SYNTHESIS AND ANTICANCER ACTIVITY TOWARDS HEPG-2 AND MCF-7 OF NEW 2-AMINO-1,3,4-THIADIAZOLE AND THEIR SUGAR DERIVATIVES

Samy A. El Assaly; Nagwan S. El Bakary; Mohammed T. Abdel Aal; Wael A. El-Sayed; Ibrahim F. Nassar; Hanem M. Awad

doi:10.22270/ujpr.v7i2.755

Samy A. El Assaly Natural and Microbial Products Chemistry Department, National Research Center (NRC), Dokki, Giza, Egypt.
Nagwan S. El Bakary Chemistry Department, Faculty of Science, Menoufia University, Shebin El-Kom, Egypt.
Mohammed T. Abdel Aal Chemistry Department, Faculty of Science, Menoufia University, Shebin El-Kom, Egypt.
Wael A. El-Sayed Natural and Microbial Products Chemistry Department, National Research Center (NRC), Dokki, Giza, Egypt. Department of chemistry, College of Science, Qassim University, KSA. PhotochemistryDepartment, National Research Centre, El-Behouth St, Dokki, Cairo, Egypt.
Ibrahim F. Nassar Faculty of Specific Education, Ain Shams University (ASU), 365 Ramsis street, Abassia, Cairo, Egypt.
Hanem M. Awad Tanning Materials and Leather Technology Department, National Research Centre, Dokki, Cairo, Egypt.

10.22270/ujpr.v7i2.755

Keywords:

1,3,4-Thiadiazol-2-amine, Cytotoxicity, HepG-2, MCF-7, Thiosemicarbazide

Abstract

Background: In recent papers, it was found that 1,3,4-oxadiazole, 1,3,4-thiadiazoleand 1,2,4-triazole pharmacophores are present in several drugs, tiodazosin and nesapidil (antihypertensive), raltegravir (antiretroviral), Furamizole, cefazolin and ceftezole (antibiotics), acetazolamide and methazolamide (carbonic anhydrase inhibitors), sulfamethizole (antibacterial), fluconazole, ravuconazole, voriconazole, itraconazole, posaconazole, and tebuconazole (antifungal).

Methods: Thiosemicarbazide was reacted with ethyl p-substituted-phenyl glycinate; namely, ethyl p-tolylglycinate (1), ethyl p-methoxyphenylglycinate (2) or ethyl p-bromophenylglycinate (3), respectively to give compounds 4-6, which then kept with conc. H₂SO₄ overnight to yield 1,3,4-thiadiazol-2-amine derivatives 7-9. Compounds 10-18 were yielded by reaction of compounds 7-9 with D-sugars namely, D-galactose, D-glucose and/ or D-xylose in ethanol and catalytic amount of acetic acid. Compounds (10-18) were then acetylated with acetic anhydride to form compounds (19-21). Finely compound 7 was reacted with chloroacetyl chloride and/or acetic anhydride to afford compounds 22 and/or 23 respectively.

Results: Six compounds were evaluated in vitro for their cytotoxic activity on the HepG-2 and MCF-7 human cancer cell lines.

Conclusion: Among the tested compounds, compounds 6 and 13 were found to be the more potent for their cytotoxic activity on the two cancer cell lines.