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

Mustafa Ceylan; Bahar Zorlu; Ayşe Şahin Yağlıoğlu; Nuray Akdoğan Üremiş; Meliha Burcu Gürdere; Meryem Keçeci Sarıkaya; Yakup Budak

doi:10.54187/jnrs.1366848

EN

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

Abstract

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).

Keywords

α, β-Unsaturated ketones, Anti-proliferative activity, C6, HeLa, 5-Fu

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Details

Primary Language

English

Subjects

Natural Products and Bioactive Compounds, Organic Chemical Synthesis

Journal Section

Research Article

Authors

Mustafa Ceylan ^*
0000-0002-9184-4385
Türkiye

Bahar Zorlu
0000-0003-4500-0584
Türkiye

Ayşe Şahin Yağlıoğlu
0000-0003-1240-0178
Türkiye

Nuray Akdoğan Üremiş
0000-0002-4056-5802
Türkiye

Meliha Burcu Gürdere
0000-0003-4285-5528
Türkiye

Meryem Keçeci Sarıkaya
0009-0006-1431-3632
Türkiye

Yakup Budak
0000-0001-7108-5548
Türkiye

Publication Date

December 31, 2023

Submission Date

September 26, 2023

Acceptance Date

November 28, 2023

Published in Issue

Year 2023 Volume: 12 Number: 3

DOI

https://doi.org/10.54187/jnrs.1366848

IZ

https://izlik.org/JA77XZ83BW

APA

Ceylan, M., Zorlu, B., Şahin Yağlıoğlu, A., Akdoğan Üremiş, N., Gürdere, M. B., Keçeci Sarıkaya, M., & Budak, Y. (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

1.Ceylan M, Zorlu B, Şahin Yağlıoğlu A, et al. 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):149-156. doi:10.54187/jnrs.1366848

Chicago

Ceylan, Mustafa, Bahar Zorlu, Ayşe Şahin Yağlıoğlu, et al. 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): 149-56. 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 (December 1, 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

[1]M. Ceylan et al., “Synthesis of (E)-7-arylidene-5-(hydroxy(aryl)methyl)bicyclo[3.2.0] heptan-6-one derivatives as anti-cancer agents”, JNRS, vol. 12, no. 3, pp. 149–156, Dec. 2023, doi: 10.54187/jnrs.1366848.

ISNAD

Ceylan, Mustafa - Zorlu, Bahar - Şahin Yağlıoğlu, Ayşe - Akdoğan Üremiş, Nuray - Gürdere, Meliha Burcu - Keçeci Sarıkaya, Meryem - Budak, Yakup. “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 (December 1, 2023): 149-156. https://doi.org/10.54187/jnrs.1366848.

JAMA

1.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, et al. “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, vol. 12, no. 3, Dec. 2023, pp. 149-56, doi:10.54187/jnrs.1366848.

Vancouver

1.Mustafa Ceylan, Bahar Zorlu, Ayşe Şahin Yağlıoğlu, Nuray Akdoğan Üremiş, Meliha Burcu Gürdere, Meryem Keçeci Sarıkaya, Yakup Budak. Synthesis of (E)-7-arylidene-5-(hydroxy(aryl)methyl)bicyclo[3.2.0] heptan-6-one derivatives as anti-cancer agents. JNRS. 2023 Dec. 1;12(3):149-56. doi:10.54187/jnrs.1366848