Synthesis of 1-(3-Chloropropyl)-4-nitroimidazole-2-carboxylic acid and N-Aminoalkylimidazole Containing Polyamides

Student Author(s)

Alex Porte, Hope CollegeFollow

Faculty Mentor(s)

Dr. Moses Lee, Hope College
Dr. Balaji Babu, Hope College
Dr. Sameer Chavda, Hope College

Document Type


Publication Date



The authors thank NSF for support.


One of the primary endeavors in modern medicinal chemistry is the development of drugs that can control specific gene expression. The naturally occurring polyamide distamycin is one such molecule that binds to A/T-rich sequences of DNA in the minor groove. By altering the number and arrangement of pyrrole and imidazole heterocycles in analogous polyamides, specific sequences can be targeted. The polyamides exhibit a wide range of binding affinities to their complementary DNA sequences. By adding amino pendants to the nitrogen atom of pyrrole within the polyamide, it is known that binding affinity is improved. In order to determine the optimal DNA binding affinity of a particular polyamide, it is necessary to include amino pendants on imidazoles as well. The focus of this research is to synthesize polyamides which contain N-aminoalkylimidazole groups and to discover the optimal number of pendant amino groups and their location within the polyamide, in regards to binding affinity.

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