DEA University of Debrecen Electronic Archive

Csősz, Éva

Tóth, Ferenc

Mahdi, Mohamed

Tsaprailis, George

Emri, Miklós

Tőzsér, József

BMC Bioinformatics

Analysis of networks of host proteins in the early time points following HIV transduction

Pusztahelyi, Tünde

Kovács, Szilvia

Pócsi, István

Prokisch, József

Journal of Trace Elements in Medicine and Biology

Selenite-stress selected mutant strains of probiotic bacteria for Se source production

Pusztai, Gabriella

Szabó, Diána

Felsőoktatási hallgatók és fogyatékossággal élő társaik

Irinyi, Beatrix

Aleksza, Magdolna

Antal-Szalmás, Péter

Sipka, Sándor

Hunyadi, János

Szegedi, Andrea

Acta Dermato Venereologica

Cytokine production of CD4+ and CD8+ peripheral T lymphocytes in patients with chronic idiopathic urticaria

Csomós, György

Földrajzi Közlemények

A társadalomföldrajz tudományterületi klasszifikációjának hazai és nemzetközi gyakorlata

Lévai, Albert

ARKIVOC

Dioxirane oxidation of sulfur-containing organic compounds

Jekő, József

Issue in Honor of Prof. Alexandru T. Balaban ARKIVOC 2005 (x) 199-205 ISSN 1424-6376 Page 199 ©ARKAT USA, Inc Synthesis of hydroxylated 3,5-diaryl-2-pyrazolines by the reaction of hydroxychalcones with hydrazines  Albert Lévai*a and József Jekőb  a Department of Organic Chemistry, University of Debrecen, P.O.Box 20, H-4010 Debrecen, Hungary, b ICN Hungary Co. Ltd., H-4440 Tiszavasvári, Hungary E-mail: alveai@puma.unideb.hu  Dedicated to Professor Dr. Alexandru T. Balaban on the occasion of his 75th birthday (received 27 Apr 05; accepted 22 Jun 05; published on the web 25 Jun 05)  Abstract New 1-substituted 3,5-diaryl-2-pyrazolines 13-27 have been synthesized by the reaction of hydroxychalcones 1-12 and hydrazines in hot acetic acid solution. Structures of all new compounds have been elucidated by microanalyses, 1H- and 13C-NMR spectroscopy.  Keywords: Hydroxychalcones, hydrazines, 3,5-diaryl-2-pyrazolines    Introduction  Pyrazolines are prominent nitrogen-containing heterocyclic compounds and, therefore, various procedures have been worked out for their synthesis.1-4 Numerous pyrazoline type compounds have been found to possess useful bioactivity, e.g. antimicrobial,5 central nervous system6 and immunosuppressive.7 Among the various pyrazoline isomers, 2-pyrazolines appear to be the most frequently investigated compounds. As a consequence, a large number of 2-pyrazolines have been described in the chemical literature, using different synthetic methods for their preparation. An especially popular procedure is based on the reaction of α,β-unsaturated aldehydes and ketones with hydrazines.8-37 However, series of specially substituted representatives have been prepared rarely. For this reason, the aim of our present study was to synthesize systematically hydroxylated 3,5-diaryl-2-pyrazolines for the study of their structure-activity relationships.  Issue in Honor of Prof. Alexandru T. Balaban ARKIVOC 2005 (x) 199-205 ISSN 1424-6376 Page 200 ©ARKAT USA, Inc Results and Discussion  Formation of 2-pyrazolines by the reaction of α,β-unsaturated ketones and hydrazines may take place under various reaction conditions using ethanol,18 acetic acid8-10,16,21,25-27 or pyridine28,29 as solvent. After some preliminary experiments, acetic acid was found to be a convenient solvent in our present case. Hydroxychalcones 1-12 were allowed to react with hydrazine hydrate or phenylhydrazine in hot acetic acid (cf. Experimental Section) to afford 1-substituted 3,5-diaryl-2-pyrazolines 13-27 in high yields (Scheme 1). N-Acetylation of all 2-pyrazolines obtained by the reaction of the appropriate chalcones with hydrazine has taken place under these reaction conditions in each case. Formation of the N-acetyl derivatives is beneficial since the 1-substituted 2-pyrazolines are stable compounds and can be used for biological and pharmaceutical trials without the risk of undesirable decomposition.  OR1 A B R2N NR3HH HR1R2XNHNH2MeCOOHX = H, Ph 123 4 51-12 13-27 1, 13: R1 = 2-OH, R2 = 4-iPr, R3 = Ac2, 14:  R1 = 2-OH, R2 = 4-Cl, R3 = Ac3, 15: R1 = 2-OH, R2 = 2,4-Cl2, R3 = Ac4, 16: R1 = 2-OH, R2 = 2,3-(MeO)2, R3 = Ac5, 17: R1 = 2-OH, R2 = 3,4,5-(MeO)3, R3 = Ac4, 18: R1 = 2-OH, R2 = 2,3-(MeO)2, R3 = Ph6, 19: R1 = 2-OH, R2 = 2-Cl, R3 = Ph7, 20: R1 = 2-OH, R2 = 3-Cl, R3 = Ph8, 21: R1 = 3-OH, R2 = 4-MeO, R3 = Ac9, 22: R1 = 3-OH, R2 = 2,6-Cl2, R3 = Ac9, 23: R1 = 3-OH, R2 = 2,6-Cl2, R3 = Ph10, 24: R1 = 4-OH, R2 = 2,4-Cl2, R3 = Ac11, 25: R1 = 4-OH, R2 = 2,6-Cl2, R3 = Ac12, 26: R1 = 4-OH, R2 = 3,4-Cl2, R3 = Ac10, 27: R1 = 4-OH, R2 = 2,4-Cl2, R3 = Ph    Scheme 1  Structures of all new compounds 13-27 have been elucidated by elemental analyses, 1H- and 13C-NMR measurements. In the 1H-NMR spectra of 2-pyrazolines 13-27, the three hydrogen atoms attached to the C-4 and C-5 carbon atoms of the heterocyclic ring gave an ABX spin system. Measured chemical shift and coupling constant values (cf. Experimental Section) unequivocally prove the 2-pyrazoline structure. In the 1H-NMR spectra of 1-acetyl-2-pyrazolines 13-17, 21, 22 and 24-36 a singlet signal at around 2.4 ppm refers to the presence of an N-acetyl group. In the 13C-NMR spectra of all new 1-substituted 3,5-diaryl-2-pyrazolines 13-27, the Issue in Honor of Prof. Alexandru T. Balaban ARKIVOC 2005 (x) 199-205 ISSN 1424-6376 Page 201 ©ARKAT USA, Inc chemical shift values of carbon atoms C-3 (154-156 ppm), C-4 (42-44 ppm) and C-5 (56-58 ppm) corroborate the 2-pyrazoline structure determined by 1H-NMR spectroscopic measurements. 13C-NMR chemical shifts of the N-acetyl group also have been assigned in the case of compounds 13-17, 21, 22 and 24-26. In conclusion, we have synthesized systematically hydroxylated 3,5-diaryl-2-pyrazolines by the reaction of hydrazines and chalcones bearing an ortho-, meta- or para-hydroxy group in their ring A. These new substances allow the investigation of the possible linkage of the 2-pyrazolines to various sites in living organisms in the course of the investigation of their bioactivities. The new 1-substituted 3,5-diaryl-2-pyrazolines described in this paper are very stable compounds, a property which may render them especially useful substances in drug research.   Experimental Section  General Procedures. Melting points were determined with a Koffler hot-stage apparatus and are uncorrected. 1H- and 13C-NMR spectra were recorded on a Varian Gemini 200 spectrometer at 200/50 MHz in CDCl3 (internal standard TMS, δ = 0.0 ppm) at room temperature. Elemental analyses were measured in-house with a Carlo Erba 1106 EA instrument. TLC was performed on Kieselgel 60 F254 (Merck) layer using hexane:acetone (7:3 v/v) or toluene:ethyl acetate (4:1 v/v) as eluents. Starting materials 1-12 were synthesized according to known procedures.38-41  General procedure for the synthesis of compounds 13-27 A mixture of hydroxychalcone (1-12, 10.0 mmoles), hydrazine hydrate (50.0 mmoles) or phenylhydrazine (50.0 mmoles) and acetic acid (40 ml) was refluxed for 3 hours then poured into water. The precipitate was separated by filtration, washed free of acid and crystallized from methanol to afford 2-pyrazolines 13-27 (Scheme 1).  1-Acetyl-3-(2-hydroxyphenyl)-5-(4-isopropylphenyl)-2-pyrazoline (13). This compound was obtained as colourless needles in 65% yield, m.p. 163-164 oC; 1H-NMR (δ): 1.22 (6H, d, J = 6.9 Hz, CH(CH3)2), 2.38 (3H, s, CH3), 2.89 (1H, m, CH(CH3)2), 3.31 (1H, dd, J = 4.6, 17.8 Hz, 4-Htrans), 3.85 (1H, dd, J = 11.8, 17.8 Hz, 4-Hcis), 5.57 (1H, dd, J = 4.6, 11.8 Hz, 5-H), 6.90-7.41 (m, 8 arom. H), 10.30 (1H, s, OH); 13C-NMR (δ): 21.9, 23.7, 33.6, 42.6, 58.1, 115.3, 117.2, 119.8, 125.7, 127.2, 128.6, 132.4, 138.7, 148.8, 156.6, 157.9, 167.9. Anal. Calcd. for C20H22N2O2: C, 74.51; H, 6.88; N, 8.68. Found: C, 74.59; H, 6.84; N, 8.76. 1-Acetyl-5-(4-chlorophenyl)-3-(2-hydroxyphenyl)-2-pyrazoline (14). This material was isolated as colourless needles in 76% yield, m.p. 146-147 oC; 1H-NMR (δ): 2.38 (3H, s, CH3), 3.28 (1H, dd, J = 4.8, 17.9 Hz, 4-Htrans), 3.84 (1H, dd, J = 12.0, 17.9 Hz, 4-Hcis), 5.54 (1H, dd, J = 4.8, 12.0 Hz, 5-H), 6.92-7.41 (m, 8 arom. H), 10.21 (1H, s, OH); 13C-NMR (δ): 21.8, 42.4, 57.7, 115.0, 117.2, 119.9, 127.2, 128.5, 129.3, 132.5, 133.9, 139.8, 156.3, 157.9, 167.9. Anal. Calcd. for C17H15ClN2O2: C, 64.87; H, 4.80; N, 8.89. Found: C, 64.98; H, 4.83; N, 8.96. Issue in Honor of Prof. Alexandru T. Balaban ARKIVOC 2005 (x) 199-205 ISSN 1424-6376 Page 202 ©ARKAT USA, Inc 1-Acetyl-5-(2,4-dichlorophenyl)-3-(2-hydroxyphenyl)-2-pyrazoline (15). This substance was prepared as pale yellow needles in 71% yield, m.p. 183-184 oC; 1NMR (δ): 2.43 (3H, s, CH3), 3.16 (1H, dd, J = 5.3, 18.0 Hz, 4-Htrans), 3.92 (1H, dd, J = 12.0, 18.0 Hz, 4-Hcis), 5.80 (1H, dd, J = 5.3, 12.0 Hz, 5-H), 6.86-7.42 (m, 7 arom. H), 10.17 (1H, s, OH); 13C-NMR (δ): 21.8, 41.6, 55.9, 114.9, 117.3, 119.9, 127.2, 127.8, 128.6, 130.1, 132.7, 134.4, 136.7, 156.8, 157.9, 168.1. Anal. Calcd. for C17H14Cl2N2O2: C, 58.47; H, 4.04; N, 8.02. Found: C, 58.57; H, 4.07; N, 8.10. 1-Acetyl-5-(2,3-dimethoxyphenyl)-3-(2-hydroxyphenyl)-2-pyrazoline (16). This comp-ound was prepared as colourless plates in 69% yield, m. p. 166-167 oC; 1H-NMR (δ): 2.39 (3H, s, CH3), 3.24 (1H, dd, J = 5.1, 17.8 Hz, 4-Htrans), 3.80 (1H, dd, J = 12.0, 17.8 Hz, 4-Hcis), 3.84 (3H, s, CH3O), 3.89 (3H, s, CH3O), 5.72 (1H, dd, J = 5.1, 12.0 Hz, 5-H), 6.72-7.37 (m, 7 arom. H), 10.34 (1H, s, OH); 13C-NMR (δ): 21.9, 42.0, 54.5, 55.6, 60.2, 112.1, 115.3, 116.9, 118.6, 119.7, 124.4, 128.6, 132.2, 134.9, 146.1, 153.1, 157.2, 157.9, 167.8. Anal. Calcd. for C19H20N2O4: C, 67.04; H, 5.92; N, 8.23. Found: C, 67.15; H, 5.86; N, 8.31. 1-Acetyl-3-(2-hydroxyphenyl)-5-(3,4,5-trimethoxyphenyl)-2-pyrazoline (17). This subs-tance was isolated as colourless needles in 68% yield, m.p. 154-155 oC; 1H-NMR (δ): 2.42 (3H, s, CH3), 3.31 (1H, dd, J = 5.0, 18.0 Hz, 4-Htrans), 3.80 (3H, s, CH3O), 3.84 (6H, s, 2CH3O), 3.90 (1H, dd, J = 11.8, 18.0 Hz, 4-Hcis), 5.49 (1H, dd, J = 5.0, 11.8 Hz, 5-H), 6.89-7.41 (m, 6 arom. H), 10.28 (1H, s, OH); 13C-NMR (δ): 21.7, 41.2, 55.3, 57.3, 111.7, 116.5, 119.3, 127.1, 127.7, 129.9, 132.5, 134.0, 137.4, 154.2, 160.0, 169.1. Anal. Calcd. for C20H22N2O5: C, 64.85; H, 5.99; N, 7.56. Found: C, 64.92; H, 5.93; N, 7.64. 5-(2,3-Dimethoxyphenyl)-3-(2-hydroxyphenyl)-1-phenyl-2-pyrazoline (18). This material was prepared as yellow needles in 70% yield, mp. 127-128 oC; 1H-NMR (δ): 3.23 (1H, dd, J = 6.9, 17.6 Hz, 4-Htrans), 3.90 (3H, s, CH3O), 3.98 (3H, s, CH3O), 4.02 (1H, dd, J = 11.3, 17.6 Hz, 4-Hcis), 5.02 (1H, dd, J = 6.9, 11.3 Hz, 5-H), 6.82-7.83 (m, 12 arom. H), 10.89 (1H, s, OH); 13C-NMR (δ): 42.8, 55.7, 58.1, 60.6, 111.9, 116.6, 118.7, 119.4, 119.8, 124.8, 127.3, 130.4, 135.5, 144.2, 146.0, 150.3, 153.1, 157.4. Anal. Calcd. for C23H22N2O3: C, 73.78; H, 5.92; N, 7.48. Found: C, 73.89; H, 5.86; N, 7.57. 5-(2-Chlorophenyl)-3-(2-hydroxyphenyl)-1-phenyl-2-pyrazoline (19). This compound was prepared as pale yellow plates in 66% yield, m.p. 121-122 oC; 1H-NMR (δ): 3.14 (1H, dd, J = 7.0, 17.6 Hz, 4-Htrans), 4.04 (1H, J = 12.1, 17.6 Hz, 4-Hcis), 5.58 (1H, dd, J = 7.0, 12.1, 5-H), 6.80-7.49 (m, 13 arom. H), 10.70 (1H, s, OH); 13C-NMR (δ): 42.2, 60.0, 113.2, 116.3, 116.7, 119.5, 120.1, 127.4, 127.9, 129.2, 129.4, 130.2, 130.7, 131.9, 138.8, 143.8, 150.2, 157.4. Anal. Calcd. for C21H17ClN2O: C,n 72.31; H, 4.91; N, 8.03. Found: C, 72.40; H, 4.87; N, 8.09. 5-(3-Chlorophenyl)-3-(2-hydroxyphenyl)-1-phenyl-2-pyrazoline (20). This substance was obtained as yellow plates in 72% yield, m.p. 122-123 oC; 1H-NMR (δ): 3.22 (1H, dd, J = 7.6, 17.3 Hz, 4-Htrans), 3.96 (1H, dd, J = 12.1, 17.3 Hz, 4-Hcis), 5.20 (1H, dd, J = 7.6, 12.1 Hz, 5-H), 6.82-7.40 (m, 13 arom. H), 10.70 (1H, s, OH); 13C-NMR (δ): 43.8, 62.8, 113.5, 116.2, 116.8, 119.5, 120.4, 124.2, 126.2, 127.3, 128.3, 129.3, 130.8, 135.3, 144.1, 149.8, 157.5. Anal. Calcd. for C21H17ClN2O: C, 72.31, H, 4.91; N, 8.03. Found: 72.22; H, 4.97; N, 7.94. Issue in Honor of Prof. Alexandru T. Balaban ARKIVOC 2005 (x) 199-205 ISSN 1424-6376 Page 203 ©ARKAT USA, Inc 1-Acetyl-3-(3-hydroxyphenyl)-5-(4-methoxyphenyl)-2-pyrazoline (21). This material was prepared as colourless plates in 62% yield, m.p. 211-212 oC; 1H-NMR (δ): 2.26 (3H, s, CH3), 3.04 (1H, dd, J = 4.5, 18.0 Hz, 4-Htrans), 3.70 (3H, s, CH3O), 3.80 (1H, dd, J = 11.7, 18.0 Hz, 4-Hcis), 5.47 (1H, dd, J = 4.5, 11.7 Hz, 5-H), 6.84-7.30 (m, 8 arom. H), 10.24 (1H, s, OH); 13C-NMR (δ): 21.6, 42.0, 55.0, 58.8, 112.9, 117.6, 117.8, 126.9, 129.9, 132.6, 134.6, 154.3, 157.8, 158.7, 167.5. Anal. Calcd. for C18H18N2O3: C, 69.66; H, 5.85; N, 9.02. Found: C, 69.78; H, 5.90; N, 9.09. 1-Acetyl-5-(2,6-dichlorophenyl)-3-(3-hydroxyphenyl)-2-pyrazoline (22). This compound was prepared as yellow needles in 70% yield, m.p. 252-253 oC; 1H-NMR (δ): 2.38 (3H, s, CH3), 3.27 (1H, dd, J = 8.5, 17.8 Hz, 4-Htrans), 3.67 (1H, dd, J = 12.8, 17.8 Hz, 4-Hcis), 6.21 (1H, dd, J = 8.5, 12.8 Hz, 5-H), 6.89-7.39 (m, 7 arom. H), 10.42 (1H, s, OH); 13C-NMR (δ): 21.2, 40.7, 56.2, 112.9, 117.6, 128.7, 129.7, 130.0, 130.2, 132.4, 133.0, 135.1, 135.5, 154.3, 157.8, 167.7. Anal. Calcd. for C17H14Cl2N2O2: C, 58.47; H, 4.04; N, 8.02. Found: C, 58.41; H, 4.01; N, 8.07. 5-(2,6-Dichlorophenyl)-3-(3-hydroxyphenyl)-1-phenyl-2-pyrazoline (23). This substance was obtained as yellow plates in 73% yield, m.p. 206-207 oC; 1H-NMR (δ): 3.31 (1H, dd, J = 7.3, 17.7 Hz, 4-Htrans), 3.79 (1H, dd, J = 11.4, 17.7 Hz, 4-Hcis), 6.08 (1H, dd, J = 7.3, 11.4 Hz, 5-H), 6.76-7.45 (m, 12 arom. H), 10.31 (1H, s, OH); 13C-NMR (δ): 39.7, 60.0, 112.3, 113.2, 115.8, 118.6, 119.5, 128.6, 129.1, 129.4, 129.9, 130.9, 134.4, 135.2, 135.3, 135.8, 144.6, 146.2, 155.9. Anal. Calcd. for C21H16Cl2N2O: C, 65.81; H, 4.21; N, 7.30. Found: C, 65.93; H, 4.27; N, 7.22. 1-Acetyl-5-(2,4-dichlorophenyl)-3-(4-hydroxyphenyl)-2-pyrazoline (24). This material was obtained as yellow plates in 64% yield, m.p. 240-241 oC; 1H-NMR (δ): 2.31 (3H, s, CH3), 3.01 (1H, dd, J = 4.8, 18.0 Hz, 4-Htrans), 3.88 (1H, dd, J = 11.8, 18.0 Hz, 4-Hcis), 5.69 (1H, dd, J = 4.8, 11.8 Hz, 5-H), 6.83-7.66 (m, 7 arom. H), 10.01 (1H, s, OH); 13C-NMR (δ): 21.4, 40.8, 56.6, 115.7, 121.9, 127.9, 128.0, 128.6, 129.3, 131.9, 132.7, 138.5, 154.6, 159.9, 167.5. Anal. Calcd. for C17H14Cl2N2O2: C, 58.47; H, 4.04; N, 8.02. Found: C, 58.53; H, 4.07; N, 8.09. 1-Acetyl-5-(2,6-dichlorophenyl)-3-(4-hydroxyphenyl)-2-pyrazoline (25). This compound was prepared as pale yellow needles in 70% yield, m.p. 261-262 oC; 1H-NMR (δ): 2.20 (3H, s, CH3), 3.15 (1H, dd, J = 7.9, 18.0 Hz, 4-Htrans), 3.80 (1H, dd, J = 12.9, 18.0 Hz, 4-Hcis), 6.06 (1H, dd, J = 7.9, 12.9 Hz, 5-H), 6.84-7.65 (m, 7 arom. H), 9.98 (1H, s, OH); 13C-NMR (δ): 21.2, 40.7, 56.0, 115.7, 122.1, 128.5, 128.8, 129.7, 130.2, 133.0, 135.1, 135.7, 154.3, 159.8, 167.4. Anal. Calcd. for C17H14Cl2N2O2: C, 58.47; H, 4.04; N, 8.02. Found: C, 58.39; H, 3.99; N, 8.08. 1-Acetyl-5-(3,4-dichlorophenyl)-3-(4-hydroxyphenyl)-2-pyrazoline (26). This substance was isolated as yellow plates in 67% yield, m.p. 254-255 oC; 1H-NMR (δ): 2.28 (3H, s, CH3), 3.12 (1H, dd, J = 4.9, 18.1 Hz, 4-Htrans), 3.79 (1H, dd, J = 11.7, 18.1 Hz, 4-Hcis), 5.51 (1H, dd, J = 4.9, 11.7 Hz, 5-H), 6.83-7.64 (m, 7 arom. H), 10.01 (1H, s, OH); 13C-NMR (δ): 21.5, 41.8, 58.2, 115.7, 122.0, 126.1, 128.1, 128.7, 129.9, 131.1, 143.7, 154.6, 159.9, 167.6. Anal. Calcd. for C17H14Cl2N2O2: C, 58.47; H, 4.04, N, 8.02. Found: C, 58.56; H, 4.07; N, 8.09. 5-(2,4-Dichlorophenyl)-3-(4-hydroxyphenyl)-1-phenyl-2-pyrazoline (27). This substance was prepared as yellow plates in 83% yield, m.p. 125-126 oC; 1H-NMR (δ): 3.01 (1H, dd, J = 6.9, 17.2 Hz, 4-Htrans), 3.94 (1H, dd, J = 11.8, 17.2 Hz, 4-Hcis), 5.51 (1H, dd, J = 6.9, 11.8 Hz, 5-H), Issue in Honor of Prof. Alexandru T. Balaban ARKIVOC 2005 (x) 199-205 ISSN 1424-6376 Page 204 ©ARKAT USA, Inc 6.75-7.62 (m, 12 arom. H), 10.30 (1H, s, OH); 13C-NMR (δ): 41.9, 60.8, 113.2, 115.7, 119.4, 125.5, 127.7, 128.1, 128.6, 129.2, 129.8, 132.6, 134.0, 138.2, 144.8, 147.4, 156.6. Anal. Calcd. for C21H16Cl2N2O: C, 65.81; H, 4.21; N, 7.30. Found: C, 65.72; H, 4.17; N, 7.38.   Acknowledgements  The present study was sponsored by the Hungarian National Research Foundation (Grant No. OTKA T049468) for which our gratitude is expressed. Technical assistance of Mrs. M. Nagy is highly appreciated.   References  1. Wiley, K. H., Ed. Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings, In The Chemistry of Heterocyclic Compounds, Weissberger, A., Ed.; Interscience Publishers: New York, 1967; Vol. 22,  p 180. 2. Elguero, J. In Comprehensive Heterocyclic Chemistry II, Katritzky, A. R.; Rees, C.W.; Scriven, E. F.V., Eds; Pergamon Press: Oxford, 1996, Vol.3, p1. 3. Lévai, A. Khim. Geterotsikl. Soedin. 1997, 747. 4. Lévai, A. J. Heterocyclic Chem. 2002, 39,1. 5. Ramalingham, K.; Thyvekikakath, G. 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