Metallocenes in biochemistry, microbiology &amp; medicine

Dombrowski, Kenneth E.; Baldwin, Wendy; Sheats, John E.

doi:10.1016/0022-328x(86)80097-3

Cited by 112 publications

(49 citation statements)

References 76 publications

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“…The N-phenylcarbodiimide 7 formed was treated with ethanol in dry pyridine to give the 2-ethoxyimidazolone 8, treatment of which with acetic acid at reflux yielded (ferrocenyl)methylidenehydantoin (9), a compound with potential biological activity. [11,12] As well as by conventional hydrolysis, this reaction may also proceed by N(3)-protonation followed by the loss of ethylene. [13] When 7 was treated with water in pyridine, 9 was contaminated by the 2-(phenylamino)imidazol-5-one 10, the formation of which is obviously due to the action of aniline originating from the partial hydrolysis of the carbodiimide precursor.…”

Section: Resultsmentioning

confidence: 99%

Ethyl α‐(Triphenylphosphoranylidene)amino‐β‐ferrocenylacrylate as a Starting Material for [2+2] Cycloadditions, Including the Aza‐Wittig Reaction

Csámpai¹,

Túrós

Kudar³

et al. 2004

Eur J Org Chem

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Ethyl α-(triphenylphosphoranylidene)amino-β-ferrocenylacrylate, synthesized from the corresponding azide, was treated with a few selected electrophilic agents potentially capable of undergoing the aza-Wittig reaction. The transformations with aroyl chlorides and phenylisocyanate afforded a series of novel 4-(ferrocenyl)methylidene-2-aryloxazolones. On treatment of the phosphorimino compound with DMAD two competitive reactions took place on the C=C and N=P bonds, giving rise to a novel amino(ferrocenyl)butadiene and a ferrocenyl-substituted aza-pentadienylphosphory-

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Section: Resultsmentioning

confidence: 99%

Ethyl α‐(Triphenylphosphoranylidene)amino‐β‐ferrocenylacrylate as a Starting Material for [2+2] Cycloadditions, Including the Aza‐Wittig Reaction

Csámpai¹,

Túrós

Kudar³

et al. 2004

Eur J Org Chem

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“…Amongst the compounds reported as a result of these efforts are the ferrocenylpyrazoles that show superb antibacterial activity against Gram positive bacteria (Damljanovic et al 2009). By coupling pyrazoles, which are known to have antimicrobial activity (Kucukguzel et al 2000;Genin et al 2000b;Adnan and Abdel-Aziem 2004;Bekhit et al 2005) with ferrocene moieties known for its advantage to cross the cell membrane (Dombrowski et al 1986), compounds 46 and 47 were isolated and shown to be active against an array of bacteria. The activities of 46 and 47 compare well with the reference compounds tetracycline and nistatine.…”

Section: Antiparasites and Antibacterialsmentioning

confidence: 99%

Perspective: the potential of pyrazole-based compounds in medicine

2011

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Pyrazoles are widely used as core motifs for a large number of compounds for various applications such as catalysis, agro-chemicals, building blocks of other compounds and in medicine. The attractiveness of pyrazole and its derivatives is their versatility that allows for synthesis of a series of analogues with different moieties in them, thus affecting the electronics and by extension the properties of the resultant compounds. In medicine pyrazole is found as a pharmacophore in some of the active biological molecules. While pyrazole derivatives have been extensively studied for many applications including anticancer, antimicrobial, anti-inflammatory, antiglycemic, anti-allergy and antiviral, much less has been reported on their metal counterparts in spite of the fact that metals have been shown to impart activity to ligands. Thus this perspective is intended to demonstrate the potential of pyrazole and pyrazolyl metal complexes in the areas of drug discovery and development. Several examples, that include palladium, platinum, copper, gold, zinc, cobalt, nickel, iron, copper, silver and gallium complexes, are used to bolster the above point. For the purposes of this review three areas are discussed, that is pyrazole metal complexes as: (i) anticancer, (ii) antibacterial/parasitic and (iii) antiviral agents.

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“…13 C NMR (50 MHz, 188.1,175.7,165.5,71.0,70.5,69.7,69.1,65.6 Fe,15.90;N,3.99;O,13.67. Found C,61.66 ;H,4.95;N,3. 1 H NMR (200 MHz, DMSO-d6): δ 4.7 (br, 2H), 4.6 (br, 2H), 4.2 (s, 5 H), 3.8 (br, 4 H), 2.8 (br, 4H). 13 C NMR (50 MHz, 188.0,175.4,165.2,70.9,70.8,69.7,69.1,49.6,46.9,45.4 1 H NMR (200 MHz, DMSO-d6): δ 9.0 (br, 1H), 7.6 (s, 1H), 6.4 (d, J = 9 Hz, 2H), 5.0 (s, 2H), 4.8 (app d, J = 3.2 Hz, 2H), 4.6 (s, 2H), 4.14 (s, 5H).…”

Section: General Procedures For the Synthesis Of Ferrocene Bissquaramimentioning

confidence: 99%

“…3 As a result, a large number of reports have appeared in the literature dealing with the synthesis and biological activity of ferrocene bioconjugates. 4 One example that stands out with respect to its antiproliferative activity on mammary tumors is a family of ferrocene-containing Tamoxifen analogues called Ferrocifen (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Study of the reactivity of squarylferrocenes. Addition of amines and aminoesters

Villanueva-García

Reyes

Pannell³

et al. 2011

Arkivoc

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The reactivity of squarylferrocenes was studied in the addition of several N-centered nucleophiles. A total of seven simple amines (primary and secondary) were added to both monosquarylferrocene and 1,1′-bissquarylferrocene to generate 14 ferrocenylsquaramides in 85-98%. Likewise, five aminoesters were added to the same scaffolds to produce a novel family of 10 ferrocene-aminoester conjugates in good to excellent yields (57-95%).

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Metallocenes in biochemistry, microbiology & medicine

Cited by 112 publications

References 76 publications

Ethyl α‐(Triphenylphosphoranylidene)amino‐β‐ferrocenylacrylate as a Starting Material for [2+2] Cycloadditions, Including the Aza‐Wittig Reaction

Ethyl α‐(Triphenylphosphoranylidene)amino‐β‐ferrocenylacrylate as a Starting Material for [2+2] Cycloadditions, Including the Aza‐Wittig Reaction

Perspective: the potential of pyrazole-based compounds in medicine

Study of the reactivity of squarylferrocenes. Addition of amines and aminoesters

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