Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential
anticancer agents and hCA I and II inhibitors

Gulcin, ilhami; Sağlamtaş, Rüya; Tuğrak Sakarya, Mehtap; Gul, Halise Inci; Sakagami, Hiroshi

doi:10.3906/kim-2009-37

Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential anticancer agents and hCA I and II inhibitors

Mehtap TUGRAK, (Atatürk Üniversitesi, Eczacılık Fakültesi, Farmasötik Kimya Anabilim Dalı, Erzurum, Türkiye)

Halise Inci GUL, (Atatürk Üniversitesi, Eczacılık Fakültesi, Farmasötik Kimya Anabilim Dalı, Erzurum, Türkiye)

Hiroshi SAKAGAMİ, (Division of Pharmacology, Meikai University School of Dentistry, Sakado, Saitama, Japan)

Rüya KAYA, (Atatürk Üniversitesi, Fen Fakültesi, Kimya Bölümü, Erzurum, Türkiye)

İlhami GÜLÇİN (Atatürk Üniversitesi, Fen Fakültesi, Kimya Bölümü, Erzurum, Türkiye)

Turkish Journal of Chemistry

5 0

Yıl: 2021 Cilt: 45 Sayı: 3 Sayfa Aralığı: 528 - 539 Metin Dili: İngilizce DOI: 10.3906/kim-2009-37 İndeks Tarihi: 28-06-2022

Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential anticancer agents and hCA I and II inhibitors

Öz:

Cancer is a disease characterized by the continuous growth of cells without adherence to the rules that healthy normal cells obey. Carbonic anhydrase I and II (CA I and CA II) inhibitors are used for the treatment of some diseases. The available drugs in the market have limitations or side effects, which bring about the need to develop new drug candidate compound(s) to overcome the problems at issue. In this study, new pyrazole-sulphonamide hybrid compounds 4-[5-(1,3-benzodioxol-5-yl)-3-aryl-4,5-dihydro-1Hpyrazol-1-yl]benzenesulphonamides (4a - 4j) were designed to discover new drug candidate compounds. The compounds 4a - 4j were synthesized and their chemical structures were confirmed using spectral techniques. The hypothesis tested was whether an introduction of methoxy and polymethoxy group(s) lead to an increased potency selectivity expression (PSE) value of the compound, which reflects cytotoxicity and selectivity of the compounds. The cytotoxicity of the compounds towards tumor cell lines were in the range of 6.7 –400 µM. The compounds 4i $(PSE_2 = 461.5)$ and 4g $(PSE_1 = 193.2)$ had the highest PSE values in cytotoxicity assays. Ki values of the compounds were in the range of 59.8 ± 3.0 - 12.7 ± 1.7 nM towards hCA I and in the range of 24.1 ± 7.1 - 6.9 ± 1.5 nM towards hCA II. While the compounds 4b, 4f, 4g, and 4i showed promising cytotoxic effects, the compounds 4c and 4g had the inhibitory potency towards hCA I and hCA II, respectively. These compounds can be considered as lead compounds for further research.

Anahtar Kelime:

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

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APA	Tuğrak Sakarya M, Gul H, Sakagami H, Sağlamtaş R, Gulcin i (2021). Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential anticancer agents and hCA I and II inhibitors. , 528 - 539. 10.3906/kim-2009-37
Chicago	Tuğrak Sakarya Mehtap,Gul Halise Inci,Sakagami Hiroshi,Sağlamtaş Rüya,Gulcin ilhami Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential anticancer agents and hCA I and II inhibitors. (2021): 528 - 539. 10.3906/kim-2009-37
MLA	Tuğrak Sakarya Mehtap,Gul Halise Inci,Sakagami Hiroshi,Sağlamtaş Rüya,Gulcin ilhami Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential anticancer agents and hCA I and II inhibitors. , 2021, ss.528 - 539. 10.3906/kim-2009-37
AMA	Tuğrak Sakarya M,Gul H,Sakagami H,Sağlamtaş R,Gulcin i Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential anticancer agents and hCA I and II inhibitors. . 2021; 528 - 539. 10.3906/kim-2009-37
Vancouver	Tuğrak Sakarya M,Gul H,Sakagami H,Sağlamtaş R,Gulcin i Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential anticancer agents and hCA I and II inhibitors. . 2021; 528 - 539. 10.3906/kim-2009-37
IEEE	Tuğrak Sakarya M,Gul H,Sakagami H,Sağlamtaş R,Gulcin i "Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential anticancer agents and hCA I and II inhibitors." , ss.528 - 539, 2021. 10.3906/kim-2009-37
ISNAD	Tuğrak Sakarya, Mehtap vd. "Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential anticancer agents and hCA I and II inhibitors". (2021), 528-539. https://doi.org/10.3906/kim-2009-37

APA	Tuğrak Sakarya M, Gul H, Sakagami H, Sağlamtaş R, Gulcin i (2021). Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential anticancer agents and hCA I and II inhibitors. Turkish Journal of Chemistry, 45(3), 528 - 539. 10.3906/kim-2009-37
Chicago	Tuğrak Sakarya Mehtap,Gul Halise Inci,Sakagami Hiroshi,Sağlamtaş Rüya,Gulcin ilhami Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential anticancer agents and hCA I and II inhibitors. Turkish Journal of Chemistry 45, no.3 (2021): 528 - 539. 10.3906/kim-2009-37
MLA	Tuğrak Sakarya Mehtap,Gul Halise Inci,Sakagami Hiroshi,Sağlamtaş Rüya,Gulcin ilhami Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential anticancer agents and hCA I and II inhibitors. Turkish Journal of Chemistry, vol.45, no.3, 2021, ss.528 - 539. 10.3906/kim-2009-37
AMA	Tuğrak Sakarya M,Gul H,Sakagami H,Sağlamtaş R,Gulcin i Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential anticancer agents and hCA I and II inhibitors. Turkish Journal of Chemistry. 2021; 45(3): 528 - 539. 10.3906/kim-2009-37
Vancouver	Tuğrak Sakarya M,Gul H,Sakagami H,Sağlamtaş R,Gulcin i Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential anticancer agents and hCA I and II inhibitors. Turkish Journal of Chemistry. 2021; 45(3): 528 - 539. 10.3906/kim-2009-37
IEEE	Tuğrak Sakarya M,Gul H,Sakagami H,Sağlamtaş R,Gulcin i "Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential anticancer agents and hCA I and II inhibitors." Turkish Journal of Chemistry, 45, ss.528 - 539, 2021. 10.3906/kim-2009-37
ISNAD	Tuğrak Sakarya, Mehtap vd. "Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential anticancer agents and hCA I and II inhibitors". Turkish Journal of Chemistry 45/3 (2021), 528-539. https://doi.org/10.3906/kim-2009-37