Synthesis and evaluation of 2,5-furan, 2,5-thiophene and 3,4-thiophene-based derivatives as CXCR4 inhibitors

Gaines, Theresa; García, Fernando Herraiz; Virani, Saniya; Liang, Zhongxing; Yoon, Younghyoun; Oum, Yoon Hyeun; Shim, Hyunsuk; Mooring, Suazette Reid

doi:10.1016/j.ejmech.2019.111562

Cited by 7 publications

(4 citation statements)

References 35 publications

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“…Gaines et al [ 62 ] performed in vivo tests (carrageenan-induced paw edema model) with symmetric thiophene and furan derivatives (bioisosteres) as CXCR4 receptor antagonists (inflammation in Irritable Bowel Disease). The authors found that compounds 18 and 19 ( Figure 5 ) substituted in positions 2 and 5 were the most active, with respective inhibition values of 30% and 5%.…”

Section: The Role Of Thiophene Derivatives In Inflammationmentioning

confidence: 99%

Thiophene-Based Compounds with Potential Anti-Inflammatory Activity

et al. 2021

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Rheumatoid arthritis, arthrosis and gout, among other chronic inflammatory diseases are public health problems and represent major therapeutic challenges. Non-steroidal anti-inflammatory drugs (NSAIDs) are the most prescribed clinical treatments, despite their severe side effects and their exclusive action in improving symptoms, without effectively promoting the cure. However, recent advances in the fields of pharmacology, medicinal chemistry, and chemoinformatics have provided valuable information and opportunities for development of new anti-inflammatory drug candidates. For drug design and discovery, thiophene derivatives are privileged structures. Thiophene-based compounds, like the commercial drugs Tinoridine and Tiaprofenic acid, are known for their anti-inflammatory properties. The present review provides an update on the role of thiophene-based derivatives in inflammation. Studies on mechanisms of action, interactions with receptors (especially against cyclooxygenase (COX) and lipoxygenase (LOX)), and structure-activity relationships are also presented and discussed. The results demonstrate the importance of thiophene-based compounds as privileged structures for the design and discovery of novel anti-inflammatory agents. The studies reveal important structural characteristics. The presence of carboxylic acids, esters, amines, and amides, as well as methyl and methoxy groups, has been frequently described, and highlights the importance of these groups for anti-inflammatory activity and biological target recognition, especially for inhibition of COX and LOX enzymes.

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Section: The Role Of Thiophene Derivatives In Inflammationmentioning

confidence: 99%

Thiophene-Based Compounds with Potential Anti-Inflammatory Activity

et al. 2021

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“…The presence of two aldehydes groups offers many possibilities for further modification via Wittig reaction, Schiff bases formation, aldol condensation, etc. [24,25] Despite this promise, few reports make use of this compound partly owing to its current high retail price (123 £.g À 1 Sigma Merck accessed 10/3/20) and instability upon prolonged storage. Additionally, the synthesis of DFF from HMF commonly requires molecular oxygen or expensive transition metal (co)-catalyst (e. g. Ru) which further reduces the applicability of DFF-derived reaction at a higher scale.…”

Section: Resultsmentioning

confidence: 99%

Work‐hardening Photopolymer from Renewable Photoactive 3,3’‐(2,5‐Furandiyl)bisacrylic Acid

et al. 2020

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The design of a photopolymer around a renewable furan‐derived chromophore is presented herein. An optimised semi‐continuous oxidation method using MnO2 affords 2,5‐diformylfuran from 5‐(hydroxymethyl)furfural in gram quantities, allowing the subsequent synthesis of 3,3’‐(2,5‐furandiyl)bisacrylic acid in good yield and excellent stereoselectivity. The photoactivity of the diester of this monomer is confirmed by reaction under UV irradiation, and the proposed [2+2] cycloaddition mechanism supported further by TD‐DFT calculations. Oligoesters of the photoreactive furan diacid with various aliphatic diols are prepared via chemo‐ and enzyme‐catalysed polycondensation. The latter enzyme‐catalysed (Candida antarctica lipase B) method results in the highest Mn (3.6 kDa), suggesting milder conditions employed with this protocol minimised unwanted side reactions, including untimely [2+2] cycloadditions, whilst preserving the monomer's photoactivity and stereoisomerism. The photoreactive polyester is solvent cast into a film where subsequent initiator‐free UV curing leads to an impressive increase in the material stiffness, with work‐hardening characteristics observed during tensile strength testing.

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“…Some CXCR4 inhibitors are in preclinical stages, even in the fundamental experiments, such as WZ811 and AMD3465. 616 , 617 …”

Section: Selective Small Molecule Nonkinase Inhibitorsmentioning

confidence: 99%

“…Phase I study (NCT04274738) mavorixafor in combination with ibrutinib in patients with WM harboring mutations in MYD88 and CXCR4 is ongoing. Some CXCR4 inhibitors are in preclinical stages, even in the fundamental experiments, such as WZ811 and AMD3465 616,617 …”

Section: Selective Small Molecule Nonkinase Inhibitorsmentioning

confidence: 99%

Small molecule inhibitors targeting the cancers

Liu

Chen

Zhang

et al. 2022

MedComm

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Compared with traditional therapies, targeted therapy has merits in selectivity, efficacy, and tolerability. Small molecule inhibitors are one of the primary targeted therapies for cancer. Due to their advantages in a wide range of targets, convenient medication, and the ability to penetrate into the central nervous system, many efforts have been devoted to developing more small molecule inhibitors. To date, 88 small molecule inhibitors have been approved by the United States Food and Drug Administration to treat cancers. Despite remarkable progress, small molecule inhibitors in cancer treatment still face many obstacles, such as low response rate, short duration of response, toxicity, biomarkers, and resistance. To better promote the development of small molecule inhibitors targeting cancers, we comprehensively reviewed small molecule inhibitors involved in all the approved agents and pivotal drug candidates in clinical trials arranged by the signaling pathways and the classification of small molecule inhibitors. We discussed lessons learned from the development of these agents, the proper strategies to overcome resistance arising from different mechanisms, and combination therapies concerned with small molecule inhibitors. Through our review, we hoped to provide insights and perspectives for the research and development of small molecule inhibitors in cancer treatment.

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Synthesis and evaluation of 2,5-furan, 2,5-thiophene and 3,4-thiophene-based derivatives as CXCR4 inhibitors

Cited by 7 publications

References 35 publications

Thiophene-Based Compounds with Potential Anti-Inflammatory Activity

Thiophene-Based Compounds with Potential Anti-Inflammatory Activity

Work‐hardening Photopolymer from Renewable Photoactive 3,3’‐(2,5‐Furandiyl)bisacrylic Acid

Small molecule inhibitors targeting the cancers

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