In vitro Anti Leukemia Cancer Activity of Some Novel Pyrazole Derivatives and Pyrazoles Containing Thiazole Moiety
American Journal of Heterocyclic Chemistry
Volume 5, Issue 3, September 2019, Pages: 55-70
Received: Jun. 30, 2019; Accepted: Aug. 1, 2019; Published: Aug. 14, 2019
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Amal Mahmoud Youssef Moustafa, Chemistry Department, Faculty of Science, Port Said University, Port Said, Egypt
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Abstract
The design and syntheses of several novel pyrazole derivatives (2, 5, 6 and 7) and pyrazole derivatives (3 and 4) containing thiazole moiety via by ethyl β-(p-chlorophenyl)–α-cyanoacrylate (1) and thiosemicarbazide as starting materials. Pyrazole derivatives (3 and 4) containing thiazole moiety were synthesized via cyclization of pyrazole derivative (2) with bromomethyl arylketones, to give compound 3, followed by acetylation. N- (3- methoxy-2-hydroxybenzal) -3- (p -chlorophenyl)-4- cyano-5-oxopyrazol-1-thiocarboxamide (6) was synthesized via reaction of compound 2 with 3-methoxy-2-hydroxybenzaldehyde. Structures of all compounds were confirmed by elemental analysis, FT-IR, 1H-NMR, 13C-NMR and mass spectrometry. The cytotoxic activity of all the synthetic compounds were evaluated against Leukemia HL-60 compared with Doxorubicicn. The cytotoxic activity was checked in vitro for the recently prepared compounds by using the MTT assay. Compounds 4, 6 and 9 were the most active against Leukemia HL-60. The IC50 values of them were less than 5 µM in the range of 1.35-4.78 µM. In addition, compounds 3 and 5 showed less antiproliferative activity against Leukemia HL-60 cells with IC50 values in the range 5.39-8.82 µM. Compound 6 was the most potent cytotoxic activity. The studies biological activity includes cell cycle analysis, apoptosis detection assay and Topoisomerase II inhibition activity assay explained that compound 6 is a strong Topo II inhibitor.
Keywords
Pyrazole, Thiazole, Antiproliferative, Cell Cycle Analysis, Annexin-V, Topoisomerase II
To cite this article
Amal Mahmoud Youssef Moustafa, In vitro Anti Leukemia Cancer Activity of Some Novel Pyrazole Derivatives and Pyrazoles Containing Thiazole Moiety, American Journal of Heterocyclic Chemistry. Vol. 5, No. 3, 2019, pp. 55-70. doi: 10.11648/j.ajhc.20190503.12
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References
[1]
Achson, A. An Introduction to the Chemistry of Heterocyclic Compounds, third ed., Willey-Intersciences, 2009.
[2]
Hamad, A. J., A. J. Kh. Atia, M. F. Al-Marjani, S. A. K. Redha, I. AL-Bayti and E. H. Batah (2019). Synthesis and anti-microbial activity of new 4-carboxylic imidazole derivatives. Journal of Pharmaceutical Sciences and Research 11 (1), 131–135.
[3]
Wipf, P. and T. D. Hopkins (2005). Total synthesis and structure validation of (+)-bistramide C. Chemical Communications 3421–3423.
[4]
Rudolph, M. J., C. R. Illig, N. L. Subasinghe, K. J. Wilson, J. B. Hoffman, T. Randle, D. Green, C. J. Molloy, R. M. Soll, F. Lewandowski, M. Zhang, R. Bone, J. C. Spurlino, I. C. Deckman, C. Manthey, C. Sharp, D. Maguire, B. L. Grasberger and Zh. Zhou (2002). Design and Synthesis of 4,5-Disubstituted-thiophene-2-amidines as Potent Urokinase Inhibitors. Bioorganic & Medicinal Chemistry Letters 12 (3), 491–495.
[5]
Weiß K. M., S. Wei and S. B. Tsogoeva (2011). Novel one-pot process for the synthesis of 1,3-thiazoles via organocatalysed epoxidation of nitro-olefins. Organic and Biomolecular Chemistry 9, 3457–3461.
[6]
An T. N. M., M. A. Kumar, S. H. Chang, M. Y. Kim, J. A. Kim and K. D. Lee (2014). Real-time Monitoring of Colloidal Nanoparticles using Light Sheet Dark-field Microscopy Combined with Microfluidic Concentration Gradient Generator (?FCGG-LSDFM). Bulletin Korean Chemical Society 35 (6), 1619–1624.
[7]
Chimenti F., A. Bolasco, D. Secci, P. Chimenti, A. Granese, S. Carradori, M. Yanez, F. Orallo, F. Ortuso and S. Alcaro (2012). Investigations on the 2-thiazolylhydrazyne scaffold: synthesis and molecular modeling of selective human monoamine oxidase inhibitors. Bioorgic Medicinal Chemistry 18 (15), 5715–5723.
[8]
Dondoni A. (2010). Heterocycles in organic synthesis: thiazoles and triazoles as exemplar cases of synthetic auxiliaries. Organic and Biomolecular Chemistry 8, 3366–3385.
[9]
Khare R., J. Sharma and A. Sharma (2016). Synthesis, characterization, and antibacterial activity of some thiazoles derived from allyl thioureas. Russian Journal of General Chemistry 86, 3, 702–707.
[10]
Chimenti F., R. Fioravanti, A. Bolasco, F. Manna, P. Chimenti, D. Secci, F. Rossi, P. Turini, F. Ortuso, S. Alcaro and M. C. Cardia (2008). Synthesis, molecular modeling studies and selective inhibitory activity against MAO of N1-propanoyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole derivatives. European Journal of Medicinal Chemistry 43 (10), 2262–2267.
[11]
Suh C. W. and D. Y. Kim (2014). Enantioselective One-Pot Synthesis of Ring-Fused Tetrahydroquinolines via Aerobic Oxidation and 1,5-Hydride Transfer/Cyclization Sequences. Organic Letters 16 (20), 5374–5377.
[12]
Bhongade B. A., S. Talath, R. A. Gadad and A. K. Gadad (2016). Biological activities of imidazo[2,1-b][1,3,4]thiadiazole derivatives: A review. Journal Saudi Chemical Society 20, S463–S475.
[13]
Rudolph J., H. Theis, R. Hanke, R. Endermann, L. Johannsen and F. M. Geschke (2014). Synthesis, Anticancer and Antioxidant Activity of Novel 2,4-Disubstituted Thiazoles. Bulletin of the Korean Chemistry Society 35 (6), 1619–1624.
[14]
Gomha S. M., A. Sayed, S. A. Ahmed and A. O. Abdelhamid (2015). Synthesis and Cytotoxicity Evaluation of Some Novel Thiazoles, Thiadiazoles, and Pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-ones Incorporating Triazole Moiety. Molecules 20, (1) 1357–1376.
[15]
Siddiqui N., F. Arshad, W. Ahsan and M. S. Alam (2009). Thiazoles: a valuable insight into the recent advances and biological activities. International Journal of Pharmaceutical Sciences and Drug Research 1 (3), 136–143.
[16]
Sayyed M., S. Mokle, M. Bokhare, A. Mankar, S. Surwase, S. Bhusare and Y. Vibhute (2006). Synthesis of some new 2, 3-diaryl-1, 3-thiazolidin-4-ones as antibacterial agents. Arkivoc ii, 187–192.
[17]
Sudbeck E. A., C. Mao, R. Vig, T. K. Venkatachalam, L. Tuel-Ahlgren and F. M. Uckun (1998). Structure-Based Design of Novel Dihydroalkoxybenzyloxopyrimidine Derivatives as Potent Nonnucleoside Inhibitors of the Human Immunodeficiency Virus Reverse Transcriptase. Antimicrobial Agents and Chemotherapy 42 (12), 3225–3233.
[18]
Trivedi A. R., A. B. Siddiqui and V. H. Shah (2008). Design, synthesis, characterization and antitubercular activity of some 2-heterocycle-substituted phenothiazines. Arkivoc ii, 210–217.
[19]
Bell F. W., A. S. Cantrell, M. Hoegberg, S. R. Jaskunas, N. G. Johansson, C. L. Jordan, M. D. Kinnick, P. Lind and J. M. Morin (1995). Phenethylthiazolethiourea (PETT) Compounds, a New Class of HIV-1 Reverse Transcriptase Inhibitors. 1. Synthesis and Basic Structure-Activity Relationship Studies of PETT Analogs. Journal of Medicinal Chemistry 38 (25), 4929–4936.
[20]
Holla B. S., K. V. Malini, B. S. Rao, B. K. Sarojini and N. S. Kumari (2003). Synthesis of some new 2,4-disubstituted thiazoles as possible antibacterial and anti-inflammatory agents. European Journal of Medicinal Chemistry 38, 313–318.
[21]
Sharma R. N., F. P. Xaurer, K. K. Vasu, S. C. Chaturvedi and S. S. Pancholi (2009). Synthesis of 4-benzyl-1, 3-thiazole derivatives as potential anti-inflammatory agents: an analogue-based drug design approach. Journal Enzyme Inhibition Medicinal Chemistry 24 (3), 890–897.
[22]
Kumar S., V. Saini, I. K. Maurya, J. Sindhu, M. Kumari, R. Kataria and V. Kumar (2018). Design, synthesis, DFT, docking studies and ADME prediction of some new coumarinyl linked pyrazolylthiazoles: Potential standalone or adjuvant antimicrobial agents. PLoS ONE 13 (4), e0196016.
[23]
Kashyap S. J., V. K. Garg, P. k. Sharma, K. Nitin, D. Rupesh and J. K. Gupta (2012). Thiazoles: having diverse biological activities. Medicinal Chemistry Research 21, 2123–2123.
[24]
Karegoudar P., M. S. Karthikeyan, D. J. Prasad, M. Mahalinga, B. S. Holla and N. S. Kumari (2008). Synthesis of some novel 2,4-disubstituted thiazoles as possible antimicrobial agents. European Journal of Medicinal Chemistry 43, 261–267.
[25]
Shih M. H. and K. F. Ying (2004). Syntheses and evaluation of antioxidant activity of sydnonyl substituted t hiazolidinone and thiazoline derivatives. Bioorganic and Medicinal Chemistry 12, 4633–4643.
[26]
Shiradkar M., G. V. S. Kumar, V. Dasari, S. Tatikonda, K. C. Akula and R. Shah (2007). Clubbed triazoles A novel approach to antitubercular drugs. European Journal of Medicinal Chemistry 42, 807–816.
[27]
Amin K. M., A. D. E. Rahman and Y. A. Al-Eryani (2008). Synthesis and preliminary evaluation of some substituted coumarins as anticonvulsant agents. Bioorganic and Medicinal Chemistry 16, 5377–5388.
[28]
Gomha S. M., S. M. Riyadh, I. M. Abbas and M. A. Bauomi (2013). Synthetic utility of ethylidene-thiosemicarbazide: Synthesis and and anti-cancer activity of 1,3-thiazines and thiazoles with imidazole moiety. Heterocycles 87, 341–356.
[29]
Gomha S. M., T. A. Salah, H. M. E. Hassaneen, H. Abdel-aziz and M. A. Khedr (2016). Synthesis, characterization and molecular docking of novel bioactive thiazolyl-thiazole derivatives as promising cytotoxic antitumor drug. Molecules 21, 1–17.
[30]
Gomha S. M., S. M. Riyadh, E. A. Mahmmoud and M. M. Elaasser (2015). Chitosan-grafted-poly(4-vinylpyridine) as a novel copolymer basic catalyst for synthesis of arylazothiazoles and 1,3,4-thiadiazoles under microwave irradiation. Chemistry of Heterocyclic Compounds 51, 1030–1038.
[31]
Gomha S. M., M. G. Badrey and M. M. Edrees, (2016). Heterocyclization of a bis-thiosemicarbazone of 2,5-diacetyl-3,4-disubstituted-thieno[2,3-b]thiophenebis-thiosemicarbazones leading to bis-thiazoles and bis-1,3,4-thiadiazoles as anti-breast cancer agents. Journal of Chemical Research 40, 120–125.
[32]
Gomha S. M., Y. H. Zaki and A. O. Abdelhamid (2015). Utility of 3-acetyl-6-bromo-2H-chromen-2-one for synthesis of new heterocycles as potential anticancer agents. Molecules 20, 21826–21839.
[33]
Dawood K. M., H. A. Gawad, E. A. Rageb, M. Ellithey and H. A. Mohamed, (2006). Synthesis, anticonvulsant, and anti-inflammatory evaluation of some new benzotriazole and benzofuran-based heterocycles. Bioorganic and Medicinal Chemistry 14, 3672–3680.
[34]
Gomha S. M., M. M. Edrees and F. M. A. Altalbawy (2016). Synthesis and Characterization of Some New Bis-Pyrazolyl-Thiazoles Incorporating the Thiophene Moiety as Potent Anti-Tumor Agents. International journal of Molecular Sciences 17, 1499.
[35]
Akbas E. and I. Berber (2005). Antibacterial and antifungal activities of new pyrazolo[3,4-d]pyridazin derivatives, European Journal of Medicinal Chemistry 40, 401-405.
[36]
Ozdemir A., G. Turan-Zitouni, Z. A. Kaplancıklı, G. Revial and K. Guven (2007). Synthesis and antimicrobial activity of 1-(4-aryl-2-thiazolyl)-3-(2-thienyl)-5-aryl-2-pyrazoline derivatives. European Journal of Medicinal Chemistry 42, 403–409.
[37]
Manfredini S., R. Bazzanini, P. G. Baraldi, M. Guarneri, D. Simoni, M. E. Marongiu, A. Pani, P. L. Colla and E. Tramontano (1992) Pyrazole-related nucleosides. Synthesis and antiviral/antitumor activity of some substituted pyrazole and pyrazolo[4,3-d]-1,2,3-triazin-4-one nucleosides, Journal of Medicinal Chemistry 35, 917-924.
[38]
Noell C. W. and C. C. Cheng (1971). Pyrazoles. 4. Analogs of 3-(3,3-dimethyl-1-triazeno)pyrazole-4-Carboxamide. Journal of Medicinal Chemistry 14, 1245-1246.
[39]
Abdel-Aziz M., G. A. Abuo-Rahma and A. A. Hassan (2009). Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activities. European Journal of Medicinal Chemistry 44, 3480-3487.
[40]
M. Shaharyar, A. A. Siddiqui, M. M. Ali, D. Sriram and P. Yogeeswari (2006). Synthesis and in vitro antimycobacterial activity of N1-nicotinoyl-3-(-40-hydroxy-30-methyl phenyl)-5-[(sub)phenyl]-2-pyrazolines. Bioorganic and Medicinal Chemistry Letters 16, 3947–3949.
[41]
Ozdemir Z., H. B. Kandilici, B. Gumusel, U. Calis and A. Bilgin (2007). Synthesis and studies on antidepressant and anticonvulsant activities of some 3-(2-furyl)-pyrazoline derivatives. European Journal of Medicinal Chemistry 42, 373-379.
[42]
Hassan S. Y. (2013). Synthesis, antibacterial and antifungal activity of some new pyrazoline and pyrazole derivatives. Molecules 3, 2683-2711.
[43]
Turan-Zitouni G., A. Ozdemir and K. Guven (2005). Synthesis of some 1[(N,N-disubstitutedthio-carbamoylthio)acetyl]-3-(2-thienyl)-5-aryl-2-prazoline derivatives and investigation of their antibacterial and antifungal activities. Archiv der Pharmazie 338, 96–104.
[44]
Pathak R. B., P. T. Chovatia and H. H. Parekh (2012). Synthesis, antitubercular and antimicrobial evaluation of 3-(4-chlorophenyl)-4-substituted pyrazole derivatives. Bioorganic and Medicinal Chemistry Letters 22, 5129-5133.
[45]
Kreutzberger A. and K. Kolter (1986). Antiviral agents. XXVII: Aminomethynylation of 5-oxo-2-pyrazoline-3-carboxylic acid derivatives. Archiv der Pharmazie 319, 18–25.
[46]
Flora F., H. H. Hosni and A. S. Girgis (2006). Novel bis(1-acyl-2-pyrazolines) of potential anti-inflammatory and molluscicidal properties. Bioorganic and Medicinal Chemistry 14, 3929–3937.
[47]
Gomha S. M., S. M. Riyadh and M. M. Abdalla (2015). Solvent-drop grinding method: Efficient synthesis, DPPH radical scavenging and anti-diabetic activities of chalcones, bis-chalcones, azolines, and bis-azolines. Current Organic Synthesis 12, 220–228.
[48]
Abid M. and A. Azam (2005). 1-N-substituted thiocarbamoyl-3-phenyl-2-pyrazolines: Synthesis and in vitro antiamoebic activities. European Journal of Medicinal Chemistry 40, 935–942.
[49]
Karrouchi Kh., S. Radi, Y. Ramli, J. Taoufik, Y. N. Mabkhot, F. A. Al-aizari and M. Ansar (2018). Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review. Molecules 23, 134.
[50]
Palomer A., F. Cabre, J. Pascual, J. Campos, M. A. Trujillo, A. Entrena, M. A. Gallo, L. Garcia, D. Mauleon and A. Espinosa (2002). Identification of novel cyclooxygenase-2 selective inhibitors using pharmacophore models. Journal of Medicinal Chemistry 45, 1402-1411.
[51]
Abid M. and A. Azam (2006). Synthesis, characterization and antimoebic activity of 1-(thiazolo[4,5-b]-quinoxalin-2-yl)-3-phenyl-2-pyrazoline derivatives. Bioorganic and Medicinal Chemistry Letters. 16, 2812–2816.
[52]
Ozdemir Z., H. B. Kandilci, B. Gumusel, U. Calis and A. A. Bilgin (2007). Synthesis and studies on antidepressant and anticonvulsant activities of some 3-(2-furyl)-pyrazoline derivatives. European Journal of Medicinal Chemistry 42, 373–379.
[53]
Wustrow D. J., T. Capiris, R. Rubin, J. A. Knobelsdorf, H. Akunne, M. D. Davis, R. MacKenzie, T. A. Pugsley, K. T. Zoski, T. G. Heffner and L. D. Wise (1998). Pyrazolo[1,5-a]pyrimidine CRF-1 receptor Antagonists. Bioorganic and Medicinal Chemistry Letters 18, 2067-2070.
[54]
Penning T. D., J. J. Talley, S. R. Bertenshaw, J. S. Carter, P. W. Collins, S. Docter, M. J. Graneto, L. F. Lee, J. W. Malecha, J. M. Miyashiro, R. S. Rogers, D. J. Rogier, S. S. Yu, G. D. Anderson, E. G. Burton, J. N. Cogburn, S. A. Gregory, C. M. Koboldt, W. E. Perkins, K. Seibert, A. W. Veenhuizen, Y. Y. Zhang and P. C. Isakson (1997), Pyrazolo[1,5-a]pyrimidine CRF-1 receptor antagonists. Journal of Medicinal Chemistry 40, 1347-1365.
[55]
Desai N. C. and M. J Bhatt (2016). Optimized Synthesis of Novel Pyrazole Based Thiazole Derivatives and their Antimicrobial Evaluation. International Letters of Chemistry. Physics and Astronomy 66, 109-118.
[56]
Farag A. M., A. S. Mayhoub, S. E. Barakat and A. H. Bayomi (2008). Regioselective synthesis and antitumor screening of some novel N-phenylpyrazole derivatives. Bioorganic Medicinal Chemistry 16, 881–889.
[57]
Xia Y., C. D. Fan, B. X. Zhao, J. Zhao, D. S. Shin and J. Y. Miaob (2008). Synthesis and structure-activity relationships of novel 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide hydrazone derivatives as potential agents against A549 lung cancer cells. European Journal of Medicinal Chemistry 43 (11), 2347–2353.
[58]
Xia Y., Z. W. Dong, X. Ge, N. Meng, D. S. Shin and J. Y. Miaob (2007). Synthesis and structure-activity relationships of novel 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide derivatives as potential agents against A549 lung cancer cells. Bioorganic Medicinal Chemistry 15 (22), 6893–6899.
[59]
El-Enany M. M., M. M. Kamel, O. M. Khalil and H. B. El-Nassan (2011). Synthesis and antitumor activity of novel pyrazolo[1,5-a]pyrimidine derivatives. European Journal of Chemistry 2 (3), 331–336.
[60]
Manetti F., C. Brullo, M. Magnani, F. Mosci, B. Chelli, E. Crespan, S. Schenone, A. Naldini, O. Bruno, M. L. Trincavelli, G. Mega, F. Carraro, C. Martini, F. Bondavalli and M. Botta (2008). Structure-based optimization of pyrazolo[3,4-d]pyrimidines as Abl inhibitors and antiproliferative agents toward human leukemia cell lines. Journal of Medicinal Chemistry 51 (5), 1252–1259.
[61]
Karai O., Y. Aouine, H. Faraj, A. Alami, M. R. Kabbour, A. El Hallaoui and M. Bouksaim (2018). Synthesis, characterization and antibacterial activity of Methyl (2R)-2-benzamido-2-{[(1R)-2-methoxy-2-oxo-1-phenylethyl]amino}acetate. Medicinal Journal of Chemistry 7 (4), 267–271.
[62]
Daidone G., S. Plescia, B. Maggio, D. Schillaci, D. Raffa and M. V. Raimondi (2004). Synthesis and in vitro antileukemic activy of new 4-trizenopyrazole derivatives. IL Farmaco 59, 413–417.
[63]
Schenone S., O. Bruno, A. Ranise, F. Bandavaui, C. Brullo, P. Fossa, L. Mosti, G. Menozzi, F. Carraro, A. Naldini, C. Bernini, F. Manetti and M. Botta (2004). New pyrazolo[3,4-d]pyrimidines endowed with A431 antiproliferative activity and inhibitory properties of Src phosphorylation. Bioorganic Medicinal Chemistry Letter 14 (10), 2511–2517.
[64]
Nosrat O. M., P. Jafar, S. Bahman and R. Mehdi (2013). Facile Regioselective Synthesis of Novel bis‐Thiazole Derivatives and Their Antimicrobial Activity. Archiv der Pharmazie Chemistry in Life Science 346, 860–864.
[65]
Zhu G. D., J. Gong, V. B. Gandhi, K. Woods, Y. Luo, X. Liu, R. Guan, V. Kinghofer, E. F. Johnson, V. S. Stoll, M. Mamo, Q. Li, S. H. Rosenberg and V. L. Giranda (2007). Design and synthesis of pyridine-pyrazolopyridine-based inhibitors of protein kinase B/Akt. Bioorganic Medicinal Chemistry 15 (6), 2441–2452.
[66]
Huang S., R. Lin, Y. Yu, Y. Lu, P. J. Connolly, G. Chiu, S. Li, S. L. Emanuel and S. A. Middleton (2007). Synthesis of 3-(1H-benzimidazol-2-yl)-5-isoquinolin-4-ylpyrazolo[1,2-b]pyridine, a potent cyclin dependent kinase 1 (CDK1) inhibitor. Bioorganic Medicinal Chemistry Letter 17 (5), 1243–1245.
[67]
Warshakoon N. C., S. Wu, A. Boyer, R. Kawamoto, S. Renock, K. Xu, M. Pokross, A. G. Evdokimov, S. Zhou, C. Winter, R. Walter and M. Mekel (2006). Design and synthesis of a series of novel pyrazolopyridines as HIF-1alpha prolyl hydroxylase inhibitors. Bioorganic Medicinal Chemistry Lette, 16 (21), 5687–5690.
[68]
Sherif M. H. and Amal M. Y. (2015). Synthesis and anticancer evaluation of some fused coumarino-[4,3-d]-pyrimidine derivatives. Research on Chemical Intermediate 41, 383–390.
[69]
Elsherbiny H. E. S, Y. M. Amal and A. A. El. Sara (2018). Synthesis of New 2-N-Substituted Amino-5-aryl-1,3-thiazoles as Antitumor Agents. Latin American Journal of Pharmacy 37 (8), 1594–1601.
[70]
Amal M. Y. Moustafa and B. Safyah (2019). Synthesis of Some Hybrid 7‑Hydroxy Quinolinone Derivatives as Anti Breast Cancer Drugs. Research on Chemical Intermediate 45 (7), 3895–3912.
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