Synthesis, Characterization, and Investigation of Antimicrobial Activities of New Naphthoquinone Compounds from 2-(butylthio)-3-chloronaphthalene-1,4-dione

Year 2023, Volume: 8 Issue: 2, 156 - 168, 28.12.2023

Şenol Yavuz

https://doi.org/10.33484/sinopfbd.1362604

Abstract

In this study, the compound 2-(butylthio)-3-chloronaphthalene-1,4-dione (3) was synthesized from the reaction of the compound 2,3-dichloro-1,4-naphthoquinone (1) with 1-butanethiol in alkaline medium. The synthesized compound 2-(butylthio)-3-chloronaphthalene-1,4-dione (3) was used as the starting compound. As a result of the nucleophilic substitution of 2-(butylthio)-3-chloronaphthalene-1,4-dione (3) with heterocyclic compounds containing nitrogen, sulfur, and oxygen atoms, a series of 10, 11, 12, 13, 14, 15, naphthoquinone derivative compounds were synthesized. The structures of the synthesized compounds were characterized by FTIR, 13C-NMR, 1H-NMR, and Mass Spectroscopy techniques. The antimicrobial properties of the synthesized compounds were examined by performing antimicrobial studies with Gram-positive and Gram-negative bacteria. The compound 2-(butylthio)-3-chloronaphthalene-1,4-dione (3) shows the highest antimicrobial activity, whereas the compound 2-(butylthio)-3-((4,5-dihydrothiazol-2-yl)thio) naphhalene-1,4-dione (10) exhibits the lowest antimicrobial activity. Compounds 3, 11, 12, 13, 14, and 15 exhibited enhanced activity against Gram-positive bacteria, such as B. subtilis and S. aureus, as well as Gram-negative E. coli and K. pneumoniae. In addition, compounds 11, 12, and 14 exhibited activity against Gram-positive B. subtilis and S. aureus, as well as Gram-negative E. coli, K. pneumoniae, and P. aeruginosa. The study aims to enhance existing literature research and create new unknown compounds through synthesis.

Keywords

Substituted quinones, nucleophilic substitution, antimicrobial activity

Project Number

Hitit Üniversitesi Bilimsel Araştırmalar Koordinatörlüğü, Proje No: ODMYO19001.19.001

2-(Butiltiyo)-3-Kloronaftalen-1,4-Dion Bileşiğinden Yeni Naftakinon Bileşiklerin Sentezi, Karakterizasyonu ve Antimikrobiyal Aktivitelerinin İncelenmesi

Abstract

Bu çalışmada, 2,3-dikloro-1,4-naftakinon (1) bileşiğinin alkali ortamda 1-butantiyol ile reaksiyoundan 2-(butiltiyo)-3-kloronaftalen-1,4-dion (3) bileşiği sentezlendi. Sentezlenen 2-(butiltiyo)-3-kloronaftalen-1,4-dion (3) bileşiği başlangıç bileşiği olarak kullanıldı. 2-(butiltiyo)-3-kloronaftalen-1,4-dion (3) bileşiğin azot, kükürt ve oksijen atomu içeren heterosiklik bileşikler ile nükleofilik sübstitüsyonu sonucu bir seri 10, 11, 12, 13, 14, 15, naftakinon türevi bileşikler sentezlendi. Sentezlenen bileşiklerin yapıları FTIR, 13C NMR, 1H NMR ve Mass Spektroskopisi ile karakterize edildi. Sentezlenen bileşiklerin Gram pozitif ve Gram negative bakteriler ile antimikrobiyal çalışması yapılarak antimikrobiyal özellikleri incelendi. 2-(butiltiyo)-3-kloronaftalen-1,4-dion (3) bileşiğinin antimikrobiyal aktivitesi en yüksek, 2-(butylthio)-3-((2,5-dihydrothiazol-5-yl) thio) naphthalene-1,4-dione (10) bileşiğinin antimikrobiyal aktivitesi en düşük olarak gözlenmiştir. 3, 11, 12, 13, 14 ve 15 bileşikleri, Gram-pozitif B. subtilis ve S. aureus ile Gram-negatif E. coli, K. pneumoniae 'ye karşı daha iyi aktivite göstermiştir. Ayrıca, 11, 12 ve 14 bileşikleri Gram-pozitif B. subtilis ve S. aureus ile Gram-negatif E. coli, K. pneumoniae ve P. aeruginosa'ya karşı aktivite gösterdi. Bu çalışma ile literatürde olan çalışmaların geliştirilmesi ve bilinmeyen yeni bileşiklerin sentezlenmesi amaçlanmıştır.

Keywords

Sübstitüe kinonlar, nükleofilik sübstitüsyon, antimikrobiyal aktivite

Ethical Statement

The study does not require ethics committee approval or any special permission.

Supporting Institution

Hitit Üniversitesi Bilimsel Araştırmalar Koordinatörlüğü

Project Number

Hitit Üniversitesi Bilimsel Araştırmalar Koordinatörlüğü, Proje No: ODMYO19001.19.001

Thanks

I would like to express my gratitude to Assoc. Prof. Dr. Demet TATAR from Hitit University and Assoc. Prof. Dr Aysel VEYİSOĞLU from Sinop University for their assistance in conducting and inter-preting the antimicrobial studies of the synthesized compounds

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