One-pot Synthesis of Pyrano[2,3-c]pyrazole Derivatives via Multicomponent Reactions (MCRs) and their Applications in Medicinal Chemistry

Medicinal Chemistry ◽

Biological Activities ◽

Biologically Active ◽

Pyrazole Derivatives ◽

One Pot ◽

Discovery Research ◽

Drug Discovery Research ◽

Biological Interest ◽

Derivatives Of

Background: Many pyrano[2,3-c]pyrazole derivatives display diverse biological activities and some of them are known as anticancer, analgesic, anticonvulsant, antimicrobial, anti-inflammatory, and anti-malarial agents. In recent years, easy convergent, multicomponent reactions (MCRs) have been adopted to make highly functionalizedpyrano[2,3-c]pyrazole derivatives of biological interest. The synthesis of 1,4-dihydropyrano[2,3-c]pyrazole (1,4-DHPP, 2), 2,4-dihydropyrano[2,3-c]pyrazole (2,4-DHPP, 3), 4-hydroxypyrano[2,3-c]pyrazole (4-HPP, 4) derivatives, 1,4,4-substitied pyranopyrazole (SPP, 5) were reported via two-, three-, four- and five-component reactions (MCRs). Methods: This review article compiles the preparation of pyrano[2,3-c]pyrazole derivatives, and it highlights the applications of various pyrano[2,3-c]pyrazole derivatives in medicinal chemistry. Results: Varieties of pyrano[2,3-c]pyrazole derivatives were achieved via “One-pot” multicomponent reactions (MCRs). Different reaction conditions in the presence of a catalyst or without catalysts were adapted to prepare the pyrano[2,3-c]pyrazole derivatives. Conclusion: Biologically active pyrano[2,3-c]pyrazole derivatives were prepared and used in drug discovery research.

Pyrazolyl-Ureas as Interesting Scaffold in Medicinal Chemistry

Molecules ◽

10.3390/molecules25153457 ◽

2020 ◽

Vol 25 (15) ◽

pp. 3457 ◽

Cited By ~ 1

Author(s):

Chiara Brullo ◽

Federica Rapetti ◽

Olga Bruno

Keyword(s):

P38 Mapk ◽

Medicinal Chemistry ◽

Biological Activities ◽

Wide Spectrum ◽

Biological Data ◽

Biologically Active ◽

Pyrazole Derivatives ◽

Intracellular Level ◽

Active Compounds ◽

Privileged Scaffold

The pyrazole nucleus has long been known as a privileged scaffold in the synthesis of biologically active compounds. Within the numerous pyrazole derivatives developed as potential drugs, this review is focused on molecules characterized by a urea function directly linked to the pyrazole nucleus in a different position. In the last 20 years, the interest of numerous researchers has been especially attracted by pyrazolyl-ureas showing a wide spectrum of biological activities, ranging from the antipathogenic activities (bacteria, plasmodium, toxoplasma, and others) to the anticarcinogenic activities. In particular, in the anticancer field, pyrazolyl-ureas have been shown to interact at the intracellular level on many pathways, in particular on different kinases such as Src, p38-MAPK, TrKa, and others. In addition, some of them evidenced an antiangiogenic potential that deserves to be explored. This review therefore summarizes all these biological data (from 2000 to date), including patented compounds.

Recent Advances in Biginelli-type Reactions

10.2174/1385272824999200616111228 ◽

2020 ◽

Vol 24 (12) ◽

pp. 1331-1366

Author(s):

Majid M. Heravi ◽

Vahideh Zadsirjan

Keyword(s):

Medicinal Chemistry ◽

Biginelli Reaction ◽

One Pot ◽

Recent Advances ◽

Active Methylene Compounds ◽

Cyclocondensation Reaction ◽

Biginelli Reactions ◽

Derivatives Of ◽

Active Methylene

The effective and high yielding synthesis of poly-functionalized pyrimidines, using multicomponent reactions (MCRs), is imperative in organic and medicinal chemistry. The classic Biginelli reaction is a typically one-pot three-component cyclocondensation reaction involving an aldehyde, a β-ketoester and urea, resulting in the construction of multi-functionalized 3,4-dihydropyrimidin-2(1H)-ones (DHPMs). In recent years, other active methylene compounds, various derivatives of urea and diversely substituted aldehydes have also been used, resulting in the preparation of a new series of various novel dihydropyrimidinones via the Biginelli-Type Reactions (BTRs) or modified Biginelli reactions (MBRs). In this review, we try to underscore the recent advances in BTRs or MBRs.

Recent Advances in the Exploitation of Kojic Acid in Multicomponent Reactions

10.2174/1385272824999200622113153 ◽

2020 ◽

Vol 24 (14) ◽

pp. 1643-1662

Author(s):

Ankita Chaudhary

Keyword(s):

Kojic Acid ◽

Biological Activities ◽

Biologically Active ◽

Atom Economy ◽

One Pot ◽

Biologically Relevant ◽

Modern Drug ◽

Wide Range ◽

Active Precursor

Kojic acid, one of the most widespread 3-hydroxypyran-4-one derivatives, displays a wide range of biological activities and found application in food as well as cosmetics industry. The synthesis of kojic acid derivatives has provoked great interest as an easily available and biologically active precursor among organic and medicinal researchers. Multicomponent reactions, involving three or more reactants in one-pot thereby resulting in a structure with functional diversity are efficient methods for the promotion of green chemistry in the context of modern drug discovery. They offer several advantages over conventional stepwise protocols like simplicity, efficiency, selectivity, convergence and atom economy. This review aims to highlight the versatility of kojic acid as an important synthon in multicomponent reactions for the construction of various biologically relevant compounds such as pyrano[3,2‐ b]chromenediones, pyrano[3,2-b]pyrans, pyrano[2′,3′:5,6]pyrano[2,3‑b]pyridines, spiro[indoline-3,4’-pyrano[3, 2-b]pyrans, 2-substituted kojic acid conjugates, etc.

Arylpyrazoles: Heterocyclic Scaffold of Immense Therapeutic Application

10.2174/1570179417999200628035645 ◽

2020 ◽

Vol 24 (14) ◽

pp. 1555-1581

Author(s):

Garima Tripathi ◽

Anil Kumar Singh ◽

Abhijeet Kumar

Keyword(s):

Biological Activities ◽

Biologically Active ◽

Present Review ◽

Pyrazole Derivatives ◽

Therapeutic Application ◽

Diverse Range ◽

Major Class ◽

Anti Inflammatory

Among the major class of heterocycles, the N-heterocycles, such as pyrazoles, are scaffolds of vast medicinal values. Various drugs and other biologically active molecules are known to contain these N-heterocycles as core motifs. Specifically, arylpyrazoles have exhibited a diverse range of biological activities, including anti-inflammatory, anticancerous, antimicrobial and various others. For instance, arylpyrazoles are present as core moieties in various insecticides, fungicides and drugs such as Celebrex and Trocoxil. The present review will be highlighting the significant therapeutic importance of pyrazole derivatives developed in the last few years.

Recent advance in ester synthesis by Multi Component Reactions (MCRs): A Review

10.2174/1385272825666210111111805 ◽

2021 ◽

Vol 25 ◽

Author(s):

Dhaval B. Patel ◽

Jagruti A. Parmar ◽

Siddharth S. Patel ◽

Unnati J. Naik ◽

Hitesh D. Patel

Keyword(s):

Medicinal Chemistry ◽

Reaction Times ◽

Synthetic Methods ◽

Ester Synthesis ◽

One Pot ◽

Wide Range ◽

Recent Developments ◽

Ester Linkage ◽

The One

: The synthesis of ester containing heterocyclic compounds via multicomponent reaction is one of the most preferable process in the synthetic organic chemistry and medicinal chemistry. Compounds containing ester linkage have a wide range of biological application in the pharmaceutical field. Therefore, many method have been developed for the synthesis of these type of derivatives. However, some of them are carried out in the presence of toxic solvents and catalysts, with lower yields, longer reaction times, low selectivities and by-products. Thus, the development of new synthetic methods for the ester synthesis is required in the medicinal chemistry. As we know, multicomponent reactions (MCRs) are a powerful tool towards the one-pot ester synthesis, so in this article we have reviewed the recent developments in ester synthesis. This work covers selected explanation of methods via multicomponent reactions to explore the methodological development in ester synthesis.

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

Molecules ◽

10.3390/molecules26164995 ◽

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.

One pot synthesis of 3, 4-dihydropyrimidine-2(1H)-thiones using orange peel powder under ultrasonic irradiation

Letters in Applied NanoBioScience ◽

10.33263/lianbs91.919923 ◽

2020 ◽

Vol 9 (1) ◽

pp. 919-923

Keyword(s):

Reaction Time ◽

Ultrasonic Irradiation ◽

Heterocyclic Compounds ◽

Orange Peel ◽

Biologically Active ◽

High Yield ◽

Atom Economy ◽

One Pot ◽

The Past

Biginelli, an important multicomponent reaction provides an avenue for the synthesis of different biologically active heterocyclic compounds. During the past decade, one pot multicomponent reactions have attracted the attention of organic and medicinal chemists due to high atom economy, time and enery saving convergent nature. The present manuscript reports a simple one pot three component synthesis of 3, 4-dihydroprimidin-2(1H)-thiones from various diversely substituted aldehydes, ethyl acetoacetate and thiourea using a orange peel powder as a natural catalyst on ultrasonic irradiation in aqueous medium as the solvent. The advantages of this reaction are less reaction time, high yield, easy availability of the catalyst and green nature.

Synthesis of Biologically Active Molecules through Multicomponent Reactions

Molecules ◽

10.3390/molecules25030505 ◽

2020 ◽

Vol 25 (3) ◽

pp. 505 ◽

Cited By ~ 16

Author(s):

Daniel Insuasty ◽

Juan Castillo ◽

Diana Becerra ◽

Hugo Rojas ◽

Rodrigo Abonia

Keyword(s):

Multicomponent Reaction ◽

Biological Property ◽

Organic Molecules ◽

Biological Activities ◽

Biologically Active ◽

Vast Number ◽

Key Points ◽

Reported Data ◽

Synthetic Approaches

Focusing on the literature progress since 2002, the present review explores the highly significant role that multicomponent reactions (MCRs) have played as a very important tool for expedite synthesis of a vast number of organic molecules, but also, highlights the fact that many of such molecules are biologically active or at least have been submitted to any biological screen. The selected papers covered in this review must meet two mandatory requirements: (1) the reported products should be obtained via a multicomponent reaction; (2) the reported products should be biologically actives or at least tested for any biological property. Given the diversity of synthetic approaches utilized in MCRs, the highly diverse nature of the biological activities evaluated for the synthesized compounds, and considering their huge structural variability, much of the reported data are organized into concise schemes and tables to facilitate comparison, and to underscore the key points of this review.

Recent applications of imines as key intermediates in the synthesis of alkaloids and novel nitrogen heterocycles

Pure and Applied Chemistry ◽

10.1351/pac-con-08-07-03 ◽

2009 ◽

Vol 81 (2) ◽

pp. 195-204 ◽

Cited By ~ 78

Author(s):

Stephen F. Martin

Keyword(s):

Organic Chemistry ◽

Natural Products ◽

Nitrogen Heterocycles ◽

Biologically Active ◽

Total Syntheses ◽

Biological Interest ◽

Cascade Processes ◽

Novel Applications ◽

Active Natural

One of the major challenges in contemporary synthetic organic chemistry is the design and development of new tactics and strategies and their application to concise and efficient syntheses of biologically active natural products. Strategies that utilize reactions that enable the rapid assembly of the skeletal framework of such targets are thus especially attractive. In this context, we have developed novel applications of imine chemistry in Mannich and related reactions, cascade processes, and multicomponent reactions (MCRs) to rapidly assemble structural subunits common to diverse families of alkaloids. The practical utility of these chemistries is evidenced by their use in the execution of facile total syntheses of (±)-epilupinine (1), (±)-tashiromine (2), (-)-epimyrtine (3), and (±)-roelactamine (4) as well as other nitrogen heterocycles of potential biological interest.

Synthesis and Screening of Biologically Active Schiff bases of Benzothiazoles and its Zinc and Lanthanum Metal Complexes

Oriental Journal Of Chemistry ◽

10.13005/ojc/370126 ◽

2021 ◽

Vol 37 (1) ◽

pp. 187-193

Author(s):

D. G. Anuse ◽

V. J. Desale ◽

B. R. Thorat ◽

D. D. Anuse ◽

S. G. Jagadhani ◽

...

Keyword(s):

Metal Complex ◽

Metal Complexes ◽

Schiff Bases ◽

Zinc Chloride ◽

Biological Activities ◽

Biologically Active ◽

Lanthanum Chloride ◽

Schiff’S Bases ◽

Schiff's Bases ◽

Derivatives Of

The substituted 2-Aminobenzothiazole and ethyl 2-(4-formyl-3-hydroxyphenyl)-4-methylthiazole-5-carboxylate in methanol mix together and heat the reaction mixture for overnight, It gives Schiff’s bases (derivatives of substituted aminobenzothiazole) 3. This compound 3 when treated with Zinc Chloride it gives Zinc metal complex of Schiff’s bases 4 and if compound 3 was treated with Lanthanum chloride gives Lanthanum metal complex of Schiff’s bases 5, which shows marked biological activities.