Araştırma Makalesi
BibTex RIS Kaynak Göster

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

Öz

-

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

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.
Toplam 20 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Konular Mühendislik
Bölüm Araştırma Makalesi
Yazarlar

Rahmi Kasımoğulları Bu kişi benim

Makbule Maden Bu kişi benim

Samet Mert Bu kişi benim

Yayımlanma Tarihi 1 Haziran 2012
Gönderilme Tarihi 30 Eylül 2011
Kabul Tarihi 14 Kasım 2011
Yayımlandığı Sayı Yıl 2012 Cilt: 16 Sayı: 1

Kaynak Göster

APA Kasımoğulları, R., Maden, M., & Mert, S. (2012). Bazı pirazol-3-karboksilik asitlerin çeşitli diamin ve diollerle reaksiyonlarının incelenmesi. Sakarya University Journal of Science, 16(1), 47-52. https://doi.org/10.16984/saufbed.11034
AMA Kasımoğulları R, Maden M, Mert S. Bazı pirazol-3-karboksilik asitlerin çeşitli diamin ve diollerle reaksiyonlarının incelenmesi. SAUJS. Nisan 2012;16(1):47-52. doi:10.16984/saufbed.11034
Chicago Kasımoğulları, Rahmi, Makbule Maden, ve Samet Mert. “Bazı Pirazol-3-Karboksilik Asitlerin çeşitli Diamin Ve Diollerle reaksiyonlarının Incelenmesi”. Sakarya University Journal of Science 16, sy. 1 (Nisan 2012): 47-52. https://doi.org/10.16984/saufbed.11034.
EndNote Kasımoğulları R, Maden M, Mert S (01 Nisan 2012) Bazı pirazol-3-karboksilik asitlerin çeşitli diamin ve diollerle reaksiyonlarının incelenmesi. Sakarya University Journal of Science 16 1 47–52.
IEEE R. Kasımoğulları, M. Maden, ve S. Mert, “Bazı pirazol-3-karboksilik asitlerin çeşitli diamin ve diollerle reaksiyonlarının incelenmesi”, SAUJS, c. 16, sy. 1, ss. 47–52, 2012, doi: 10.16984/saufbed.11034.
ISNAD Kasımoğulları, Rahmi vd. “Bazı Pirazol-3-Karboksilik Asitlerin çeşitli Diamin Ve Diollerle reaksiyonlarının Incelenmesi”. Sakarya University Journal of Science 16/1 (Nisan 2012), 47-52. https://doi.org/10.16984/saufbed.11034.
JAMA Kasımoğulları R, Maden M, Mert S. Bazı pirazol-3-karboksilik asitlerin çeşitli diamin ve diollerle reaksiyonlarının incelenmesi. SAUJS. 2012;16:47–52.
MLA Kasımoğulları, Rahmi vd. “Bazı Pirazol-3-Karboksilik Asitlerin çeşitli Diamin Ve Diollerle reaksiyonlarının Incelenmesi”. Sakarya University Journal of Science, c. 16, sy. 1, 2012, ss. 47-52, doi:10.16984/saufbed.11034.
Vancouver Kasımoğulları R, Maden M, Mert S. Bazı pirazol-3-karboksilik asitlerin çeşitli diamin ve diollerle reaksiyonlarının incelenmesi. SAUJS. 2012;16(1):47-52.

30930 This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.