Molecular docking, synthesis and biological evaluation (enzyme inhibition, antimicrobial and antioxidant) of methoxy benzoin/benzil/stilbenoid derivatives

YAYLI, Nurettin; SELLİTEPE, Hasan Erdinç; BOZDAL, Gözde; Tatar Yılmaz, Gizem; Kahriman, Nuran; aliyazicioglu, rezzan; Alpay Karaoğlu, Şengül; Serdaroğlu, Vildan

Molecular docking, synthesis and biological evaluation (enzyme inhibition, antimicrobial and antioxidant) of methoxy benzoin/benzil/stilbenoid derivatives

Nurettin YAYLI, (Karadeniz Teknik Üniversitesi, Eczacılık Fakültesi, Farmakognozi Anabilim Dalı, 61080, Trabzon, Türkiye)

Nuran KAHRİMAN, (Karadeniz Teknik Üniversitesi, Fen Fakültesi, Kimya Bölümü, 61080, Trabzon, Türkiye)

Gözde KILIÇ, (Karadeniz Teknik Üniversitesi, Eczacılık Fakültesi, Farmakognozi Anabilim Dalı, 61080, Trabzon, Türkiye)

Vildan SERDAROĞLU, (Karadeniz Teknik Üniversitesi, Fen Fakültesi, Kimya Bölümü, 61080, Trabzon, Türkiye)

Rezzan ALİYAZICIOĞLU, (Karadeniz Teknik Üniversitesi, Eczacılık Fakültesi Biyokimya Bölümü, 61080, Trabzon, Türkiye)

Hasan Erdinç SELLİTEPE, (Karadeniz Teknik Üniversitesi, Kimya Anabilim Dalı, Farmasötik Eczacılık Fakültesi, 61080, Trabzon, Türkiye)

Şengül Alpay KARAOĞLU, (Recep Tayyip Erdoğan Üniversitesi, Fen-Edebiyat Fakültesi, Biyoloji Bölümü, 53100, Rize, Türkiye)

Gizem TATAR (Karadeniz Teknik Üniversitesi, Tıp Fakültesi, Biyoistatistik ve Tıp Bilişimi Anabilim Dalı, 61080, Trabzon, Türkiye)

Organic Communications

14 1

Yıl: 2022 Cilt: 15 Sayı: 2 Sayfa Aralığı: 129 - 147 Metin Dili: İngilizce İndeks Tarihi: 05-07-2022

Molecular docking, synthesis and biological evaluation (enzyme inhibition, antimicrobial and antioxidant) of methoxy benzoin/benzil/stilbenoid derivatives

Öz:

In this study, methoxy benzoin compounds (1-10) were synthesized from the corresponding aromatic aldehydes based on a screening of biological activity. Oxidation and reduction of benzoins (1-10) yielded the corresponding benzils (11-20) and stilbenoids (21-29), respectively. The enzyme inhibition, antimicrobial, and antioxidant activities of 1-29 were evaluated. 1, 14, 19, and 28 against α-amylase, 15 and 19 against α-glucosidase, 2, 4, 14, 18, 25 and 26 against tyrosinase, 2, 7, and 23 against AChE, and 7, and 13 against BChE showed similar activity to the standard used. Among the methoxy benzoin derivatives, 4 proved to be the most active compound against E.coli, Y.pseudotuberculosis, M. smegmatis, and C.albicans in the range of 41-82 μg/mL MIC values. All benzil derivatives displayed bioactivity against M.smegmatis and C. albicans. Compounds 18 and 11 were found to be most effective against M.smegmatis, and compounds 11 and 17 were found to be the most effective against C.albicans. All stilbenoid type compounds showed selective activity against B.cereus. Compounds 21 and 22 were the most effective stilbenoid compounds against M. smegmatis. Benzoins (1-10) were the most effective antioxidants among all three groups compared to the tested methods, which can be attributed to the free hydroxyl at the benzylic position. As a result, the change of carbon skeleton and substitution at different positions of synthesized organic compounds also caused the variation of biological activity

Anahtar Kelime:

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

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APA	YAYLI N, Kahriman N, BOZDAL G, Serdaroğlu V, aliyazicioglu r, SELLİTEPE H, Alpay Karaoğlu Ş, Tatar Yılmaz G (2022). Molecular docking, synthesis and biological evaluation (enzyme inhibition, antimicrobial and antioxidant) of methoxy benzoin/benzil/stilbenoid derivatives. , 129 - 147.
Chicago	YAYLI Nurettin,Kahriman Nuran,BOZDAL Gözde,Serdaroğlu Vildan,aliyazicioglu rezzan,SELLİTEPE Hasan Erdinç,Alpay Karaoğlu Şengül,Tatar Yılmaz Gizem Molecular docking, synthesis and biological evaluation (enzyme inhibition, antimicrobial and antioxidant) of methoxy benzoin/benzil/stilbenoid derivatives. (2022): 129 - 147.
MLA	YAYLI Nurettin,Kahriman Nuran,BOZDAL Gözde,Serdaroğlu Vildan,aliyazicioglu rezzan,SELLİTEPE Hasan Erdinç,Alpay Karaoğlu Şengül,Tatar Yılmaz Gizem Molecular docking, synthesis and biological evaluation (enzyme inhibition, antimicrobial and antioxidant) of methoxy benzoin/benzil/stilbenoid derivatives. , 2022, ss.129 - 147.
AMA	YAYLI N,Kahriman N,BOZDAL G,Serdaroğlu V,aliyazicioglu r,SELLİTEPE H,Alpay Karaoğlu Ş,Tatar Yılmaz G Molecular docking, synthesis and biological evaluation (enzyme inhibition, antimicrobial and antioxidant) of methoxy benzoin/benzil/stilbenoid derivatives. . 2022; 129 - 147.
Vancouver	YAYLI N,Kahriman N,BOZDAL G,Serdaroğlu V,aliyazicioglu r,SELLİTEPE H,Alpay Karaoğlu Ş,Tatar Yılmaz G Molecular docking, synthesis and biological evaluation (enzyme inhibition, antimicrobial and antioxidant) of methoxy benzoin/benzil/stilbenoid derivatives. . 2022; 129 - 147.
IEEE	YAYLI N,Kahriman N,BOZDAL G,Serdaroğlu V,aliyazicioglu r,SELLİTEPE H,Alpay Karaoğlu Ş,Tatar Yılmaz G "Molecular docking, synthesis and biological evaluation (enzyme inhibition, antimicrobial and antioxidant) of methoxy benzoin/benzil/stilbenoid derivatives." , ss.129 - 147, 2022.
ISNAD	YAYLI, Nurettin vd. "Molecular docking, synthesis and biological evaluation (enzyme inhibition, antimicrobial and antioxidant) of methoxy benzoin/benzil/stilbenoid derivatives". (2022), 129-147.

APA	YAYLI N, Kahriman N, BOZDAL G, Serdaroğlu V, aliyazicioglu r, SELLİTEPE H, Alpay Karaoğlu Ş, Tatar Yılmaz G (2022). Molecular docking, synthesis and biological evaluation (enzyme inhibition, antimicrobial and antioxidant) of methoxy benzoin/benzil/stilbenoid derivatives. Organic Communications, 15(2), 129 - 147.
Chicago	YAYLI Nurettin,Kahriman Nuran,BOZDAL Gözde,Serdaroğlu Vildan,aliyazicioglu rezzan,SELLİTEPE Hasan Erdinç,Alpay Karaoğlu Şengül,Tatar Yılmaz Gizem Molecular docking, synthesis and biological evaluation (enzyme inhibition, antimicrobial and antioxidant) of methoxy benzoin/benzil/stilbenoid derivatives. Organic Communications 15, no.2 (2022): 129 - 147.
MLA	YAYLI Nurettin,Kahriman Nuran,BOZDAL Gözde,Serdaroğlu Vildan,aliyazicioglu rezzan,SELLİTEPE Hasan Erdinç,Alpay Karaoğlu Şengül,Tatar Yılmaz Gizem Molecular docking, synthesis and biological evaluation (enzyme inhibition, antimicrobial and antioxidant) of methoxy benzoin/benzil/stilbenoid derivatives. Organic Communications, vol.15, no.2, 2022, ss.129 - 147.
AMA	YAYLI N,Kahriman N,BOZDAL G,Serdaroğlu V,aliyazicioglu r,SELLİTEPE H,Alpay Karaoğlu Ş,Tatar Yılmaz G Molecular docking, synthesis and biological evaluation (enzyme inhibition, antimicrobial and antioxidant) of methoxy benzoin/benzil/stilbenoid derivatives. Organic Communications. 2022; 15(2): 129 - 147.
Vancouver	YAYLI N,Kahriman N,BOZDAL G,Serdaroğlu V,aliyazicioglu r,SELLİTEPE H,Alpay Karaoğlu Ş,Tatar Yılmaz G Molecular docking, synthesis and biological evaluation (enzyme inhibition, antimicrobial and antioxidant) of methoxy benzoin/benzil/stilbenoid derivatives. Organic Communications. 2022; 15(2): 129 - 147.
IEEE	YAYLI N,Kahriman N,BOZDAL G,Serdaroğlu V,aliyazicioglu r,SELLİTEPE H,Alpay Karaoğlu Ş,Tatar Yılmaz G "Molecular docking, synthesis and biological evaluation (enzyme inhibition, antimicrobial and antioxidant) of methoxy benzoin/benzil/stilbenoid derivatives." Organic Communications, 15, ss.129 - 147, 2022.
ISNAD	YAYLI, Nurettin vd. "Molecular docking, synthesis and biological evaluation (enzyme inhibition, antimicrobial and antioxidant) of methoxy benzoin/benzil/stilbenoid derivatives". Organic Communications 15/2 (2022), 129-147.