Bromination and conversion of tetrahydro-1H-indene to bisoxirane with a new approach: synthesis, structural characterization by spectroscopic and theoretical methods, and biological analysis supported by DFT and docking

YILMAZ, RAŞİT FİKRET; erkan, sultan; Ökten, Salih; Tutar, Ahmet; Sahin, Ertan

doi:10.55730/1300-0527.3628

Bromination and conversion of tetrahydro-1H-indene to bisoxirane with a new approach: synthesis, structural characterization by spectroscopic and theoretical methods, and biological analysis supported by DFT and docking

Raşit Fikret YILMAZ, (Milli Savunma Üniversitesi, Deniz Harp Okulu, Temel Bilimler Bölümü, İstanbul, Türkiye)

Sultan ERKAN, (Sivas Cumhuriyet Üniversitesi, Fen Fakültesi, Kimya Bölümü, Sivas, Türkiye)

Salih ÖKTEN, (Kırıkkale Üniversitesi, Eğitim Fakültesi, Matematik ve Fen Bilimleri Eğitimi Bölümü, Kırıkkale, Türkiye)

Ahmet TUTAR, (Sakarya Üniversitesi, Fen Fakültesi, Kimya Bölümü, Sakarya, Türkiye)

Ertan ŞAHİN (Atatürk Üniversitesi, Fen Fakültesi, Kimya Bölümü, Erzurum, Türkiye)

Turkish Journal of Chemistry

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Yıl: 2023 Cilt: 47 Sayı: 6 Sayfa Aralığı: 1459 - 1478 Metin Dili: İngilizce DOI: 10.55730/1300-0527.3628 İndeks Tarihi: 16-01-2024

Bromination and conversion of tetrahydro-1H-indene to bisoxirane with a new approach: synthesis, structural characterization by spectroscopic and theoretical methods, and biological analysis supported by DFT and docking

Öz:

In this study, a new method for synthesizing diepoxides is proposed. Tetrahydroindene 1 was brominated with NBS in the presence of LiClO4 and acetic acid, resulting in the formation of dibromodiacetate derivatives 2 and 3. Treatment of compounds 2 and 3 with NaOH in methanol produced a mixture of diepoxides 4 and 5. Additionally, direct bromination of tetrahydro-1H-indene yielded tetrabromo octahydroindene isomers 6 and 7. The structures of the compounds were characterized using spectroscopic techniques such as 1H NMR, 13C NMR, APT, COSY, and XRD. The new method provides an easy and selective route to access epoxides for the synthesis of various chemicals. This study also highlights the selective formation of endo-exo and exo-exo orientations of the obtained diepoxides, distinguishing it from previous studies. The stability and properties of the stereoisomers were investigated using computational methods, revealing the most stable configurations. Reactive sites in the molecules were identified using contour diagrams and molecular electrostatic potential maps. The anticancer properties of the compounds were evaluated in silico, comparing them to 5-fluorouracil (5-FU) against several cancer cell lines. The compounds exhibited the most effective anticancer activity against MCF-7 cells, with the order of anticancer activities generally determined as 2 > 7 > 3 > 6 > 5 > 4 > 5-FU.

Anahtar Kelime: Octahydroindene dibromodiacetate diepoxide tetrabromo octahydroindene density functional theory molecular docking

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

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APA	YILMAZ R, erkan s, Ökten S, Tutar A, Sahin E (2023). Bromination and conversion of tetrahydro-1H-indene to bisoxirane with a new approach: synthesis, structural characterization by spectroscopic and theoretical methods, and biological analysis supported by DFT and docking. , 1459 - 1478. 10.55730/1300-0527.3628
Chicago	YILMAZ RAŞİT FİKRET,erkan sultan,Ökten Salih,Tutar Ahmet,Sahin Ertan Bromination and conversion of tetrahydro-1H-indene to bisoxirane with a new approach: synthesis, structural characterization by spectroscopic and theoretical methods, and biological analysis supported by DFT and docking. (2023): 1459 - 1478. 10.55730/1300-0527.3628
MLA	YILMAZ RAŞİT FİKRET,erkan sultan,Ökten Salih,Tutar Ahmet,Sahin Ertan Bromination and conversion of tetrahydro-1H-indene to bisoxirane with a new approach: synthesis, structural characterization by spectroscopic and theoretical methods, and biological analysis supported by DFT and docking. , 2023, ss.1459 - 1478. 10.55730/1300-0527.3628
AMA	YILMAZ R,erkan s,Ökten S,Tutar A,Sahin E Bromination and conversion of tetrahydro-1H-indene to bisoxirane with a new approach: synthesis, structural characterization by spectroscopic and theoretical methods, and biological analysis supported by DFT and docking. . 2023; 1459 - 1478. 10.55730/1300-0527.3628
Vancouver	YILMAZ R,erkan s,Ökten S,Tutar A,Sahin E Bromination and conversion of tetrahydro-1H-indene to bisoxirane with a new approach: synthesis, structural characterization by spectroscopic and theoretical methods, and biological analysis supported by DFT and docking. . 2023; 1459 - 1478. 10.55730/1300-0527.3628
IEEE	YILMAZ R,erkan s,Ökten S,Tutar A,Sahin E "Bromination and conversion of tetrahydro-1H-indene to bisoxirane with a new approach: synthesis, structural characterization by spectroscopic and theoretical methods, and biological analysis supported by DFT and docking." , ss.1459 - 1478, 2023. 10.55730/1300-0527.3628
ISNAD	YILMAZ, RAŞİT FİKRET vd. "Bromination and conversion of tetrahydro-1H-indene to bisoxirane with a new approach: synthesis, structural characterization by spectroscopic and theoretical methods, and biological analysis supported by DFT and docking". (2023), 1459-1478. https://doi.org/10.55730/1300-0527.3628

APA	YILMAZ R, erkan s, Ökten S, Tutar A, Sahin E (2023). Bromination and conversion of tetrahydro-1H-indene to bisoxirane with a new approach: synthesis, structural characterization by spectroscopic and theoretical methods, and biological analysis supported by DFT and docking. Turkish Journal of Chemistry, 47(6), 1459 - 1478. 10.55730/1300-0527.3628
Chicago	YILMAZ RAŞİT FİKRET,erkan sultan,Ökten Salih,Tutar Ahmet,Sahin Ertan Bromination and conversion of tetrahydro-1H-indene to bisoxirane with a new approach: synthesis, structural characterization by spectroscopic and theoretical methods, and biological analysis supported by DFT and docking. Turkish Journal of Chemistry 47, no.6 (2023): 1459 - 1478. 10.55730/1300-0527.3628
MLA	YILMAZ RAŞİT FİKRET,erkan sultan,Ökten Salih,Tutar Ahmet,Sahin Ertan Bromination and conversion of tetrahydro-1H-indene to bisoxirane with a new approach: synthesis, structural characterization by spectroscopic and theoretical methods, and biological analysis supported by DFT and docking. Turkish Journal of Chemistry, vol.47, no.6, 2023, ss.1459 - 1478. 10.55730/1300-0527.3628
AMA	YILMAZ R,erkan s,Ökten S,Tutar A,Sahin E Bromination and conversion of tetrahydro-1H-indene to bisoxirane with a new approach: synthesis, structural characterization by spectroscopic and theoretical methods, and biological analysis supported by DFT and docking. Turkish Journal of Chemistry. 2023; 47(6): 1459 - 1478. 10.55730/1300-0527.3628
Vancouver	YILMAZ R,erkan s,Ökten S,Tutar A,Sahin E Bromination and conversion of tetrahydro-1H-indene to bisoxirane with a new approach: synthesis, structural characterization by spectroscopic and theoretical methods, and biological analysis supported by DFT and docking. Turkish Journal of Chemistry. 2023; 47(6): 1459 - 1478. 10.55730/1300-0527.3628
IEEE	YILMAZ R,erkan s,Ökten S,Tutar A,Sahin E "Bromination and conversion of tetrahydro-1H-indene to bisoxirane with a new approach: synthesis, structural characterization by spectroscopic and theoretical methods, and biological analysis supported by DFT and docking." Turkish Journal of Chemistry, 47, ss.1459 - 1478, 2023. 10.55730/1300-0527.3628
ISNAD	YILMAZ, RAŞİT FİKRET vd. "Bromination and conversion of tetrahydro-1H-indene to bisoxirane with a new approach: synthesis, structural characterization by spectroscopic and theoretical methods, and biological analysis supported by DFT and docking". Turkish Journal of Chemistry 47/6 (2023), 1459-1478. https://doi.org/10.55730/1300-0527.3628