- Synthesis, spectral, X-ray crystallography, electrochemistry, DNA/protein binding and radical scavenging activity of new palladium(II) complexes containing triphenylarsine
-
The reactions of [PdCl2(AsPh3)2] with equimolar amount of salicylaldehyde-4(N)-phenylthiosemicarbaz-one [H 2-(Sal-ptsc)] (H2L1) and 2-hydroxy-1- naphthaldehyde-4(N)-methylthiosemicarbazone
- Kalaivani,Prabhakaran,Kaveri,Huang,Staples,Natarajan
-
-
Read Online
- Two thiosemicarbazones derived from salicylaldehyde: Very specific hydrogen-bonding inter-actions of the N - H...S=C type
-
The mol-ecular structures of two salicylaldehyde thio-semi-carba-zone derivatives, namely salicylaldehyde 4-phenylthio-semicarbazone, C 14H13N3OS, (I), and 4-methoxysalicyl aldehyde 4-phenylthiosemicarbazone, C15/sub
- Rubcic, Mirta,Dstrokeilovic, Ivica,Cindric, Marina,Matkovic-Calogovic, Dubravka
-
-
Read Online
- Pharmacomodulations of the benzoyl-thiosemicarbazide scaffold reveal antimicrobial agents targeting D-alanyl-D-alanine ligase in bacterio
-
D-Alanyl-D-alanine ligase (Ddl) is a validated and attractive target among the bacterial enzymes involved in peptidoglycan biosynthesis. In the present work, we investigated the pharmacomodulations of the benzoylthiosemicarbazide scaffold to identify new Ddl inhibitors with antibacterial potency. Five novel series of thiosemicarbazide analogues, 1,2,4-thiotriazole-3-thiones, 1,3,4-thiadiazoles, phenylthiosemicarbazones, diacylthiosemicarbazides and thioureas were synthesized via straightforward procedures, then tested against Ddl and on susceptible or resistant bacterial strains. Among these, the thiosemicarbazone and thiotriazole were identified as the most promising scaffolds with Ddl inhibition potency in the micromolar range. Antimicrobial evaluation of salicylaldehyde-4(N)-(3,4-dichlorophenyl) thiosemicarbazone 33, one of the best compounds in our study, revealed interesting antimicrobial activities with values of 3.12–6.25 μM (1.06–2.12 μg/mL) against VRE strains and 12.5–25.0 μM (4.25–8.50 μg/mL) towards MRSA and VRSA strains. A detailed mechanistic study was conducted on the Ddl inhibitors 4-(3,4-dichlorophenyl)-5-(2-hydroxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 20 and compound 33, and revealed a bactericidal effect at 5 × MIC concentration after 7 h and 24 h, respectively, and a bacteriostatic effect at 1 × MIC or 2 × MIC without any sign of bacterial membrane disruption at these lower concentrations. Finally, 20 and 33 were proved to target Ddl in bacterio via intracellular LC-MS dosage of D-Ala, L-Ala and D-Ala-D-Ala. Although, at this stage, our results indicate that other mechanisms might be involved to explain the antimicrobial potency of our compounds, their ability to inhibit the growth of strains resistant to usual antibiotics, as well as strains that express alternative ligases, sets the stage for the development of new antimicrobial agents potentially less sensitive to resistance mechanisms.
- Ameryckx, Alice,Pochet, Lionel,Wang, Gang,Yildiz, Esra,Saadi, Bouazza Es,Wouters, Johan,Van Bambeke, Fran?oise,Frédérick, Rapha?l
-
supporting information
(2020/06/03)
-
- Synthesis and in vitro anti-toxoplasma gondii activity of novel thiazolidin-4-one derivatives
-
Recent findings on the biological activity of thiazolidin-4-ones and taking into account the lack of effective drugs used in the treatment of toxoplasmosis, their numerous side effects, as well as the problem of drug resistance of parasites prompted us to
- Trotsko, Nazar,Bekier, Adrian,Paneth, Agata,Wujec, Monika,Dzitko, Katarzyna
-
-
- A thiosemicarbazone derivative induces triple negative breast cancer cell apoptosis: possible role of miRNA-125a-5p and miRNA-181a-5p
-
Background: Breast cancer, the most commonly diagnosed malignancy in women, accounts for the highest cancer-related deaths worldwide. Triple negative breast cancer (TNBC), lacking the expression of estrogen, progesterone and HER2 receptors, has an aggressive clinical phenotype and is susceptible to chemotherapy but not to hormonal or targeted immunotherapy. In an attempt to identify potent and selective anti-TNBC agents, a set of thiosemicarbazone derivatives were screened for their cytotoxic activity against MDA-MB 231 breast cancer cell line. Methods: MTT assay was used to examine cell viability. P53 phosphorylation status, poly (ADP-ribose) polymerase (PARP) cleavage as well as Bcl2 and Bax protein levels were assessed by Western blot. Quantitative Real Time-PCR was carried out to characterize miRNAs expression levels. Results: Combining Cisplatin + thiosemicarbazone compound 4 showed potent anti-TNBC potential. Cisplatin + compound 4 significantly enhanced p53 phosphorylation, induced Bax amount, reduced Bcl2 protein levels, enhanced PARP cleavage and modulated miRNAs expression profile in TNBCs, with a particular overexpression of miR-125a-5p and miR-181a-5p. Intriguingly, miR-125a-5p and miR-181a-5p could significantly downregulate BCL2 expression by binding to their target sites in the 3′UTR. Conclusions: Collectively, our results demonstrate an anti-TNBC activity of Cisplatin + thiosemicarbazone compound 4 combination mediated via induction of apoptosis.
- El Majzoub, Rania,Fayyad-kazan, Mohammad,Nasr El Dine, Assaad,Makki, Rawan,Hamade, Eva,Grée, René,Hachem, Ali,Talhouk, Rabih,Fayyad-Kazan, Hussein,Badran, Bassam
-
p. 1431 - 1443
(2019/11/03)
-
- Impact and correlation of p: K a and dn electrons of some selected thiosemicarbazone Schiff base metal Co, Ni, Cu complexes: A study of electrochemical behavior, excitation and optical energies
-
The electron-transfer and coordination mechanism of Schiff bases with metal ions, correlation of the electrochemical and optical properties for their potential applications in various fields of chemistry and biochemistry are underexplored. Thus, detailed
- El-Shahawi,Ahmad,Mohammed,Moustafa,Al-Hazmi,El-Asmy
-
p. 4853 - 4861
(2017/07/12)
-
- Synthesis and characterization of some new Cu(II), Ni(II) and Zn(II) complexes with salicylidene thiosemicarbazones: Antibacterial, antifungal and in vitro antileukemia activity
-
Thirty two new Cu(II), Ni(II) and Zn(II) complexes (1-32) with salicylidene thiosemicarbazones (H2L1-H2L10) were synthesized. Salicylidene thiosemicarbazones, of general formula (X)N-NH-C(S)-NH(Y), were prepared
- Pahontu, Elena,Fala, Valeriu,Gulea, Aurelian,Poirier, Donald,Tapcov, Victor,Rosu, Tudor
-
p. 8812 - 8836
(2013/09/23)
-
- Synthesis, structural and spectral characterization of Zn(II) complexes, derived from thiourea and thiosemicarbazide
-
Novel mono- and binuclear complexes of Zn(II) with thiourea derivatives (H2L) (N-2-propenyl-N′-2-pyridinylthiourea) and thiosemicarbazide, H3L (2-[(2-hydroxyphenyl)methylene]hydrazine-N-(2- propenyl)carbothioamide, (2-[(2-hydroxyphen
- Orysyk,Bon,Obolentseva,Zborovskii, Yu. L.,Orysyk,Pekhnyo,Staninets,Vovk
-
experimental part
p. 127 - 138
(2012/04/11)
-
- Thiosemicarbazone copper complexes as competent catalysts for olefin cyclopropanations
-
New copper complexes of several thiosemicarbazones have been prepared and characterized. All complexes have been prepared by employing Cu (II) acetate hydrate, but analytical and spectroscopical data for the isolated complexes revealed that in most cases
- Youssef, Nabil S.,El-Seidy, Ahmed M.A.,Schiavoni, Marco,Castano, Brunilde,Ragaini, Fabio,Gallo, Emma,Caselli, Alessandro
-
experimental part
p. 94 - 103
(2012/09/25)
-
- One-pot and catalyst-free synthesis of thiosemicarbazones via multicomponent coupling reactions
-
A novel and efficient procedure for the synthesis of thiosemicarbazones has been achieved via a multicomponent and catalyst-free reaction of phenyl or p-chlorophenyl isothiocyanate, hydrazine, and aldehydes or ketones. The method afforded 20 thiosemicarba
- Cunha, Silvio,Silva, Tiago Lima da
-
experimental part
p. 2090 - 2093
(2009/09/05)
-
- Synthesis and Ribonucleotide reductase inhibitory activity of thiosemicarbazones
-
Ribonucleotide reductase (RR) is an important therapeutic target for anticancer drugs. The structure of human RR features a 1:1 complex of two homodimeric subunits, hRRM1 and hRRM2. Prokaryotically expressed and highly purified recombinant human RR subunits, hRRM1 and hRRM2, were used for holoenzyme-based [3H]CDP reduction in vitro assay. Ten new thiosemicarbazones (7-16) were synthesized and screened for their RR inhibitory activity. Two thiosemicarbazones derived from p-hydroxy benzaldehyde (9 and 10) were found to be active but less potent than the standard, Hydroxyurea (HU). Guided by the activity of compounds 9 and 10, 11 new thiosemicarbazones (17-27) derived from p-hydroxy benzaldehyde were prepared and screened for their RR inhibitory activity. All the 11 compounds were more potent than HU.
- Krishnan, Kesavan,Prathiba, Kumari,Jayaprakash, Venkatesan,Basu, Arijit,Mishra, Nibha,Zhou, Bingsen,Hu, Shuya,Yen, Yun
-
supporting information; experimental part
p. 6248 - 6250
(2009/08/07)
-
- Spectroscopic, thermal and electrochemical studies on some nickel(II) thiosemicarbazone complexes
-
Several complexes of thiosemicarbazone derivatives with Ni(II) have been prepared. Structural investigation of the ligands and their complexes has been made based on elemental analysis, magnetic moment, spectral (UV-Vis, i.r., 1H NMR, ms), and
- El-Shazly,Al-Hazmi,Ghazy,El-Shahawi,El-Asmy
-
p. 243 - 252
(2007/10/03)
-
- Organotin(IV) complexes of thiohydrazones: Synthesis, characterization and antifungal study
-
Some new organotin(IV) complexes with salicylaldehyde aniline-N- thiohydrazone (L1) and cinamaldehyde aniline-N-thiohydrazone (L 2) of the type (p-ClC6H4)3Sn[L] Cl and (p-ClC6H4)2Sn[L]Cl2 have been synthesized (where L = L1 and L2). The complexes and ligands were characterized by elemental analysis and spectral (UV-vis, IR and 1H NMR) studies. In all the complexes, ligands act as bidentate, coordination through sulphur and azomethane nitrogen. Complexes are 1:1 metal ligands complexes. Antifungal studies of some complexes against Rhizoctonia bataticola fungal strain have been carried out.
- Mishra,Manav,Kaushik
-
p. 3097 - 3101
(2007/10/03)
-
- On the synthesis of fused thiazolo[5,4-d]isoxazoles and a novel rearrangement involving conversion of 5(4H)-isoxazolones to 4(5H)-isoxazolones
-
The interaction of 4-bromo-3-substituted-(4H)-isoxazol-5-ones (1) with alkyl/aryl thiocarbamides (2), 4-alkyl/aryl thiosemicarbazides (7) and 2, 4-disubstituted thiosemicarbazides (12) afford 5-alkyl/ arylamino-3-substituted-thiazolo [5, 4-d]isoxazoles (3) and 6-amino/anilino-5-alkyl/arylimino-3-substituted-thiazolo[5, 4-d]isoxazoles respectively. An alternate unambiguous one step synthesis is described. The compounds have been characterised by chemical reactions and spectral data.
- Chande,Joshi
-
p. 403 - 409
(2007/10/03)
-
- Novel synthesis of new 5,7-disubstituted-2-alkyl/arylamino-4H-pyrazolothiadiazines and 4,6-disubstituted-3-amino/anilino-2-alkyl/aryliminopyrazolothiazolines
-
The title compounds have been prepared by the interaction of substituted 4-bromopyrazolin-5-ones with thiosemicarbazides.An alternate unambiguous synthesis of pyrazolothiazolines has been described.All the compounds have been characterised by spect
- Chande, Madhukar S.,Joshi, Rajesh D.
-
p. 289 - 301
(2007/10/02)
-