scholarly journals Revisiting the Structure and Chemistry of 3(5)-Substituted Pyrazoles

Molecules ◽  
2019 ◽  
Vol 25 (1) ◽  
pp. 42 ◽  
Author(s):  
Alina Secrieru ◽  
Paul Michael O’Neill ◽  
Maria Lurdes Santos Cristiano
Keyword(s):  
Organic Synthesis ◽  
Medicinal Chemistry ◽  
Positive Impact ◽  
Biological Activities ◽  
Experimental Methods ◽  
Synthetic Methods ◽  
Conformational Preferences ◽  
Substituted Pyrazoles ◽  
Present Subject

Pyrazoles are known as versatile scaffolds in organic synthesis and medicinal chemistry, often used as starting materials for the preparation of more complex heterocyclic systems with relevance in the pharmaceutical field. Pyrazoles are also interesting compounds from a structural viewpoint, mainly because they exhibit tautomerism. This phenomenon may influence their reactivity, with possible impact on the synthetic strategies where pyrazoles take part, as well as on the biological activities of targets bearing a pyrazole moiety, since a change in structure translates into changes in properties. Investigations of the structure of pyrazoles that unravel the tautomeric and conformational preferences are therefore of upmost relevance. 3(5)-Aminopyrazoles are largely explored as precursors in the synthesis of condensed heterocyclic systems, namely pyrazolo[1,5-a]pyrimidines. However, the information available in the literature concerning the structure and chemistry of 3(5)-aminopyrazoles is scarce and disperse. We provide a revision of data on the present subject, based on investigations using theoretical and experimental methods, together with the applications of the compounds in synthesis. It is expected that the combined information will contribute to a deeper understanding of structure/reactivity relationships in this class of heterocycles, with a positive impact in the design of synthetic methods, where they take part.

scholarly journals Substituted Pyrazoles and Their Heteroannulated Analogs—Recent Syntheses and Biological Activities

Molecules ◽  
2021 ◽  
Vol 26 (16) ◽  
pp. 4995
Author(s):  
Mohamed Ramadan ◽  
Ashraf A. Aly ◽  
Lamiaa E. Abd El-Haleem ◽  
Mohammed B. Alshammari ◽  
Stefan Bräse
Keyword(s):  
Medicinal Chemistry ◽  
Biological Activities ◽  
Biologically Active ◽  
Substituted Pyrazoles ◽  
Privileged Scaffolds

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.

Alternative Routes to the Click Method for the Synthesis of 1,2,3-Triazoles, an Important Heterocycle in Medicinal Chemistry

2018 ◽  
Vol 18 (17) ◽  
pp. 1428-1453 ◽  
Author(s):  
Luana da S.M. Forezi ◽  
Mariana F.C. Cardoso ◽  
Daniel T.G. Gonzaga ◽  
Fernando de C. da Silva ◽  
Vitor F. Ferreira
Keyword(s):  
Medicinal Chemistry ◽  
Biological Activities ◽  
Triazole Ring ◽  
Synthetic Methods ◽  
Synthetic Method ◽  
Molecular Fragments ◽  
Biological Aspects ◽  
Practical Guidance ◽  
Alternative Routes ◽  
Extensive Family

Heterocyclic rings having nitrogen atoms are the molecular fragments most used in drug design by using the tools of medicinal chemistry. The 1,2,4-triazole rings are part of an extensive family of drugs that are in use in the pharmaceutical market. More recently, 1,2,3-triazole rings have begun to arouse the great interest of scientists and therefore, many researches have been developed seeking the synthesis of new substances and their possible biological activities. A number of articles have been published by us and others highlighting the synthetic and biological aspects of 1,2,3-triazoles. The growth of new substances of this class was largely due to the simple and selective synthetic method of 1,2,3- triazole ring developed by Sharpless et al. However, some 1,2,3-triazole cannot be synthesized by this method. This review focuses on other synthetic methods that give access to other variations around the 1,2,3-triazole core. The systematic arrangement in this review explores the possibility of providing practical guidance to alternatives of this heterocycle. It has been divided into sections according to the types of starting materials and reactions.

Pyrazole Carboxylic Acid and Derivatives: Synthesis and Biological Applications

2020 ◽  
Vol 17 ◽  
Author(s):  
Adnan Cetin
Keyword(s):  
Organic Chemistry ◽  
Biological Activity ◽  
Carboxylic Acid ◽  
Heterocyclic Compounds ◽  
Medicinal Chemistry ◽  
Biological Activities ◽  
Building Blocks ◽  
Literature Survey ◽  
Synthetic Methods ◽  
Biological Applications

: The heterocyclic compounds are the building blocks for synthesis of the different biological active compounds in the organic chemistry. Heterocyclic compounds have versatile synthetic applicability and biological activity. Pyrazole carboxylic acid derivatives are significant scaffold structures in heterocyclic compounds due to biologic activities such as antimicrobial, anticancer, inflammatory, antidepressant, antifungal anti-tubercular and antiviral etc. The aim of this mini-review is an overview synthesis of pyrazole carboxylic acid derivatives and their biologic applications. The summarized literature survey presents in detail biological activities of pyrazole carboxylic acid derivatives and their various synthetic methods. This mini-review can be guide to many scientists in medicinal chemistry.

Green Chemistry Synthesis Methods of Oxazine and Thiazine Derivatives as Promising Scaffolds in Medicinal Chemistry: A Mini-Review

2020 ◽  
Vol 17 ◽  
Author(s):  
Mohammad Asif ◽  
Mohammad Imran
Keyword(s):  
Green Chemistry ◽  
Green Synthesis ◽  
Medicinal Chemistry ◽  
Biological Activities ◽  
Synthetic Methods ◽  
Bioactive Molecules ◽  
Synthesis Methods ◽  
Design And Development ◽  
Pharmacological Activities ◽  
Oxazine Derivatives

: Green synthesis of oxazine and thiazine derivatives have concerned a great impact of concern of medicinal researchers and provided a lead molecule for the design and development of various potential bioactive molecules. This review associated additional green synthetic information and it would extend a great deal of help to researchers in synthesizing the most productive, economical, and clinically important thiazine and oxazine derivatives which will be expected to show potent pharmacological activities. This has led to the discovery of various compounds that have diverse types of interesting biological activities. Propose of this article is to study the various synthetic methods of oxazine and thiazine derivatives by green chemistry methods and their biological activities. We expect that this article will be interesting for researchers concerned with oxazine and thiazine compounds.

scholarly journals A Review on Green Synthesis and Biological Activities of Nitrogen and Oxygen Containing Heterocycles

2021 ◽  
Author(s):  
Susheel Gulati ◽  
Rajvir Singh ◽  
Suman Sangwan
Keyword(s):  
Analytical Chemistry ◽  
Green Chemistry ◽  
Organic Synthesis ◽  
Material Science ◽  
Biological Activities ◽  
Review Article ◽  
Synthetic Methods ◽  
Mild Conditions ◽  
Environmental Friendly ◽  
Benign Solvents

Heterocycles are unique precursors for the synthesis of various pharmaceuticals and agrochemicals particularly those possessing N- or O- moieties. The development of methods to prepare heterocycles is of great importance in synthesis of organic compounds, especially the heterocycles which can be found in natural products. The synthesis of nitrogen and oxygen containing heterocycles viz. coumarins, dihydropyrimidinones, imidazoles, isoxazoles and benzimidazoles represented an attractive and demanding work for chemists as these nucleus has found extensive applications in several fields such as material science, analytical chemistry and most importantly in medicinal chemistry. Organic synthesis has been attracted towards the development of new environmental friendly procedures to achieve the goals of green chemistry. The fundamental aspects of green chemistry are use of biocatalysts and environmental benign solvents under mild conditions. The present review article summarized the green synthetic methods and biological activities of nitrogen and oxygen containing heterocycles.

scholarly journals Triterpene sapogenins with oleanene skeleton: chemotypes and biological activities.

2014 ◽  
Vol 61 (2) ◽  
Author(s):  
Kamil Jatczak ◽  
Grzegorz Grynkiewicz
Keyword(s):  
Drug Development ◽  
Current Literature ◽  
Medicinal Chemistry ◽  
Biological Activities ◽  
Renewable Resource ◽  
Synthetic Methods ◽  
Critical Survey ◽  
Natural Sources ◽  
Development Potential ◽  
Pentacyclic Triterpenes

Critical survey of a selected class of pentacyclic triterpenes--the oleanane family, is presented based on current literature in order to underline their value for medicinal chemistry and drug development potential. Oleanenes may be considered as a renewable resource of valuable research materials which are structurally diverse, inherently biocompatible and have built-in affinity for many categories of functional proteins. Although availability of particular compounds from natural sources may be very low, synthetic methods elaborated by generations of chemists, secure a way to obtaining desirable structures from commercial starting materials.

Regioselective Synthesis of Diverse Thio-, Seleno-substituted 1,2,3-Triazoles

2020 ◽  
Vol 23 (22) ◽  
pp. 2379-2401
Author(s):  
Lin-Lin Zhang ◽  
Qin-Pei Wu ◽  
Zhi-Bin Xu
Keyword(s):  
Organic Synthesis ◽  
Reaction Mechanisms ◽  
Material Science ◽  
Medicinal Chemistry ◽  
Synthetic Methods ◽  
Regioselective Synthesis ◽  
Internal Alkynes ◽  
Synthetic Approaches

: Thio-, seleno-substituted triazoles are useful scaffolds employed in the fields of organic synthesis, medicinal chemistry, and material science. A number of synthetic approaches to efficient formation of thio- and seleno-triazoles have been disclosed, including the interception of copper(I) triazolides generated in-situ, cycloaddition of internal alkynes (thio-, halo-, and metalated alkynes) to azides, and the coupling of azides and nonalkyne substrates. This mini-review intends to summarize the synthetic methods toward thio-, seleno-1,2,3-triazoles and the relative reaction mechanisms.

Methyl linked pyrazoles: Synthetic and Medicinal Perspective

2021 ◽  
Vol 21 ◽  
Author(s):  
Tulika Sharma ◽  
Joginder Singh ◽  
Bijender Singh ◽  
Ramesh Kataria ◽  
Vinod Kumar
Keyword(s):  
Medicinal Chemistry ◽  
Biological Activities ◽  
Wide Spectrum ◽  
Review Article ◽  
Present Review ◽  
Pyrazole Derivatives ◽  
High Efficacy ◽  
Depth Analysis ◽  
Synthetic Approaches ◽  
Substituted Pyrazoles

: Pyrazoles, an important and well known class of the azole family, have been found to show a large number of applications in various fields specially of medicinal chemistry. Among pyrazole derivatives, particularly, methyl substituted pyrazoles have been reported as the 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 in depth analysis of their respective medical significances till March2021. It is hoped that literature sum-up in the form of present review article would certainly be a great tool to assist the medicinal chemists for generating new leads possessing pyrazole nucleus with high efficacy and less microbial resistance.

Cascade CuH-Catalyzed Conversion of Alkynes to Enantioenriched 1,1-Disubstituted Products

2019 ◽  
Author(s):  
De-Wei Gao ◽  
Yang Gao ◽  
Huiling Shao ◽  
Tian-Zhang Qiao ◽  
Xin Wang ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Medicinal Chemistry ◽  
Proteasome Inhibitors ◽  
Building Blocks ◽  
Unique Role ◽  
Efficient Strategy ◽  
Carbon Centers ◽  
Rapid Access ◽  
Cascade Catalysis ◽  
Privileged Scaffolds

Enantioenriched <i>α</i>-aminoboronic acids play a unique role in medicinal chemistry and have emerged as privileged pharmacophores in proteasome inhibitors. Additionally, they represent synthetically useful chiral building blocks in organic synthesis. Recently, CuH-catalyzed asymmetric alkene hydrofunctionalization has become a powerful tool to construct stereogenic carbon centers. In contrast, applying CuH cascade catalysis to achieve reductive 1,1-difunctionalization of alkynes remains an important, but largely unaddressed, synthetic challenge. Herein, we report an efficient strategy to synthesize <i>α</i>-aminoboronates <i>via </i>CuH-catalyzed hydroboration/hydroamination cascade of readily available alkynes. Notably, this transformation selectively delivers the desired 1,1-heterodifunctionalized product in favor of alternative homodifunctionalized, 1,2-heterodifunctionalized, or reductively monofunctionalized byproducts, thereby offering rapid access to these privileged scaffolds with high chemo-, regio- and enantioselectivity.<br>

Catalytic, Enantioselective Syn-Diamination of Alkenes

2019 ◽  
Author(s):  
Zhonglin Tao ◽  
Brad Gilbert ◽  
Scott Denmark
Keyword(s):  
General Solution ◽  
Organic Synthesis ◽  
Medicinal Chemistry ◽  
Catalytic Cycle ◽  
Bifunctional Nucleophile

The enantioselective, vicinal diamination of alkenes represents one of the stereocontrolled additions that remains an outstanding challenge in organic synthesis. A general solution to this problem would enable the efficient and selective preparation of widely useful, enantioenriched diamines for applications in medicinal chemistry and catalysis. In this Article we describe the first enantioselective, <i>syn-</i>diamination of simple alkenes mediated by a chiral, enantioenriched organoselenium catalyst together with a <i>N,N’-</i>bistosyl urea as the bifunctional nucleophile and <i>N-</i>fluorocollidinium tetrafluoroborate as the stoichiometric oxidant. Diaryl, aryl-alkyl, and alkyl-alkyl olefins bearing a variety of substituents are all diaminated in consistently high enantioselectivities selectivities but variable yields. The reaction likely proceeds through a Se(II)/Se(IV) redox catalytic cycle reminiscent of the <i>syn-</i>dichlorination reported previously. Furthermore, the <i>syn</i>-stereospecificity of the transformation shows promise for highly enantioselective diaminations of alkenes with no strong steric or electronic bias.

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