Synthesis and Biological Evaluation of Novel Genistein Amino Acid Ester Derivatives as Potential Anti‐Tumor Agents

Long, Xiaokang; Liao, Lanqing; Zeng, Yao‐Fu; Zhang, Ye; Xiao, Fang; Li, Chong; Guo, Yu

doi:10.1002/slct.201900857

Cited by 5 publications

(4 citation statements)

References 23 publications

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“…Particularly, compound 15 (Figure 5) having the tryptophan chain showed the most potent cytotoxicity against HCT‐116 cells with an IC 50 value of 2.76 μM. Mode of action studies further revealed that compound 15 suppressed the metastasis of HCT‐116 cells and induced the apoptosis in a concentration dependent manner and produces the cell cycle arrest at G1 phase [135] …”

Section: Semi‐synthetic Modification Of Genistein During the Period 2...mentioning

confidence: 98%

“…Mode of action studies further revealed that compound 15 suppressed the metastasis of HCT-116 cells and induced the apoptosis in a concentration dependent manner and produces the cell cycle arrest at G1 phase. [135] Bai et al in 2018 reported the antitumor activity of a new synthetic genistein derivative, 5-hydroxy-4'-nitro-7-propionyloxy-genistein (HNPG) 16 (Figure 5) in human ovarian cancer cells A2780. The compound has shown to inhibit the proliferation, invasion and metastasis and induced the apoptosis in a dose and time dependent manner.…”

Section: Human Breast Cancer Cells (Mcf-7)mentioning

confidence: 99%

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Therapeutic Potential of Genistein and its Derivatives as a Target for Anticancer Agents

Gupta

Kumar³

et al. 2023

ChemistrySelect

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Genistein is a natural isoflavone and a phytoestrogen known to possess broad range of pharmacological properties specifically explored for anticancer effects. The compound is under clinical trials for different types of cancer treatment. Structural modification of genistein has been done to prepare analogs with improved anticancer potential and pharmaceutical properties. Also, novel formulations of genistein have been developed to further improve water solubility and bioavailability for better clinical effectiveness. In the present review, we have summarized the recent available literature on genistein anticancer effects along with mechanism of action and clinical trial studies, reported analogs and novel formulations developed for improving the anticancer efficacy of genistein during the period 2013–2022. Also, the structure activity relationship (SAR) study of reported genistein analogs is described. Further, articles published in this period showed that both genistein and its various derivatives exhibit promising potential for the development of effective chemotherapeutic agents against different types of cancer. Further, the present review will help the researchers in design and development of genistein formulation with desired drug profile.

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Section: Semi‐synthetic Modification Of Genistein During the Period 2...mentioning

confidence: 98%

Section: Human Breast Cancer Cells (Mcf-7)mentioning

confidence: 99%

Therapeutic Potential of Genistein and its Derivatives as a Target for Anticancer Agents

Gupta

Kumar³

et al. 2023

ChemistrySelect

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“…Amino acid has played an important role in therapeutics from the earliest days of modern drug discovery . Recently, nonproteinogenic α-amino acids are found as substructures in various pharmaceuticals, such as antibiotic, antiparkinsonian, and antitumor drugs (Scheme ). As a result, there have been extensive studies on the synthesis of amino acids, especially the construction of amino acid skeleton since it avoids restriction from the derivatization of naturally occurring compounds .…”

mentioning

confidence: 99%

“…99 mg (60%): colorless oil. 1 H NMR (400 MHz, CDCl 3 ) δ 8.43 (ddd, J = 4.9, 2.0, 0.8 Hz,1H),7.58 (ddd,J = 8.2,7.4,2.0 Hz,1H),2H),3H),1H),7.04 (ddd,J = 7.3,4.9, 1.0 Hz, 1H), 5.78 (q, J = 7.1 Hz, 1H), 1.70 (d,J = 7.1 Hz,3H), 1.27 (s, 9H). 13 C{ 1 H} NMR (100 MHz, CDCl 3 ) δ 154.…”

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confidence: 99%

Synthesis of Unnatural α-Amino Acids from (Pyridin-2-yl) Carbamate via CIPE-Induced Carbonyl Migration

Wang

Huo

et al. 2022

J. Org. Chem.

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Synthetic methods of unnatural α-amino acids have always been the focus of extensive research due to their significant bioactivities. However, convenient transition-metal-free catalyzed methods are still in demand. Herein, we report a novel strategy for the construction of an unnatural α-amino acid skeleton via intramolecular rearrangement of carbamates, which are readily available from amines and their common protecting groups. This rearrangement could afford a variety of amino ester products in up to 98% yield, even in gram-scale reaction. The reaction mechanism was studied in detail through experiments and theoretical calculations. The complex-induced proximity effect (CIPE) from the 2-pyridyl group is shown to be indispensable for this transformation.

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Synthesis of Cinnamoyl‐Amino Acid Ester Derivatives and Structure‐Activity Relationship Based on Thermal Stability, Dielectric, and Theoretical Analysis

et al. 2022

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In this study, cinnamic acid derivatives were synthesized from the reaction of benzaldehyde derivatives with malonic acid in the presence of pyridine and piperidine. These compounds were then respectively reacted with glycine and L‐alanine methyl ester hydrochloride based on triazine methodology to obtain novel cinnamoyl‐amino acid ester derivatives. The structure of these compounds were established via 1H, 13C APT, FT‐IR, MS and elemental analysis. The synthesized novel compounds were studied in terms of structure‐activity relationship based on dielectric, thermal stability, and theoretical analysis. Dielectric analysis was carried out in terms of amino acid type and aromatic substituted group (electron‐withdrawing or releasing group factor). Amino acid side chain differences make alanine conjugates have higher ϵ′ values compared to glycine conjugates. Thermal stability analysis was performed for the compounds (10 and 16) with the highest dielectric constants. Thermal decomposition activation energies were calculated as 95 kJ mol−1 and 100 kJ mol−1 for 10 and 16, respectively. HOMO‐LUMO energy levels and other related properties of the target compounds were analyzed and a correlation was observed between HOMO‐LUMO energy band gap and dielectric constant.

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Synthesis and Biological Evaluation of Novel Genistein Amino Acid Ester Derivatives as Potential Anti‐Tumor Agents

Cited by 5 publications

References 23 publications

Therapeutic Potential of Genistein and its Derivatives as a Target for Anticancer Agents

Therapeutic Potential of Genistein and its Derivatives as a Target for Anticancer Agents

Synthesis of Unnatural α-Amino Acids from (Pyridin-2-yl) Carbamate via CIPE-Induced Carbonyl Migration

Synthesis of Cinnamoyl‐Amino Acid Ester Derivatives and Structure‐Activity Relationship Based on Thermal Stability, Dielectric, and Theoretical Analysis

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