Ferrocene-containing tetrahydropyrazolopyrazolones: Antioxidant and antimicrobial activity

Bugarinović, Jovana P.; Pešić, Marko; Minić, Aleksandra; Katanić, Jelena; Ilić-Komatina, Danijela; Pejović, Anka; Mihailović, Vladimir; Stevanović, Dragana; Nastasijević, Branislav; Damljanović, Ivan

doi:10.1016/j.jinorgbio.2018.09.015

Cited by 28 publications

(11 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Notably, the inclusion of ferrocene increased the antileishmanial activity of quinazoline, isatinoxamohydrazide, trypanosomal activity of nucleobases . antitoxoplasma activity of atovaquone, antibacterial and antifungal activities of tetrahydropyrazolopyrazolones, Ru (II) arene complrexes, penem, sedaxicene, and antiHCV activity of daclatasvir . Interestingly, ferrocene analogues have also exhibited selectivity for Gram-positive over Gram-negative bacterial strains in 133h .…”

Section: Discussionmentioning

confidence: 99%

“…Bugarinovic et al synthesized ferrocene-derivatized tetrahydropyrazolopyrazolones 223−224 to improve the antimicrobial activity of tetrahydropyrazolopyrazolones 222. 119 The resulting compounds were screened for antimicrobial activity against a panel of bacterial, that is, Gram-positive E. coli ATCC25922, S. enteritidis ATCC13076, and Gram-negative B. cereus ATCC10876, S. aureus ATCC25923 strains. As anticipated, the addition of ferrocene substantially increased the antibacterial activity over the parent compound 222 (MIC > 11.49 mM for all antibacterial strains), but these analogues were not as active as commercial antibiotics, erythromycin and ciprofloxacin (Figure 62).…”

Section: Effect Of Amalgamation/replacement Of Ferrocene On Antimicro...mentioning

confidence: 93%

“…Bugarinovic et al synthesized ferrocene-derivatized tetrahydropyrazolopyrazolones 223 – 224 to improve the antimicrobial activity of tetrahydropyrazolopyrazolones 222 . The resulting compounds were screened for antimicrobial activity against a panel of bacterial, that is, Gram-positive E. coli ATCC25922, S. enteritidis ATCC13076, and Gram-negative B. cereus ATCC10876, S. aureus ATCC25923 strains.…”

Section: Effect Of Amalgamation/replacement Of Ferrocene On Antimicro...mentioning

confidence: 99%

“…The majority of these compounds had lower to moderate activity than the standard drug, isoniazid. The lipophilic nature of ferrocene, which contributes to the partial accessibility of these moieties to penetrate the hydrophobic mycobacterial cell wall, could explain the moderate anti-TB effects of ferrocene-based compounds . Undoubtedly, anti-TB activities of ferrocene-based compounds have not been thoroughly investigated.…”

Section: Effect Of Amalgamation/replacement Of Ferrocene On Antimicro...mentioning

confidence: 99%

See 3 more Smart Citations

Has Ferrocene Really Delivered Its Role in Accentuating the Bioactivity of Organic Scaffolds?

Sharma

Kumar

2021

J. Med. Chem.

View full text Add to dashboard Cite

Ferrocene is an important structural core in bioorganometallic chemistry because of its inherent stability, excellent redox properties, and low toxicity. Ferroquine and ferrocifen are two of the most notable contributions of ferrocene to medicinal chemistry with remarkable antimalarial and anticancer properties. The improved medicinal properties of these drug candidates highlight the impact that ferrocene can have on the molecular and biological properties of the bioactive compounds. In this Perspective, we investigate the scope and limitations of ferrocene incorporation into organic compounds/natural products on their mode of action and biological activities. We have also discussed the detailed role of ferrocene modifications in influencing the anticancer, antimalarial, and antimicrobial properties of various bioactive moieties to design safer and promising ferrocene-based drugs.

show abstract

Section: Discussionmentioning

confidence: 99%

Section: Effect Of Amalgamation/replacement Of Ferrocene On Antimicro...mentioning

confidence: 93%

Section: Effect Of Amalgamation/replacement Of Ferrocene On Antimicro...mentioning

confidence: 99%

Section: Effect Of Amalgamation/replacement Of Ferrocene On Antimicro...mentioning

confidence: 99%

See 2 more Smart Citations

Has Ferrocene Really Delivered Its Role in Accentuating the Bioactivity of Organic Scaffolds?

Sharma

Kumar

2021

J. Med. Chem.

View full text Add to dashboard Cite

show abstract

“…Compounds containing metallocene building units, and particularly ferrocene derivatives, have been studied extensively both in academic and industrial settings (Santos et al, 2017;Singh et al, 2019;Ong & Gasser, 2020). Owing to a favorable combination of chemical and physical properties, ferrocene derivatives are often biologically active, making them attractive pharmacophores for drug design and useful templates in medicinal chemistry research and therapeutic applications including as antioxidant (Bugarinović et al, 2018;Naz et al, 2020), anti-inflammatory (Yun Guo et al, 2019), antimalarial (Peter & Aderibigbe, 2019;Xiao et al, 2020), antileishmanial (Rauf et al, 2016), anticancer (Wang et al, 2020;Ismail et al, 2020), antiplasmodial (García- Barrantes et al, 2013), anticonvulsant (Adil et al, 2018) and antimicrobial (Damljanović et al, 2009) agents. A wide range of therapeutic activities is also associated with ferrocenyl Schiff bases, which have shown exceptionally high activities against pathogenic microbes (Chohan & Praveen, 2000;Chohan et al 2001), and these molecules exhibit potent antioxidant and DNAprotecting properties (Li & Liu, 2011).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis study of (E)-1-(4-chlorophenyl)-N-(4-ferrocenylphenyl)methanimine

Sghyar¹,

Moussaoui²,

Sebbar³

et al. 2021

Acta Crystallogr E Cryst Commun

View full text Add to dashboard Cite

The substituted cyclopentadienyl ring in the title molecule, [Fe(C5H5)(C18H13ClN)], is nearly coplanar with the phenyl-1-(4-chlorophenyl)methanimine substituent, with dihedral angles between the planes of the phenylene ring and the Cp and 4-(chlorophenyl)methanimine units of 7.87 (19) and 9.23 (10)°, respectively. The unsubstituted cyclopentadienyl ring is rotationally disordered, the occupancy ratio for the two orientations refined to a 0.666 (7)/0.334 (7) ratio. In the crystal, the molecules pack in `bilayers' parallel to the ab plane with the ferrocenyl groups on the outer faces and the substituents directed towards the regions between them. The ferrocenyl groups are linked by C—H...π(ring) interactions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (46.1%), H...C/C... H (35.4%) and H...Cl/Cl...H (13.8%) interactions. Thus C—H...π(ring) and van der Waals interactions are the dominant interactions in the crystal packing.

show abstract

[3 + 2] Cycloadditions of Azomethine Imines

Grošelj

Svete

2020

Organic Reactions

View full text Add to dashboard Cite

In spite of their late discovery in the middle of 20 th century, the importance of azomethine imines and their [3+2] cycloaddition reactions has grown constantly throughout the decades. Today, [3+2] cycloadditions of azomethine imines have become indispensable in the preparation of pyrazole derivatives with all degrees of saturation. The structural diversity of azomethine imines is wide and comprises acyclic, C , N ‐cyclic, N , N ‐cyclic, and C , N , N ‐cyclic 1,3‐dipoles. Although electron‐deficient dipolarophiles are preferred, electron‐rich dipolarophiles, such as enol ethers and enamines, are also commonly used in these reactions. Compared to cyclocondensation methods and [3+2] cycloadditions with diazoalkanes and nitrile imines, [3+2] cycloadditions with azomethine imines provide access to a greater diversity of pyrazole derivatives with all degrees of saturation. As with other 1,3‐dipolar cycloadditions, a concerted and nearly synchronous mechanism has been proposed for most [3+2] cycloadditions of azomethine imines, although a stepwise mechanism may be viable in some cases. Several examples of asymmetric [3+2] cycloadditions of azomethine imines that afford non‐racemic cycloadducts with high enantioselectivity have been reported. These asymmetric cycloadditions are performed with various types of transition metal catalysts and organocatalysts, and indicate their potential for the asymmetric synthesis of saturated pyrazole derivatives. Finally, many examples of copper‐catalyzed and thermal, strain‐promoted [3+2] cycloadditions of azomethine imines (in particular sydnones) clearly indicate wide applicability of these reactions in bioconjugation, fluorescent labelling, materials functionalization, and other applications outside the realm of pure organic synthesis.

show abstract

Ferrocene-containing tetrahydropyrazolopyrazolones: Antioxidant and antimicrobial activity

Cited by 28 publications

References 38 publications

Has Ferrocene Really Delivered Its Role in Accentuating the Bioactivity of Organic Scaffolds?

Has Ferrocene Really Delivered Its Role in Accentuating the Bioactivity of Organic Scaffolds?

Crystal structure and Hirshfeld surface analysis study of (E)-1-(4-chlorophenyl)-N-(4-ferrocenylphenyl)methanimine

[3 + 2] Cycloadditions of Azomethine Imines

Contact Info

Product

Resources

About