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Molecules (Basel, Switzerland) Oct 2017Chromones, six-membered oxygen heterocycles, and pyrazoles, five-membered two-adjacent-nitrogen-containing heterocycles, represent two important classes of biologically... (Review)
Review
Chromones, six-membered oxygen heterocycles, and pyrazoles, five-membered two-adjacent-nitrogen-containing heterocycles, represent two important classes of biologically active compounds. Certain derivatives of these scaffolds play an important role in medicinal chemistry and have been extensively used as versatile building blocks in organic synthesis. In this context, we will discuss the most relevant advances on the chemistry that involves both chromone and pyrazole rings. The methods reviewed include the synthesis of chromone-pyrazole dyads, synthesis of chromone-pyrazole-fused compounds, and chromones as starting materials in the synthesis of 3(5)-(2-hydroxyaryl)pyrazoles, among others. This review will cover the literature on the chromone and pyrazole dual chemistry and their outcomes in the 21st century.
Topics: Antineoplastic Agents; Chromones; Drug Design; Humans; Molecular Structure; Pyrazoles; Structure-Activity Relationship
PubMed: 28981465
DOI: 10.3390/molecules22101665 -
Molecules (Basel, Switzerland) Mar 2020The present review presents an overview of antitumor pyrazoles of natural or bioinspired origins. Pyrazole compounds are relatively rare in nature, the first ones having... (Review)
Review
The present review presents an overview of antitumor pyrazoles of natural or bioinspired origins. Pyrazole compounds are relatively rare in nature, the first ones having been reported in 1966 and being essentially used as somniferous drugs. Cytotoxic pyrazoles of natural sources were first isolated in 1969, and a few others have been reported since then, most of them in the last decade. This paper presents a perspective on the current knowledge on antitumor natural pyrazoles, organized into two sections. The first focuses on the three known families of cytotoxic pyrazoles that were directly isolated from plants, for which the knowledge of the medicinal properties is in its infancy. The second section describes pyrazole derivatives of natural products, discussing their structure-activity relationships.
Topics: Animals; Antineoplastic Agents; Biological Products; Biomimetic Materials; Humans; Pyrazoles
PubMed: 32192149
DOI: 10.3390/molecules25061364 -
Molecules (Basel, Switzerland) Aug 2021Pyrazoles are considered privileged scaffolds in medicinal chemistry. Previous reviews have discussed the importance of pyrazoles and their biological activities;... (Review)
Review
Pyrazoles are considered privileged scaffolds in medicinal chemistry. Previous reviews have discussed the importance of pyrazoles and their biological activities; however, few have dealt with the chemistry and the biology of heteroannulated derivatives. Therefore, we focused our attention on recent topics, up until 2020, for the synthesis of pyrazoles, their heteroannulated derivatives, and their applications as biologically active moieties. Moreover, we focused on traditional procedures used in the synthesis of pyrazoles.
Topics: Chemistry Techniques, Synthetic; Humans; Pyrazoles
PubMed: 34443583
DOI: 10.3390/molecules26164995 -
Mini Reviews in Medicinal Chemistry 2022Pyrazoles, an important and well-known class of the azole family, have been found to show a large number of applications in various fields, especially medicinal... (Review)
Review
Pyrazoles, an important and well-known class of the azole family, have been found to show a large number of applications in various fields, especially medicinal chemistry. Pyrazole derivatives, particularly methyl-substituted pyrazoles, have been reported as potent medicinal scaffolds that exhibit a wide spectrum of biological activities. The present review is an attempt to highlight the detailed synthetic approaches for methyl-substituted pyrazoles along with an in-depth analysis of their respective medical significances till March 2021. It is hoped that literature sum-up in the form of present review article would certainly be a great tool in assisting medicinal chemists in generating new leads possessing pyrazole nucleus with high efficacy and less microbial resistance.
Topics: Chemistry, Pharmaceutical; Pyrazoles
PubMed: 34521325
DOI: 10.2174/1389557521666210914124914 -
Medicinal Chemistry (Shariqah (United... 2022Pyrazole scaffolds have gained importance in drug discovery and development for various pharmacological activities like antiviral, antifungal, anticancer,... (Review)
Review
BACKGROUND
Pyrazole scaffolds have gained importance in drug discovery and development for various pharmacological activities like antiviral, antifungal, anticancer, antidepressant, antiinflammatory, antibacterial, etc. Additionally, the pyrazole moiety has shown potent anti-HIV activity as a core heterocycle or substituted heterocycles derivatives (mono, di, tri, tetra, and fused pyrazole derivatives). To assist the development of further potential anti-HIV agents containing pyrazole nucleus, here we have summarized pyrazole containing anti-HIV compounds that have been reported by researchers all over the world for the last two decades.
OBJECTIVE
The present review concentrates on an assortment of pyrazole containing compounds, particularly for potential therapeutic activity against HIV.
METHODS
Google Scholar, Pubmed, and SciFinder were searched databases with ''pyrazol'' keywords. Further, the year of publication and keywords ''Anti-HIV'' filter was applied to obtain relevant reported literature for anti-HIV agents containing pyrazole as a core or substituted derivatives.
RESULTS
This review article has shown the comprehensive compilation of 220 compounds containing pyrazole nucleus and possessing anti-HIV activity by sorting approximately 40 research articles from 2001 to date. 1-(4-Benzoylpiperazin-1-yl)-2-(4-fluoro-7-(1H-pyrazol-3-yl)-1H-pyrrolo[2,3-c]pyridin- 3-yl)ethane-1,2-dione (13), 3-(3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-fluoro-1H-pyrrolo[2,3- c]pyridin-7-yl)-1H-pyrazole-5-carboxamide (31), 3-(3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4- fluoro-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-pyrazole-5-carboxamide (88), 3-cyanophenoxypyrazole derivative (130), and 4-(4-chlorophenyl)-5-(4-methyl-5-((4-nitrophenyl)diazenyl)thiazol-2-yl)-3- phenyl-5,6-dihydro-4H-pyrazolo[4,3-d]isoxazole (178) were the most potent mono-, di-, tri-, tetrasubstituted, and fused pyrazole derivatives, respectively, which have shown potent anti-HIV activity among all the described derivatives as compared with standard anti-HIV drugs.
CONCLUSION
This review article provides an overview of the potential therapeutic activity of pyrazole derivatives against HIV that will be helpful for designing pyrazole containing compounds for anti-HIV activity.
Topics: Anti-HIV Agents; Anti-Inflammatory Agents; Antifungal Agents; HIV Infections; Humans; Pyrazoles
PubMed: 34994333
DOI: 10.2174/1573406418666220106163846 -
European Journal of Medicinal Chemistry Jun 2015Pyrazole is a five membered and two-nitrogen containing heterocyclic ring. These structures have been investigated in the development of novel compounds with... (Review)
Review
Pyrazole is a five membered and two-nitrogen containing heterocyclic ring. These structures have been investigated in the development of novel compounds with hypoglycemic, analgesic, anti-inflammatory, antimicrobial, anticonvulsant, antidepressant, antimycobacterial, antioxidant, antiviral, insecticidal and antitumor activities. Therefore, these compounds have been synthesized as target structures by many researchers and were evaluated for their biological activities. We hope that the bioactivity of pyrazole derivatives will be beneficial for the rational design of new generation of small molecule drugs. In this review, we report the structures of 1H-pyrazoles with their corresponding biological activities for 21st (in 2000-2014 years) century.
Topics: Animals; Drug Discovery; Humans; Pyrazoles
PubMed: 25555743
DOI: 10.1016/j.ejmech.2014.11.059 -
Bioorganic Chemistry Oct 2023Tumor selectivity is yet a challenge in chemotherapy-based cancer treatment. A series of calixarenes derivatized at the lower rim with 3-phenyl-1H-pyrazole units with...
Tumor selectivity is yet a challenge in chemotherapy-based cancer treatment. A series of calixarenes derivatized at the lower rim with 3-phenyl-1H-pyrazole units with variable upper-rim substituent and conformations of macrocyclic core, alkyl chain length between heterocycle and core, as well as phenolic monomer (5-(4-tert-butylphenyloxy)methoxy-3-phenyl-1H-pyrazole) have been synthesized and characterized in a range of therapeutically relevant cellular models (M-HeLa, MCF7, A-549, PC3, Chang liver, and Wi38) from different target organs/systems. Specific cytotoxicity for M-HeLa cells has been observed in tert-butylcalix[4]arene pyrazoles in 1,3-alternate (compound 7b) and partial cone (compound 7c) conformations with low mutagenicity and haemotoxicity and in vivo toxicity in mice. Compounds 7b,c have induced mitochondrial pathway of apoptosis of M-HeLa cells through caspase-9 activation preceded by the cell cycle arrest at G0/G1 phase. A concomitant overexpression of DNA damage markers in pyrazole-treated M-HeLa cells suggests that calixarene pyrazoles target DNA, which was supported by the presence of interactions between calixarenes and ctDNA at the air-water interface.
Topics: Animals; Humans; Mice; Calixarenes; HeLa Cells; Neoplasms; Porifera; Pyrazoles
PubMed: 37480816
DOI: 10.1016/j.bioorg.2023.106742 -
Molecules (Basel, Switzerland) Dec 2020The pyrazole nucleus and its reduced forms, pyrazolines and pyrazolidine, are privileged scaffolds in medicinal chemistry due to their remarkable biological activities.... (Review)
Review
The pyrazole nucleus and its reduced forms, pyrazolines and pyrazolidine, are privileged scaffolds in medicinal chemistry due to their remarkable biological activities. A huge number of pyrazole derivatives have been studied and reported over time. This review article gives an overview of pyrazole derivatives that contain a styryl (2-arylvinyl) group linked in different positions of the pyrazole backbone. Although there are studies on the synthesis of styrylpyrazoles dating back to the 1970s and even earlier, this type of compound has rarely been studied. This timely review intends to summarize the properties, biological activity, methods of synthesis and transformation of styrylpyrazoles; thus, highlighting the interest and huge potential for application of this kind of compound.
Topics: Animals; Humans; Molecular Structure; Pyrazoles
PubMed: 33322752
DOI: 10.3390/molecules25245886 -
Anti-inflammatory & Anti-allergy Agents... 2018
Topics: Analgesics; Anti-Inflammatory Agents; Benzimidazoles; Phthalazines; Pyrazoles
PubMed: 30277139
DOI: 10.2174/187152301701180827120421 -
Future Medicinal Chemistry Nov 2023Pyrazole or 1-pyrazole, a five-membered 1,2-diazole, is found in several approved drugs and some bioactive natural products. A myriad number of derivatives of this small... (Review)
Review
Pyrazole or 1-pyrazole, a five-membered 1,2-diazole, is found in several approved drugs and some bioactive natural products. A myriad number of derivatives of this small molecule have been reported in clinical and preclinical studies for the potential treatment of several diseases. The number of drugs containing a pyrazole nucleus has increased significantly in the last 10 years. Some of the best-selling drugs in this class are ibrutinib, ruxolitinib, axitinib, niraparib and baricitinib, and are used to treat different types of cancers; lenacapavir to treat HIV; riociguat to treat pulmonary hypertension; and sildenafil to treat erectile dysfunction. Several aniline-derived pyrazole compounds have been reported as potent antibacterial agents with selective activity against methicillin-resistant and vancomycin-resistant enterococci. Here, we discuss the pyrazole-derived drugs reported up to September 2023.
Topics: Male; Humans; Methicillin-Resistant Staphylococcus aureus; Anti-Bacterial Agents; Pyrazoles; Drug Discovery; Microbial Sensitivity Tests
PubMed: 37933613
DOI: 10.4155/fmc-2023-0207