Synthesis and Structure?Activity Relationship of Omaezallene Derivatives
Synthesis and Structure?Activity Relationship of Omaezallene Derivatives
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Omaezallene衍生物的合成及构效关系
DOI：
10.1002/cbdv.201800451
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发表时间：
2019
影响因子：
2.9
通讯作者：
Matsuda Fuyuhiko
中科院分区：
文献类型：
--
作者：
Umezawa Taiki;Prakoso Nurcahyo Iman;Kannaka Miho;Nogata Yasuyuki;Yoshimura Erina;Okino Tatsufumi;Matsuda Fuyuhiko
成功地合成了三种新的Omaezallene衍生物(去溴烯丙烯、去溴二烯和溴烯炔类)。研究了它们的抗污活性、对两栖藤壶幼虫的毒性和对海洋甲壳类老虎的生态毒性。结果表明，Omaazallene的两个侧链对其阻垢活性是必需的，因为Nor-Bromoallene和Nor-Brobiene的活性显著降低。结果表明，该化合物具有与奥美沙林相当的高效防污活性，且毒性和生态毒性均较低。在Omaazallene中，溴烯炔骨架的制备比溴二烯骨架的制备容易得多。在此基础上，合成了荧光探针，并对其生物活性进行了评价。
Omaezallene derivatives (nor‐bromoallene,nor‐bromodiene, and bromoenynes) were successfully synthesized. Their antifouling activity and toxicity to the cypris larvae of the barnacleAmphibalanus amphitriteand ecotoxicity to the marine crustaceanTigriopus japonicuswere studied. It was revealed that the two side chains of omaezallene were essential to its antifouling activity because the activities ofnor‐bromoallene andnor‐bromodiene were significantly diminished. The bromoenyne was found to exhibit potent antifouling activities comparable to omaezallene with low toxicity and ecotoxicity. Preparation of bromoenyne framework is much easier than that of bromodiene moiety in omaezallene. Based on the antifouling activities of the bromoenynes, the synthesis of fluorescent probes and evaluation of their biological activities were also carried out.