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

Rahmi Kasımoğulları Hamdiye Duran Samet Mert

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.

Anahtar Kelimeler

pyrazole-3-carboxylic acid, pyrazole, ester, ureide, carboxamide

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

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.

Anahtar Kelimeler

pirazol-3-karboksilik asit, pirazol, ester, üreid, karboksamit

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).