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***

^#Phone: + 966-534292860; fax: +966014670560; e-mail: [email protected]

*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