Synthesis of alnustone-like diarylpentanoids via a 4 + 1 strategy and assessment of their potential anticancer activity

Neslihan ÇELEBİOĞLU, (Atatürk Üniversitesi, Fen Fakültesi, Kimya Bölümü, Erzurum, Türkiye)
Özlem ÖZDEMİR TOZLU, (Erzurum Teknik Üniversitesi, Fen Fakültesi, Moleküler Biyoloji ve Genetik Bölümü, Erzurum, Türkiye)
Hasan TÜRKEZ, (Atatürk Üniversitesi, Tıp Fakültesi, Tıbbi Biyoloji Anabilim Dalı, Erzurum, Türkiye)
Hasan SEÇEN (Atatürk Üniversitesi, Fen Fakültesi, Kimya Bölümü, Erzurum, Türkiye)
Turkish Journal of Chemistry
10 0
Yıl: 2023 Cilt: 47 Sayı: 5 Sayfa Aralığı: 1249 - 1259 Metin Dili: İngilizce DOI: 10.55730/1300-0527.3609 İndeks Tarihi: 21-11-2023

Synthesis of alnustone-like diarylpentanoids via a 4 + 1 strategy and assessment of their potential anticancer activity

Öz:
Twelve compounds with a 1,5-diaryl-1-penten-3-one structure were synthesized and their cytotoxic activities were evaluated. The 1,5-diaryl-1-penten-3-one compounds were obtained via in situ enaminations of 4-phenyl-2-butanone and 4-(4-hydroxyphenyl)-2- butanone in the presence of pyrrolidine-AcOH, followed by condensation with six different benzaldehydes. The synthesized compounds were tested for their cytotoxic activity against human glioblastoma (U87-MG), breast (MCF-7), and prostate (PC-3) cancer cell lines. Some of the novel compounds exhibited remarkable cytotoxic action, especially against MCF-7 cancer cells.
Anahtar Kelime: 1 5-Diarylpentanoid cytotoxic activity breast cancer prostate cancer glioblastoma anticancer effect

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
  • [1] Claeson P, Tuchinda P, Reutrakul V. Naturally occurring 1,7-diarylheptanoids. Journal of the Indian Chemical Society 1994; 71 (6-8): 509- 521.
  • [2] Claeson P, Claseon UP, Tuchinda P, Reutrakul V. Occurrence, structure and bioactivity of 1,7-diarylheptanoids. Studies in Natural Products Chemistry 2002; 26: 881-905. https://doi.org/10.1016/S1572-5995(02)80021-7
  • [3] Keserü GM, Nogradi M. The chemistry of natural diarylheptanoids. Studies in Natural Products Chemistry 1995; 17: 357-394. https://doi. org/10.1016/S1572-5995(05)80090-0
  • [4] Lv H, She G. Naturally occurring diarylheptanoids. Natural Product Communications 2010; 5 (10): 1687-1708. https://doi. org/10.1177/1934578X1000501035
  • [5] Mirzaei H, Shakeri A, Rashidi B, Jalili A, Banikazemi Z et al. Phytosomal curcumin: a review of pharmacokinetic, experimental and clinical studies. Biomedicine & Pharmacotherapy 2017; 85: 102-112. https://doi.org/10.1016/j.biopha.2016.11.098
  • [6] Celebioglu N, Ozgen U, Secen H. Naturally occurring 1,5-diarylpentanoids: a review. Organic Communications 2017; 10 (4): 250-258. https://doi.org/10.25135/acg.oc.33.17.10.052
  • [7] Goel A, Kunnumakkara AB, Aggarwal BB. Curcumin as “curecumin”: from kitchen to clinic. Biochemical Pharmacology 2008; 75: 787- 809. https://doi.org/10.1016/j.bcp.2007.08.016
  • [8] Anand P, Thomas SG, Kunnumakkara AB, Sundaram C, Harikumar KB et al. Biological activities of curcumin and its analogues (congeners) made by man and mother nature. Biochemical Pharmacology 2008; 76: 1590-1611. https://doi.org/10.1016/j.bcp.2008.08.008
  • [9] Anand P, Sundaram C, Jhurani S, Kunnumakkara AB, Aggarwal BB. Curcumin and cancer: an “old-age” disease with an “age-old” solution. Cancer Letters 2008; 267: 133-164. https://doi.org/10.1016/j.canlet.2008.03.025
  • [10] Aggarwal BB, Harikumar KB. Potential therapeutic effects of curcumin, the anti-inflammatory agent, against neurodegenerative, cardiovascular, pulmonary, metabolic, autoimmune and neoplastic diseases. International Journal of Biochemistry & Cell Biology 2009; 41: 40-59. https://doi.org/10.1016/j.biocel.2008.06.010
  • [11] Agrawal DK, Mishra PK. Curcumin and its analogues: potential anticancer agents. Medicinal Research Reviews 2010; 30: 818-860. https:// doi.org/10.1002/med.20188
  • [12] Moreira J, Saraiva L, Pinto MM, Cidade H. Diarylpentanoids with antitumor activity: a critical review of structure-activity relationship studies. European Journal of Medicinal Chemistry 2020; 192: 112177. https://doi.org/10.1016/j.ejmech.2020.112177
  • [13] Leong SW, Chia SL, Abas F, Yusoff K. Synthesis and in-vitro anti-cancer evaluations of multi-methoxylated asymmetrical diarylpentanoids as intrinsic apoptosis inducer against colorectal cancer. Bioorganic & Medicinal Chemistry Letters 2020; 30 (8): 127065. https://doi. org/10.1016/j.bmcl.2020.127065
  • [14] Wang L, Cheng L, Ma L, Farooqi AA, Qiao G et al. Alnustone inhibits the growth of hepatocellular carcinoma via ROS-mediated PI3K/ Akt/mTOR/p70S6K Axis. Phytotherapy Research 2022; 36 (1): 525-542. https://doi.org/10.1002/ptr.7337
  • [15] Kucukoglu K, Secinti H, Ozgur A, Secen H, Tutar Y. Synthesis, molecular docking, and antitumoral activity of alnustone-like compounds against estrogen receptor alpha-positive human breast cancer. Turkish Journal of Chemistry 2015; 39 (1): 179-193. https://doi.org/10.3906/ KIM-1408-72
  • [16] Nyandoro SS, Joseph CC, Nkunya HHM, Hosea MMK. New antimicrobial, mosquito larvicidal and other metabolites from two Artabotrys species. Natural Product Research 2013; 27 (16): 1450-1458. https://doi.org/10.1080/14786419.2012.725397
  • [17] Gao K, Tang HF, Lu YY, Wang XY, Zhang W et al. Chemical constituents in fruits of Lycium barbarum L. Zhongnan Yaoxue 2014; 12: 324- 327. https://doi.org/10.3390/molecules24081585
  • [18] Chen J, McKay RM, Parada LF. Malignant glioma: lessons from genomics, mouse models, and stem cells. Cell 2012; 149 (1): 36-47. https:// doi.org/10.1016/j.cell.2012.03.009
  • [19] Cancer.Net Editorial Board. Brain Tumor: Statistics 2016. Alexandria, VA, USA: American Society of Clinical Oncology, 2016. Available at https://www.cancer.net/cancer-types/brain-tumor/statistics
  • [20] Louis DN, Perry A, Reifenberger G, von Deimling A, Figarella-Branger D et al. The 2016 World Health Organization Classification of Tumors of the Central Nervous System: A summary. Acta Neuropathologica 2016; 131 (6): 803-820. https://doi.org/10.1007/s00401-016- 1545-1
  • [21] Hanif F, Muzaffar K, Perveen K, Malhi SM, Simjee SU. Glioblastoma multiforme: a review of its epidemiology and pathogenesis through clinical presentation and treatment. Asian Pacific Journal of Cancer Prevention 2017; 18 (1): 3-9. https://doi.org/10.22034/APJCP.2017.18.1.3
  • [22] Tamimi AF, Juweid M. Epidemiology and outcome of glioblastoma. In: Vleeschouwer SD (editor). Epidemiology of Glioblastoma. Brisbane, Australia: Codon Publications, 2017, pp. 143-153. https://doi.org/10.15586/codon.glioblastoma.2017.ch8
  • [23] Li K, Lu D, Guo Y, Wang C, Liu X et al. Trends and patterns of incidence of diffuse glioma in adults in the United States, 1973-2014. Cancer Medicine 2018; 7 (10): 5281-5290. https://doi.org/10.1002/cam4.1757
  • [24] Behl T, Sharma A, Sharma L, Sehgal A, Singh S et al. Current perspective on the natural compounds and drug delivery techniques in glioblastoma multiforme. Cancers 2021; 13 (11): 2765. https://doi.org/10.3390/cancers13112765
  • [25] Yi M, Li T, Niu M, Luo S, Chu Q et al. Epidemiological trends of women’s cancers from 1990 to 2019 at the global, regional, and national levels: a population-based study. Biomarker Research 2021; 9: 55. https://doi.org/10.1186/s40364-021-00310-y
  • [26] Sung H, Ferlay J, Siegel RL, Laversanne M, Soerjomataram I et al. Global Cancer Statistics 2020: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA Cancer Journal for Clinicians 2021; 71 (3): 209-249. https://doi.org/10.3322/ caac.21660
  • [27] Heer E, Harper A, Escandor N, Sung H, McCormack V et al. Global burden and trends in premenopausal and postmenopausal breast cancer: a population-based study. Lancet Global Health 2020; 8: e1028. https://doi.org/10.1016/S2214-109X(20)30215-1
  • [28] Rebello RJ, Oing C, Knudsen KE, Loeb S, Johnson DC et al. Prostate cancer. Nature Reviews Disease Primers 2021; 7: 9. https://doi. org/10.1038/s41572-020-00243-0
  • [29] Göksu S, Çelik H, Seçen H. An efficient synthesis of alnustone, a naturally occurring compound. Turkish Journal of Chemistry 2003; 27: 31-34.
  • [30] Demir ŞB, Seçinti H, Çelebioğlu N, Özdal M, Sezen A et al. Syntheses and antibacterial activities of 4 linear nonphenolic diarylheptanoids. Turkish Journal of Chemistry 2020; 4 (3): 589-601. https://doi.org/10.3906/kim-1911-61
  • [31] Burmaoglu S, Celik H, Göksu S, Maraş A, Altundaş R et al. Synthesis of two alnustone-like natural diarylheptanoids via $C_4+C_3$ strategy. Synthesis Communications 2009; 39: 1549-1562. https://doi.org/10.1080/00397910802542036
  • [32] Castro E, Moreira J, Silva PMA, Saraiva L, Pinto M et al. Biological evaluation of new diarylpentanoid analogues for antitumor activity (Proceeding abstract). Scientific Letters 2023; 1 (Suppl. 1): 26. https://doi.org/10.48797/sl.2023.26
  • [33] Leong SW, Chia SL, Abas F, Yusoff K. Synthesis and in-vitro anti-cancer evaluations of multi-methoxylated asymmetrical diarylpentanoids as intrinsic apoptosis inducer against colorectal cancer. Bioorganic & Medicinal Chemistry Letters 2020; 30 (8): 127065. https://doi. org/10.1016/j.bmcl.2020.127065
  • [34] Paulraj F, Abas F, Lajis NH, Othman I, Naidu R. Molecular pathways modulated by curcumin analogue, diarylpentanoids in cancer. Biomolecules 2019; 9 (7): 270. https://doi.org/10.3390/biom9070270
  • [35] López-Lázaro M. Two preclinical tests to evaluate anticancer activity and to help validate drug candidates for clinical trials. Oncoscience 2015; 2 (2): 91-98. https://doi.org/10.18632/oncoscience.132
  • [36] López-Lázaro M. How many times should we screen a chemical library to discover an anticancer drug? Drug Discovery Today 2015; 20 (2): 167-169. https://doi.org/10.1016/j.drudis.2014.12.006
  • [37] Li W, Wu XF. Ruthenium-catalyzed conjugate hydrogenation of α,β-enones by in situ generated dihydrogen paraformaldehyde and water. European Journal of Organic Chemistry 2015; 20: 331-335. https://doi.org/10.1002/ejoc.201403359
  • [38] Lao Z, Zhang H, Toy PH. Reductive halogenation reactions: selective synthesis of unsymmetrical α-haloketones. Organic Letters 2019; 21: 8149-8152. https://doi.org/10.1021/acs.orglett.9b02324
  • [39] Oh S, Jang S, Kim D, Han IO, Jung JC. Synthesis and evaluation of biological properties of benzylideneacetophenone derivatives. Archives of Pharmacal Research 2006; 29 (6): 469-475. https://doi.org/10.1007/BF02969418
  • [40] Doiron JA, Leblanc LM, Hebert MJG, Levesque NA, Pare AF et al. Structure-activity relationship of caffeic acid phenethyl ester analogs as new 5-lipoxygenase inhibitors. Chemical Biology & Drug Design 2017; 89 (4): 514-528. https://doi.org/10.1111/cbdd.12874
  • [41] Özdemir Ö , Marinelli L, Cacciatore I, Ciulla M, Emsen B et al. Anticancer effects of novel NSAIDs derivatives on cultured human glioblastoma cells. Zeitschrift fur Naturforschung C 2020; 76 (7-8): 329-335. https://doi.org/10.1515/znc-2020-0093
  • [42] Özgeriş B, Akbaba Y, Özdemir Ö, Türkez H, Göksu S. Synthesis and anticancer activity of novel ureas and sulfamides incorporating 1-aminotetralins. Archives of Medical Research 2007; 48 (6): 513-519. https://doi.org/10.1016/j.arcmed.2017.12.002
APA Çelebioğlu N, Özdemir Tozlu Ö, Turkez H, Seçen H (2023). Synthesis of alnustone-like diarylpentanoids via a 4 + 1 strategy and assessment of their potential anticancer activity. , 1249 - 1259. 10.55730/1300-0527.3609
Chicago Çelebioğlu Neslihan,Özdemir Tozlu Özlem,Turkez Hasan,Seçen Hasan Synthesis of alnustone-like diarylpentanoids via a 4 + 1 strategy and assessment of their potential anticancer activity. (2023): 1249 - 1259. 10.55730/1300-0527.3609
MLA Çelebioğlu Neslihan,Özdemir Tozlu Özlem,Turkez Hasan,Seçen Hasan Synthesis of alnustone-like diarylpentanoids via a 4 + 1 strategy and assessment of their potential anticancer activity. , 2023, ss.1249 - 1259. 10.55730/1300-0527.3609
AMA Çelebioğlu N,Özdemir Tozlu Ö,Turkez H,Seçen H Synthesis of alnustone-like diarylpentanoids via a 4 + 1 strategy and assessment of their potential anticancer activity. . 2023; 1249 - 1259. 10.55730/1300-0527.3609
Vancouver Çelebioğlu N,Özdemir Tozlu Ö,Turkez H,Seçen H Synthesis of alnustone-like diarylpentanoids via a 4 + 1 strategy and assessment of their potential anticancer activity. . 2023; 1249 - 1259. 10.55730/1300-0527.3609
IEEE Çelebioğlu N,Özdemir Tozlu Ö,Turkez H,Seçen H "Synthesis of alnustone-like diarylpentanoids via a 4 + 1 strategy and assessment of their potential anticancer activity." , ss.1249 - 1259, 2023. 10.55730/1300-0527.3609
ISNAD Çelebioğlu, Neslihan vd. "Synthesis of alnustone-like diarylpentanoids via a 4 + 1 strategy and assessment of their potential anticancer activity". (2023), 1249-1259. https://doi.org/10.55730/1300-0527.3609
APA Çelebioğlu N, Özdemir Tozlu Ö, Turkez H, Seçen H (2023). Synthesis of alnustone-like diarylpentanoids via a 4 + 1 strategy and assessment of their potential anticancer activity. Turkish Journal of Chemistry, 47(5), 1249 - 1259. 10.55730/1300-0527.3609
Chicago Çelebioğlu Neslihan,Özdemir Tozlu Özlem,Turkez Hasan,Seçen Hasan Synthesis of alnustone-like diarylpentanoids via a 4 + 1 strategy and assessment of their potential anticancer activity. Turkish Journal of Chemistry 47, no.5 (2023): 1249 - 1259. 10.55730/1300-0527.3609
MLA Çelebioğlu Neslihan,Özdemir Tozlu Özlem,Turkez Hasan,Seçen Hasan Synthesis of alnustone-like diarylpentanoids via a 4 + 1 strategy and assessment of their potential anticancer activity. Turkish Journal of Chemistry, vol.47, no.5, 2023, ss.1249 - 1259. 10.55730/1300-0527.3609
AMA Çelebioğlu N,Özdemir Tozlu Ö,Turkez H,Seçen H Synthesis of alnustone-like diarylpentanoids via a 4 + 1 strategy and assessment of their potential anticancer activity. Turkish Journal of Chemistry. 2023; 47(5): 1249 - 1259. 10.55730/1300-0527.3609
Vancouver Çelebioğlu N,Özdemir Tozlu Ö,Turkez H,Seçen H Synthesis of alnustone-like diarylpentanoids via a 4 + 1 strategy and assessment of their potential anticancer activity. Turkish Journal of Chemistry. 2023; 47(5): 1249 - 1259. 10.55730/1300-0527.3609
IEEE Çelebioğlu N,Özdemir Tozlu Ö,Turkez H,Seçen H "Synthesis of alnustone-like diarylpentanoids via a 4 + 1 strategy and assessment of their potential anticancer activity." Turkish Journal of Chemistry, 47, ss.1249 - 1259, 2023. 10.55730/1300-0527.3609
ISNAD Çelebioğlu, Neslihan vd. "Synthesis of alnustone-like diarylpentanoids via a 4 + 1 strategy and assessment of their potential anticancer activity". Turkish Journal of Chemistry 47/5 (2023), 1249-1259. https://doi.org/10.55730/1300-0527.3609
Sayfa Oluşturulma Tarihi
24-04-2024 9:47

İLETİŞİM

TÜBİTAK ULAKBİM TR Dizin

Yüzüncüyıl, İşçi Blokları Mahallesi

Muhsin Yazıcıoğlu Caddesi No:51/C

06530 Çankaya / ANKARA +90 (312) 298 92 00

trdizin@tubitak.gov.tr

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