Araştırma Makalesi
BibTex RIS Kaynak Göster
Yıl 2023, Cilt: 12 Sayı: 3, 149 - 156, 31.12.2023
https://doi.org/10.54187/jnrs.1366848

Öz

Kaynakça

  • V. V. Loza, Z. R. Valiullina, M. S. Miftakhov, Adducts of dichloroketene with 1,3-cyclopen-tadienes in the synthesis of bioactive cyclopentanoids, Russian Chemical Bulletin 70 (1) (2021) 1–31.
  • V. E. Marquez, M. Lim, Carbocyclic Nucleosides, Medicinal Research Reviews 6 (1) (1986) 1–40.
  • K. Tonari, K. Sameshima, Antibacterial activity of 3-methylcyclopentanone derivatives in relation to methylenomycins, Journal of Japonian Oil Chemists’ Society 49 (6) (2000) 583–590.
  • L. F. Silva Jr., Construction of cyclopentyl units by ring contraction reactions, Tetrahedron 58 (45) (2002) 9137–9161.
  • E. J. Corey, X. Cheng, The logic of chemical synthesis, John Wiley & Sons, New York, 1989.
  • D. J. Faulkner, Marine natural products, Natural Product Reports 18 (1) (2001) 1R–49R.
  • B. M. Fraga, Natural sesquiterpenoids, Natural Product Reports 18 (6) (2001) 650–673.
  • D. H. Grayson, Monoterpenoids, Natural Product Reports 17 (4) (2000) 385–419.
  • J. R. Hanson, Diterpenoids, Natural Product Reports 20 (1) (2003) 70–78.
  • J. D. Connoly, R. A. Hill, Triterpenoids, Natural Product Reports 18 (2001) 560–578.
  • C. Morozzi, M. Sauerland, L. F. Gamon, A. Manandhar, T. Ulven, M. J. Davies, Synthesis and cellular evaluation of click-chemistry probes to study the biological effects of alpha, beta-unsaturated carbonyls, Redox Biology, 52 (2022) Article Number 102299 8 pages.
  • D. N. Dhar, The chemistry of chalcones and related compounds, Wiley, New York, 1981.
  • F. L. Ansari, S. Nazir, H. Noureen, B. Mirza, Combinatorial synthesis and evaluation of an indexed chalcone library, Chemistry and Biodiversity 2 (12) (2005) 1656–1664.
  • M. Ceylan, H. Gezegen, Preparation of 1,5-diketones by addition of cyclohexanone to chalcones under solvent-free phase transfer catalyst condition, Turkish Journal of Chemistry 32 (1) (2008) 55–61.
  • M. Ceylan, E. Fındık, Synthesis and characterization of new chalcone derivatives from cis-bicyclo [3.2.0]hept-2-en-6-one, Synthetic Communications 39 (6) (2009) 1046–1054.
  • M. Ceylan, S. Erkan, A. Sahin Yaglioglu, N. Akdogan Uremis, E. Koç, Antiproliferative evaluation of some 2-[2-(2-phenylethenyl)-cyclopent-3-en-1-yl]-1,3-benzothiazoles: dft and molecular docking study , Chemistry and Biodiversity 17 (4) (2020) Article Number e1900675 15 pages.
  • R. J. Anto, K. Sukumaran, G. Kuttan, M. N. A. Rao, V. Subbaraju, R. Kuttan, Anticancer and antioxidant activity of synthetic chalcones and related compounds, Cancer Letter 97 (1) (1995) 33–37.
  • H. H. Ko, L. T. Tsao, K. L. Yu, C. T. Liu, J. P. Wang, C. N. Lin, Structure-activity relationship studies on chalcone derivatives: The potent inhibition of chemical mediator release, Bioorganic and Medicinal Chemistry 11 (1) (2003) 105–111.
  • H. K. Hesieh, L. T. Tsao, J. P. Wang, C. N. Lin, Synthesis and antiinflammatory effect of chalcones, Journal of Pharmacy and Pharmacology 52 (2) (2000) 163–171.
  • Y. M. Lin, Y. Zhou, M. T. Flavin, L. M. Zhou, W. Nie, F. C. Chen, Chalcones and flavonoids as anti tuberculosis agents, Bioorganic and Medicinal Chemistry 10 (8) (2002) 2795–2802.
  • M. Khalid, A. Ali, Z. U. Din, M. N. Tahir, S. F. de A. Alcantara Morais, A. A. C. Braga, M. N. Akhtar, M. Imran, E. R. Filho, β-Hydroxy Carbonyl compounds via aldol reaction: Single crystal investigation and quantum chemical exploration for the unveiling of supramolecular behavior, Journal of Molecular Structure, 1241 (2021) Article Number 130650 10 pages.
  • H. B. Küçük, G. Kantürk, Ş. Yerlikaya, T. Yıldız, A. M. Sentürk, M. Güzel, Novel β–hydroxy ketones: Synthesis, spectroscopic characterization, molecular docking, and anticancer activity studies, Journal of Molecular Structure 1250 (2022) Article Number 131772 14 pages.
  • D. Acetti, E. Brenna, C. Fuganti, F .G. Gatti, S. Serra, Baker’s yeast reduction of β-hydroxy ketones, European Journal of Organic Chemistry 2010 (1) (2010) 142–151.
  • H. Kohls, M. Anderson, J. Dickerhoff, K. Weisz, A. Córdova, P. Berglund, H. Brundiek, U.T. Bornscheuer, M. Höhne, Selective access to all four diastere- omers of a 1,3-amino alcohol by combination of a keto reductase- and an amine transaminase-catalysed reaction, Advanced Synthesis & Catalysis 357 (8) (2015) 1808–1814.
  • R. A. Fernandes, The potential of β-hydroxy- γ-vinyl- γ-lactone in the synthesis of natural products and beyond, European Journal of Organic Chemistry 2020 (6) (2020) 634–645.
  • G. Ceyhan, M. Kose, M. Tumer, I. Demirtas, A. S. Yaglioglu, V. McKee, Structural characterization of some Schiff base compounds: Investigation of their electrochemical, photoluminescence, thermal and anticancer activity properties, Journal of Luminescence 143 (2013) 623–634.
  • G. Karakuş, Z. A. Polat, A. S. Yaglioglu, M. Karahan, A. F. Yenidünya, Synthesis, characterization, and assessment of cytotoxic, anti-proliferative, and antiangiogenic effects of a novel procainamide hydrochloride-poly (maleic anhydride-co-styrene) conjugate, Journal of Biomaterial Science, Polymer Edition 24 (10) (2013) 1260–1276.

Synthesis of (E)-7-arylidene-5-(hydroxy(aryl)methyl)bicyclo[3.2.0] heptan-6-one derivatives as anti-cancer agents

Yıl 2023, Cilt: 12 Sayı: 3, 149 - 156, 31.12.2023
https://doi.org/10.54187/jnrs.1366848

Öz

7,7-Dichlorobicyclo [3.2.0]heptan-6-one was prepared by adding dichloroketene to cyclopentene. Reduction of 7,7-dichlorobicyclo[3.2.0]heptan-6-one with Zn in acetic acid afforded the bicyclo[3.2.0]heptan-6-one. (E)-7-Arylidene-5-(hydroxy(aryl)methyl)bicyclo [3.2.0]heptan-6-ones were synthesized by addition of related benzaldehydes to bicyclo[3.2.0]heptan-6-one. The anti-proliferative activities of synthesized compounds were elucidated against rat brain tumor (C6) and human cervical carcinoma cells (HeLa) cell lines. The most active compound was chloro derivative against C6 cell lines with IC50 = 2.45 μM value (5-FU, IC50 = 14.82 μM). Moreover, the most active compound was methyl derivative against HeLa cell lines with IC50 = 26.30 μM (5-FU, IC50 = 29.30 μM).

Kaynakça

  • V. V. Loza, Z. R. Valiullina, M. S. Miftakhov, Adducts of dichloroketene with 1,3-cyclopen-tadienes in the synthesis of bioactive cyclopentanoids, Russian Chemical Bulletin 70 (1) (2021) 1–31.
  • V. E. Marquez, M. Lim, Carbocyclic Nucleosides, Medicinal Research Reviews 6 (1) (1986) 1–40.
  • K. Tonari, K. Sameshima, Antibacterial activity of 3-methylcyclopentanone derivatives in relation to methylenomycins, Journal of Japonian Oil Chemists’ Society 49 (6) (2000) 583–590.
  • L. F. Silva Jr., Construction of cyclopentyl units by ring contraction reactions, Tetrahedron 58 (45) (2002) 9137–9161.
  • E. J. Corey, X. Cheng, The logic of chemical synthesis, John Wiley & Sons, New York, 1989.
  • D. J. Faulkner, Marine natural products, Natural Product Reports 18 (1) (2001) 1R–49R.
  • B. M. Fraga, Natural sesquiterpenoids, Natural Product Reports 18 (6) (2001) 650–673.
  • D. H. Grayson, Monoterpenoids, Natural Product Reports 17 (4) (2000) 385–419.
  • J. R. Hanson, Diterpenoids, Natural Product Reports 20 (1) (2003) 70–78.
  • J. D. Connoly, R. A. Hill, Triterpenoids, Natural Product Reports 18 (2001) 560–578.
  • C. Morozzi, M. Sauerland, L. F. Gamon, A. Manandhar, T. Ulven, M. J. Davies, Synthesis and cellular evaluation of click-chemistry probes to study the biological effects of alpha, beta-unsaturated carbonyls, Redox Biology, 52 (2022) Article Number 102299 8 pages.
  • D. N. Dhar, The chemistry of chalcones and related compounds, Wiley, New York, 1981.
  • F. L. Ansari, S. Nazir, H. Noureen, B. Mirza, Combinatorial synthesis and evaluation of an indexed chalcone library, Chemistry and Biodiversity 2 (12) (2005) 1656–1664.
  • M. Ceylan, H. Gezegen, Preparation of 1,5-diketones by addition of cyclohexanone to chalcones under solvent-free phase transfer catalyst condition, Turkish Journal of Chemistry 32 (1) (2008) 55–61.
  • M. Ceylan, E. Fındık, Synthesis and characterization of new chalcone derivatives from cis-bicyclo [3.2.0]hept-2-en-6-one, Synthetic Communications 39 (6) (2009) 1046–1054.
  • M. Ceylan, S. Erkan, A. Sahin Yaglioglu, N. Akdogan Uremis, E. Koç, Antiproliferative evaluation of some 2-[2-(2-phenylethenyl)-cyclopent-3-en-1-yl]-1,3-benzothiazoles: dft and molecular docking study , Chemistry and Biodiversity 17 (4) (2020) Article Number e1900675 15 pages.
  • R. J. Anto, K. Sukumaran, G. Kuttan, M. N. A. Rao, V. Subbaraju, R. Kuttan, Anticancer and antioxidant activity of synthetic chalcones and related compounds, Cancer Letter 97 (1) (1995) 33–37.
  • H. H. Ko, L. T. Tsao, K. L. Yu, C. T. Liu, J. P. Wang, C. N. Lin, Structure-activity relationship studies on chalcone derivatives: The potent inhibition of chemical mediator release, Bioorganic and Medicinal Chemistry 11 (1) (2003) 105–111.
  • H. K. Hesieh, L. T. Tsao, J. P. Wang, C. N. Lin, Synthesis and antiinflammatory effect of chalcones, Journal of Pharmacy and Pharmacology 52 (2) (2000) 163–171.
  • Y. M. Lin, Y. Zhou, M. T. Flavin, L. M. Zhou, W. Nie, F. C. Chen, Chalcones and flavonoids as anti tuberculosis agents, Bioorganic and Medicinal Chemistry 10 (8) (2002) 2795–2802.
  • M. Khalid, A. Ali, Z. U. Din, M. N. Tahir, S. F. de A. Alcantara Morais, A. A. C. Braga, M. N. Akhtar, M. Imran, E. R. Filho, β-Hydroxy Carbonyl compounds via aldol reaction: Single crystal investigation and quantum chemical exploration for the unveiling of supramolecular behavior, Journal of Molecular Structure, 1241 (2021) Article Number 130650 10 pages.
  • H. B. Küçük, G. Kantürk, Ş. Yerlikaya, T. Yıldız, A. M. Sentürk, M. Güzel, Novel β–hydroxy ketones: Synthesis, spectroscopic characterization, molecular docking, and anticancer activity studies, Journal of Molecular Structure 1250 (2022) Article Number 131772 14 pages.
  • D. Acetti, E. Brenna, C. Fuganti, F .G. Gatti, S. Serra, Baker’s yeast reduction of β-hydroxy ketones, European Journal of Organic Chemistry 2010 (1) (2010) 142–151.
  • H. Kohls, M. Anderson, J. Dickerhoff, K. Weisz, A. Córdova, P. Berglund, H. Brundiek, U.T. Bornscheuer, M. Höhne, Selective access to all four diastere- omers of a 1,3-amino alcohol by combination of a keto reductase- and an amine transaminase-catalysed reaction, Advanced Synthesis & Catalysis 357 (8) (2015) 1808–1814.
  • R. A. Fernandes, The potential of β-hydroxy- γ-vinyl- γ-lactone in the synthesis of natural products and beyond, European Journal of Organic Chemistry 2020 (6) (2020) 634–645.
  • G. Ceyhan, M. Kose, M. Tumer, I. Demirtas, A. S. Yaglioglu, V. McKee, Structural characterization of some Schiff base compounds: Investigation of their electrochemical, photoluminescence, thermal and anticancer activity properties, Journal of Luminescence 143 (2013) 623–634.
  • G. Karakuş, Z. A. Polat, A. S. Yaglioglu, M. Karahan, A. F. Yenidünya, Synthesis, characterization, and assessment of cytotoxic, anti-proliferative, and antiangiogenic effects of a novel procainamide hydrochloride-poly (maleic anhydride-co-styrene) conjugate, Journal of Biomaterial Science, Polymer Edition 24 (10) (2013) 1260–1276.
Toplam 27 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Doğal Ürünler ve Biyoaktif Bileşikler, Organik Kimyasal Sentez
Bölüm Articles
Yazarlar

Mustafa Ceylan 0000-0002-9184-4385

Bahar Zorlu 0000-0003-4500-0584

Ayşe Şahin Yağlıoğlu 0000-0003-1240-0178

Nuray Akdoğan Üremiş 0000-0002-4056-5802

Meliha Burcu Gürdere 0000-0003-4285-5528

Meryem Keçeci Sarıkaya 0009-0006-1431-3632

Yakup Budak 0000-0001-7108-5548

Yayımlanma Tarihi 31 Aralık 2023
Yayımlandığı Sayı Yıl 2023 Cilt: 12 Sayı: 3

Kaynak Göster

APA Ceylan, M., Zorlu, B., Şahin Yağlıoğlu, A., Akdoğan Üremiş, N., vd. (2023). Synthesis of (E)-7-arylidene-5-(hydroxy(aryl)methyl)bicyclo[3.2.0] heptan-6-one derivatives as anti-cancer agents. Journal of New Results in Science, 12(3), 149-156. https://doi.org/10.54187/jnrs.1366848
AMA Ceylan M, Zorlu B, Şahin Yağlıoğlu A, Akdoğan Üremiş N, Gürdere MB, Keçeci Sarıkaya M, Budak Y. Synthesis of (E)-7-arylidene-5-(hydroxy(aryl)methyl)bicyclo[3.2.0] heptan-6-one derivatives as anti-cancer agents. JNRS. Aralık 2023;12(3):149-156. doi:10.54187/jnrs.1366848
Chicago Ceylan, Mustafa, Bahar Zorlu, Ayşe Şahin Yağlıoğlu, Nuray Akdoğan Üremiş, Meliha Burcu Gürdere, Meryem Keçeci Sarıkaya, ve Yakup Budak. “Synthesis of (E)-7-Arylidene-5-(hydroxy(aryl)methyl)bicyclo[3.2.0] Heptan-6-One Derivatives As Anti-Cancer Agents”. Journal of New Results in Science 12, sy. 3 (Aralık 2023): 149-56. https://doi.org/10.54187/jnrs.1366848.
EndNote Ceylan M, Zorlu B, Şahin Yağlıoğlu A, Akdoğan Üremiş N, Gürdere MB, Keçeci Sarıkaya M, Budak Y (01 Aralık 2023) Synthesis of (E)-7-arylidene-5-(hydroxy(aryl)methyl)bicyclo[3.2.0] heptan-6-one derivatives as anti-cancer agents. Journal of New Results in Science 12 3 149–156.
IEEE M. Ceylan, B. Zorlu, A. Şahin Yağlıoğlu, N. Akdoğan Üremiş, M. B. Gürdere, M. Keçeci Sarıkaya, ve Y. Budak, “Synthesis of (E)-7-arylidene-5-(hydroxy(aryl)methyl)bicyclo[3.2.0] heptan-6-one derivatives as anti-cancer agents”, JNRS, c. 12, sy. 3, ss. 149–156, 2023, doi: 10.54187/jnrs.1366848.
ISNAD Ceylan, Mustafa vd. “Synthesis of (E)-7-Arylidene-5-(hydroxy(aryl)methyl)bicyclo[3.2.0] Heptan-6-One Derivatives As Anti-Cancer Agents”. Journal of New Results in Science 12/3 (Aralık 2023), 149-156. https://doi.org/10.54187/jnrs.1366848.
JAMA Ceylan M, Zorlu B, Şahin Yağlıoğlu A, Akdoğan Üremiş N, Gürdere MB, Keçeci Sarıkaya M, Budak Y. Synthesis of (E)-7-arylidene-5-(hydroxy(aryl)methyl)bicyclo[3.2.0] heptan-6-one derivatives as anti-cancer agents. JNRS. 2023;12:149–156.
MLA Ceylan, Mustafa vd. “Synthesis of (E)-7-Arylidene-5-(hydroxy(aryl)methyl)bicyclo[3.2.0] Heptan-6-One Derivatives As Anti-Cancer Agents”. Journal of New Results in Science, c. 12, sy. 3, 2023, ss. 149-56, doi:10.54187/jnrs.1366848.
Vancouver Ceylan M, Zorlu B, Şahin Yağlıoğlu A, Akdoğan Üremiş N, Gürdere MB, Keçeci Sarıkaya M, Budak Y. Synthesis of (E)-7-arylidene-5-(hydroxy(aryl)methyl)bicyclo[3.2.0] heptan-6-one derivatives as anti-cancer agents. JNRS. 2023;12(3):149-56.


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