New pyrimidine-N-β-D-glucosides: synthesis, biological evaluation, and molecular docking investigations

PEKER, KIVANC; Kahriman, Nuran; Serdaroğlu, Vildan; aydin, ali; TÜRKMENOĞLU, BURÇİN; Usta, Asu; YAYLI, Nurettin

doi:10.55730/1300-0527.3553

New pyrimidine-N-β-D-glucosides: synthesis, biological evaluation, and molecular docking investigations

Nuran KAHRİMAN, (Karadeniz Teknik Üniversitesi, Fen Fakültesi, Kimya Bölümü, Trabzon, Türkiye)

KIVANC PEKER, (Karadeniz Teknik Üniversitesi, Fen Fakültesi, Kimya Bölümü, Trabzon, Türkiye)

Vildan SERDAROĞLU, (Karadeniz Teknik Üniversitesi, Fen Fakültesi, Kimya Bölümü, Trabzon, Türkiye)

Ali AYDIN, (Bozok Üniversitesi, Tıp Fakültesi, Temel Tıp Bilimleri Anabilim Dalı, Yozgat, Türkiye)

Burçin TÜRKMENOĞLU, (Erzincan Binali Yıldırım Üniversitesi, Eczacılık Fakültesi, Analitik Kimya Anabilim Dalı, Erzincan, Türkiye)

Asu USTA, (Recep Tayyip Erdoğan Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Rize, Türkiye)

Nurettin YAYLI (Karadeniz Teknik Üniversitesi, Eczacılık Fakültesi, Trabzon, Türkiye)

Turkish Journal of Chemistry

12 0

Yıl: 2023 Cilt: 47 Sayı: 2 Sayfa Aralığı: 476 - 494 Metin Dili: İngilizce DOI: 10.55730/1300-0527.3553 İndeks Tarihi: 12-06-2023

New pyrimidine-N-β-D-glucosides: synthesis, biological evaluation, and molecular docking investigations

Öz:

In this study, syntheses of new pyrimidine-coupled N-β-glucosides and tetra-O-acetyl derivatives were carried out. All glycoconjugates were investigated in comparison with known chemotherapeutic agents in terms of their antimicrobial and anticancer functions and DNA/protein binding affinities. Spectral data showed that all glycoside derivatives were obtained by diastereoselectivity as β-anomers. Both tested groups exhibited strong antiproliferative activity (2.29–66.84 μg/mL), but some of them had sufficiently ideal % cytotoxicity values (10.01%–16.78%). And also all synthetic compounds exhibited remarkable antibacterial activity against human pathogenic bacteria. Binding of these compounds to CT-DNA resulted in significant changes in spectral properties, consistent with groove binding. Molecular docking studies of some compounds revealed that the docking score, complex energy, and MM-GBSA $ΔG_{Bind}$ energy values were consistent with the experimental results, which showed that the new compounds were potent chemotherapeutic agents. Overall bioactivity results suggest that these compounds may be candidates as new chemotherapeutic agents and deserve further pharmacological evaluation.

Anahtar Kelime: 2 4 6-trisubstituted pyrimidine N-β-D-glucosides biological activity molecular docking

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

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APA	Kahriman N, PEKER K, Serdaroğlu V, aydin a, TÜRKMENOĞLU B, Usta A, YAYLI N (2023). New pyrimidine-N-β-D-glucosides: synthesis, biological evaluation, and molecular docking investigations. , 476 - 494. 10.55730/1300-0527.3553
Chicago	Kahriman Nuran,PEKER KIVANC,Serdaroğlu Vildan,aydin ali,TÜRKMENOĞLU BURÇİN,Usta Asu,YAYLI Nurettin New pyrimidine-N-β-D-glucosides: synthesis, biological evaluation, and molecular docking investigations. (2023): 476 - 494. 10.55730/1300-0527.3553
MLA	Kahriman Nuran,PEKER KIVANC,Serdaroğlu Vildan,aydin ali,TÜRKMENOĞLU BURÇİN,Usta Asu,YAYLI Nurettin New pyrimidine-N-β-D-glucosides: synthesis, biological evaluation, and molecular docking investigations. , 2023, ss.476 - 494. 10.55730/1300-0527.3553
AMA	Kahriman N,PEKER K,Serdaroğlu V,aydin a,TÜRKMENOĞLU B,Usta A,YAYLI N New pyrimidine-N-β-D-glucosides: synthesis, biological evaluation, and molecular docking investigations. . 2023; 476 - 494. 10.55730/1300-0527.3553
Vancouver	Kahriman N,PEKER K,Serdaroğlu V,aydin a,TÜRKMENOĞLU B,Usta A,YAYLI N New pyrimidine-N-β-D-glucosides: synthesis, biological evaluation, and molecular docking investigations. . 2023; 476 - 494. 10.55730/1300-0527.3553
IEEE	Kahriman N,PEKER K,Serdaroğlu V,aydin a,TÜRKMENOĞLU B,Usta A,YAYLI N "New pyrimidine-N-β-D-glucosides: synthesis, biological evaluation, and molecular docking investigations." , ss.476 - 494, 2023. 10.55730/1300-0527.3553
ISNAD	Kahriman, Nuran vd. "New pyrimidine-N-β-D-glucosides: synthesis, biological evaluation, and molecular docking investigations". (2023), 476-494. https://doi.org/10.55730/1300-0527.3553

APA	Kahriman N, PEKER K, Serdaroğlu V, aydin a, TÜRKMENOĞLU B, Usta A, YAYLI N (2023). New pyrimidine-N-β-D-glucosides: synthesis, biological evaluation, and molecular docking investigations. Turkish Journal of Chemistry, 47(2), 476 - 494. 10.55730/1300-0527.3553
Chicago	Kahriman Nuran,PEKER KIVANC,Serdaroğlu Vildan,aydin ali,TÜRKMENOĞLU BURÇİN,Usta Asu,YAYLI Nurettin New pyrimidine-N-β-D-glucosides: synthesis, biological evaluation, and molecular docking investigations. Turkish Journal of Chemistry 47, no.2 (2023): 476 - 494. 10.55730/1300-0527.3553
MLA	Kahriman Nuran,PEKER KIVANC,Serdaroğlu Vildan,aydin ali,TÜRKMENOĞLU BURÇİN,Usta Asu,YAYLI Nurettin New pyrimidine-N-β-D-glucosides: synthesis, biological evaluation, and molecular docking investigations. Turkish Journal of Chemistry, vol.47, no.2, 2023, ss.476 - 494. 10.55730/1300-0527.3553
AMA	Kahriman N,PEKER K,Serdaroğlu V,aydin a,TÜRKMENOĞLU B,Usta A,YAYLI N New pyrimidine-N-β-D-glucosides: synthesis, biological evaluation, and molecular docking investigations. Turkish Journal of Chemistry. 2023; 47(2): 476 - 494. 10.55730/1300-0527.3553
Vancouver	Kahriman N,PEKER K,Serdaroğlu V,aydin a,TÜRKMENOĞLU B,Usta A,YAYLI N New pyrimidine-N-β-D-glucosides: synthesis, biological evaluation, and molecular docking investigations. Turkish Journal of Chemistry. 2023; 47(2): 476 - 494. 10.55730/1300-0527.3553
IEEE	Kahriman N,PEKER K,Serdaroğlu V,aydin a,TÜRKMENOĞLU B,Usta A,YAYLI N "New pyrimidine-N-β-D-glucosides: synthesis, biological evaluation, and molecular docking investigations." Turkish Journal of Chemistry, 47, ss.476 - 494, 2023. 10.55730/1300-0527.3553
ISNAD	Kahriman, Nuran vd. "New pyrimidine-N-β-D-glucosides: synthesis, biological evaluation, and molecular docking investigations". Turkish Journal of Chemistry 47/2 (2023), 476-494. https://doi.org/10.55730/1300-0527.3553