Synthesis and evaluation of bile acid amides of $$\alpha $$ α -cyanostilbenes as anticancer agents
| Autor: | Rajdeep Chowdhury, Devesh S. Agarwal, K. Lohitesh, Rajeev Sakhuja, Prabhat Jha, Rajnish Prakash Singh |
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| Rok vydání: | 2017 |
| Předmět: |
0301 basic medicine
Bile acid Stereochemistry medicine.drug_class Organic Chemistry Deoxycholic acid Cholic acid Alpha (ethology) General Medicine Catalysis Inorganic Chemistry Cell cycle analysis 03 medical and health sciences chemistry.chemical_compound 030104 developmental biology 0302 clinical medicine chemistry 030220 oncology & carcinogenesis Drug Discovery medicine Physical and Theoretical Chemistry Cancer cell lines Molecular Biology Information Systems |
| Zdroj: | Molecular Diversity. 22:305-321 |
| ISSN: | 1573-501X 1381-1991 |
| Popis: | A series of amino-substituted $$\alpha $$ -cyanostilbene derivatives and their bile acid (cholic and deoxycholic acid) amides were designed and synthesized. A comparative study on the anticancer and antibacterial activity evaluation on the synthesized analogs was carried against the human osteosarcoma (HOS) cancer cell line, and two gram −ve (E. coli and S. typhi) and two gram $$+$$ ve (B. subtilis and S. aureus) bacterial strains. All the cholic acid $$\alpha $$ -cyanostilbene amides showed an $$\hbox {IC}_{50}$$ in the range 2–13 $$\upmu \hbox {M}$$ against human osteosarcoma cells (HOS) with the most active analog (6g) possessing an $$\hbox {IC}_{50}$$ of $$2\,\upmu \hbox {M}$$ . One of the amino-substituted $$\alpha $$ -cyanostilbene, 4e, was found to possess an $$\hbox {IC}_{50}$$ of $$3\,\upmu \hbox {M}$$ . An increase in the number of cells at the sub- $$\hbox {G}_{1}$$ phase of the cell was observed in the in vitro cell cycle analysis of two most active compounds in the series (4e, 6g) suggesting a clear indication toward induction of apoptotic cascade. With respect to antibacterial screening, amino-substituted $$\alpha $$ -cyanostilbenes were found to be more active than their corresponding bile acid amides. The synthesized compounds were also subjected to in silico study to predict their physiochemical properties and drug-likeness score. |
| Databáze: | OpenAIRE |
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