Halogenated flavanones as potential apoptosis-inducing agents: Synthesis and biological activity evaluation

Safavi, Maliheh; Esmati, Nasim; Ardestani, Sussan K.; Emami, Saeed; Ajdari, Soheila; Davoodi, Jamshid; Shafiee, Abbas; Foroumadi, Alireza

doi:10.1016/j.ejmech.2012.10.043

Cited by 68 publications

(36 citation statements)

References 26 publications

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“…The isomerization equilibrium between the flavanone and chalcone forms can be correlated with this conformational disorder [26]. This conformational behavior has major impact on the diverse biological activities of this class of compounds [27]. Crystal data and structure refinement details of compounds (1 and 2) are shown in Table 1.…”

Section: Resultsmentioning

confidence: 99%

Isolation, Characterization, Crystal Structure Elucidation of Two Flavanones and Simultaneous RP-HPLC Determination of Five Major Compounds from Syzygium campanulatum Korth

et al. 2015

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Two flavanones named (2S)-7-Hydroxy-5-methoxy-6,8-dimethyl flavanone (1), (S)-5,7-dihydroxy-6,8-dimethyl-flavanone (2), along with known chalcone, namely, (E)-2ʹ,4ʹ-dihydroxy-6ʹ-methoxy-3ʹ,5ʹ-dimethylchalcone (3) and two triterpenoids, namely, betulinic and ursolic acids (4 and 5), were isolated from the leaves of Syzygium campanulatum Korth (Myrtaceae). The structures of compounds (1 and 2) were determined on the basis of UV-visible, FTIR, NMR spectroscopies and LC-EIMS analytical techniques. Furthermore, new, simple, precise, selective, accurate, highly sensitive, efficient and reproducible RP-HPLC method was developed and validated for the quantitative analysis of the compounds (1-5) from S. campanulatum plants of five different age. RP-HPLC method was validated in terms of specificity, linearity (r 2 ≤ 0.999), precision (2.0% RSD), and recoveries (94.4%-105%). The LOD and LOQ of these compounds ranged from 0.13-0.38 and 0.10-2.23 µg·mL −1 , OPEN ACCESSMolecules 2015, 20 14213 respectively. Anti-proliferative activity of isolated flavanones (1 and 2) and standardized extract of S. campanulatum was evaluated on human colon cancer (HCT 116) cell line. Compounds (1 and 2) and extract revealed potent and dose-dependent activity with IC50 67.6, 132.9 and 93.4 µg·mL −1 , respectively. To the best of our knowledge, this is the first study on isolation, characterization, X-ray crystallographic analysis of compounds (1 and 2) and simultaneous RP-HPLC determination of five major compounds (1-5) from different age of S. campanulatum plants.

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Section: Resultsmentioning

confidence: 99%

Isolation, Characterization, Crystal Structure Elucidation of Two Flavanones and Simultaneous RP-HPLC Determination of Five Major Compounds from Syzygium campanulatum Korth

et al. 2015

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“…The most active compound 8c was selected to determine its potential to induce apoptosis in MCF-7 cells morphologically by acridine orange/ethidiumbromide (AO/EB) double staining test [40] (Fig. 2).…”

Section: Acridine Orange/ethidium Bromide Double Stainingmentioning

confidence: 99%

Design, synthesis, in vitro cytotoxic activity evaluation, and apoptosis-induction study of new 9(10H)-acridinone-1,2,3-triazoles

Mohammadi-Khanaposhtani

Safavi

Sabourian

et al. 2015

Mol Divers

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A new series of 9(10H)-acridinone-1,2,3-triazole derivatives were designed, synthesized and evaluated for their cytotoxic activity against human breast cancer cell lines. The acridone skeleton was prepared through the Ullman condensation of 2-bromobenzoic acid and anilines. Subsequently, it was functionalized with propargyl bromide. Then, a click reaction of the latter compound and in situ prepared 1-(azidomethyl)-4-methoxybenzene derivatives led to the formation of the desired triazole products. Finally, all products were investigated for their capability to cause cytotoxicity against MCF-7, T-47D, and MDA-MB-231 cell lines. Among them, 2-methoxy-10-((1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)acridin-9(10H)-one 8c exhibited the most potency [Formula: see text] against MCF-7 cells, being more potent than etoposide [Formula: see text]. Also, apoptosis induced by compound 8c was confirmed via acridine orange/ethidium bromide and Annexin V-FITC/propidium iodide (PI) double staining.

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“…These are consistent with the literature ones. 2,4,7,[24][25][26][27] Synthesis of flavanones 4a-m (General method). In a 25 ml round-bottom flask, a mixture of 2'-hydroxychalcone 3a-m (1 mmol) and NSSDAIL (0.20 g) was heated at 80°C and stirred until TLC monitoring indicated no further progress (35 to 70 min).…”

Section: -Methyl-3-(4-sulfobutyl)imidazolium Hydrogen Sulfatementioning

confidence: 99%

“…1 Due to this wide range of biological activities, many researchers have been interested in the synthesis of these materials. [1][2][3][4][5][6][7][8][9][10][11][12][13] In general, flavanones are synthesized in two steps: in the first step, 2'-hydroxychalcones are synthesized via the Claisen-Schmidt condensation between benzaldehyde derivatives and 2'-hydroxyacetophenone in alkaline media. In the second step, the corresponding flavanone is obtained by cyclization of 2'-hydroxychalcone.…”

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confidence: 99%

Nanosilica-supported dual acidic ionic liquid as a heterogeneous and reusable catalyst for the synthesis of flavanones under solvent-free conditions

Rostamizadeh

Zekri

Tahershamsi

2015

Chem Heterocycl Comp

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A nanosilica-supported dual acidic ionic liquid on the basis of 1-methyl-3-(4-sulfobutyl)imidazolium hydrogen sulfate was synthesized and used as an efficient, green, non-corrosive, non-toxic, heterogeneous, and reusable catalyst for the synthesis of some new and known substituted flavanones. The synthesis was done by the condensation of 2'-hydroxyacetophenone with different aldehydes and the subsequent cyclization of the resulting 2'-hydroxychalcone in the presence of the catalyst. High yields of the products, short reaction times, and solvent-free conditions characterize this new method.

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Halogenated flavanones as potential apoptosis-inducing agents: Synthesis and biological activity evaluation

Cited by 68 publications

References 26 publications

Isolation, Characterization, Crystal Structure Elucidation of Two Flavanones and Simultaneous RP-HPLC Determination of Five Major Compounds from Syzygium campanulatum Korth

Isolation, Characterization, Crystal Structure Elucidation of Two Flavanones and Simultaneous RP-HPLC Determination of Five Major Compounds from Syzygium campanulatum Korth

Design, synthesis, in vitro cytotoxic activity evaluation, and apoptosis-induction study of new 9(10H)-acridinone-1,2,3-triazoles

Nanosilica-supported dual acidic ionic liquid as a heterogeneous and reusable catalyst for the synthesis of flavanones under solvent-free conditions

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