30290-15-4Relevant academic research and scientific papers
Synthesis of 4-azo-butenolides
Pissurno, Ana Paula da Rocha,de Laurentiz, Rosangela da Silva
supporting information, p. 1874 - 1878 (2017/10/07)
An efficient, catalyst-free, microwave-assisted approach has been developed for the synthesis of 4-azo-butyenolides derivatives by condensing tetronic acid with various anilines. This approach exhibited good functional group compatibility and produced the
Highly active magnetically separable CuFe2O4 nanocatalyst: An efficient catalyst for the green synthesis of tetrahydrofuro[3,4-b]quinoline-1,8(3H,4H) dione derivatives
Ghahremanzadeh, Ramin,Rashid, Zahra,Zarnani, Amir-Hassan,Naeimi, Hossein
, p. 1407 - 1419 (2014/10/16)
A facile and efficient procedure has been reported for the synthesis of tetrahydrofuro[3,4-b]quinoline-1,8(3H,4H)-diones by the condensation reaction of benzaldehydes, 1,3-cyclohexanediones and anilinolactones in the presence of CuFe2O4 as a reusable nanocatalyst with high catalytic activity in water. The notable advantages of this method are excellent isolated yields, short reaction times, simple workup procedure and little environmental impact. Graphical Abstract: [Figure not available: see fulltext.].
Synthesis of novel spirooxindoles in water by using MnFe2O 4 nanoparticles as an efficient magnetically recoverable and reusable catalyst
Ghahremanzadeh, Ramin,Rashid, Zahra,Zarnani, Amir Hassan,Naeimi, Hossein
, p. 270 - 278 (2013/09/02)
An efficient, clean, atom-economical and simple method for the one-pot synthesis of novel spirooxindole derivatives via a three-component reaction of isatins, dimedone and anilinolactones was reported. This reaction was performed by using MnFe2O4 nanoparticles (5 mol%) as an efficient magnetically heterogeneous catalyst in water as green solvent. Prominent among the advantages of this method is the use of magnetically recoverable and reusable catalyst, simple work up procedure, good to high product yields and use of water as a solvent that is considered to be relatively environmentally benign.
Synthesis and comparative evaluation of 4-oxa- and 4-aza-podophyllotoxins as antiproliferative microtubule destabilizing agents
Chernysheva, Natalia B.,Tsyganov, Dmitry V.,Philchenkov, Alex A.,Zavelevich, Michael P.,Kiselyov, Alex S.,Semenov, Roman V.,Semenova, Marina N.,Semenov, Victor V.
supporting information; experimental part, p. 2590 - 2593 (2012/05/05)
A series of novel 4-oxa-podophyllotoxin derivatives 7 featuring the intact lactone ring D and various substituents in rings B and E has been synthesized and evaluated in a phenotypic sea urchin embryo assay along with the representative 4-aza-analogs 5 for their antimitotic and microtubule destabilizing activity. The most active compounds exhibited myristicin-derived or a 3′,5′-dimethoxy substitution pattern in the ring E and a 6-methoxy moiety replacing the methylenedioxy ring A. Compounds 5xb, 5xe, 5yb, 7xa, 7xb, and 7xc showed potent antiproliferative effects in the NCI60 cytotoxicity screen. Notably, growth of the multi-drug resistant NCI/ADR-RES cells was more affected by these agents than the parent OVCAR-8 cell line. Although generally 4-oxa-podophyllotoxins were less potent than the respective 4-aza-derivatives in these assays, stability of the former series towards oxidation may prove to be of interest for the development of anticancer agents with in vivo activity.
Synthesis of 3-bromotetronamides via amination of 3,4-dibromofuran-2(5H)- one
Cunha, Silvio,Oliveira, Caio C.,Sabino, Jose? R.
experimental part, p. 598 - 603 (2011/10/17)
This work describes the direct synthesis of 3-bromotetronamides in good yields through the reaction of 3,4-dibromofuran-2(5H)-one, obtained from furfural, with primary and secondary amines. Aromatic amines were more tolerated than aliphatic and heteroaromatic ones. The X-ray structures of five derivatives are described.
Polyalkoxybenzenes from plants. 5. parsley seed extract in synthesis of azapodophyllotoxins featuring strong tubulin destabilizing activity in the sea urchin embryo and cell culture assays
Semenova, Marina N.,Kiselyov, Alex S.,Tsyganov, Dmitry V.,Konyushkin, Leonid D.,Firgang, Sergei I.,Semenov, Roman V.,Malyshev, Oleg R.,Raihstat, Mikhail M.,Fuchs, Fabian,Stielow, Anne,Lantow, Margareta,Philchenkov, Alex A.,Zavelevich, Michael P.,Zefirov, Nikolay S.,Kuznetsov, Sergei A.,Semenov, Victor V.
experimental part, p. 7138 - 7149 (2011/12/04)
A series of 4-azapodophyllotoxin derivatives with modified rings B and E have been synthesized using allylpolyalkoxybenzenes from parsley seed oil. The targeted molecules were evaluated in vivo in a phenotypic sea urchin embryo assay for antimitotic and tubulin destabilizing activity. The most active compounds identified by the in vivo sea urchin embryo assay featured myristicin-derived ring E (4e, 6e, and 8e). These molecules were determined to be more potent than podophyllotoxin. Cytotoxic effects of selected molecules were further confirmed and evaluated by conventional assays with A549 and Jurkat human leukemic T-cell lines including cell growth inhibition, cell cycle arrest, cellular microtubule disruption, and induction of apoptosis. The ring B modification yielded 6-OMe substituted molecule 8e as the most active compound. Finally, in Jurkat cells, compound 8e induced caspase-dependent apoptosis mediated by the apical caspases-2 and -9 and not caspase-8, implying the involvement of the intrinsic caspase-9-dependent apoptotic pathway.
