548-39-0Relevant articles and documents
Synthesis of perinaphthenones through rhodium-catalyzed dehydrative annulation of 1-naphthoic acids with alkynes
Fukuyama, Takahide,Sugimori, Taiki,Maetani, Shinji,Ryu, Ilhyong
, p. 7583 - 7587 (2018)
An efficient approach to the synthesis of perinaphthenones via the rhodium-catalyzed dehydrative annulation of 1-naphthoic acids with internal alkynes was developed. Norbornadiene can act as an acetylene equivalent to give unsubstituted perinaphthenones at the 2- and 3-positions via dehydrative annulation followed by a retro Diels-Alder reaction.
Synthesis and insecticidal evaluation of phytoalexin phenalenones derivatives
Zhang, Ya-Nan,Feng, Yi-An,Li, Zhong,Shao, Xu-Sheng
, p. 1228 - 1231 (2017)
Phenalenone is a kind of defensive compound biosynthesized inside plants in response to the outside attack such as fungus and nematodes. A set of derivatives encompassing structural modifications on the privileged phenalenone scaffold were synthesized through introduction of phenyl and hydroxyl substitutes at 9-positon and 2-position and assessed their insecticidal activities against armyworm (Mythimna separata Walker) and cowpea aphids (Aphis craccivora). No obvious insecticidal activities of the synthesized compounds were observed against armyworm. Some of the 9-phenyl and 2-hydroxy substituted phenalenone analogues showed potential activities against cowpea aphids with 33%–41% mortality at 500?mg/L.
A Green-Absorbing, Red-Fluorescent Phenalenone-Based Photosensitizer as a Theranostic Agent for Photodynamic Therapy
Kaye, Esther G.,Kailass, Karishma,Sadovski, Oleg,Beharry, Andrew A.
supporting information, p. 1295 - 1301 (2021/08/01)
Phenalenone is a synthetically accessible, highly efficient photosensitizer with a near-unity singlet oxygen quantum yield. Unfortunately, its UV absorption and lack of fluorescence has made it unsuitable for fluorescence-guided photodynamic therapy against cancer. In this work, we synthesized a series of phenalenone derivatives containing electron-donating groups to red-shift the absorption spectrum and bromine(s) to permit good singlet oxygen production via the heavy-atom effect. Of the derivatives synthesized, the phenalenone containing an amine at the 6-position with bromines at the 2- and 5-positions (OE19) exhibited the longest absorption wavelength (i.e., green) and produced both singlet oxygen and red fluorescence efficiently. OE19 induced photocytotoxicity with nanomolar potency in 2D cultured PANC-1 cancer cells as well as light-induced destruction of PANC-1 spheroids with minimal dark toxicity. Overall, OE19 opens up the possibility of employing phenalenone-based photosensitizers as theranostic agents for photodynamic cancer therapy.
