Design and synthesis of 3-benzylaminocoumarin-7-O-sulfamate derivatives as steroid sulfatase inhibitors

Hng, Yue; Lin, Mei‐Hsiang; Lin, Tzung-Sheng; Liu, I-Chen; Lin, I-Chun; Lu, Yeh‐Lin; Chang, Chiao-Nien; Chiu, Pei-Fang; Tsai, Keng‐Chang; Chen, Mei-Jou; Liang, Pi‐Hui

doi:10.1016/j.bioorg.2020.103618

Cited by 15 publications

(3 citation statements)

References 27 publications

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“…The synthetic methods of saponins have been well reviewed, providing complete information on the organic synthesis to perform SAR optimization [6,7]. Based on the research experiences on carbohydrate [8,9] and medicinal [10][11][12][13][14][15][16][17][18][19][20][21][22] chemistry in our lab, we summarize the biological effects and preliminary SAR results of synthetic saponins over the last five years to serve as a bridge between chemistry and biology, providing an insight for further structure optimization and mechanism studies, finally facilitating the development of saponin-based bioactive compounds.…”

Section: Introductionmentioning

confidence: 99%

Biological and Pharmacological Effects of Synthetic Saponins

Juang

Liang

2020

Molecules

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Saponins are amphiphilic molecules consisting of carbohydrate and either triterpenoid or steroid aglycone moieties and are noted for their multiple biological activities—Fungicidal, antimicrobial, antiviral, anti-inflammatory, anticancer, antioxidant and immunomodulatory effects have all been observed. Saponins from natural sources have long been used in herbal and traditional medicines; however, the isolation of complexed saponins from nature is difficult and laborious, due to the scarce amount and structure heterogeneity. Chemical synthesis is considered a powerful tool to expand the structural diversity of saponin, leading to the discovery of promising compounds. This review focuses on recent developments in the structure optimization and biological evaluation of synthetic triterpenoid and steroid saponin derivatives. By summarizing the structure–activity relationship (SAR) results, we hope to provide the direction for future development of saponin-based bioactive compounds.

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Section: Introductionmentioning

confidence: 99%

Biological and Pharmacological Effects of Synthetic Saponins

Juang

Liang

2020

Molecules

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“…Similarly, 3-benzylamino coumarin-7-O-sulfamate derivatives (compound 80 ) developed by Hng et al showed efficacy toward MCF-7 cells, with an IC 50 value of 1.3 µM. The substitution of the methoxy group at the ortho and meta position of the benzyl ring adjacent to the amine linkage was desirable for the activity of the compound, while a change in the position or the removal of the methoxy group led to a decrease in its activity ( Figure 22 ) [ 167 ].…”

Section: Synthetic Coumarin-inspired Derivatives With Anti-breast Can...mentioning

confidence: 99%

Coumarin as an Elite Scaffold in Anti-Breast Cancer Drug Development: Design Strategies, Mechanistic Insights, and Structure–Activity Relationships

Singh,

Kaur

et al. 2024

Biomedicines

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Breast cancer is the most common cancer among women. Currently, it poses a significant threat to the healthcare system due to the emerging resistance and toxicity of available drug candidates in clinical practice, thus generating an urgent need for the development of new potent and safer anti-breast cancer drug candidates. Coumarin (chromone-2-one) is an elite ring system widely distributed among natural products and possesses a broad range of pharmacological properties. The unique distribution and pharmacological efficacy of coumarins attract natural product hunters, resulting in the identification of numerous natural coumarins from different natural sources in the last three decades, especially those with anti-breast cancer properties. Inspired by this, numerous synthetic derivatives based on coumarins have been developed by medicinal chemists all around the globe, showing promising anti-breast cancer efficacy. This review is primarily focused on the development of coumarin-inspired anti-breast cancer agents in the last three decades, especially highlighting design strategies, mechanistic insights, and their structure–activity relationship. Natural coumarins having anti-breast cancer efficacy are also briefly highlighted. This review will act as a guideline for researchers and medicinal chemists in designing optimum coumarin-based potent and safer anti-breast cancer agents.

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“…Presented results showed that these compounds could represent new leads for potential development after further preclinical studies. A wide range of novel sulphamoylated derivatives of coumarin has been also synthesised by Hng et al recently 60 . In the course of undertaken research, the modifications at the 3-position of a coumarin core have been evaluated.…”

Section: Nonsteroidal Sts Inhibitors Containing a Sulphamate Moietymentioning

confidence: 99%

Recent progress in the development of steroid sulphatase inhibitors – examples of the novel and most promising compounds from the last decade

Daśko

Demkowicz

Biernacki

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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The purpose of this review article is to provide an overview of recent achievements in the synthesis of novel steroid sulphatase (STS) inhibitors. STS is a crucial enzyme in the biosynthesis of active hormones (including oestrogens and androgens) and, therefore, represents an extremely attractive molecular target for the development of hormone-dependent cancer therapies. The inhibition of STS may effectively reduce the availability of active hormones for cancer cells, causing a positive therapeutic effect. Herein, we report examples of novel STS inhibitors based on steroidal and nonsteroidal cores that contain various functional groups (e.g. sulphamate and phosphorus moieties) and halogen atoms, which may potentially be used in therapies for hormone-dependent cancers. The presented work also includes examples of multitargeting agents with STS inhibitory activities. Furthermore, the fundamental discoveries in the development of the most promising drug candidates exhibiting STS inhibitory activities are highlighted.

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Design and synthesis of 3-benzylaminocoumarin-7-O-sulfamate derivatives as steroid sulfatase inhibitors

Cited by 15 publications

References 27 publications

Biological and Pharmacological Effects of Synthetic Saponins

Biological and Pharmacological Effects of Synthetic Saponins

Coumarin as an Elite Scaffold in Anti-Breast Cancer Drug Development: Design Strategies, Mechanistic Insights, and Structure–Activity Relationships

Recent progress in the development of steroid sulphatase inhibitors – examples of the novel and most promising compounds from the last decade

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