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Design and Synthesis of Potential Anticancer Agents

Zhang, Weihe
http://rave.ohiolink.edu/etdc/view?acc_num=ohiou1288896777

Abstract Details

2010, Doctor of Philosophy (PhD), Ohio University, Chemistry and Biochemistry (Arts and Sciences).
Most cancers mainly rely on glucose as a source of biosynthesis material and energy for their fast growth and proliferation. We proposed inhibiting glucose uptake might kill cancer cells by restricting their energy supply. Based on this hypothesis, we designed and synthesized small molecules which can inhibit the glucose uptake and cell growth in lung cancer line H1299. These small molecules acted as potential novel anticancer agents. First, we designed and synthesized phenolic benzoate esters, from which most compounds displayed mild to good inhibitory activity in glucose uptake and cell growth. The Structure-Activity-Relationship (SAR) was studied by changing different substituents on the core aromatic ring and the pendant aromatic rings, as well as changing the number of hydroxyl groups on the pendant aromatic rings. SAR showed the meta-hydroxyl group played an important role in both inhibitory activity. Due to the instability of the benzoate esters, we designed and synthesized hydrolytically more stable analogs-phenolic ethers, N-linked and S-linked phenolic derivatives. The phenolic ethers showed better inhibitory activity than the N-linked and S-linked phenolic analogs. Finally, the nitro phenolic ether WZB-173 was selected as the lead compound.
Stephen C Bergmeier, PhD (Advisor)
Xiaozhuo Chen, PhD (Committee Member)
Mark C McMills, PhD (Committee Member)
Shiyong Wu, PhD (Committee Member)
233 p.
Biochemistry; Chemistry
Anticancer; GLUT1; Glucose uptake, Inhibitory activity; Polyphenols; phenlic ether; phenolic amide; phenolic amine; Glucose transporter;

Recommended Citations

Citations

  • Zhang, W. (2010). Design and Synthesis of Potential Anticancer Agents [Doctoral dissertation, Ohio University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=ohiou1288896777

    APA Style (7th edition)

  • Zhang, Weihe. Design and Synthesis of Potential Anticancer Agents. 2010. Ohio University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=ohiou1288896777.

    MLA Style (8th edition)

  • Zhang, Weihe. "Design and Synthesis of Potential Anticancer Agents." Doctoral dissertation, Ohio University, 2010. http://rave.ohiolink.edu/etdc/view?acc_num=ohiou1288896777

    Chicago Manual of Style (17th edition)

ohiou1288896777
3,364
© 2010, all rights reserved.
This open access ETD is published by Ohio University and OhioLINK.