2026-09-22T20:33:47Z https://www.ideals.illinois.edu/oai-pmh

oai:www.ideals.illinois.edu:2142/67237 2023-07-11 col_2142_5131 col_2142_14789 com_2142_5130 com_2142_14788 com_2142_8903

Cheng, Michael Tung-Hai 2014-12-13T20:11:00Z 2014-12-13T20:11:00Z 10000-01-01 1980 1980 The marine tunicate Polyandrocarpa sp. contains anti-microbial and cytotoxic metabolites, polyandrocarpidines, whose structures include a polymethylenediamine chain; one nitrogen is acylated with a twelve-carbon fatty acid which contains a cyclopropene ring in conjugation with a diene system, the other nitrogen is part of a primary guanidine function. It was advantageous to convert the guanidine to the dimethylpyrimidyl moiety by condensing with 2,4-pentanedione in the presence of sodium bicarbonate, because the dimethylpyrimidyl derivatives can be gas chromatographed, and the dimethylpyrimidyl moiety institutes very characteristic mass spectrometric fragmentations for the rest of the molecule. Attempts to synthesize polyandrocarpidines were unsuccessful; however, hexahydropolyandrocarpidines were synthesized. Therefore, various analogs of hexahydropolyandrocarpidine were synthesized to study the structure-activity relationship against Bacillus subtilis. It was determined that the compound with five methylene groups between the two nitrogens has the highest activity, that the cyclopropane ring is not required for activity but its presence enhances the antimicrobial activity, and that the chain length of the acyl part is important to the activity. Made available in DSpace on 2014-12-13T20:11:00Z (GMT). No. of bitstreams: 1 8108462.pdf: 4396998 bytes, checksum: 3d4d0142b1a7d626309208b256ec2cfb (MD5) Previous issue date: 1980 Embargo set by: Seth Robbins for item 67415 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs U of I Only 170 p. Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1980. http://hdl.handle.net/2142/67237 (UMI)AAI8108462 eng Chemistry, Organic Polyandrocarpidines: Antimicrobial and Cytotoxic Compounds From the Marine Tunicate Polyandrocarpa Sp text Chemistry Chemistry University of Illinois at Urbana-Champaign Dissertation Ph.D.