Synthesis of nordihydroguaiaretic acid derivatives and their bioactivities on S. pombe and K562 cell lines

Xu, Li; Jiang, Jian‐Hong; Chen, Qingqi; Xiao, Shengxiong; Li, Chuanhua; Gu, Hui‐Wen; Zhang, Hui; Hu, Jilin; Yao, Fei-Hong; Li, Qiang‐Guo

doi:10.1016/j.ejmech.2013.01.028

Cited by 23 publications

(7 citation statements)

References 19 publications

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“…The slow conversion of 6 to 7 is possibly attributed to the Kornblum oxidation mediated by DMSO. [48] The analogs of 6 and 7 have been proven to be important intermediates of some known bioactive compounds, such as nordihydroguaiaretic acid (antioxidant and anticancer), [49] SMART analogs (tubulin inhibitor), [50] corbasil, [51] imidazopyridines, [52] quinoxalines. [53] (Schemes S1-S4).…”

Section: Difunctionalization Of Propenylcatecholmentioning

confidence: 99%

Sustainable Production of Bioactive Molecules from C‐Lignin‐Derived Propenylcatechol

Song

et al. 2022

ChemSusChem

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Catechyl lignin (C-lignin) is a naturally occurring linear homogeneous biopolymer composed solely of caffeyl alcohol subunits with cleavable benzodioxane linkages. The inherent structural features of propenylcatechol, a direct depolymerized product of castor seed coats C-lignin, render it a sustainable and promising platform for the synthesis of bioactive molecules. Herein, diversified transformations of propenylcatechol, including C=C bond difunctionalization, β-modification, β,γ-rearrangement, and γ-methyl derivatization, were reported based on known or developed methods. A series of functional molecular skeletons involved in the current synthetic routes for the preparation of pharmaceuticals and bioactive molecules were obtained. Starting from castor seed coats, annuloline (natural product) and CC-5079 (antitumor) were synthesized using facile and inexpensive reagents in only four-and five-sequence reactions, respectively, thereby demonstrating a superior step-efficiency to that of reported synthetic routes. Almost all atoms in the Clignin biopolymer were incorporated into the final products owing to the intrinsic structures of naturally occurring C-lignin. Bioactive molecules produced from C-lignin integrate a lowcarbon footprint with high-quality and economical manufacture of pharmaceuticals.

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Section: Difunctionalization Of Propenylcatecholmentioning

confidence: 99%

Sustainable Production of Bioactive Molecules from C‐Lignin‐Derived Propenylcatechol

Song

et al. 2022

ChemSusChem

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“…According to the literature data, the synthesis of the Schiff base ligand was carried out first [28][29][30]. Complexes were synthesized after it was understood that the structural characterization data of the obtained ligand molecule were compatible with the literature data.…”

Section: Synthesis Studiesmentioning

confidence: 99%

“…The Schiff base ligand, N,N'-bis(2-hydroxy-3methoxyphenylmethylidene)-2,6pyridinediamine, was prepared according to the references [28][29][30].…”

Section: Synthesis Of Bhmp As a Ligandmentioning

confidence: 99%

Investigation of The Effects of Diaminopyridine and o-Vanillin Derivative Schiff Base Complexes of Mn(II), Mn(III), Co(II) and Zn(II) Metals on The Oxidative Bleaching Performance of H2O2

Uğur¹,

Tuna

2021

Sakarya University Journal of Science

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Catalytic applications are widely used in industrial and individual applications today due to their many advantages, especially the energy and time they provide. For this purpose, many coordination compounds have been synthesized, and their catalytic performances have been investigated in recent years. In this study, the Schiff base ligand, (N,N'-bis(2-hydroxy-3methoxyphenylmethylidene)-2,6-pyridinediamine, BHMP), was synthesized with 2,6diaminopyridine with o-vanillin. Mn(II), Mn(III), Co(II), Zn(II) complexes were obtained with the synthesized ligand. Spectroscopic methods such as FT-IR, 1 H-NMR, UV-vis, Mass, and melting point determination methods were used for the structure elucidation of the synthesized compounds. The performances of the obtained complexes as bleach catalysts, which are an important application area of Schiff base complexes, were investigated. According to the bleaching measurement results, the highest catalytic effect on the bleaching performance of H2O2 in pH 10.5 buffer at 25 °C under homogeneous conditions was obtained with Co(II) complex. It was understood that this complex was followed by Mn(II), Mn(III), and Zn(II) complexes, respectively.

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“…It was approved in the USA for topical use in treatment of actinic keratosis (Billinsky, Krol, 2008). In addition, Masoprocol, that is the generic name of NDGA, demonstrated promising activity as a new antineoplastic agent for topical use (Li et al, 2013;Olsen et al, 1991).…”

Section: Introductionmentioning

confidence: 99%

Chemical and biological properties of nordihydroguaiaretic acid

Macena

Renzi

Grigoletto

2022

Braz. J. Pharm. Sci.

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Nordihydroguaiaretic acid (NDGA) is a natural product obtained by the alkaline extraction of dried plants of Larrea tridentata species. Due to the biological properties presented, such as antioxidant, anti-inflammatory, antiviral and cytotoxic capacity, this compound is being increasingly studied. In this review, it was evaluated the benefits of NDGA against different animal models. Besides that, it was found that this compound has antitumor activity similar to its synthetic derivative terameprocol in prostate tumors. The hypoglycemic effect may be evidenced by the inhibition of sugar uptake by NDGA; in obesity, studies have observed that NDGA presented a positive regulatory effect for Peroxisome proliferator-activated receptors (PPAR-α) involved in the oxidation of hepatic fatty acids and reduced the expression of lipogenic genes. Regarding its antioxidant potential, its mechanism is related to the ability to in vitro scavenging reactive substances. Although there are several studies demonstrating the benefits of using NDGA, there are also reports of its toxicity, mainly of liver damage and nephrotoxicity.

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Synthesis of nordihydroguaiaretic acid derivatives and their bioactivities on S. pombe and K562 cell lines

Cited by 23 publications

References 19 publications

Sustainable Production of Bioactive Molecules from C‐Lignin‐Derived Propenylcatechol

Sustainable Production of Bioactive Molecules from C‐Lignin‐Derived Propenylcatechol

Investigation of The Effects of Diaminopyridine and o-Vanillin Derivative Schiff Base Complexes of Mn(II), Mn(III), Co(II) and Zn(II) Metals on The Oxidative Bleaching Performance of H2O2

Chemical and biological properties of nordihydroguaiaretic acid

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