Thiosemicarbazone copper complexes as competent catalysts for olefin cyclopropanations

Youssef, Nabil S.; El‐Seidy, Ahmed M. A.; Schiavoni, Marco; Castano, B.; Ragaini, Fabio; Gallo, Emma; Caselli, Alessandro

doi:10.1016/j.jorganchem.2012.03.018

Cited by 29 publications

(17 citation statements)

References 53 publications

(44 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…35 Non-activated aliphatic alkenes are known to be less reactive in comparison with aromatic or activated alkenes towards copper mediated cyclopropanations. 36 Chiral catalysts for the …”

Section: Paper Dalton Transactionsmentioning

confidence: 99%

Asymmetric cyclopropanation of olefins catalysed by Cu(i) complexes of chiral pyridine-containing macrocyclic ligands (Pc-L*)

et al. 2013

Self Cite

View full text Add to dashboard Cite

The synthesis and characterisation of copper(I) complexes of chiral pyridine-containing macrocyclic ligands (Pc-L*) and their use as catalysts in asymmetric cyclopropanation reactions are reported.All ligands and metal complexes were fully characterised, including crystal structures of some species determined by X-ray diffraction on single crystals. This allowed characterising the very different conformations of the macrocycles which could be induced by different substituents or by metal complexation.The strategy adopted for the ligand synthesis is very flexible allowing several structural modifications. A small library of macrocyclic ligands possessing the same donor properties but with either C 1 or C 2 symmetry was synthesized. Cyclopropane products with both aromatic and aliphatic olefins were obtained in good yields and enantiomeric excesses up to 99%.

show abstract

“…35 Non-activated aliphatic alkenes are known to be less reactive in comparison with aromatic or activated alkenes towards copper mediated cyclopropanations. 36 Chiral catalysts for the …”

Section: Paper Dalton Transactionsmentioning

confidence: 99%

Asymmetric cyclopropanation of olefins catalysed by Cu(i) complexes of chiral pyridine-containing macrocyclic ligands (Pc-L*)

et al. 2013

Self Cite

View full text Add to dashboard Cite

show abstract

“…Such disorders have been frequently observed in crystallography at the terminal chains 44,45 . Furthermore, the salicylaldimine plane of 1 which includes O1, N1 and C1-C7 found to be rotated approximately 180 o around C6-C7 bond compared to that in the other compounds (2)(3)(4). This led to change the anti geometry between the C1 or C5 atom and N1 atom to syn geometry.…”

Section: Crystallographic Studymentioning

confidence: 88%

“…New thiosemicarbazones (1)(2)(3)(4) were prepared by condensation of 4-ethyl-3-thiosemicarbazide with corresponding aldehyde derivatives. Compounds were collected either as white or yellow powderous material.…”

Section: Synthesismentioning

confidence: 99%

“…The S1-C8 bond distance is longer than compared to that of N2-C8 which indicates that the compounds are present in thione form. The N3-C8 [1.268(17) Å] bond distance of 1 is shorter that compared to that of N3-C9 [1.51(2) Å] that is different compared to the other compounds (2)(3)(4). This phenomenon leads to decrease the S1-C8-N3 [117.5 (8) …”

Section: Crystallographic Studymentioning

confidence: 99%

“…Metal-thiosemicarbazone complexes have been found to have interesting catalytic [3][4][5][6] as well as biological applications 5,[7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24] . However, it has been also reported that by suitable structural variations thiosemicarbazone ligands could also become potential anticarcinogenic agents [25][26][27][28][29][30] .…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Asynthesis, Crystal Structures and in Vitro Anticancer Studies of New Thiosemicarbazone Derivatives

Hussein

Iqbal

Asif

et al. 2015

Phosphorus, Sulfur, and Silicon and the Related Elements

View full text Add to dashboard Cite

Thiosemicarbazones are an important class of compounds having significant biological properties. These compounds are used as stable ligands for the synthesis of coordination compounds of biological worth. The current study describes syntheses of four new N(3)-ethyl thiosemicarbazone derivatives and their in vitro anticancer testing. The purpose of the study was to observe the effect of various subtitutions at the aromatic ring against the growth of cancerous cell. The synthesized compounds were characterized by NMR ( 1 H & 13 C) spectroscopy and the molecular structures of each of the compounds were determined using single crystal X-ray crystallographic technique. Interestingly, compound 4 appeared to have two crystallographically different units (A and B), having slightly different bond lengths and angles compared to each other. All the compounds were tested for their in vitro anticancer properties against Human Colon Cancer (HCT 116) and Breast Cancer (MCF-7) cell lines. The compounds (1-2), having halide (Cl and Br) substitutions, showed significant activity compared to those having ethoxy and allyl substitutions (3-4), indicating the possible involvement of halides against cancerous cells.

show abstract

Synthesis, characterization, biological screening and molecular docking of Zn(II) and Cu(II) complexes of 3,5‐dichlorosalicylaldehyde‐N⁴‐cyclohexylthiosemicarbazone

Mathews

Begum

Kurup

2019

Applied Organom Chemis

View full text Add to dashboard Cite

A 3,5‐dichlorosalicylaldehyde‐N4‐cyclohexylthiosemicarbazone (C14H16Cl2N3OS) and its complexes [Zn(dsct)(phen)]·DMF (1), [Zn(dsct)(bipy)]·DMF (2), [Cu(dsct)(bipy)]·DMF (3) (phen = 1,10‐phenathroline, bipy = 2,2’bipyridine) were synthesized and characterized by CHN analysis, FT‐IR, UV–vis and NMR spectra. The molecular structure of the thiosemicarbazone (H2dsct) and its complexes have been resolved using single crystal XRD studies. In the complexes, thiosemicarbazone exist in the thioiminolate form and acts as dideprotonated tridentate ligand coordinating through phenolic oxygen, thioiminolate sulfur and azomethine nitrogen. The antibacterial activity of the prepared compounds were screened against Escherichia coli, Salmonella typhi, Enterobacter aerogenes, Shigella dysentriae, Bacillus cereus, Staphylococcus aureus. All the complexes showed activity against bacterial strains E.coli and Salmonella typhi. The thiosemicarbazone showed activity against three bacterial strains such as E. coli, Enterobacter aerogenes and Shigella dysentriae. Complex 2 showed very good antibacterial activity as compared to standard drug (Ampicillin) against the bacterial strain, Salmonella typhi. Finally, the thiosemicarbazone and its complexes have been used to accomplish molecular docking studies against an Epidermal Growth Factor Receptor (EGFR) and breast cancer mutant 3hb5‐oxidoreductase to determine the most preferred mode of interaction. The results confirm that the complex [Cu (dsct)(bipy)]·DMF(3) showed the highest docking score as compared to other complexes under study. The [Cu(dsct)(bipy)]·DMF(3) complex was evaluated for their anticancer activities against breast cancer cell line (MCF‐7) and normal L929 (Mouse Fibroblast) cell line. It was found that the compound showed an LC50 of 6.25 μg/mL against breast cancer cell line (MCF‐7).

show abstract

Thiosemicarbazone copper complexes as competent catalysts for olefin cyclopropanations

Cited by 29 publications

References 53 publications

Asymmetric cyclopropanation of olefins catalysed by Cu(i) complexes of chiral pyridine-containing macrocyclic ligands (Pc-L*)

Asymmetric cyclopropanation of olefins catalysed by Cu(i) complexes of chiral pyridine-containing macrocyclic ligands (Pc-L*)

Asynthesis, Crystal Structures and in Vitro Anticancer Studies of New Thiosemicarbazone Derivatives

Synthesis, characterization, biological screening and molecular docking of Zn(II) and Cu(II) complexes of 3,5‐dichlorosalicylaldehyde‐N⁴‐cyclohexylthiosemicarbazone

Contact Info

Product

Resources

About

Thiosemicarbazone copper complexes as competent catalysts for olefin cyclopropanations

Cited by 29 publications

References 53 publications

Asymmetric cyclopropanation of olefins catalysed by Cu(i) complexes of chiral pyridine-containing macrocyclic ligands (Pc-L*)

Asymmetric cyclopropanation of olefins catalysed by Cu(i) complexes of chiral pyridine-containing macrocyclic ligands (Pc-L*)

Asynthesis, Crystal Structures and in Vitro Anticancer Studies of New Thiosemicarbazone Derivatives

Synthesis, characterization, biological screening and molecular docking of Zn(II) and Cu(II) complexes of 3,5‐dichlorosalicylaldehyde‐N4‐cyclohexylthiosemicarbazone

Contact Info

Product

Resources

About

Synthesis, characterization, biological screening and molecular docking of Zn(II) and Cu(II) complexes of 3,5‐dichlorosalicylaldehyde‐N⁴‐cyclohexylthiosemicarbazone