Synthesis and biological evaluation of pyrroloiminoquinone derivatives

Passarella, Daniele; Belinghieri, Francesca; Scarpellini, Michele; Pratesi, Graziella; Zunino, Franco; Gia, Ornella; Via, Lisa Dalla; Santoro, Giuseppe E.; Danieli, Bruno

doi:10.1016/j.bmc.2007.11.063

Cited by 11 publications

(4 citation statements)

References 36 publications

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“…Topoisomerases inhibition. Based on our previous efforts in this field, [25][26][27][28][29] both (R)-and (S)boehmeriasin A were tested for their capacity to affect the activity of opoisomerases. Similar experiments were performed to assay the effect on topoisomerase I relaxation activity as well, and the obtained results indicate the occurrence of a higher inhibitory effect compared to that obtained on topoisomerase II.…”

Section: Biological Evaluationmentioning

confidence: 99%

Boehmeriasin A as new lead compound for the inhibition of topoisomerases and SIRT2

Christodoulou

Calogero

Baumann

et al. 2015

European Journal of Medicinal Chemistry

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Two synthetic approaches to boehmeriasin A are described. A gram scale racemic preparation is accompanied by an efficient preparation of both the pure enantiomers using the conformationally stable 2-piperidin-2-yl acetaldehyde as starting material. The anti-proliferative activity in three cancer cell lines (CEM, HeLa and L1210) and two endothelial cell lines (HMEC-1, BAEC) indicates promising activity at the nanomolar range. Topoisomerases and SIRT2 are identified as biological targets and the experimental data has been supported by docking studies.

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Section: Biological Evaluationmentioning

confidence: 99%

Boehmeriasin A as new lead compound for the inhibition of topoisomerases and SIRT2

Christodoulou

Calogero

Baumann

et al. 2015

European Journal of Medicinal Chemistry

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“…8 The inability of discorhabdin A to inhibit topoisomerase II is indicative of the fact that this potent cytotoxicity most probably acts by a different mechanism than the makaluvamines. [53][54][55][56][57]…”

Section: Biological Activitymentioning

confidence: 99%

The synthetic and biological studies of discorhabdins and related compounds

et al. 2011

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Various analogues of the marine alkaloids, discorhabdins, have been synthesized. The strategy contains spirocyclization with phenyliodine(III) bis(trifluoroacetate) (PIFA), oxidative fragmentation of the β-amino alcohols with the hypervalent iodine reagent C(6)F(5)I(OCOCF(3))(2), the detosylation and dehydrogenation reaction of the pyrroloiminoquinone unit in the presence of a catalytic amount of NaN(3) and the bridged ether synthesis with HBr-AcOH as the key reactions. All the synthesized compounds were evaluated by in vitro MTT assay for cytotoxic activity against the human colon cancer cell line HCT-116. Furthermore, the discorhabdin A oxa analogues were also evaluated against four kinds of tumor model cells, a human colon cancer cell line (WiDr), a human prostate cancer cell line (DU-145) and murine leukemia cell lines (P388 and L1210). For the identification of the target, discorhabdin A and the discorhabdin A oxa analogue were evaluated by an HCC panel assay. In the test, discorhabdins could have a novel mode of action with the tumor cells.

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“…[1][2][3][4][5] Given our interests in: a) the total synthesis of piperidine-based natural products, [6][7][8][9][10][11][12][13][14] b) the modification of natural products, [15][16][17][18][19][20][21][22][23][24][25][26] and c) the discovery and generation of new anticancer compounds, [27][28][29][30][31] we considered the natural product pironetin [32] due to its capacity for α-tubulin binding. [1][2][3][4][5] Given our interests in: a) the total synthesis of piperidine-based natural products, [6][7][8][9][10][11][12][13][14] b) the modification of natural products, [15][16][17]…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Pironetin–Dumetorine Hybrids as Tubulin Binders

et al. 2016

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The synthesis of the eight stereoisomers of 6-[2-methoxy-3-(piperidinyl)propyl]-5,6-dihydropyran-2-one is reported. The configuration at C2′ and C6 is induced by a sterecontrolled allylation reaction with DIP-Cl. The general structure is the result of merging the structures of two natural products (pironetin and dumetorine) with the aim of discovering a new scaffold for tubulin binders. Docking studies and biological evaluations confirm the validity of the approach

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Synthesis and biological evaluation of pyrroloiminoquinone derivatives

Cited by 11 publications

References 36 publications

Boehmeriasin A as new lead compound for the inhibition of topoisomerases and SIRT2

Boehmeriasin A as new lead compound for the inhibition of topoisomerases and SIRT2

The synthetic and biological studies of discorhabdins and related compounds

Synthesis of Pironetin–Dumetorine Hybrids as Tubulin Binders

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