pyrrole derivatives
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2022 ◽  
Vol 25 ◽  
pp. 24-40
Author(s):  
Emilio Mateev ◽  
Maya Georgieva ◽  
Alexander Zlatkov

With the significant increase of patients suffering from different types of cancer, it is evident that prompt measures in the development of novel and effective agents need to be taken. Pyrrole moiety has been found in various active compounds with anti-inflammatory, antiseptic, antibacterial, lipid-lowering and anticancer properties. Recent advances in the exploration of highly active and selective cytotoxic structures containing pyrrole motifs have shown promising data for future investigations. Accordingly, this review presents an overview of recent developments in the pyrrole derivatives as anticancer agents, with a main focus towards the key moieties required for the anti-tumor activities. Pyrrole molecules comprising prominent targeting capacities against microtubule polymerization, tyrosine kinases, cytochrome p450 family 1, histone deacetylase and bcl-2 proteins were reported. In addition, several mechanisms of action, such as apoptosis, cell cycle arrest, inhibiting kinases, angiogenesis, disruption of cell migration, modulation of nuclear receptor responsiveness and others were analyzed. Furthermore, in most of the discussed cases we provided synthesis schemes of the mentioned molecules. Overall, the utilization of pyrrole scaffold for the design and synthesis of novel anticancer drugs could be a promising approach for future investigations.  


2021 ◽  
Vol 14 (4) ◽  
pp. 1730-1736
Author(s):  
Kalpana. P. R

Chitosan, a cationic biopolymer is a major derivative of chitin. It is biocompatible, non-toxic and environ-friendly material and has broad spectrum antimicrobial activity. However, it is less effective in neutral or basic conditions due to its solubility only in acidic medium. Therefore, chemical modification with suitable groups is necessary to enhance the potency of chitosan. The present study was mainly conducted to explore the effect of structural modifications on antimicrobial potential of chitosan. N-Methyl, N-Ethyl and N-Propyl pyrrole were reacted with N-chloroacyl-6-O-triphenylmethylchitosan prepared by stepwise modification of chitosan to form N-Methyl, N-Ethyl and N-Propyl pyrrole derivatives of chitosan. Structural characterization of these pyrrole derivatives was done by IR, NMR, XRD, DSC and Elemental Analysis. The gram-negative bacterium Escherichia coli, gram-positive bacterium Staphylococcus aureus were selected for antibacterial activity and the fungus C. albicans was selected for antifungal activity by agar diffusion method and MIC method. Antimicrobial activity of the N-Methyl, N-Ethyl and N-Propyl pyrrole derivatives on E. coli, S. aureus and C. albicans showed an inhibitory effect on all the organisms. The potency of inhibition was found to be varied with the substitutions. The maximum activity was shown by N-pyrrolylpropylchitosan against E. coli (zone of inhibition 1.2±0.05cm, MIC 0.15±0.03mg/ml), S. aureus (zone of inhibition 1.4±0.03cm, MIC 0.15±0.01mg/ml), C. albicans (zone of inhibition 0.8±0.03cm, MIC 0.2±0.03mg/ml). The study also confirmed that all the three derivatives exhibited higher inhibition than that of chitosan against E. coli (zone of inhibition 0.7±0.03cm, MIC 0.09±0.02mg/ml), S. aureus (zone of inhibition 0.8±0.03cm, MIC 0.09±0.02mg/ml), C. albicans (zone of inhibition 0.6±0.03cm, MIC 0.09±0.03mg/ml). Results demonstrated that these three N-alkylpyrrole chitosan derivatives exhibited improved potency and hence can have the more applicability as antimicrobials.


Author(s):  
Saurabh Bhardwaj ◽  
Gyanendra Kumar Sharma

The Pyrrole is one of the significant classes of heterocyclic mixes having pharmacological and natural exercises, for example, antibacterial, antifungal, anthelmintic. The subbed pyrroles with chose functionalities at various position fill in as antecedents for the combination of different new functionalities. Pyrrole has additionally indicated wide organic exercises, for example, treatment of hyperlipidemias, mitigating, COX1/COX-2 inhibitors, 6 cytotoxic action against strong tumor model and assortment of marine and human models. A progression of new Schiff base (E)- N'- Substituted benzylidene-1H-pyrrole-2-carbohydrazide subsidiary (3a-3j) were combined by the response of 1H-pyrrole-2-carbohydrazide and fragrant aldehyde within the sight of ethanol with barely any drops of frosty acidic corrosive. The response blend was observed by TLC and recrystallized from wanted dissolvable. FTIR, 1HNMR, mass spectral and natural investigation were affirmed the structure of the blended mixes. All orchestrated mixes were screened against traditional strains for their antibacterial, antifungal and anthelmintic tasks: gram positive is B.subtilis, and S.aureus and gram negative are E. coli. Antifungal movement was screened against C. Albicans and A. niger and anthelmintic movement was screened against M. konkanensis and P. corethruses. The outcomes uncovered that 3f, 3g and 3i display increasingly strong action against the both two microorganism (gram negative and gram positive bacteria) on the opposite side compound 3a, 3g and 3h show progressively intense movement against the two growths (C. Albicans and A. niger) and compound 3c and 3d having most powerful movement with mean paralyzing time of 11.27 mins and 15.83 mins and mean death time of 19.25 mins and 24.45 mins individually when contrasted with standard medication.


Molecules ◽  
2021 ◽  
Vol 26 (21) ◽  
pp. 6435
Author(s):  
Beatrice-Cristina Ivan ◽  
Florea Dumitrascu ◽  
Adriana Iuliana Anghel ◽  
Robert Viorel Ancuceanu ◽  
Sergiu Shova ◽  
...  

A series of new pyrrole derivatives were designed as chemical analogs of the 1,4-dihydropyridines drugs in order to develop future new calcium channel blockers. The new tri- and tetra-substituted N-arylpyrroles were synthesized by the one-pot reaction of 1-methyl-3-cyanomethyl benzimidazolium bromide with substituted alkynes having at least one electron-withdrawing substituent, in 1,2-epoxybutane, acting both as the solvent and reagent to generate the corresponding benzimidazolium N3-ylide. The structural characterization of the new substituted pyrroles was based on IR, NMR spectroscopy as well as on single crystal X-ray analysis. The toxicity of the new compounds was assessed on the plant cell using Triticum aestivum L. species and on the animal cell using Artemia franciscana Kellogg and Daphnia magna Straus crustaceans. The compounds showed minimal phytotoxicity on Triticum rootlets and virtually no acute toxicity on Artemia nauplii, while on Daphnia magna, it induced moderate to high toxicity, similar to nifedipine. Our research indicates that the newly synthetized pyrrole derivatives are promising molecules with biological activity and low acute toxicity.


Author(s):  
Dilek Şeyma KIZILCAN ◽  
Burçin TÜRKMENOĞLU ◽  
Yahya GÜZEL ◽  
Ertuğrul ASLAN

2021 ◽  
pp. 100373
Author(s):  
Ana Carolina F. de Lyra ◽  
Luis P.A. da Silva ◽  
Jorge de Lima Neto ◽  
Cristiane V. Costa ◽  
Alexandro M.L. de Assis ◽  
...  

2021 ◽  
Vol 15 (3) ◽  
pp. 17-28
Author(s):  
I. P. Kotlyar ◽  
◽  
H. M. Kuznietsova ◽  
V. K. Rybalchenko ◽  
◽  
...  

Background. Previously, we have detected the antitumor and anti-inflammatory activities of pyrrole-derived protein kinase inhibitors - MI-1 (1-(4-Cl-benzyl)-3-Cl-4-(CF3-phenylamino) -1H-pyrrole-2,5-dione 1) and D1 (5-amino-4-(1,3-benzothiazole-2-yl)-1-(3-methoxyphenyl)-1,2-dihydro-3H-pyrrole-3-one) using rat colon cancer model. Therefore, pyrrole derivatives was aimed at detecting the anti-inflammatory effect on the model of ulcerative colitis caused by acetic acid in rats. Materials and Methods. Prednisolone was used as a reference anti-inflammatory drug of glucocorticoid nature. It was administered intraperitoneally at a dose of 0.7 mg/kg. The compounds were administered in 2 h after the first administration of acetic acid. Total protein was estimated quantitatively, as described by Lowry et al., 1951. Content of the malonic dialdehyde, protein carbonyl groups, and the activity of antioxidant enzymes as indicators of colon mucosa redox status were measured spectrophotometrically. Statistical analysis of the results was performed using MS Excel-2013. Results and Discussion. In case of chronic colitis, the number of carbonyl groups and lipid peroxidation products in the colonic mucosa are increased, indicating the development of oxidative stress. The injection of pyrrole derivatives separately contributes to the approaching these indicators to normal. Adding prednisolone does not have this effect. Colitis has been shown to have a decrease in superoxide dismutase activity, which is a typical phenomenon for chronic inflammation and may indicate depletion of the enzyme. In case of colitis, alanine aminotransferase activity and the content of direct bilirubin are increased, which indicates a liver injury and are systemic manifestations of inflammation of the colon. Pyrrole derivatives help to reduce the liver injury, which indicates the restoration of normal alanine aminotransferase activity and direct bilirubin content. Conclusion. It has been found that at chronic colitis pyrrole derivatives reduce the manifestations of inflammation, contribute to the normal structure of the mucous membrane (comparative to prednisolone as a standard anti-inflammatory drug). It suggests their anti-inflammatory effectiveness, while an increase in total bilirubin under exposition to pyrrole derivatives may be a sign of the adverse effects on the rat’s liver.


PeerJ ◽  
2021 ◽  
Vol 9 ◽  
pp. e12209
Author(s):  
Yuntian Xing ◽  
Jiakai Yao ◽  
Guoli Qu ◽  
Jianrong Dai ◽  
Bainian Feng

The snail Oncomelania hupensis is the only intermediate host of the highly invasive parasite Schistosoma japonicum. Molluscicide is often used to curb transmission of S. japonicum. Niclosamide, the only World Health Organization (WHO) recognized molluscicide, presents major drawbacks, including high cost and toxicity towards aquatic animals. In the present study, a number of aryl pyrrole derivatives (ADs) were synthesized to serve as potential molluscicides and were tested on O. hupensis. To uncover the underlying mechanisms, adenosine triphosphate (ATP) and adenosine diphosphate (ADP) levels were assessed in the soft body of ADs-exposed O. hupensis, using high performance liquid chromatography (HPLC). The effect of C6 on key points of energy metabolism (the activities of complexes I, III, IV and the membrane potential) was determined. We demonstrated that the Compound 6 (C6, 4-bromo-1-(bromomethyl)-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile) exerted the strongest molluscicidal activity against adult O. hupensis at LC50 of 0.27, 0.19, and 0.13 mg/L for 24, 48, and 72 h respectively. Moreover, we found that the bromide on the pyrrole ring of C6 was essential for molluscicidal activity. Furthermore, the ATP content reduced from 194.46 to 139.75 μg/g after exposure to 1/2 LC50, and reduced to 93.06 μg/g after exposure to LC50. ADP, on the other hand, remained the same level before and after C6 exposure. We found that C6, at 1/2 LC50, reduced the membrane potential of O. hupensis, while no significant changes were observed in the activities of complexes I, III, and IV. C6 was identified with excellent activities on O. hupensis. The obtained structure−activity relationship and action mechanism study results should be useful for further compound design and development.


2021 ◽  
Vol 17 ◽  
pp. 2462-2476
Author(s):  
Yi Liu ◽  
Puying Luo ◽  
Yang Fu ◽  
Tianxin Hao ◽  
Xuan Liu ◽  
...  

Great progress has been made in the tandem annulation of enynes in the past few years. This review only presents the corresponding reactions of 1,3-enyne structural motifs to provide the functionalized pyridine and pyrrole derivatives. The functionalization reactions cover iodination, bromination, trifluoromethylation, azidation, carbonylation, arylation, alkylation, selenylation, sulfenylation, amidation, esterification, and hydroxylation. We also briefly introduce the applications of the products and the reaction mechanisms for the synthesis of corresponding N-heterocycles.


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