Tổng hợp và đánh giá độc tính đối với tế bào của một số dẫn xuất naphthalenyl-benzimidazole
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Abstract
field with many pharmacological activitives such as antiinflamatory, antimicrobial, antiviral, antidiabetic and anticancer activity. In this study, four naphthalenyl-benzimidazole derivatives have been successfully synthesized in good yield through a fivestep sequence starting from 2,5‑dimethoxybenzaldehyde. The synthesis made use of the Stobbe condensation followed by cyclization to afford the ethyl 4-acetoxy-5,8-dimethoxy-2-naphthoate core. The ethyl ester moiety was then further converted into the corresponding aldehyde which was then condensed with o‑phenylenediamine and o-nitroaniline derivatives under different conditions to provide 2-naphthalyl-1H-benzimidazole derivatives. The structures of these new compounds were fully confirmed by various spectroscopic methods such as MS, IR, 1H-NMR and 13C-NMR. Cytotoxicity evaluation of two derivatives named 5,8-dimethoxy-3-(5-methyl-1H-benzo[d]imidazol-2-yl)naphthalene-1-ol (6a) and 3-(1H-benzo[d]imidazol-2-yl)-5,8-dimethoxynaphthalen-1-ol (7a) showed that these two compounds possess weak activity against Mouse skin B16 melanoma cell line.
Tóm tắt
trong lĩnh vực y học với nhiều hoạt tính dược lý như kháng viêm, kháng khuẩn, kháng virus, chống đái tháo đường và kháng ung thư. Trong nghiên cứu này, bốn dẫn xuất naphthalene-benzimidazole đã được tổng hợp thành công với hiệu suất tốt qua năm bước bắt đầu từ 2,5-dimethoxybenzaldehyde. Phương pháp tổng hợp sử dụng phản ứng ngưng tụ Stobbe, sau đó đóng vòng tạo khung sườn ethyl-4-acetoxy-5,8-dimethoxy-2-napthoate. Chuyển hóa nhóm chức ethyl ester thành nhóm aldehyde, sau đó ngưng tụ với các dẫn xuất o-phenyldiamine và o-nitroaniline trong những điều kiện khác nhau để tạo thành các dẫn xuất 2-naphthalyl-1H-benzimidazole tương ứng. Cấu trúc của các hợp chất này được xác nhận đầy đủ bằng một số phương
pháp quang phổ như phổ MS, IR, 1H-NMR và 13C-NMR. Kết quả đánh giá độc tính đối với tế bào ung thư cho thấy hai dẫn xuất
5,8-dimethoxy-3-(5-methyl-1H-benzo[d]imidazol-2-yl)naphthalene-1-ol (6a) và 3-(1H-benzo[d]imidazol-2-yl)-5,8-dimethoxynaphthalen-1-ol (7a) thể hiện độc tính yếu đối với dòng tế bào ung thư da ác tính Mouse skin B16 melanoma.
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