7731-10-4Relevant articles and documents
Reprint of: Antiproliferative activity of the Antrodia camphorata secondary metabolite 4,7-dimethoxy-5-methylbenzo[d][1,3]dioxole and analogues
Yeung, Sing Yee,Piggott, Matthew J.
, p. 40 - 44 (2018)
Both the traditional Chinese medicinal fungus, Antrodia camphorata, and its secondary metabolite, 4,7-dimethoxy-5-methylbenzo[d][1,3]dioxole, have been reported to possess promising anticancer activity. In this work the natural product and analogues bearing more polar substituents were synthesised and assessed for antiproliferative activity in the NCI-60 screen. Although each compound inhibited the growth of some cell lines at 10 μM, none had sufficient activity to warrant further investigation.
Dill and parsley seed extracts in scale up synthesis of aminopolyalkoxybenzenes - Beneficial synthons for fused nitrogen polyalkoxyheterocycles
Karmanova, Irina B.,Firgang, Sergei I.,Konyushkin, Leonid D.,Khrustalev, Victor N.,Ignatov, Alexander V.,Kuznetsov, Leonid A.,Pinchuk, Yuriy A.,Kozlov, Ivan A.,Semenov, Victor V.
, p. 66 - 68 (2016/02/12)
Ecologically friendly transformation of readily accessible plant allylpolyalkoxybenzenes to hardly available aminotetraalkoxybenzenes has been developed. The efficacy of hydrogenation stage is substantially increased by the application of highly porous ceramic block Pd-catalysts featuring a large surface area, low hydraulic resistance, significant thermal and mechanical stabililty, multiple cycling and easy regeneration.
Cis -restricted 3-aminopyrazole analogues of combretastatins: Synthesis from plant polyalkoxybenzenes and biological evaluation in the cytotoxicity and phenotypic sea urchin embryo assays
Tsyganov, Dmitry V.,Konyushkin, Leonid D.,Karmanova, Irina B.,Firgang, Sergei I.,Strelenko, Yuri A.,Semenova, Marina N.,Kiselyov, Alex S.,Semenov, Victor V.
, p. 1485 - 1491 (2013/09/23)
We have synthesized a series of novel cis-restricted 4,5-polyalkoxydiaryl- 3-aminopyrazole analogues of combretastatins via short synthetic sequences using building blocks isolated from dill and parsley seed extracts. The resulting compounds were tested in vivo in the phenotypic sea urchin embryo assay to reveal their antimitotic and antitubulin effects. The most potent aminopyrazole, 14a, altered embryonic cell division at 10 nM concentration, exhibiting microtubule-destabilizing properties. Compounds 12a and 14a displayed pronounced cytotoxicity in the NCI60 anticancer drug screen, with the ability to inhibit growth of multi-drug-resistant cancer cells.
Application of plant allylpolyalkoxybenzenes in synthesis of antimitotic phenstatin analogues
Titov, Ilia Y.,Sagamanova, Irina K.,Gritsenko, Roman T.,Karmanova, Irina B.,Atamanenko, Olga P.,Semenova, Marina N.,Semenov, Victor V.
, p. 1578 - 1581 (2011/05/04)
Phenstatin and its derivatives with the modified ring A have been synthesized, using plant allylpolyalkoxybenzenes as a starting material. The targeted molecules were evaluated in a phenotypic sea urchin embryo assay for antiproliferative activity. It was found that phenstatin ring A modifications yielded antimitotic compounds. The most effective myristicin derivative 7d (combretastatin A-2 analogue) was determined to be ca. 10 times more potent than phenstatin, displaying antimitotic tubulin-destabilizing activity at the same concentration range as combretastatins. In contrast to combretastatins, 7d featured the steric stability with potential for further design as anticancer agent.
