Synthesis and anti-barnacle activities of novel isocyanocyclohexane compounds containing an ester or an ether functional group.
Ten novel isocyanocyclohexane compounds that possess an oxygenic functional group at the 4-position were synthesized and evaluated for their antifouling activity against the larvae of the barnacle Balanus amphitrite with the aim of exploring the structure-activity relationships further. The anti-barnacle effect of the synthesized compounds was in the EC50 range of 0.0096-17.0 microg ml(-1). Some ester derivatives exhibited extremely high antifouling activities, and none of the synthesized isocyanocyclohexane compounds showed significant toxicity. The results suggest that the ester function is one of the important groups in the expression of potent antifouling activity in isocyano compounds.
Kitano
Yoshikazu
Y
Laboratory of Bio-organic Chemistry Tokyo University of Agriculture and Technology 3-5-8 Saiwai-cho Fuchu Tokyo 183-8509 Japan. kitayo@cc.tuat.ac.jp
Nogata
Yasuyuki
Y
Shinshima
Kyouji
K
Yoshimura
Erina
E
Chiba
Kazuhiro
K
Tada
Masahiro
M
Sakaguchi
Isamu
I
D000818:Animals; D003486:Cyanides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D003510:Cyclohexanes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D007814:Larva / Q000187:drug effects; D008386:Marine Biology; D013329:Structure-Activity Relationship; D001468:Thoracica / Q000187:drug effects* / Q000254:growth & development
D003486:Cyanides; D003510:Cyclohexanes