87580-07-2Relevant academic research and scientific papers
Synthesis and biological evaluation of purealin and analogues as cytoplasmic dynein heavy chain inhibitors
Zhu, Guangyu,Yang, Fanglong,Balachandran, Raghavan,H??k, Peter,Vallee, Richard B.,Curran, Dennis P.,Day, Billy W.
, p. 2063 - 2076 (2007/10/03)
Cytoplasmic dynein plays important roles in membrane transport, mitosis, and other cellular processes. A few small-molecule inhibitors of cytoplasmic dynein have been identified. We report here the first synthesis of purealin, a natural product isolated from the sea sponge Psammaplysilla purea, which is known to inhibit axonemal dynein. Also described are the first syntheses, by modular amide coupling reactions, of the natural product purealidin A (a component of purealin) and a small library of analogues. The library was examined for inhibition of cytoplasmic dynein heavy chain and cell growth. The compounds showed effective antiproliferative activity against a mouse leukemia cell line but selective activities against human carcinoma cell lines. Purealin and some of the analogues inhibited the microtubule-stimulated ATPase activity of recombinant cytoplasmic dynein heavy chain motor domain. The inhibitory effect of purealin was concentration dependent and uncompetitive, supporting the hypothesis that it does not compete with the binding of ATP.
Total synthesis, structural revision, and biological evaluation of calafianin, a marine spiroisoxazoline from the sponge, Aplysina gerardogreeni
Ogamino, Takahisa,Obata, Rika,Tomoda, Hiroshi,Nishiyama, Shigeru
, p. 134 - 139 (2007/10/03)
The reported structure of the natural calafianin (1) and its isomer in the epoxide region 13 were successfully synthesized through the cis- and trans-spiroisoxazoline compounds, which were produced by electrochemical oxidation of the hydroxyimino-phenol d
Synthesis and structural revision of calafianin, a member of the spiroisoxazole family isolated from the marine sponge, Aplysina gerardogreeni
Ogamino, Takahisa,Nishiyama, Shigeru
, p. 1083 - 1086 (2007/10/03)
Calafianin 1 was successfully synthesized by employing a spiroisoxazoline compound, which was produced by electrochemical oxidation of the oximino-phenol derivative 7 followed by reduction. This investigation revealed a structural revision of 1, the trans
Electrochemical synthesis of spiroisoxazole derivatives and its application to natural products
Ogamino, Takahisa,Ishikawa, Yuichi,Nishiyama, Shigeru
, p. 73 - 78 (2007/10/03)
Efficient synthesis of the trans-spiroisoxazole (1) and its unnatural cis-isomer (2) was accomplished by employing anodic oxidation of 4, followed by Zn(BH4)2 reduction. This method was applied to an assembly of the carbon framework of zamamistatin (12).
Oxidative cyclisation of o-phenolic oxime-acid derivatives using phenyliodonium diacetate: Synthesis of spiroisoxazoline derivatives
Murakata, Masatoshi,Yamada, Kohei,Hoshino, Osamu
, p. 14713 - 14722 (2007/10/03)
An efficient formation of spiroisoxazoline ring system by intramolecular oxidative cyclisation of o-phenolic oxime-esters and oxime-amides using phenyliodonium diacetate (PIDA) is described. The intramolecular oxidative cyclisation of various o-phenolic o
Total syntheses of (±)-aerothionin, (±)-homoaerothionin, and (±)-aerophobin-1
Nishiyama,Yamamura
, p. 3453 - 3456 (2007/10/02)
(±)-Aerothionin, (±)-homoaerothionin, and (±)-aerophobin-1 have been successfully synthesized using phenolic oxidation of the methyl pyruvate oxime derivative with thallium(III) trifluoroacetate as a key step. The stereostructure of aerophobin-2 has been also established by comparison of the 1H NMR spectrum with those of related compounds.
TOTAL SYNTHESES OF (+/-)-AEROTHIONIN AND (+/-)-HOMOAEROTHIONIN
Nishiyama, Shigeru,Yamamura, Shosuke
, p. 3351 - 3352 (2007/10/02)
Both aerothionin and homoaerothionin, the novel metabolites of the sponges Aplysina aerophoba, A. fistularis and Verongia thiona, have been synthesized in racemic form.
