Synthesis and biological evaluation of 7-O-modified oroxylin A derivatives

Fu, Wei; Wang, Jubo; Yu, Liqin; Zhao, Li; Lu, Na; Qin, You; Guo, Qing; Li, Zhiyu

doi:10.1016/j.bmcl.2011.11.117

Cited by 13 publications

(6 citation statements)

References 13 publications

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“…The difference of 3cc between the inhibition of cell proliferation and the apoptotic induction indicated that 3cc was more likely to be a necrosis-inducing agent or both apoptosis/necrosis inducer. Thus, the novel 7-O-alkylamino derivative of oroxylin A, compound 3cc, could be a promising antitumor candidate, and further in vitro and in vivo biological character evaluations are warranted 27 .…”

Section: Biological Effects Of Natural Products Containing the Piperazinyl Moietymentioning

confidence: 99%

Piperazine skeleton in the structural modification of natural products: a review

Zhang

Guo

Deng

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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Piperazine moiety is a cyclic molecule containing two nitrogen atoms in positions 1 and 4, as well as four carbon atoms. Piperazine is one of the most sought heterocyclics for the development of new drug candidates with a wide range of applications. Over 100 molecules with a broad range of bioactivities, including antitumor, antibacterial, anti-inflammatory, antioxidant, and other activities, were reviewed. This article reviewed investigations regarding piperazine groups for the modification of natural product derivatives in the last decade, highlighting parameters that affect their biological activity.

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Section: Biological Effects Of Natural Products Containing the Piperazinyl Moietymentioning

confidence: 99%

Piperazine skeleton in the structural modification of natural products: a review

Zhang

Guo

Deng

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…In this work, we functionalized the -OH group at position 7 of chrysin with alkyl chains with or without terminal groups (Br, piperidine), in order to modulate their biological properties (see Figure 2). The introduction of the piperidine moiety was based on previous positive effects in the cytotoxic activity after the introduction of this group in chrysin or related derivatives [90,91]. After deprotonation of the chrysin compounds, the anionic species will be able to act as chelators for the metal centers and, in fact, they coordinate to p-cymene-Ru, Cp*-Rh and Cp*-Ir fragments to afford the corresponding half-sandwich complexes.…”

Section: Introductionmentioning

confidence: 99%

“…In this manner, potential multi-targeted compounds will be obtained. Furthermore, the coordination will eliminate the intramolecular hydrogen bond between the C=O group on the 5-OH position, a bond that has been proposed to produce low bioavailability [90]. The aim of this work was to carry out a SAR study evaluating the influence not only of the substitution on the ligand but also that of the metal center in their biological properties.…”

Section: Introductionmentioning

confidence: 99%

Anticancer Activity of Half-Sandwich Ru, Rh and Ir Complexes with Chrysin Derived Ligands: Strong Effect of the Side Chain in the Ligand and Influence of the Metal

et al. 2021

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An important challenge in the field of anticancer chemotherapy is the search for new species to overcome the resistance of standard drugs. An interesting approach is to link bioactive ligands to metal fragments. In this work, we have synthesized a set of p-cymene-Ru or cyclopentadienyl-M (M = Rh, Ir) complexes with four chrysin-derived pro-ligands with different -OR substituents at position 7 of ring A. The introduction of a piperidine ring on chrysin led to the highly cytotoxic pro-ligand HL4 and its metal complexes L4-M (SW480 and A549 cell lines, cytotoxic order: L4-Ir > L4-Ru ≈ L4-Rh). HL4 and its complexes induce apoptosis and can overcome cis-platinum resistance. However, HL4 turns out to be more cytotoxic in healthy than in tumor cells in contrast to its metal complexes which displayed higher selectivity than cisplatin towards cancer cells. All L4-M complexes interact with double stranded DNA. Nonetheless, the influence of the metal is clear because only complex L4-Ir causes DNA cleavage, through the generation of highly reactive oxygen species (1O2). This result supports the hypothesis of a potential dual mechanism consisting of two different chemical pathways: DNA binding and ROS generation. This behavior provides this complex with a great effectivity in terms of cytotoxicity.

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“…Chrysin is reported to exhibit various biological activities, which includes antibacterial [31], anti-inflammatory [32] anti-allergic [33], antioxidant [34], and anticancer [35] activities. Several attempts have been made to synthesize the structural derivatives of chrysin and to study their biological activities [36,37,38]. These studies indicated that synthetic analogues of chrysin are found to have more potent biological activities than standard drugs.…”

Section: Introductionmentioning

confidence: 99%

Molecular Design, Synthesis, and Biological Evaluation of 2-Hydroxy-3-Chrysino Dithiocarbamate Derivatives

et al. 2019

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A series of 2-hydroxy-3-chrysino dithiocarbamate derivatives (3a–k) were designed, synthesized, and characterized for their structure determination by 1H NMR, 13C NMR, and HRMS (ESI) spectral data. They were screened for their in vitro biological activities against a panel of selected bacterial and fungal strains. These antimicrobial studies indicate that some of the analogues manifested significant activity compared to standard drugs. Among the synthetic analogues (3a–k), compounds 3d, 3f, and 3j exhibited very good antibacterial activity and compounds 3d, 3f, and 3h showed very good antifungal activity compared to the standard drugs penicillin and itrazole, respectively. The compounds 3e, 3g, and 3h showed moderate antibacterial activity and the compounds 3j and 3k showed moderate antifungal activity. Molecular docking studies were performed and the experimental antimicrobial screening results were also correlated with the binding energy values obtained by molecular docking. The synthesized chrysin analogues (3a–k) have obeyed Lipinski’s “rule of five” and have drug-likeness.

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Synthesis and biological evaluation of 7-O-modified oroxylin A derivatives

Cited by 13 publications

References 13 publications

Piperazine skeleton in the structural modification of natural products: a review

Piperazine skeleton in the structural modification of natural products: a review

Anticancer Activity of Half-Sandwich Ru, Rh and Ir Complexes with Chrysin Derived Ligands: Strong Effect of the Side Chain in the Ligand and Influence of the Metal

Molecular Design, Synthesis, and Biological Evaluation of 2-Hydroxy-3-Chrysino Dithiocarbamate Derivatives

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