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Special Issue "Pyrazole Derivatives"

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Medicinal Chemistry".

Deadline for manuscript submissions: 30 November 2017

Special Issue Editor

Guest Editor
Prof. Dr. Wolfgang Holzer

Division of Drug Synthesis, Department of Pharmaceutical Chemistry, Faculty of Life Sciences, University of Vienna, Althanstrasse 14, 1090 Vienna, Austria
Website | E-Mail
Interests: chemistry of azoles; chemistry of azines; heterocyclic tautomerism; NMR spectroscopy in structural elucidation; medicinal heterocyclic chemistry; chemistry of carbenoides

Special Issue Information

Dear Colleagues,

The pyrazole nucleus has been the core of the first synthetic drug molecule and is still a frequently-occurring motif in many biologically active compounds, including several pharmaceuticals currently on the market. Moreover, pyrazole derivatives have found numerous applications in agrochemicals, dyes, fluorescent materials, and more. Hence, there is ongoing interest in pyrazole chemistry also in recent times, what is reflected by a plethora of correspondent publications.

In this respect, researchers in the field are cordially invited to submit their manuscripts relevant to the synthesis of pyrazoles, pyrazolidines and pyrazolinones, their functionalization and their use in the construction of condensed systems for a Special Issue, ‘Pyrazole Derivatives’, within the journal Molecules. Moreover, contributions regarding spectroscopic data and tautomerism studies with appropriate pyrazole derivatives are welcome.

Prof. Dr. Wolfgang Holzer
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All papers will be peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1800 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Synthesis of pyrazoles via ring-closure reactions
  • Functionalization of the pyrazole nucleus
  • Cross-coupling reactions with appropriate pyrazoles
  • N-alkylation and N-arylation of NH-pyrazoles
  • Synthesis of condensed systems starting from pyrazole derivatives
  • Tautomerism of pyrazoles and pyrazolones
  • Bioactive pyrazole derivatives
  • Spectroscopic data of pyrazoles
  • Pyrazole-containing ligands

Published Papers (4 papers)

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Research

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Open AccessArticle 19F‐NMR Diastereotopic Signals in Two N-CHF2 Derivatives of (4S,7R)-7,8,8-Trimethyl-4,5,6,7-tetrahydro-4,7-methano-2H-indazole
Molecules 2017, 22(11), 2003; doi:10.3390/molecules22112003
Received: 2 November 2017 / Revised: 14 November 2017 / Accepted: 16 November 2017 / Published: 17 November 2017
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Abstract
In this paper, we report the anisochrony of the fluorine atoms of a CHF2 group when linked to a pyrazole ring. The pyrazole is part of (4S,7R)-7,8,8-trimethyl-4,5,6,7-tetrahydro-4,7-methano-2H-indazole also known as (4S,7R)-campho[2,3-c
[...] Read more.
In this paper, we report the anisochrony of the fluorine atoms of a CHF2 group when linked to a pyrazole ring. The pyrazole is part of (4S,7R)-7,8,8-trimethyl-4,5,6,7-tetrahydro-4,7-methano-2H-indazole also known as (4S,7R)-campho[2,3-c]pyrazole, which has two stereogenic centers. Gauge-Independent Atomic Orbital (GIAO)/Becke, 3-parameter, Lee-Yang-Parr (B3LYP)/6-311++G(d,f) calculated 19F chemical shifts of the minimum energy conformations satisfactorily agree with the experimental data. The energy differences between minima need to consider solvent effects (continuum model) to be satisfactorily reproduced. Full article
(This article belongs to the Special Issue Pyrazole Derivatives)
Figures

Open AccessArticle Synthesis and Structure–Activity Relationships of 4-Morpholino-7,8-Dihydro-5H-Thiopyrano[4,3-d]pyrimidine Derivatives Bearing Pyrazoline Scaffold
Molecules 2017, 22(11), 1870; doi:10.3390/molecules22111870
Received: 6 September 2017 / Revised: 20 October 2017 / Accepted: 25 October 2017 / Published: 31 October 2017
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Abstract
Phosphatidylinositol 3-kinase/Protein kinase B/Mammalian target of rapamycin (PI3K/Akt/mTOR) signaling pathway is abnormally active in the growth and proliferation of cancer cells. The inhibition of PI3K kinase can effectively block the conduction of signaling pathways and is an ideal target for drug design. In
[...] Read more.
Phosphatidylinositol 3-kinase/Protein kinase B/Mammalian target of rapamycin (PI3K/Akt/mTOR) signaling pathway is abnormally active in the growth and proliferation of cancer cells. The inhibition of PI3K kinase can effectively block the conduction of signaling pathways and is an ideal target for drug design. In this paper; two series of 4-morpholino-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidine derivatives bearing pyrazoline moiety (7a–l; 8a–l) were synthesized; and their cytotoxicity in vitro were evaluated by 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method against four human cancer cell lines including A549; PC-3; MCF-7; and HepG2 cell lines. The activity of the most promising compound 8d against PI3Kα kinase was further evaluated. The results indicated that most of the target compounds showed moderate to excellent cytotoxicity and the most promising compound 8d showed excellent cytotoxicity against four cancer cell lines with half maximal inhibitory concentration (IC50) values of 6.02–10.27 μM. In addition; the compound 8d was found to have a moderate inhibitory activity in the PI3Kα enzyme assay. What’s more; the compounds of which the substituents of benzene ring at the C-4 position are electron-withdrawing groups such as substituents (Cl; F; Br) have better activity than the compounds containing the electron donating groups (OCH3; H). However; the exact action mechanism is not quite clear right now. Further study will be carried out to identify the exact target in near future. Full article
(This article belongs to the Special Issue Pyrazole Derivatives)
Figures

Open AccessArticle Solvent and Copper Ion-Induced Synthesis of Pyridyl–Pyrazole-3-One Derivatives: Crystal Structure, Cytotoxicity
Molecules 2017, 22(11), 1813; doi:10.3390/molecules22111813
Received: 12 September 2017 / Revised: 19 October 2017 / Accepted: 24 October 2017 / Published: 25 October 2017
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Abstract
Five novel compounds, methyl 5-(acetyloxy)-1-(6-bromo-2-pyridinyl)-1H-pyrazole-3-carboxylate (1), methyl 1-(6-bromo-2-pyridinyl)-5-hydroxy-1H-pyrazole-3-carboxylate (2), Trimethyl 1,1′,1′′-tris(6-bromo-2-pyridinyl)-5,5′′-dihydroxy-5′-oxo-1′,5′-dihydro-1H,1′′H-4,4′: 4′,4′′-terpyrazole-3,3′,3′′-tricarboxylate (H2L1, 3), [Cu2(L2)2]·CH3OH (4), H2L2A·CH3
[...] Read more.
Five novel compounds, methyl 5-(acetyloxy)-1-(6-bromo-2-pyridinyl)-1H-pyrazole-3-carboxylate (1), methyl 1-(6-bromo-2-pyridinyl)-5-hydroxy-1H-pyrazole-3-carboxylate (2), Trimethyl 1,1′,1′′-tris(6-bromo-2-pyridinyl)-5,5′′-dihydroxy-5′-oxo-1′,5′-dihydro-1H,1′′H-4,4′: 4′,4′′-terpyrazole-3,3′,3′′-tricarboxylate (H2L1, 3), [Cu2(L2)2]·CH3OH (4), H2L2A·CH3CN (5) were synthesized. Compounds 15 characterized by elemental analysis, IR, and X-ray single-crystal diffraction. And 13 were also characterized by 1H NMR, 13C NMR and ESI-MS. The H2L1, H2L2 were formed by in-situ reaction. H2L2 and H2L2A are mesomer compounds which have two chiral carbons. The antitumor activity of compounds 15 against BEL-7404, HepG2, NCI-H460, T-24, A549 tumor cell lines were screened by methylthiazolyl tetrozolium (MTT) assay. The compounds 1, 2 showed weakly growth inhibition on the HepG2 cell lines. The HepG2 and A549 cell lines showed higher sensitivity to compound 4, while the IC50 values are 10.66, 28.09 μM, respectively. It is worth noting that compounds 15 did not show cytotoxicity to human normal liver cell line HL-7702, suggesting its cytotoxic selectivity on these tumor cell lines. Full article
(This article belongs to the Special Issue Pyrazole Derivatives)
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Review

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Open AccessReview Synthesis of Chromone-Related Pyrazole Compounds
Molecules 2017, 22(10), 1665; doi:10.3390/molecules22101665
Received: 28 August 2017 / Revised: 22 September 2017 / Accepted: 28 September 2017 / Published: 5 October 2017
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Abstract
Chromones, six-membered oxygen heterocycles, and pyrazoles, five-membered two-adjacentnitrogen- 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
[...] Read more.
Chromones, six-membered oxygen heterocycles, and pyrazoles, five-membered two-adjacentnitrogen- 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. Full article
(This article belongs to the Special Issue Pyrazole Derivatives)
Figures

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