 2001. European Journal of
- Sakane, K., Tanaka, H. The anti-inflammatory effect of FR188582, a highly selective inhibitor of cyclooxygenase-2, with an ulcerogenic sparing effect in rats, Japanese Journal of Pharmacology, 85 (2), 175–182, 2001.
- Mantione, L., Cutuli, V.M.C., Mangano, N.G., Caruso, A. Synthesis and pharmacological study of ethyl 1-methyl-5- (substituted pyrazole-4-acetates, European Journal of Medicinal Chemistry, 36 (9), 737–742, 2001.
- Antioxidant and Antimicrobial Activity of 5-methyl-2-(5- methyl-1,3-diphenyl-1H-pyrazole-4-carbonyl)-2,4-dihydro- pyrazol-3-one, International Journal of Biomedical Science, (4), 359–368, 2009.
- G.E.D.A.A., Abdel-Aziz, M., Radwan, M.F., Farag, H.H. Design, synthesis and biological investigation of certain pyrazole-3-carboxylic acid derivatives as novel carriers for nitric oxide, Bioorganic & Medicinal Chemistry, 17 (11), –3837, 2009. E.S.M.N., Abuo-Rahma,
- Scatturin, A., Romagnoli, C., Mares, D. Synthesis of a novel series of imidazo[4,5-c]pyrazole derivatives and their evaluation as herbicidal agents, Archiv der Pharmazie, 332 (10), 337–342, 1999.
- Marr, C.L.P., Mason, A.M., Mo, C.L., Myers, P.L., Noble, S.A., Penn, C.R., Weir, N.G., Woods, J.M., Coe, P.L. The synthesis and antiviral activity of 4-fluoro-1-beta-D- ribofuranosyl-1H-pyrazole-3-carboxamide, Nucleosides & Nucleotides, 18 (2), 203–216, 1999.
- Mascarella, S.W., Page, K., Seltzman, H.H., Thomas, B.F. Conformationally constrained analogues of N-(piperidinyl)- (4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H- pyrazole-3-carboxamide (SR141716): Design, synthesis, computational analysis, and biological evaluations, Journal of Medicinal Chemistry, 51 (12), 3526–3539, 2008.
- J.Z., Soni, R., Raval, P., Gite, A., Goswami, A., Sadhwani, N., Gandhi, N., Patel, H., Mishra, B., Solanki, M., Pandey, B., Jain, M.R., Patel, P.R. Diaryl dihydropyrazole-3- carboxamides with significant in vivo antiobesity activity related to CBI receptor antagonism: Synthesis, biological evaluation, and molecular modeling in the homology model, Journal of Medicinal Chemistry, 50 (24), 5951–5966, 2007.
- Venkatesham, B., Balasubrahmanyam, D., Kannan, M., Srinivas, P., Kumar, K.S., Devi, B.N., Jadhav, V.P., Khan, S.K., Mohan, P., Chaudhury, H., Bhuniya, D., Iqbal, J., Chakrabarti, R.. Novel pyrazole-3-carboxamide derivatives as cannabinoid-1 (CB1) antagonists: Journey from non-polar to polar amides, Bioorganic & Medicinal Chemistry Letters, (1), 562–568, 2011.
- Buisson, I., Bribes, E., Péleraux, A., Pénarier, G., Soubrié, P., Le Fur, G., Galiègue, S., Casellas, P. The CB1 receptor antagonist rimonabant reverses the diet-induced obesity phenotype through the regulation of lipolysis and energy balance, The FASEB Journal, 19 (11), 1567–1569, 2005.
- Shedage, S.A., Gandhi, N., Sairam, K.V.V.M., Pawar, V., Sadhwani, N., Mitra, P., Jain, M.R., Patel, P.R. Facile synthesis, ex-vivo and in vitro screening of 3-sulfonamide derivative of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4- methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide (SR141716) a potent CB1 receptor antagonist, Bioorganic &
- Medicinal Chemistry Letters, 18 (14), 3882–3886, 2008.
- Lazzari, P., Reali, R., Pani, L., Toma, L., Pinna, G.A. Tricyclic pyrazoles. 3. Synthesis, biological evaluation, and molecular modeling of analogues of the cannabinoid antagonist 8-chloro-1-(2',4'-dichlorophenyl)-N-piperidin-1- yl-1,4,5,6-tetrahydrobenzo[6,7]cyclohepta[1,2-c]pyrazole-3- carboxamide, Journal of Medicinal Chemistry, 48 (23), –7362, 2005.
- A., Erdelyi, P., Vukics, K., Szikra, J., Hegyi, E., Vastag, M., Kiss, B., Laszy, J., Gyertyan, I., Fischer, J. Chemical and biological investigation of cyclopropyl containing diaryl- pyrazole-3-carboxamides as novel and potent cannabinoid type 1 receptor antagonists, Journal of Medicinal Chemistry, (14), 4329–4337, 2009.
- Gokce, B. Synthesis, characterization and antiglaucoma activity of some novel pyrazole derivatives of 5-amino- ,3,4-thiadiazole-2-sulfonamide, European Journal of Medicinal Chemistry, 45 (11), 4769–4773, 2010.
- Guleryuz, H. Synthesis of 5-amino-1,3,4-thiadiazole-2- sulfonamide derivatives and their inhibition effects on human carbonic anhydrase isozymes, Journal of Enzyme Inhibition and Medicinal Chemistry, 26 (2), 231–237, 2011.
- Guleryuz, H. Effects of new 5-amino-1,3,4-thiadiazole-2- sulfonamide derivatives on human carbonic anhydrase isozymes, Bioorganic & Medicinal Chemistry, 17 (9), 3295– , 2009.
- Bildirici, I., Akcamur, Y. Studies on the reactions of cyclic oxalyl compounds with hydrazines or hydrazones II [1]: Synthesis and reactions of 4-benzoyl-1-(3-nitrophenyl)-5- phenyl-1H-pyrazole-3-carboxylic Heterocyclic Chemistry, 39 (5), 869–875, 2002. acid, Journal of characterization of some pyrazole derivatives of 1,5- diphenyl-1H-pyrazole-3,4-dicarboxylic acid, Journal of
- Heterocyclic Chemistry, 47 (5), 1040–1048, 2010.
Bazı pirazol-3-karboksilik asitlerin çeşitli diamin ve diollerle reaksiyonlarının incelenmesi
Yıl 2012,
Cilt: 16 Sayı: 1, 47 - 52, 01.06.2012
Rahmi Kasımoğulları
Makbule Maden
Samet Mert
Öz
In this study, some new derivatives were synthesized of 4-benzoyl-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid (1) and 4-(ethoxycarbonyl)-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid (2) that they were pyrazole carboxylic acid derivatives. Firstly, 1 and 2 reacted with SOCl2 to transform them into acyl chlorides (3, 4). Then various bis-carboxamide derivatives (58) were obtained from the reaction of 3 and 4 with various diamines and also a β-hydroxy ester (9) derivative was obtained from the reaction of 3 with ethylene glycol. The structures of synthesized compounds were elucidated with using FT-IR, 1H NMR, 13C NMR and elemental analysis methods.
Kaynakça
- inflammatory activities of cannabinoid receptor ligands in mouse peritonitis models, Pharmacology, 432 (1), 107–119, 2001. European Journal of
- Sakane, K., Tanaka, H. The anti-inflammatory effect of FR188582, a highly selective inhibitor of cyclooxygenase-2, with an ulcerogenic sparing effect in rats, Japanese Journal of Pharmacology, 85 (2), 175–182, 2001.
- Mantione, L., Cutuli, V.M.C., Mangano, N.G., Caruso, A. Synthesis and pharmacological study of ethyl 1-methyl-5- (substituted pyrazole-4-acetates, European Journal of Medicinal Chemistry, 36 (9), 737–742, 2001.
- Antioxidant and Antimicrobial Activity of 5-methyl-2-(5- methyl-1,3-diphenyl-1H-pyrazole-4-carbonyl)-2,4-dihydro- pyrazol-3-one, International Journal of Biomedical Science, (4), 359–368, 2009.
- G.E.D.A.A., Abdel-Aziz, M., Radwan, M.F., Farag, H.H. Design, synthesis and biological investigation of certain pyrazole-3-carboxylic acid derivatives as novel carriers for nitric oxide, Bioorganic & Medicinal Chemistry, 17 (11), –3837, 2009. E.S.M.N., Abuo-Rahma,
- Scatturin, A., Romagnoli, C., Mares, D. Synthesis of a novel series of imidazo[4,5-c]pyrazole derivatives and their evaluation as herbicidal agents, Archiv der Pharmazie, 332 (10), 337–342, 1999.
- Marr, C.L.P., Mason, A.M., Mo, C.L., Myers, P.L., Noble, S.A., Penn, C.R., Weir, N.G., Woods, J.M., Coe, P.L. The synthesis and antiviral activity of 4-fluoro-1-beta-D- ribofuranosyl-1H-pyrazole-3-carboxamide, Nucleosides & Nucleotides, 18 (2), 203–216, 1999.
- Mascarella, S.W., Page, K., Seltzman, H.H., Thomas, B.F. Conformationally constrained analogues of N-(piperidinyl)- (4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H- pyrazole-3-carboxamide (SR141716): Design, synthesis, computational analysis, and biological evaluations, Journal of Medicinal Chemistry, 51 (12), 3526–3539, 2008.
- J.Z., Soni, R., Raval, P., Gite, A., Goswami, A., Sadhwani, N., Gandhi, N., Patel, H., Mishra, B., Solanki, M., Pandey, B., Jain, M.R., Patel, P.R. Diaryl dihydropyrazole-3- carboxamides with significant in vivo antiobesity activity related to CBI receptor antagonism: Synthesis, biological evaluation, and molecular modeling in the homology model, Journal of Medicinal Chemistry, 50 (24), 5951–5966, 2007.
- Venkatesham, B., Balasubrahmanyam, D., Kannan, M., Srinivas, P., Kumar, K.S., Devi, B.N., Jadhav, V.P., Khan, S.K., Mohan, P., Chaudhury, H., Bhuniya, D., Iqbal, J., Chakrabarti, R.. Novel pyrazole-3-carboxamide derivatives as cannabinoid-1 (CB1) antagonists: Journey from non-polar to polar amides, Bioorganic & Medicinal Chemistry Letters, (1), 562–568, 2011.
- Buisson, I., Bribes, E., Péleraux, A., Pénarier, G., Soubrié, P., Le Fur, G., Galiègue, S., Casellas, P. The CB1 receptor antagonist rimonabant reverses the diet-induced obesity phenotype through the regulation of lipolysis and energy balance, The FASEB Journal, 19 (11), 1567–1569, 2005.
- Shedage, S.A., Gandhi, N., Sairam, K.V.V.M., Pawar, V., Sadhwani, N., Mitra, P., Jain, M.R., Patel, P.R. Facile synthesis, ex-vivo and in vitro screening of 3-sulfonamide derivative of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4- methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide (SR141716) a potent CB1 receptor antagonist, Bioorganic &
- Medicinal Chemistry Letters, 18 (14), 3882–3886, 2008.
- Lazzari, P., Reali, R., Pani, L., Toma, L., Pinna, G.A. Tricyclic pyrazoles. 3. Synthesis, biological evaluation, and molecular modeling of analogues of the cannabinoid antagonist 8-chloro-1-(2',4'-dichlorophenyl)-N-piperidin-1- yl-1,4,5,6-tetrahydrobenzo[6,7]cyclohepta[1,2-c]pyrazole-3- carboxamide, Journal of Medicinal Chemistry, 48 (23), –7362, 2005.
- A., Erdelyi, P., Vukics, K., Szikra, J., Hegyi, E., Vastag, M., Kiss, B., Laszy, J., Gyertyan, I., Fischer, J. Chemical and biological investigation of cyclopropyl containing diaryl- pyrazole-3-carboxamides as novel and potent cannabinoid type 1 receptor antagonists, Journal of Medicinal Chemistry, (14), 4329–4337, 2009.
- Gokce, B. Synthesis, characterization and antiglaucoma activity of some novel pyrazole derivatives of 5-amino- ,3,4-thiadiazole-2-sulfonamide, European Journal of Medicinal Chemistry, 45 (11), 4769–4773, 2010.
- Guleryuz, H. Synthesis of 5-amino-1,3,4-thiadiazole-2- sulfonamide derivatives and their inhibition effects on human carbonic anhydrase isozymes, Journal of Enzyme Inhibition and Medicinal Chemistry, 26 (2), 231–237, 2011.
- Guleryuz, H. Effects of new 5-amino-1,3,4-thiadiazole-2- sulfonamide derivatives on human carbonic anhydrase isozymes, Bioorganic & Medicinal Chemistry, 17 (9), 3295– , 2009.
- Bildirici, I., Akcamur, Y. Studies on the reactions of cyclic oxalyl compounds with hydrazines or hydrazones II [1]: Synthesis and reactions of 4-benzoyl-1-(3-nitrophenyl)-5- phenyl-1H-pyrazole-3-carboxylic Heterocyclic Chemistry, 39 (5), 869–875, 2002. acid, Journal of characterization of some pyrazole derivatives of 1,5- diphenyl-1H-pyrazole-3,4-dicarboxylic acid, Journal of
- Heterocyclic Chemistry, 47 (5), 1040–1048, 2010.