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SYNTHESIS AND CHARACTERISATION OF SOME ESTER, AMIDE AND UREIDE DERIVATIVES OF 4-(ETHOXYCARBONYL)-1-(3-NITROPHENYL)-5-PHENYL-1H-PYRAZOLE-3-CARBOXYLIC ACID

Yıl 2011, Sayı: 026, 47 - 56, 15.12.2011

Öz

In this study, some new derivatives were synthesized of 4-(ethoxycarbonyl)-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid (1) which was a pyrazole carboxylic acid
derivative. For this aim, ester derivatives were obtained from the reaction of 1 with various alcohols; amide (7) and ureide (8) derivatives were obtained from the reaction with amonnia and
urea respectively. Also a new pyrazole derivative (9) was synthesized from decarboxylation of 1. The structures of synthesized compounds were elucidated with FT-IR,
1H NMR and 13C
NMR analysis methods.

Kaynakça

  • [1] A. M. Farghaly, N. S. Habib, M. A. Khalil, and O. A. El-Sayed, “Synthesis of 1H-pyrazole[3,4-b] quinoline derivatives of possible therapeutic interest”, Alex. J. Pharm. Sci, 3(1), 90–91 (1989).
  • [2] R. N. Mahajan, F. H. Havaldar, and P. S. Fernandes, “Syntheses and biological activity of heterocycles derived from 3-methoxy-1-phenyl-1H-pyrazole-5-carboxylate”, J. Indian Chem. Soc, 68(4), 245–246 (1991).
  • [3] P. G. Baraldi, S. Manfredini, R. Romagnoli, L. Stevanato, A. N. Zaid, and R. Mans ervigi, “Synthesis and anti-HSV-1 activity of 6 substituted pyrazolo[3,4-d]pyridazin-7-one nucleosides”, Nucleos. Nucleot, 17(12), 2165–2173 (1998).
  • [4] J. S. Larsen, M. A. Zahran, E. B. Pedersen, and C. Nielsen, “Synthesis of triazenopyrazole derivatives as potential inhibitors of HIV-1”, Monatsh. Chem, 130(9), 1167–1174 (1999).
  • [5] S. Suzuki, and A. Inoue, “Anticancer agents containing 1H-pyrazolo[3,4-b] pyrazines”, Jpn. Kokai Tokyo Koho JP 02 172 988 [90172988]; (Cl. C07D487/04) [Chem. Abstr. 113 218276t] (1990).
  • [6] G. J. Hatheway, C. Hansch, K. H. Kim, S. R. Milstein, C. L. Schmidt, R. N. Smith, and F. R. Quinn, “Antitumor 1-(X-aryl)-3,3-dialkyltriazenes. 1. Quantitative structure-activity relationships vs. L1210 Leukemia in mice”, J. Med. Chem, 21(6), 563–574 (1978).
  • [7] H. Katayama, and T. Oshiyama, “Preparation and bioactivity of pyrazole derivatives as potential cross-linking agent”, Can. J. Chem, 75(6), 913–919 (1997).
  • [8] R. Riedel, “Lonazolac-Ca= Calcium [3-(para chlorophenyl)-1-phenylpyrazole-4]-acetate-pharmacological properties of a new antiinflammatory-antirheumatic drug”, Arzneim. Forsch. / Drug. Res, 31–1(4), 655–665 (1981).
  • [9] E. A. M. Badawey, and I. M. El-Ashmawey, “Nonsteroidal antiinflammatory agents - Part 1: Antiinflammatory, analgesic and antipyretic activity of some new 1-(pyrimidin-2-yl)-3-pyrazolin-5-ones and 2-(pyrimidin-2-yl)-1,2,4,5,6,7-hexahydro-3H-indazol-3-ones”, Eur. J. Med. Chem, 33(5), 349–361 (1998).
  • [10] O. Bruno, A. Ranise, F. Bondavalli, P. Schenone, M. D’amico, E. Lampa, C. Falzarano, F. Rossi, “3,5-Diphenyl-1H-pyrazole derivatives. 10. N-Substituted 1-(2-aminopropyl)-3,5-diphenyl-1H-pyrazoles and 1-(3-amino-2-hydroxypropyl)-3,5-diphenyl-1H-pyrazoles with antiinflammatory and other activities”, Farmaco, 47(10), 1235–1248 (1992).
  • [11] P. D. Mishra, S. Wahidullah, and S. Y. Kamat, “A heteroaromatic acid from marine sponge Suberites vestigium”, Indian J. Chem. Soc. Sec. B, 37(2), 199–200 (1998).
  • [12] W. T., Thomson, “Agricultural Chemicals-Book II Herbicides”, 13th. Ed., Thomson Publications, California-USA, pp 268,269,278 (1997).
  • [13] M. Londershausen, “Approaches to new parasiticides”, Pestic. Sci, 48(4), 269–292 (1996).
  • [14] V. V. Badiger, and S. C. Bennur, “Synthesis and biological activity of pyrazolopyrimidines”, Indian J. Heterocycl. Chem, 6(1), 63–66. (1996).
  • [15] C.-Y. Zhang, X.-H. Liu, B.-L. Wang, S.-H. Wang, and Z.-M. Li, “Synthesis and antifungal activities of new pyrazole derivatives via 1,3-dipolar cycloaddition reaction” Chem. Biol. Drug Des, 75(5), 489–493 (2010).
  • [16] M. Kurowski, A. Dunky, and M. Geddawi, “Transsynovial distribution and protein binding of pirazolac in patients with rheumatoid arthritis”, Eur. J. Clin. Pharmacol, 31(3), 307–311 (1986).
  • [17] F. Lepage, and B. Hublot, “Dérivés hétérocycliques doués d'activité anticonvulsivante, procédé de préparation et composition pharmaceutique”, Eur. Pat. Appl. EP.459 887 A1; 1–21, [Chem.Abstr., 116, 128917] (1991).
  • [18] D. M. Bailey, P. E. Hansen, A. G. Hlavac, E. R. Baizman, J. Pearl, A. F. Defelice, and M. E. Feigenson, “3,4-Diphenyl-1H-pyrazole-1-propanamine antidepressants”, J. Med. Chem, 28(2), 256–260 (1985).
  • [19] R. H., Wiley, and P., Wiley, “Pyrazolones, pyrazolidones and derivatives”, John Wiley and Sons, New York, pp.102. (1964).
  • [20] G. A. Hanson, “1-Phényl, 2-pyrazolines substituées”, Bull. Soc. Chim. Belg, 67(11–12), 707–711 (1958).
  • [21] O. Neunhoeffer, G. Alsdorf, and H. Ulrich, “Hyperkonjugation und fluoreszenzverhalten”, Chem. Ber, 92(1), 252–255 (1959).
  • [22] E. E. Baroni, and K. A. Kovyrzina, “Synthesis of luminescent heterocyclic compounds”, Zh. Obshchei. Khim, 31, 1641–1643 (1961).
  • [23] R. Kasimogullari, M. Bulbul, S. Mert, H. Guleryuz, “Synthesis of 5-amino-1,3,4-thiadiazole-2-sulfonamide derivatives and their inhibition effects on human carbonic anhydrase isozymes”, J. Enzyme Inhib, 26(2), 231–237 (2011).
  • [24] R. Kasımoğulları, M. Bülbül, B. S. Arslan, and B. Gökçe, “Synthesis, characterization and antiglaucoma activity of some novel pyrazole derivatives of 5-amino-1,3,4-thiadiazole-2-sulfonamide.” Eur. J. Med. Chem, 45(9), 4769–4773 (2010).
  • [25] R. Kasımoğulları, M. Bülbül, H. Günhan, and H. Güleryüz, “Effects of new 5-amino-1,3,4-thiadiazole-2-sulfonamide derivatives on human carbonic anhydrase isozymes” Bioorg. Med. Chem, 17(11), 3295-3301 (2009).
  • [26] M. Bulbul, R. Kasimogullari, O. I. Kufrevioglu, “Amide derivatives with pyrazole carboxylic acids of 5-amino-1,3,4-thiadiazole 2-sulfonamide as new carbonic anhydrase inhibitors: Synthesis and investigation of inhibitory effects”, J. Enzyme Inhib, 23(6), 895–900 (2008).
  • [27] Y. Akcamur, G. Penn, E. Ziegler, H. Sterk, G. Kollenz, K. Peters, E.M. Peters, H.G. Vonschnering, “Reactions of cyclic oxalyl compounds .24. Reaction of 4-benzoyl-5-phenyl-furan-2,3-dione with phenylhydrazones and phenylhydrazine” Monatsh. Chem, 117(2), 231–245 (1986).
  • [28] A. Sener, R. Kasimogullari, M. K. Sener, I. Bildirici, Y. Akcamur, “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 acid”, J. Heterocycl. Chem, 39(5), 869–875 (2002).
  • [29] R. Kasimogullari and B. S. Arslan, “Synthesis and characterization of some pyrazole derivatives of 1,5-diphenyl-1H-pyrazole-3,4-dicarboxylic acid”, J. Heterocycl. Chem, 47(5), 1040–1048 (2010).
  • [30] R. Kasimogullari, B. Zengin, M. Maden, S. Mert, C. Kazaz, “Synthesis of new derivatives of 1-(3-amino-phenyl)-4-benzoyl-5-phenyl-1H-pyrazole-3-carboxylic acid”, J. Serb. Chem. Soc., 75(12), 1625–1635 (2010).
  • [31] M. Balcı, “Nükleer Manyetik Rezonans Spektroskopisi”, METU Yayınları, Ankara, (1999).
  • [32] R. M. Silverstein, G. G. Bassler, T. C. Morrill, “Spectrometric Identification of Organic Compound”, John Wiley & Sons, New York, (1991).

4-(ETOKSİKARBONİL)-1-(3-NİTROFENİL)-5-FENİL-1H-PİRAZOL-3-KARBOKSİLİK ASİDİN BAZI ESTER AMİT VE ÜREİD TÜREVLERİNİN SENTEZİ VE KARAKTERİZASYONU

Yıl 2011, Sayı: 026, 47 - 56, 15.12.2011

Öz

Bu çalışmada bir
pirazol karboksilik asit türevi olan 4-(etoksikarbonil)-1-(3-nitrofenil)-5-fenil-1H-pirazol-3-karboksilik asit (1) bileşiğinin bazı yeni türevleri
sentezlendi. Bunun için, 1
bileşiğinin çeşitli alkollerle reaksiyonundan ester türevleri (3–6), amonyak ve üre ile reaksiyonundan
ise sırasıyla amit (7) ve üreid (8) türevleri elde edildi. Ayrıca 1 bileşiğinin dekarboksilasyonu ile de
yeni bir pirazol türevi (9)
sentezlendi. Sentezlenen bileşiklerin yapıları, FT-IR, 1H NMR ve 13C NMR
spektroskopik yöntemleri kullanılarak aydınlatıldı.

Kaynakça

  • [1] A. M. Farghaly, N. S. Habib, M. A. Khalil, and O. A. El-Sayed, “Synthesis of 1H-pyrazole[3,4-b] quinoline derivatives of possible therapeutic interest”, Alex. J. Pharm. Sci, 3(1), 90–91 (1989).
  • [2] R. N. Mahajan, F. H. Havaldar, and P. S. Fernandes, “Syntheses and biological activity of heterocycles derived from 3-methoxy-1-phenyl-1H-pyrazole-5-carboxylate”, J. Indian Chem. Soc, 68(4), 245–246 (1991).
  • [3] P. G. Baraldi, S. Manfredini, R. Romagnoli, L. Stevanato, A. N. Zaid, and R. Mans ervigi, “Synthesis and anti-HSV-1 activity of 6 substituted pyrazolo[3,4-d]pyridazin-7-one nucleosides”, Nucleos. Nucleot, 17(12), 2165–2173 (1998).
  • [4] J. S. Larsen, M. A. Zahran, E. B. Pedersen, and C. Nielsen, “Synthesis of triazenopyrazole derivatives as potential inhibitors of HIV-1”, Monatsh. Chem, 130(9), 1167–1174 (1999).
  • [5] S. Suzuki, and A. Inoue, “Anticancer agents containing 1H-pyrazolo[3,4-b] pyrazines”, Jpn. Kokai Tokyo Koho JP 02 172 988 [90172988]; (Cl. C07D487/04) [Chem. Abstr. 113 218276t] (1990).
  • [6] G. J. Hatheway, C. Hansch, K. H. Kim, S. R. Milstein, C. L. Schmidt, R. N. Smith, and F. R. Quinn, “Antitumor 1-(X-aryl)-3,3-dialkyltriazenes. 1. Quantitative structure-activity relationships vs. L1210 Leukemia in mice”, J. Med. Chem, 21(6), 563–574 (1978).
  • [7] H. Katayama, and T. Oshiyama, “Preparation and bioactivity of pyrazole derivatives as potential cross-linking agent”, Can. J. Chem, 75(6), 913–919 (1997).
  • [8] R. Riedel, “Lonazolac-Ca= Calcium [3-(para chlorophenyl)-1-phenylpyrazole-4]-acetate-pharmacological properties of a new antiinflammatory-antirheumatic drug”, Arzneim. Forsch. / Drug. Res, 31–1(4), 655–665 (1981).
  • [9] E. A. M. Badawey, and I. M. El-Ashmawey, “Nonsteroidal antiinflammatory agents - Part 1: Antiinflammatory, analgesic and antipyretic activity of some new 1-(pyrimidin-2-yl)-3-pyrazolin-5-ones and 2-(pyrimidin-2-yl)-1,2,4,5,6,7-hexahydro-3H-indazol-3-ones”, Eur. J. Med. Chem, 33(5), 349–361 (1998).
  • [10] O. Bruno, A. Ranise, F. Bondavalli, P. Schenone, M. D’amico, E. Lampa, C. Falzarano, F. Rossi, “3,5-Diphenyl-1H-pyrazole derivatives. 10. N-Substituted 1-(2-aminopropyl)-3,5-diphenyl-1H-pyrazoles and 1-(3-amino-2-hydroxypropyl)-3,5-diphenyl-1H-pyrazoles with antiinflammatory and other activities”, Farmaco, 47(10), 1235–1248 (1992).
  • [11] P. D. Mishra, S. Wahidullah, and S. Y. Kamat, “A heteroaromatic acid from marine sponge Suberites vestigium”, Indian J. Chem. Soc. Sec. B, 37(2), 199–200 (1998).
  • [12] W. T., Thomson, “Agricultural Chemicals-Book II Herbicides”, 13th. Ed., Thomson Publications, California-USA, pp 268,269,278 (1997).
  • [13] M. Londershausen, “Approaches to new parasiticides”, Pestic. Sci, 48(4), 269–292 (1996).
  • [14] V. V. Badiger, and S. C. Bennur, “Synthesis and biological activity of pyrazolopyrimidines”, Indian J. Heterocycl. Chem, 6(1), 63–66. (1996).
  • [15] C.-Y. Zhang, X.-H. Liu, B.-L. Wang, S.-H. Wang, and Z.-M. Li, “Synthesis and antifungal activities of new pyrazole derivatives via 1,3-dipolar cycloaddition reaction” Chem. Biol. Drug Des, 75(5), 489–493 (2010).
  • [16] M. Kurowski, A. Dunky, and M. Geddawi, “Transsynovial distribution and protein binding of pirazolac in patients with rheumatoid arthritis”, Eur. J. Clin. Pharmacol, 31(3), 307–311 (1986).
  • [17] F. Lepage, and B. Hublot, “Dérivés hétérocycliques doués d'activité anticonvulsivante, procédé de préparation et composition pharmaceutique”, Eur. Pat. Appl. EP.459 887 A1; 1–21, [Chem.Abstr., 116, 128917] (1991).
  • [18] D. M. Bailey, P. E. Hansen, A. G. Hlavac, E. R. Baizman, J. Pearl, A. F. Defelice, and M. E. Feigenson, “3,4-Diphenyl-1H-pyrazole-1-propanamine antidepressants”, J. Med. Chem, 28(2), 256–260 (1985).
  • [19] R. H., Wiley, and P., Wiley, “Pyrazolones, pyrazolidones and derivatives”, John Wiley and Sons, New York, pp.102. (1964).
  • [20] G. A. Hanson, “1-Phényl, 2-pyrazolines substituées”, Bull. Soc. Chim. Belg, 67(11–12), 707–711 (1958).
  • [21] O. Neunhoeffer, G. Alsdorf, and H. Ulrich, “Hyperkonjugation und fluoreszenzverhalten”, Chem. Ber, 92(1), 252–255 (1959).
  • [22] E. E. Baroni, and K. A. Kovyrzina, “Synthesis of luminescent heterocyclic compounds”, Zh. Obshchei. Khim, 31, 1641–1643 (1961).
  • [23] R. Kasimogullari, M. Bulbul, S. Mert, H. Guleryuz, “Synthesis of 5-amino-1,3,4-thiadiazole-2-sulfonamide derivatives and their inhibition effects on human carbonic anhydrase isozymes”, J. Enzyme Inhib, 26(2), 231–237 (2011).
  • [24] R. Kasımoğulları, M. Bülbül, B. S. Arslan, and B. Gökçe, “Synthesis, characterization and antiglaucoma activity of some novel pyrazole derivatives of 5-amino-1,3,4-thiadiazole-2-sulfonamide.” Eur. J. Med. Chem, 45(9), 4769–4773 (2010).
  • [25] R. Kasımoğulları, M. Bülbül, H. Günhan, and H. Güleryüz, “Effects of new 5-amino-1,3,4-thiadiazole-2-sulfonamide derivatives on human carbonic anhydrase isozymes” Bioorg. Med. Chem, 17(11), 3295-3301 (2009).
  • [26] M. Bulbul, R. Kasimogullari, O. I. Kufrevioglu, “Amide derivatives with pyrazole carboxylic acids of 5-amino-1,3,4-thiadiazole 2-sulfonamide as new carbonic anhydrase inhibitors: Synthesis and investigation of inhibitory effects”, J. Enzyme Inhib, 23(6), 895–900 (2008).
  • [27] Y. Akcamur, G. Penn, E. Ziegler, H. Sterk, G. Kollenz, K. Peters, E.M. Peters, H.G. Vonschnering, “Reactions of cyclic oxalyl compounds .24. Reaction of 4-benzoyl-5-phenyl-furan-2,3-dione with phenylhydrazones and phenylhydrazine” Monatsh. Chem, 117(2), 231–245 (1986).
  • [28] A. Sener, R. Kasimogullari, M. K. Sener, I. Bildirici, Y. Akcamur, “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 acid”, J. Heterocycl. Chem, 39(5), 869–875 (2002).
  • [29] R. Kasimogullari and B. S. Arslan, “Synthesis and characterization of some pyrazole derivatives of 1,5-diphenyl-1H-pyrazole-3,4-dicarboxylic acid”, J. Heterocycl. Chem, 47(5), 1040–1048 (2010).
  • [30] R. Kasimogullari, B. Zengin, M. Maden, S. Mert, C. Kazaz, “Synthesis of new derivatives of 1-(3-amino-phenyl)-4-benzoyl-5-phenyl-1H-pyrazole-3-carboxylic acid”, J. Serb. Chem. Soc., 75(12), 1625–1635 (2010).
  • [31] M. Balcı, “Nükleer Manyetik Rezonans Spektroskopisi”, METU Yayınları, Ankara, (1999).
  • [32] R. M. Silverstein, G. G. Bassler, T. C. Morrill, “Spectrometric Identification of Organic Compound”, John Wiley & Sons, New York, (1991).
Toplam 32 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Konular Mühendislik
Bölüm Makaleler
Yazarlar

Rahmi Kasımoğulları

Hamdiye Duran Bu kişi benim

Samet Mert Bu kişi benim

Yayımlanma Tarihi 15 Aralık 2011
Yayımlandığı Sayı Yıl 2011 Sayı: 026

Kaynak Göster

APA Kasımoğulları, R., Duran, H., & Mert, S. (2011). 4-(ETOKSİKARBONİL)-1-(3-NİTROFENİL)-5-FENİL-1H-PİRAZOL-3-KARBOKSİLİK ASİDİN BAZI ESTER AMİT VE ÜREİD TÜREVLERİNİN SENTEZİ VE KARAKTERİZASYONU. Journal of Science and Technology of Dumlupınar University(026), 47-56.