An insight on synthetic and medicinal aspects of pyrazolo[1,5-a]pyrimidine scaffold

Cherukupalli, Srinivasulu; Karpoormath, Rajshekhar; Chandrasekaran, Balakumar; Hampannavar, Girish A.; Thapliyal, Neeta; Palakollu, Venkata Narayana

doi:10.1016/j.ejmech.2016.11.019

Cited by 150 publications

(127 citation statements)

References 110 publications

Supporting

Mentioning

127

Contrasting

Order By: Relevance

“…The rich reactivity of pyrazoles is linked to their challenging structure, with the possibility of tautomerism [12] and the presence of a multifarious framework, offering versatility for applications in synthetic organic chemistry [13,14]. Derivatives of 3-or 5-amino pyrazole, generally referred to as 3(5)-aminopyrazoles, are especially interesting in this context, serving as starting materials for the synthesis of condensed heterocycles, including pyrazolo [1,5-a]pyrimidines, another privileged motif that attracted interest for many years and is extensively reviewed, in the past and also in recent literature [15][16][17][18]. However, to this date, a thorough investigation regarding the chemistry and diverse reactivity of 3(5)-aminopyrazoles leading to more complex heterocyclic systems has not been performed.…”

Section: Introductionmentioning

confidence: 99%

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

2019

View full text Add to dashboard Cite

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.

show abstract

Section: Introductionmentioning

confidence: 99%

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

2019

View full text Add to dashboard Cite

show abstract

“…Pyrimidine is one of the privileged hetrocycles in drug discovery because its derivatives have highly pronounced biological profiles including anti‐TB activity . Thus, combination of pyrimidine and isatin has the potential to provide more active anti‐TB candidates.…”

Section: Isatin‐pyrimidine Hybridsmentioning

confidence: 99%

Isatin Derivatives with Potential Antitubercular Activities

Jiang

Wang

Liu

et al. 2018

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Tuberculosis is a life‐threatening chronic infectious disease, which primarily affects the lungs but can spread to other vital organs. The re‐emergence and wide spread of new virulent forms of Mycobacterium tuberculosis that are resistant to some or all first and second line antitubercular agents has reached an alarming level in recent decades. Thus, it is imperative to develop more effective agents. Isatin derivatives are endowed with diverse biological properties, therefore thousands of isatin derivatives have been synthesized in hopes of discovering new candidates with potential antitubercular activities against both drug‐susceptible and drug‐resistant strains. This review summarizes the recent developments of isatin derivatives with potential antitubercular activities.

show abstract

“…The substitution point at C¼C bond and methoxy groups are also briefly mentioned in this article [6e9]. The modifications in these frameworks lead to the broadening of activity continuum of TMCA analogues [10,11].…”

Section: Introductionmentioning

confidence: 99%

Research progress in the biological activities of 3,4,5-trimethoxycinnamic acid (TMCA) derivatives

Zhao

Song

Xie

et al. 2019

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

a b s t r a c t TMCA (3,4,5-trimethoxycinnamic acid) ester and amide are privileged structural scaffolds in drug discovery which are widely distributed in natural products and consequently produced diverse therapeutically relevant pharmacological functions. Owing to the potential of TMCA ester and amide analogues as therapeutic agents, researches on chemical syntheses and modifications have been carried out to druglike candidates with broad range of medicinal properties such as antitumor, antiviral, CNS (central nervous system) agents, antimicrobial, anti-inflammatory and hematologic agents for a long time. At the same time, SAR (structure-activity relationship) studies have draw greater attention among medicinal chemists, and many of the lead compounds were derived for various disease targets. However, there is an urgent need for the medicinal chemists to further exploit the precursor in developing chemical entities with promising bioactivity and druggability. This review concisely summarizes the synthesis and biological activity for TMCA ester and amide analogues. It also comprehensively reveals the relationship of significant biological activities along with SAR studies.

show abstract

An insight on synthetic and medicinal aspects of pyrazolo[1,5-a]pyrimidine scaffold

Cited by 150 publications

References 110 publications

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

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

Isatin Derivatives with Potential Antitubercular Activities

Research progress in the biological activities of 3,4,5-trimethoxycinnamic acid (TMCA) derivatives

Contact Info

Product

Resources

About