Discovery and biological evaluation of some (1H-1,2,3-triazol-4-yl)methoxybenzaldehyde derivatives containing an anthraquinone moiety as potent xanthine oxidase inhibitors

Zhang, Tingjian; Li, Songye; Wei, Yuan; Wu, Qing-xia; Wang, Lin; Sai, Yang; Sun, Qi; Meng, Fan‐hao

doi:10.1016/j.bmcl.2017.01.049

Cited by 29 publications

(12 citation statements)

References 26 publications

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“…Anthraquinone (chemical formula: C 14 H 8 O 2 , molecular weight: 208.21, 9,10-Anthracenedione) possesses the structural core of anthracyclines. (1 H -1,2,3-triazol-4-yl)methoxybenzaldehyde derivatives containing an anthraquinone moiety were synthesised and identified as novel xanthine oxidase inhibitors 168 . Among them, the most promising compounds ( 94a [IC 50 = 0.6 µM] and 94b [IC 50 = 0.8 µM]) ( Figure 22 ) were obtained, and these compounds exhibited greater than 10-fold higher potencies compared to that of the reference xanthine oxidase inhibitor allopurinol.…”

Section: Biological Activitiesmentioning

confidence: 99%

Application of triazoles in the structural modification of natural products

Guo

Zheng-ai

Shen

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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Nature products have been extensively used in the discovery and development of new drugs, as the most important source of drugs. The triazole ring is one of main pharmacophore of the nitrogen-containing heterocycles. Thus, a new class of triazole-containing natural product conjugates has been synthesised. These compounds reportedly exert anticancer, anti-inflammatory, antimicrobial, antiparasitic, antiviral, antioxidant, anti-Alzheimer, and enzyme inhibitory effects. This review summarises the research progress of triazole-containing natural product derivatives involved in medicinal chemistry in the past six years. This review provides insights and perspectives that will help scientists in the fields of organic synthesis, medicinal chemistry, phytochemistry, and pharmacology.

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Section: Biological Activitiesmentioning

confidence: 99%

Application of triazoles in the structural modification of natural products

Guo

Zheng-ai

Shen

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Professor Sharpless in 2014 (Dong et al, 2014;Barrow et al, 2019), have already gained wide application in the synthesis of drug screening libraries (Kitamura et al, 2020;Smedley et al, 2020), late-stage modification of drugs and natural products (Li S. et al, 2017;Liu et al, 2018), DNA-encoded library synthesis (Liu et al, 2019;Xu H. et al, 2019;Zhang et al, 2021), and the synthesis of 18 F radio tracers (Zheng et al, 2021).…”

Section: Sufex Chemistry Another Ideal Click Reaction Proposed Bymentioning

confidence: 99%

“…Taking advantage of the emerging SuFEx click chemistry, several steroid derivatives such as fluorosulfate L7 (Liu et al, 2018), iminosulfur oxydifluoride L8 (Li S. et al, 2017), bis(trifluoromethyl)sulfur oxyimine L9 (Smedley et al, 2019), sulfurofluoridoimidate L10 (Li S. et al, 2017), sulfonimidoyl fluoride L11 and sulfonimidate L12 have been synthesized by using SO 2 F 2 or its sister gas SOF 4 as key reagents in the presence of tertiary amine additives (e.g., TEA, DIPEA, DBU) (Li S. et al, 2017;Gao et al, 2018;Smedley et al, 2019). Among them, the fluorosulfate version of fulvestrant L7 (IC 50 4.8-5.5 nM) could exert more potent inhibitory activity than fulvestrant (IC 50 7.7-14.8 nM).…”

Section: Click Chemistry-based Modification Of Steroidsmentioning

confidence: 99%

Click Chemistry in Natural Product Modification

Zhang

Zhao

et al. 2021

Front. Chem.

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Click chemistry is perhaps the most powerful synthetic toolbox that can efficiently access the molecular diversity and unique functions of complex natural products up to now. It enables the ready synthesis of diverse sets of natural product derivatives either for the optimization of their drawbacks or for the construction of natural product-like drug screening libraries. This paper showcases the state-of-the-art development of click chemistry in natural product modification and summarizes the pharmacological activities of the active derivatives as well as the mechanism of action. The aim of this paper is to gain a deep understanding of the fruitful achievements and to provide perspectives, trends, and directions regarding further research in natural product medicinal chemistry.

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“…The anthraquinone moiety was exploited by Zhang et al [145] to increase enzyme-inhibitor interactions outside the active site while the portion of the molecule interacting inside the active site was made of various acylaminoa cids. Of the eight amino acid derivatives synthesized, only the one with phenylalanine 220 (IC 50 = 3.0 mm)d emonstrated bettera ctivity than allopurinol (IC 50 = 8.1 mm).…”

Section: Other Miscellaneous Compoundsmentioning

confidence: 99%

Inhibitors of Xanthine Oxidase: Scaffold Diversity and Structure‐Based Drug Design

2019

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Xanthine oxidase (XO) is the enzyme responsible for the catabolism of purines and their conversion into uric acid. XO is thus the target for the treatment of hyperuricemia and gout. For more than 50 years the only XO inhibitor drug available on the market was the purine analogue allopurinol. In the last decade there has been a resurgence in the search for new inhibitors of XO, as the activity of XO and hyperuricemia have also been associated with a variety of conditions such as diabetes, hypertension, and other cardiovascular diseases. In recent years the non‐purine inhibitor febuxostat was approved in Europe and the USA for the treatment of hyperuricemia. This drug was followed by another XO inhibitor called topiroxostat. This review discusses the molecular structures and activities of the multiple classes of inhibitors that have been developed since the discovery of allopurinol, with a brief review of the molecular interactions between inhibitors and XO active site residues for the most important molecules. The challenges ahead for the discovery of new inhibitors of XO with novel chemical structures are discussed.

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Discovery and biological evaluation of some (1H-1,2,3-triazol-4-yl)methoxybenzaldehyde derivatives containing an anthraquinone moiety as potent xanthine oxidase inhibitors

Cited by 29 publications

References 26 publications

Application of triazoles in the structural modification of natural products

Application of triazoles in the structural modification of natural products

Click Chemistry in Natural Product Modification

Inhibitors of Xanthine Oxidase: Scaffold Diversity and Structure‐Based Drug Design

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