DESIGN, SYNTHESIS, AND ANTICANCER EVALUATION OF SOME NOVEL THIOUREA, CARBAMIMIDOTHIOIC ACID, OXAZOLE, OXAZOLIDINE, AND 2-AMINO-1-PHENYLPROPYL-2-CHLOROACETATE DERIVED FROM L-NOREPHEDRINE
© 2016 Maged S. Abdel-Kader*, **, Mostafa M. Ghorab***, ****, #, Mansour S. Alsaid***, and Saleh I. Alqasoumi***
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*Department of Pharmacognosy, College of Pharmacy, Prince Sattam Bin Abdulaziz University, Saudi Arabia; **Department of Pharmacognosy, College of Pharmacy, Alexandria University, Alexandria, Egypt; ***Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh, 11451 Saudi Arabia; ****Department of Drug Radiation Research, National Center for Radiation Research and Technology, P.O. Box 29, Nasr City, Cairo, Egypt
Received February 8, 2016; in final form, March 6, 2016
A novel series of thiourea, carbamimidothioic acid, 4, 5-dihydrooxazole-2-thiol, oxazolidine-2-thine, and 2-amino-1-phenylpropyl-2-chloroacetate derivatives was designed and synthesized using 2-amino-1-phenylpropan-1-ol (L-norephedrine) as a strategic starting material. The structures of the newly synthesized compounds were established by elemental analyses, IR, and 1H NMR and 13C NMR spectral data. The compounds were evaluated for their in vitro anticancer activity against various cancer cell lines. The corresponding acetamide, carbamimidothioic acid, and 2-2-amino-1-phenylpropyl-2-chloroacetate derivatives showed almost the same activity as the standard drug doxorubicin against human breast cancer cell line (MCF-7). Also, the acetamide and 2-thioxoimidazolidin-4-one derivatives exhibited higher activity than the reference drug doxorubicin against human colon cancer cell line (HCT 116).
Keywords: thiourea carbamimidothioic acid, oxazole, oxazolidine, 2-amino-1-phenylpropyl-2-chloroacetate, anticancer activity.
Биоорг. химия 2016, 42 (4): 481-487