Pyrrole: An insight into recent pharmacological advances with structure activity relationship

Ahmad, Shujauddin; Alam, Ozair; Naim, Mohd. Javed; Shaquiquzzaman, Mohammad; Alam, Mohammad Mumtaz; Iqbal, Muzaffar

doi:10.1016/j.ejmech.2018.08.002

Cited by 185 publications

(93 citation statements)

References 196 publications

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“…The pentacyclic iminosugar compounds were constructed by fusing triazolo[5,1-c] [1,4]oxazepine scaffolds and were investigated for their HIV reverse-transcriptase inhibitory potentials. 127 All synthesised samples demonstrated inhibitory activity against reverse-transcriptase.…”

Section: Antiviral Activitymentioning

confidence: 99%

“…Novel fused triazole 6-methyl-4,5,6,7-tetrahydro-1H- [1,2,3]triazolo [4,5-c]pyridine derivatives were synthesised as P2X7 receptor antagonists by Chrovian et al 138 The 1,2,3-triazole-fused lead 109 (Fig. 14) increased the plasma free fraction that exhibited potential P2X7 receptor occupancy in the hippocampus of rats, with a low ED 50 value of 0.07 mg/kg, and unbound plasma EC 50 value of 12 ng/mL.…”

Section: 23-triazoles As Neuroprotective Agentsmentioning

confidence: 99%

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1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Bozorov

Zhao

Aisa

2019

Bioorganic & Medicinal Chemistry

582

289

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A B S T R A C TThe 1,2,3-triazole ring is a major pharmacophore system among nitrogen-containing heterocycles. These fivemembered heterocyclic motifs with three nitrogen heteroatoms can be prepared easily using 'click' chemistry with copper-or ruthenium-catalysed azide-alkyne cycloaddition reactions. Recently, the 'linker' property of 1,2,3-triazoles was demonstrated, and a novel class of 1,2,3-triazole-containing hybrids and conjugates was synthesised and evaluated as lead compounds for diverse biological targets. These lead compounds have been demonstrated as anticancer, antimicrobial, anti-tubercular, antiviral, antidiabetic, antimalarial, anti-leishmanial, and neuroprotective agents. The present review summarises advances in lead compounds of 1,2,3-triazolecontaining hybrids, conjugates, and their related heterocycles in medicinal chemistry published in 2018. This review will be useful to scientists in research fields of organic synthesis, medicinal chemistry, phytochemistry, and pharmacology. Chemistry: synthesis and properties of the 1,2,3-triazolesThe general synthetic route of 1,2,3-triazoles using click chemistry is described in Scheme 1A. The most popular route to 1,2,3-triazoles is Cu(I)-catalysed Huisgen 1,3-dipolar cycloaddition, which is the https://doi.

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Section: Antiviral Activitymentioning

confidence: 99%

Section: 23-triazoles As Neuroprotective Agentsmentioning

confidence: 99%

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Bozorov

Zhao

Aisa

2019

Bioorganic & Medicinal Chemistry

582

289

View full text Add to dashboard Cite

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“…Pyrrole is one of the most relevant N-heterocyclic unit because of its presence in diverse natural and synthetic compounds with a broad range of applications in medicinal chemistry, drug discovery and materials science [115][116][117]. Although, several synthetic approaches for this scaffold have been developed, there remains a great need to find simpler and atom-economical approaches for the construction of functionalized pyrrole-fused derivatives, which have been considered of interest in view of their pharmacological importance [118][119][120].…”

Section: Pyrrole Derivativesmentioning

confidence: 99%

Synthesis of Biologically Active Molecules through Multicomponent Reactions

et al. 2020

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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.Molecules 2020, 25, 505 2 of 71 acetylcholinesterase inhibitors, anti-HIV, antimicrobial, antioxidant, anti-mycobacterial and anticancer activities ( Figure 1). It is noteworthy that 64% and 16% of the supporting literature found for this review correspond to heterocyclic structures with anticancer and antimicrobial activities, respectively. Scheme 2. Three-component synthesis of 3,4-dihydropyrimidinones/thiones type 7 under microwave irradiation, for anti-inflammatory activity.Patil et al., reported a one-pot pseudo-five-component synthesis of highly functionalized tetrahydropyridines 9 using Cu(OTf) 2 as catalyst, Scheme 3. In vitro anti-inflammatory activity of the obtained compounds 9 was determined against matrix metalloproteinases (MMPs) as MMP-2 and MMP-9 by using gelatin zymography [29]. Scheme 3. Multicomponent Cu(OTf) 2 catalyzed synthesis of substituted tetrahydropyridines 9 for anti-inflammatory activity.A highly diastereoselective synthesis (exclusively the cis isomer is formed), of chromeno β-lactam hybrids 13/14 was also achieved by an efficient one-pot three-component reaction between either 5,5-dimethylcyclohexane-1,3-dione (10a) or 4-hydroxycoumarin (10b), diverse benzaldehydes 11 and malononitrile (12), in the presence of DABCO under reflux conditions (Scheme 4). Scheme 4. Three-component synthesis of β-lactam hybrids 13/14 for anti-inflammatory activity.The synthesized compounds (13 in 80-95% yield) and (14 in 82-95% yield) were screened for anti-inflammatory activity (as well as for anticancer activity, please see Section 3.13.13. Compound 13b (Ar = 4-ClC 6 H 4 , Ar 1 = 4-MeC 6 H 4 ) was the most active of all the chromeno β-lactam hybrids 13/14 tested, with a 19.8 anti-inflammatory ratio, although, it resulted less active than the reference drug dexamethasone corticosteroid used for the treatment of rheumatoid and skin inflammation [30].

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“…As a continuation of our interest in the chemistry of seven-membered sultams, we have focused on the development of the synthetic route to azasultams fused with azole heterocycle (pyrrole, indole, benzimidazole, pyrazole) forming the 1,2,4-thiadiazepine framework. Pyrrole 21 and indole 22 scaffolds can be found in many vital synthetic drugs and natural products that were highlighted in numerous reports. Hence, it was of interest for us to explore these promising heterocyclic templates for the construction of novel seven-membered sultams.…”

Section: Figure 1 Naturally Occurring Sulfonamidesmentioning

confidence: 99%

Synthetic Approach to Fused Azasultams with 1,2,4-Thiadiazepine Framework

et al. 2020

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Synthetic approach to fused azasultams with 1,2,4-thiadiazepine framework via base promoted protocols has been developed. 1H-Azole-2-carboxylates and N-(chloromethyl)-N-methylmethanesulfonamide were used as ambiphilic building blocks in the one-pot and two-step reaction sequences. Chemical behavior of the obtained azasultams in reactions with amines, hydrazine, DMFDMA, and NaBH4 was investigated. An enamino ketone derived from an azasultam was exploited in the synthesis of new pyrazole and pyrimidine heterocycles.

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Pyrrole: An insight into recent pharmacological advances with structure activity relationship

Cited by 185 publications

References 196 publications

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Synthesis of Biologically Active Molecules through Multicomponent Reactions

Synthetic Approach to Fused Azasultams with 1,2,4-Thiadiazepine Framework

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