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3-(2-氨基恶唑-5-基)-2H-色烯-2-酮衍生物的设计、合成及生物学评价

Design, synthesis and biological evaluation of 3-(2-aminooxazol-5-yl)-2H-chromen-2-one derivatives.

作者信息

Kakkar Saloni, Kumar Sanjiv, Lim Siong Meng, Ramasamy Kalavathy, Mani Vasudevan, Shah Syed Adnan Ali, Narasimhan Balasubramanian

机构信息

Faculty of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak, 124001, India.

Faculty of Pharmacy, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300, Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia.

出版信息

Chem Cent J. 2018 Dec 4;12(1):130. doi: 10.1186/s13065-018-0499-x.

DOI:10.1186/s13065-018-0499-x
PMID:30515643
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6768039/
Abstract

BACKGROUND

In view of wide range of biological activities of oxazole, a new series of oxazole analogues was synthesized and its chemical structures were confirmed by spectral data (Proton/Carbon-NMR, IR, MS etc.). The synthesized oxazole derivatives were screened for their antimicrobial and antiproliferative activities.

RESULTS AND DISCUSSION

The antimicrobial activity was performed against selected fungal and bacterial strains using tube dilution method. The antiproliferative potential was evaluated against human colorectal carcinoma (HCT116) and oestrogen- positive human breast carcinoma (MCF7) cancer cell lines using Sulforhodamine B assay and, results were compared to standard drugs, 5-fluorouracil and tamoxifen, respectively.

CONCLUSION

The performed antimicrobial activity indicated that compounds 3, 5, 6, 8 and 14 showed promising activity against selected microbial species. Antiproliferative screening found compound 14 to be the most potent compound against HCT116 (IC = 71.8 µM), whereas Compound 6 was the most potent against MCF7 (IC = 74.1 µM). Further, the molecular docking study has been carried to find out the interaction between active oxazole compounds with CDK8 (HCT116) and ER-α (MCF7) proteins indicated that compound 14 and 6 showed good dock score with better potency within the ATP binding pocket and may be used as a lead for rational drug designing of the anticancer molecule.

摘要

背景

鉴于恶唑具有广泛的生物活性，合成了一系列新的恶唑类似物，并通过光谱数据（质子/碳核磁共振、红外光谱、质谱等）确认了其化学结构。对合成的恶唑衍生物进行了抗菌和抗增殖活性筛选。

结果与讨论

采用试管稀释法对选定的真菌和细菌菌株进行抗菌活性测试。使用磺酰罗丹明B测定法评估对人结肠直肠癌（HCT116）和雌激素阳性人乳腺癌（MCF7）癌细胞系的抗增殖潜力，并将结果分别与标准药物5-氟尿嘧啶和他莫昔芬进行比较。

结论

所进行的抗菌活性表明，化合物3、5、6、8和14对选定的微生物物种显示出有前景的活性。抗增殖筛选发现化合物14是对HCT116最有效的化合物（IC = 71.8 μM），而化合物6对MCF7最有效（IC = 74.1 μM）。此外，进行了分子对接研究以找出活性恶唑化合物与CDK8（HCT116）和ER-α（MCF7）蛋白之间的相互作用，结果表明化合物14和6在ATP结合口袋内显示出良好的对接分数和更好的效力，可作为抗癌分子合理药物设计的先导。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c31/6768039/76d920816462/13065_2018_499_Fig10_HTML.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c31/6768039/03ec29ad9e62/13065_2018_499_Fig9_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c31/6768039/76d920816462/13065_2018_499_Fig10_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c31/6768039/4971acbdf363/13065_2018_499_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c31/6768039/231342b8b12a/13065_2018_499_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c31/6768039/a8671f6f057b/13065_2018_499_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c31/6768039/00d3dda3ed25/13065_2018_499_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c31/6768039/ce6d5fe33ca2/13065_2018_499_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c31/6768039/35a3797da47f/13065_2018_499_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c31/6768039/47e27f571ca2/13065_2018_499_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c31/6768039/ebf26fc65926/13065_2018_499_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c31/6768039/7aca1e0587e6/13065_2018_499_Fig8_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c31/6768039/03ec29ad9e62/13065_2018_499_Fig9_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c31/6768039/76d920816462/13065_2018_499_Fig10_HTML.jpg

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