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Aly MR, Saad HA, Abdel-Hafez SH. Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners. Beilstein J Org Chem. 2015;11:1922-32doi: 10.3762/bjoc.11.208.
Aly, M. R., Saad, H. A., & Abdel-Hafez, S. H. (2015). Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners. Beilstein journal of organic chemistry, 111922-32. https://doi.org/10.3762/bjoc.11.208
Aly, Mohamed Ramadan El Sayed, et al. "Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners." Beilstein journal of organic chemistry vol. 11 (2015): 1922-32. doi: https://doi.org/10.3762/bjoc.11.208
Aly MR, Saad HA, Abdel-Hafez SH. Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners. Beilstein J Org Chem. 2015 Oct 16;11:1922-32. doi: 10.3762/bjoc.11.208. eCollection 2015. PMID: 26664612; PMCID: PMC4661006.
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Beilstein J Org Chem. 2015 Oct 16;11:1922-32. doi: 10.3762/bjoc.11.208. eCollection 2015.

Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners.

Beilstein journal of organic chemistry

Mohamed Ramadan El Sayed Aly, Hosam Ali Saad, Shams Hashim Abdel-Hafez

Affiliations

  1. Chemistry Department, Faculty of Science, Taif University, 21974-Hawyah-Taif, Kingdom of Saudi Arabia ; Chemistry Department, Faculty of Applied Science, Port Said University, 42522-Port Said, Egypt.
  2. Chemistry Department, Faculty of Science, Taif University, 21974-Hawyah-Taif, Kingdom of Saudi Arabia ; Chemistry Department, Faculty of Science, Zagazig University, Zagazig, 44511, Egypt.
  3. Chemistry Department, Faculty of Science, Taif University, 21974-Hawyah-Taif, Kingdom of Saudi Arabia ; Chemistry Department, Faculty of Science, Assuit University, 71516-Assuit, Egypt.

PMID: 26664612 PMCID: PMC4661006 DOI: 10.3762/bjoc.11.208

Abstract

3β-Azidocholest-5-ene (3) and (3β)-3-(prop-2-yn-1-yloxy)cholest-5-ene (10) were prepared as substrates to synthesize a variety of three-motif pharmacophoric conjugates through CuAAC. Basically, these conjugates included cholesterol and 1,2,3-triazole moieties, while the third, the pharmacophore, was either a chalcone, a lipophilic residue or a carbohydrate tag. These compounds were successfully prepared in good yields and characterized by NMR, MS and IR spectroscopic techniques. Chalcone conjugate 6c showed the best antimicrobial activity, while the lactoside conjugate 27 showed the best cytotoxic effect in vitro.

Keywords: antimicrobial; chalcone; cholesterol; cytotoxicity; glycoside; triazole

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