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Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Research Article

A Facile Synthesis and Reactions of Some Novel Pyrazole-based Heterocycles

Author(s): Ahmed A.O. Abeed*, Talaat I. El-Emary and Mohamed S.K. Youssef

Volume 16, Issue 3, 2019

Page: [405 - 412] Pages: 8

DOI: 10.2174/1570179416666181210160908

Price: $65

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Abstract

Aim and Objective: This work presents the synthetic capability and the exploitation of 1,3-diphenyl- 1H-pyrazole-4-carboxladehyde 1 and 5-diphenyl pyrazolyl-2-pyrazoline analogue 8 to serve as excellent precursors for the synthesis of substituted indol-2,3-dione, trizolo[3,4-a]benzazoles, thiazolo[2,3- a]benzimidazole-3-one, substituted 2-pyrazoline and pyrazole-substituted-pyrazolines using various reagents.

Materials and Methods: Using chemicals from Aldrich, Fluka, or Merck, and pure solvents, we apply the synthetic procedures for the synthesis of novel heterocycles. The melting points of these compounds were determined using APP. Digital ST 15 melting point apparatus. SP3-100 spectrophotometer recorded FT-IR spectra (KBr) (cm-1). NMR spectra (δ, ppm) were recorded on 400 MHz AVANCE-III High-Performance FT-NMR Spectrometer BRUCKER (Switzerland) and some 1H NMR spectra were recorded on Varian EM-360L NMR Spectrophotometer (90 MHz) (USA) in CDCl3 or DMSO-d6 as a solvent. Elemental analyses were carried out at a Vario EL C, H, N, and S Analyzer. Bromine was determined using direct titration method after carius combustion.

Results: The structures of the compounds were confirmed by IR, 1H NMR, 13C NMR, and elemental analyses.

Conclusion: 1,3-Diphenyl-1H-pyrazole-4-carboxladehyde 1 and 2-pyrazoline derivative 9 confirmed their importance in the synthetic organic chemistry. Depending on the formyl group of aldehyde 1 and active methylene of pyrazoline 8, we synthesized new series of heterocycles; indol-2,3-dione, trizolo[3,4-a]benzazole, thiazolo[2,3-a]benzimidazole-3-one and pyrazolyl-pyrazoline derivatives expecting their pharmacological applications. The targeted compounds were substantiated from its spectral data.

Keywords: 1, 3-Diphenyl pyrazole, 2-pyrazoline, thiazolidine-4-one, thiazolo[2, 3-a]benzimidazole, heterocycles, pyrazole.

Graphical Abstract
[1]
Thumar, N.J.; Patel, M.P. Synthesis and in vitro antimicrobial evaluation of 4H-pyrazolopyran, -benzopyran and naphthopyran derivatives of 1H-pyrazole. Arkivoc, 2009, 13, 363-380.
[2]
Bondock, S.; Fadaly, W.; Metwally, M.A. Synthesis and antimicrobial activity of some new thiazole, thiophene and pyrazole derivatives containing benzothiazole moiety. Eur. J. Med. Chem., 2010, 45, 3692-3701.
[3]
Aneja, D.K.; Lohan, P.; Arora, S.; Sharma, C.; Aneja, K.R.; Prakash, O. Synthesis of new pyrazolyl-2,4-thiazolidinediones as antibacterial and antifungal agents. Org. Med. Chem. Lett., 2011, 1, 15-26.
[4]
Rathelot, P.; Azas, N.; El-Kashef, H.; Delmas, F.; Giorgio, C.D.; Timon-David, P.; Maldonado, J.; Vanelle, P. 1,3-Diphenyl pyrazoles: synthesis and antiparasitic activities of azomethine derivatives. Eur. J. Med. Chem., 2002, 37, 671-679.
[5]
Bondock, S.; Khalifa, W.; Fadda, A.A. Synthesis and antimicrobial activity of some new 4-hetarylpyrazole and furo[2,3-c]pyrazole derivatives. Eur. J. Med. Chem., 2011, 46, 2555-2561.
[6]
Rostom, S.H.A.F.; El-Ashmawy, I.M.; Abd El-Razik, H.A.E.; Badr, M.H.; Ashour, H.M.A. Design and synthesis of some thiazolyl and thiadiazolyl derivatives of antipyrine as potential non-acidic anti-inflammatory, analgesic and antimicrobial agents. Bioorg. Med. Chem., 2009, 17, 882-895.
[7]
Abd-El Gawad, N.M.; Hassan, G.S.; Georgey, H.H. Design and synthesis of some pyrazole derivatives of expected anti-inflamm-atory and analgesic activities. Med. Chem. Res., 2012, 21, 983-994.
[8]
Huang, H.X.F.; Xiang, L.; Yong, Z.; Guo-Qiang, S.; Qi-Long, H.; Qing-Shan, L.; Xian-Hui, Y.; Yao, W.; Hai-Liang, Z. Synthesis of biological evaluation, and molecular docking of N-((1,3-diphenyl-1H-pyrazol-4-yl)methyl)aniline derivatives as novel anticancer agents. Bioorg. Med. Chem., 2012, 20, 4895-4900.
[9]
Srinivasa, R.T.; Ganga, R.V.; Kulhari, H.; Shukla, R.; Kamal, A.; Bansal, V. A series of (Z)-1-(1,3-diphenyl-1H-pyrazole-4-yl)-3-(phenylamino)-prop-2-en-1-one derivatives as potential anticancer and apoptosis inducing agents. Eur. J. Med. Chem., 2016, 117, 157-166.
[10]
Srinivasa, R.T.; Hitesh, H.; Reddy, V.G.; Bansal, V.; Kamal, A.; Shukla, R. Design, synthesis and biological evaluation of 1,3-diphenyl-1H-pyrazole derivatives containing benzimidazole skeleton as potential anticancer and apoptosis inducing agents. Eur. J. Med. Chem., 2015, 101, 790-805.
[11]
Reddy, T.S.; Kulhari, K.; Reddy, V.G.; Rao, A.V.S.; Bansal, V.; Kamal, A.; Shukla, R. Synthesis and biological evaluation of pyrazolotriazole hybrids as cytotoxic and apoptosis inducing agents. Org. Biomol. Chem., 2015, 13, 10136.
[12]
Singh, P.; Negi, J.S.; Pant, G.J.N.P.; Rawat, M.S.M. Synthesis, and characterization of novel 1-chloroacetyl derivatives of 2-pyrazolines. Heterocycl. Commun., 2011, 17, 61-63.
[13]
Abeed, A.A.O. 2-Pyraolin-5-One-based heterocycles: Synthesis and characterization. J. Heterocycl. Chem., 2015, 52, 1175-1184.
[14]
Palaskaa, E.; Aytemira, M.; Uzbay, I.; Erola, D. Synthesis and antidepressant activities of some 3,5-diphenyl-2-pyrazolines. Eur. J. Med. Chem., 2001, 36, 539-543.
[15]
Prasad, Y.R.; Rao, A.L.; Prasoona, L.; Murali, K.; Kumar, P.R. Synthesis and antidepressant activity of some 1,3,5-triphenyl-2-pyrazolines and 3-(2-hydroxynaphthalen-1-yl)-1,5-diphenyl-2-pyrazolines. Bioorg. Med. Chem. Lett., 2005, 15, 5030-5034.
[16]
Kelekci, N.G.; Koyunoglu, S.; Yabanoglu, S.; Yelekci, K.; Ozgen, O.; Ucar, G.; Erol, K.; Kendi, E.; Yesilada, A. New pyrazoline bearing 4-(3H)-quinazolinone inhibitors of monoamine oxidase: Synthesis, biological evaluation and structural determinants of MAO-A and MAO-B selectivity. Bioorg. Med. Chem., 2008, 22, 23-25.
[17]
Amir, M.; Kumar, H.; Khan, S.A. Synthesis and pharmacological evaluation of pyrazoline derivatives as new anti-inflammatory and analgesic agents. Bioorg. Med. Chem. Lett., 2008, 18, 918-922.
[18]
Rathish, I.G.; Javed, K.; Ahmad, S.; Bano, S.; Alam, M.S.; Pillai, K.K.; Singh, S.; Bagchi, V. Synthesis and anti-inflammatory activity of some new 1,3,5-trisubstituted pyrazolines bearing benzene sulfonamide. Bioorg. Med. Chem. Lett., 2008, 21, 212-213.
[19]
Amir, M.; Kumar, H.; Khan, S.A. Synthesis and pharmacological evaluation of pyrazoline derivatives as new anti-inflammatory and analgesic agents. Bioorg. Med. Chem. Lett., 2008, 18, 918-922.
[20]
Ozdemir, A.; Turan Zitouni, G.; Kaplancıklı, Z.A.; Revial, G.; Guven, K. Synthesis and antimicrobial activity of 1-(4-aryl-2-thiazolyl)-3-(2-thienyl)-5-aryl-2-pyrazoline derivatives. Eur. J. Med. Chem., 2007, 42, 403-409.
[21]
Stirrett, K.L.; Ferreras, J.A.; Jayaprakash, V.; Sinha, B.N.; Renc, T.; Quadri, L.E.N. Small molecules with structural similarities to siderophores as novel antimicrobials against Mycobacterium tuberculosis and Yersinia pestis. Bioorg. Med. Chem. Lett., 2008, 18, 2662-2668.
[22]
Sharma, M.; Sharma, S.; Buddhiraja, A.; Saxena, A.K.; Nepali, K.; Bedi, P.M.S. Synthesis and cytotoxicity studies of 3,5-diaryl N-acetyl pyrazoline-isatin hybrids. Med. Chem. Res., 2014, 23, 4337-4344.
[23]
Zhou, Z.; Zhuo, J.; Yan, S.; Ma, L. Design and synthesis of 3,5- diaryl-4,5-dihydro-1H-pyrazoles as new tyrosinase inhibitors. Bioorg. Med. Chem., 2013, 21, 2156-2162.
[24]
Havrylyuk, D.; Zimenkovsky, B.; Vasylenko, O.; Day, C.W.; Smee, D.F.; Grellier, P.; Lesyk, R. Synthesis and biological activity evaluation of 5-pyrazoline substituted 4-thiazolidinones. Eur. J. Med. Chem., 2013, 66, 228-237.
[25]
Girisha, K.S.; Kalluraya, B.; Narayana, V. Padmashree. Synthesis, and pharmacological study of 1-acetyl/propyl-3-aryl-5-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-2-pyrazoline. Eur. J. Med. Chem., 2010, 45, 4640-4644.
[26]
Youssef, M.S.K.; Abeed, A.A.O. Synthesis, characterization and pharmacological activities of pyrimidine derivatives containing 2-pyrazolin-5-one. Int. J. Pharm. Sci. Res., 2014, 5, 1705-1720.
[27]
Youssef, M.S.K.; Omar, A.A. Synthesis and reactions of 5-amino-3-(3-methyl-5-oxo-1-phenyl-2-pyrazolin-4-yl)-7-phenyl-7H-thiazolo[3,2-a]pyrim-idine-6-carbonitrile. Monatsh. Chem., 2007, 138, 989-995.
[28]
Youssef, M.S.K.; Abbady, M.S.; Ahmed, R.A.; Omar, A.A. Synthesis of some new heterocycles derived from ethyl 7-amino-3-(3-methyl-5-oxo-1-phenyl-2-pyrazolin-4-yl)-5-aryl-5H-thiazolo[3, 2-a]pyrimidine-6-carboxylate of biological importance. J. Heterocycl. Chem., 2013, 50, 179-187.
[29]
Youssef, M.S.K.; Abbady, M.S.; Ahmed, R.A.; Omar, A.A. Preparation and reactions of 2‐methyl‐7‐(3‐methyl‐5‐oxo‐1‐ phenyl‐2‐pyrazolin‐4‐yl)‐5‐aryl-thiazolo[3,2‐a]pyrimido[4,5‐d]oxazin‐4(5H)‐one. Chin. J. Chem., 2001, 29, 1473-1482.
[30]
Abeed, A.A.O.; Youssef, M.S.K.; Hegazy, R. Synthesis, anti-diabetic and renoprotective activity of some new benzazole, thiazolidin-4-one and azetidin-2-one derivatives. J. Braz. Chem. Soc., 2017, 28, 2054-2063.
[31]
Youssef, M.S.K.; Abeed, A.A.O.; El-Emary, T.I. Synthesis and evaluation of chromene-based compounds containing pyrazole moiety as antimicrobial agents. Heterocycl. Comm., 2017, 23, 55-64.
[32]
Makineni, S.; McCorkindale, Wm.; Syme, A.C. A direct titration method for determining chlorine in organic compounds after carius combustion. J. Chem. Tech. Biotech., 1958, 8, 310-313.

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