Novel Mannich bases with strong carbonic anhydrases and acetylcholinesterase
inhibition effects: 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)-
benzoxazolones

KOCA, MEHMET; Gulcin, ilhami; ANIL, BARIŞ; Bilginer, Sinan; Demir, Yeliz

doi:10.3906/kim-2101-25

Novel Mannich bases with strong carbonic anhydrases and acetylcholinesterase inhibition effects: 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)- benzoxazolones

Sinan BiLGiNER, (Atatürk Üniversitesi, Eczacılık Fakültesi, Farmasötik Kimya Anabilim Dalı, Erzurum, Türkiye)

Baris ANIL, (Atatürk Üniversitesi, Fen Fakültesi, Kimya Bölümü, Erzurum, Türkiye)

Mehmet KOCA, (Atatürk Üniversitesi, Eczacılık Fakültesi, Farmasötik Kimya Anabilim Dalı, Erzurum, Türkiye)

Yeliz DEMİR, (Ardahan Üniversitesi, Nihat Delibalta Göle Meslek Yüksekokulu, Ardahan, Türkiye)

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

Turkish Journal of Chemistry

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Yıl: 2021 Cilt: 45 Sayı: 3 Sayfa Aralığı: 805 - 818 Metin Dili: İngilizce DOI: 10.3906/kim-2101-25 İndeks Tarihi: 28-06-2022

Novel Mannich bases with strong carbonic anhydrases and acetylcholinesterase inhibition effects: 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)- benzoxazolones

Öz:

In this study, a new series of Mannich bases, 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)- benzoxazolones (1a–g), were synthesized by the Mannich reaction. Inhibitory effects of the newly synthesized compounds towards carbonic anhydrases (CAs) and acetylcholinesterase (AChE) enzymes were evaluated to find out new potential drug candidate compounds. According to the inhibitory activity results, $K_i$ values of the compounds 1 and 1a–g were in the range of 12.3 ± 1.2 to 154.0 ± 9.3 nM against hCA I, and they were in the range of 8.6 ± 1.9 to 41.0 ± 5.5 nM against hCA II. Ki values of acetazolamide (AZA) that was used as a reference compound were 84.4 ± 8.4 nM towards hCA I and 59.2 ± 4.8 nM towards hCA II. Ki values of the compounds 1 and 1a–g were in the range of 35.2 ± 2.0 to 158.9 ± 33.5 nM towards AChE. Ki value of Tacrine (TAC), the reference compound, was 68.6 ± 3.8 nM towards AChE. Furthermore, docking studies were done with the most potent compounds 1d, 1g, and 1f (in terms of hCA I, hCA II, and AChE inhibition effects, respectively) to determine the binding profiles of the series with these enzymes. Additionally, the prediction of ADME profiles of the compounds pointed out that the newly synthesized compounds had desirable physicochemical properties as lead compounds for further studies.

Anahtar Kelime:

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

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APA	Bilginer S, ANIL B, KOCA M, Demir Y, Gulcin i (2021). Novel Mannich bases with strong carbonic anhydrases and acetylcholinesterase inhibition effects: 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)- benzoxazolones. , 805 - 818. 10.3906/kim-2101-25
Chicago	Bilginer Sinan,ANIL BARIŞ,KOCA MEHMET,Demir Yeliz,Gulcin ilhami Novel Mannich bases with strong carbonic anhydrases and acetylcholinesterase inhibition effects: 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)- benzoxazolones. (2021): 805 - 818. 10.3906/kim-2101-25
MLA	Bilginer Sinan,ANIL BARIŞ,KOCA MEHMET,Demir Yeliz,Gulcin ilhami Novel Mannich bases with strong carbonic anhydrases and acetylcholinesterase inhibition effects: 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)- benzoxazolones. , 2021, ss.805 - 818. 10.3906/kim-2101-25
AMA	Bilginer S,ANIL B,KOCA M,Demir Y,Gulcin i Novel Mannich bases with strong carbonic anhydrases and acetylcholinesterase inhibition effects: 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)- benzoxazolones. . 2021; 805 - 818. 10.3906/kim-2101-25
Vancouver	Bilginer S,ANIL B,KOCA M,Demir Y,Gulcin i Novel Mannich bases with strong carbonic anhydrases and acetylcholinesterase inhibition effects: 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)- benzoxazolones. . 2021; 805 - 818. 10.3906/kim-2101-25
IEEE	Bilginer S,ANIL B,KOCA M,Demir Y,Gulcin i "Novel Mannich bases with strong carbonic anhydrases and acetylcholinesterase inhibition effects: 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)- benzoxazolones." , ss.805 - 818, 2021. 10.3906/kim-2101-25
ISNAD	Bilginer, Sinan vd. "Novel Mannich bases with strong carbonic anhydrases and acetylcholinesterase inhibition effects: 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)- benzoxazolones". (2021), 805-818. https://doi.org/10.3906/kim-2101-25

APA	Bilginer S, ANIL B, KOCA M, Demir Y, Gulcin i (2021). Novel Mannich bases with strong carbonic anhydrases and acetylcholinesterase inhibition effects: 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)- benzoxazolones. Turkish Journal of Chemistry, 45(3), 805 - 818. 10.3906/kim-2101-25
Chicago	Bilginer Sinan,ANIL BARIŞ,KOCA MEHMET,Demir Yeliz,Gulcin ilhami Novel Mannich bases with strong carbonic anhydrases and acetylcholinesterase inhibition effects: 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)- benzoxazolones. Turkish Journal of Chemistry 45, no.3 (2021): 805 - 818. 10.3906/kim-2101-25
MLA	Bilginer Sinan,ANIL BARIŞ,KOCA MEHMET,Demir Yeliz,Gulcin ilhami Novel Mannich bases with strong carbonic anhydrases and acetylcholinesterase inhibition effects: 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)- benzoxazolones. Turkish Journal of Chemistry, vol.45, no.3, 2021, ss.805 - 818. 10.3906/kim-2101-25
AMA	Bilginer S,ANIL B,KOCA M,Demir Y,Gulcin i Novel Mannich bases with strong carbonic anhydrases and acetylcholinesterase inhibition effects: 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)- benzoxazolones. Turkish Journal of Chemistry. 2021; 45(3): 805 - 818. 10.3906/kim-2101-25
Vancouver	Bilginer S,ANIL B,KOCA M,Demir Y,Gulcin i Novel Mannich bases with strong carbonic anhydrases and acetylcholinesterase inhibition effects: 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)- benzoxazolones. Turkish Journal of Chemistry. 2021; 45(3): 805 - 818. 10.3906/kim-2101-25
IEEE	Bilginer S,ANIL B,KOCA M,Demir Y,Gulcin i "Novel Mannich bases with strong carbonic anhydrases and acetylcholinesterase inhibition effects: 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)- benzoxazolones." Turkish Journal of Chemistry, 45, ss.805 - 818, 2021. 10.3906/kim-2101-25
ISNAD	Bilginer, Sinan vd. "Novel Mannich bases with strong carbonic anhydrases and acetylcholinesterase inhibition effects: 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)- benzoxazolones". Turkish Journal of Chemistry 45/3 (2021), 805-818. https://doi.org/10.3906/kim-2101-25