Synthesis and biological evaluation of 6-phenylpurine linked hydroxamates as novel histone deacetylase inhibitors

Chen, Dizhong; Soh, Chang Kai; Goh, Wei Huang; Wang, Zilong; Wang, Haishan

doi:10.1016/j.bioorg.2020.103724

Cited by 12 publications

(3 citation statements)

References 37 publications

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“…Purine-hydroximic acid hybrid 58 (IC 50 : 0.22-1.42 µM, Sulforhodamine B/SRB assay) was superior to vorinostat (IC 50 : 0.43-3.07 µM) against leukemia (K562, MOLT4, MV4-11), lymphomas (Raji, Ramos, SU-DHL-6), liver (HepG2, HuH-7, PLC/PRF/5, SK-HEP1, SNU-387, SNU-398), breast (MCF-7), and prostate (PC-3) cancer cell lines. [72] Hybrid 58 (IC 50 : 35 nM) was also more active than vorinostat against SU-DHL-4, SU-DHL-6, and JEKO-1 non-Hodgkin's lymphoma cell lines. [73] Mechanistically, WNY1613 could exert anticancer activity by inducing cancer cell apoptosis and inhibiting the phosphorylation of [74] Hybrid 60 inhibited the phosphorylation of EGFR/HER2, which suppressed the downstream signaling, and induced apoptosis.…”

Section: Purine Derivativesmentioning

confidence: 99%

Current scenario of fused pyrimidines with in vivo anticancer therapeutic potential

Xu,

Wang,

2024

Archiv der Pharmazie

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Cancer, characterized by uncontrolled cell growth and metastasis, is responsible for nearly one in six deaths and represents a severe threat to public health worldwide. Chemotherapy can substantially improve the quality of life and survival of patients with cancer, but anticancer chemotherapeutics are associated with a range of adverse effects. Moreover, almost all currently available anticancer chemotherapeutics could develop drug resistance over a period of time of application in cancer patients and ultimately lead to cancer relapse and death in 90% of patients, creating an urgent need to develop new anticancer agents. Fused pyrimidines trait the inextricable part of DNA and RNA and are vital in numerous biological processes. Fused pyrimidines can act on various biological cancer targets and have the potential to address drug resistance. In addition, more than 20 fused pyrimidines have already been approved for clinical treatment of different cancers and occupy a prominent place in the current therapeutic arsenal, revealing that fused pyrimidines are privileged scaffolds for the development of novel anticancer chemotherapeutics. The purpose of this review is to summarize the current scenario of fused pyrimidines with in vivo anticancer therapeutic potential along with their acute toxicity, metabolic profiles as well as pharmacokinetic properties, toxicity and mechanisms of action developed from 2020 to the present to facilitate further rational exploitation of more effective candidates.

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Section: Purine Derivativesmentioning

confidence: 99%

Current scenario of fused pyrimidines with in vivo anticancer therapeutic potential

Xu,

Wang,

2024

Archiv der Pharmazie

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“…Substitution of the free phenol group of compound 120 may remove bioavailability disadvantage of phenol compound such as PI-103, as demonstrated via replacement of the phenol group of PI-103 [ 110 ] with different hydrogen bond donor/acceptor heterocycles to produce bioavailable clinical drug candidates, namely VS-5584/SB2343. In view of this, Chen et al [ 111 ] reported the synthesis and biological evaluation of a series of 6-phenylpurine-based hydroxamates as anticancer agents. Among the synthesized compounds, 123 appears to be a promising HDAC inhibitor and modulates HDAC targets in PC-3, MCF7, and MV4-11 cells in a dose-dependent manner.…”

Section: Six-membered Heterocyclic Compoundsmentioning

confidence: 99%

An Overview of the Biological Evaluation of Selected Nitrogen-Containing Heterocycle Medicinal Chemistry Compounds

Ebenezer

Jordaan

Carena

et al. 2022

IJMS

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Heterocyclic compounds are a class of compounds of natural origin with favorable properties and hence have major pharmaceutical significance. They have an exceptional adroitness favoring their use as diverse smart biomimetics, in addition to possessing an active pharmacophore in a complex structure. This has made them an indispensable motif in the drug discovery field. Heterocyclic compounds are usually classified according to the ring size, type, and the number of heteroatoms present in the ring. Among different heterocyclic ring systems, nitrogen heterocyclic compounds are more abundant in nature. They also have considerable pharmacological significance. This review highlights recent pioneering studies in the biological assessment of nitrogen-containing compounds, namely: triazoles, tetrazoles, imidazole/benzimidazoles, pyrimidines, and quinolines. It explores publications between April 2020 and February 2022 and will benefit researchers in medicinal chemistry and pharmacology. The present work is organized based on the size of the heterocyclic ring.

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“…Chen et al prepared thirty-one 6-phenylpurines linked to hydroxamate via an alkoxy chain of variable length [ 128 ]. Compound 131 (see Figure 12 for structures of compounds 131 – 141 ) exhibited promising activity against MV4-11 and PC-3 cancer cell lines, with IC 50 values of 0.16 and 1.16 µM, respectively.…”

Section: Imidazoles As Inhibitors Of Other Targetsmentioning

confidence: 99%

Imidazoles as Potential Anticancer Agents: An Update on Recent Studies

et al. 2021

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Nitrogen-containing heterocyclic rings are common structural components of marketed drugs. Among these heterocycles, imidazole/fused imidazole rings are present in a wide range of bioactive compounds. The unique properties of such structures, including high polarity and the ability to participate in hydrogen bonding and coordination chemistry, allow them to interact with a wide range of biomolecules, and imidazole-/fused imidazole-containing compounds are reported to have a broad spectrum of biological activities. This review summarizes recent reports of imidazole/fused imidazole derivatives as anticancer agents appearing in the peer-reviewed literature from 2018 through 2020. Such molecules have been shown to modulate various targets, including microtubules, tyrosine and serine-threonine kinases, histone deacetylases, p53-Murine Double Minute 2 (MDM2) protein, poly (ADP-ribose) polymerase (PARP), G-quadraplexes, and other targets. Imidazole-containing compounds that display anticancer activity by unknown/undefined mechanisms are also described, as well as key features of structure-activity relationships. This review is intended to provide an overview of recent advances in imidazole-based anticancer drug discovery and development, as well as inspire the design and synthesis of new anticancer molecules.

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Synthesis and biological evaluation of 6-phenylpurine linked hydroxamates as novel histone deacetylase inhibitors

Cited by 12 publications

References 37 publications

Current scenario of fused pyrimidines with in vivo anticancer therapeutic potential

Current scenario of fused pyrimidines with in vivo anticancer therapeutic potential

An Overview of the Biological Evaluation of Selected Nitrogen-Containing Heterocycle Medicinal Chemistry Compounds

Imidazoles as Potential Anticancer Agents: An Update on Recent Studies

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