Browsing by Author "Gaetano Marverti"

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Copper (I) complexes based on novel N, N′-disubstituted thiocarbamides: Synthesis, spectroscopic, in vitro cytotoxicity, DNA damage and G0/G1 cell cycle arrest studies
(Elsevier S.A., 2019) Sunil K. Pandey; Seema Pratap; Sandeep Pokharia; Hirdyesh Mishra; Gaetano Marverti; Manpreet Kaur; Jerry P. Jasinski
Four trigonal planar copper (I) complexes with novel N, N′-disubstituted isobutoxycarbonyl thiocarbamide ligands were synthesized and characterized by elemental analysis, spectroscopic (FT–IR, 1H and 13C NMR, UV–Visible), TG analysis and single crystal X-ray studies of ligands 1 and 2. The synthesized copper (I) complexes (1a–4a) bear the general formula [Cu(ROCONHCSNHR1)2Cl] where R = –CH2CH(CH3)2 and R1 = 2, 4-dichlorophenyl (1), 2-chloro 4-nitrophenyl (2), 2-methoxyphenyl (3), 4-chloro-2-nitrophenyl (4). All the complexes are mononuclear coordinating through thione sulfur only. Coordination through carbonyl oxygen would have not been possible owing to the presence of strong intramolecular hydrogen bonding (N–H⋯O[dbnd]C) in the ligands. The proposed trigonal planar geometry of complexes has been validated by density functional theory (DFT) study of complex 1a. Computational details of theoretical calculations (DFT) of complex have been discussed. Cyclic voltammogram of complexes 1a–4a displayed quasireversible redox behaviour corresponding to Cu(I)/Cu(II) couple. In vitro cytotoxicity results of ligands and complexes against five human cancer cell lines indicated that all the complexes displayed stronger inhibitory properties than the ligands. The most effective were complexes 3a, 4a and 5a. All the complexes exhibit IC50 values even lower than cisplatin against C13* cell line (cisplatin resistant). The comet assay test of all the complexes against 2008, C13* and IGROV-1 cell lines indicated significant damage to the DNA structure. All the complexes induce apoptosis in 2008, C13* and IGROV-1 cells by blocking cell cycle progression of these cells in G0/G1 phase. © 2019 Elsevier B.V.
Copper(I) complexes of N-(2/4 methoxy/2-chloro-4-nitro)phenyl-N′ (methoxycarbonyl)thiocarbamides as potential anticancer agents: Synthesis, crystal structure, in vitro cytotoxicity and DNA damage studies
(Elsevier Ltd, 2019) Sunil K. Pandey; Durga P. Singh; Seema Pratap; Gaetano Marverti; R.J. Butcher
Synthesis and structural assignment of four trigonal planar copper(I) complexes (1a–4a) having the general formula [Cu(CH3OCONHCSNHR)2Cl] where R = 2-methoxyphenyl (1), 4-methoxyphenyl (2), 2-chloro 4-nitrophenyl (3) and 2-methoxy 4-nitrophenyl (4) have been described. The characterization were done by elemental, spectroscopic (FT-IR, 1H, 13C NMR, UV–Vis), TG analysis and single crystal X-ray studies of ligands 1, 3 and complex 2a. In the complex 2a the methoxycarbonyl groups adopt cis conformation with respect to chlorine atom and are nearly coplanar with the central plane in a trigonal planar geometry. Cyclic voltammogram of complexes 1a–4a displayed quasi-irreversible redox behaviour corresponding to Cu(I)/Cu(II) couple. In vitro cytotoxicity of the ligands and their copper(I) complexes screened against five human cancer cell lines revealed that complexes were two to three times more potent than the ligands against all the cell lines. DNA damage study of complexes against 2008, C13* (cervical cancer) and IGROV-1 (ovarian cancer) cell lines indicated that cytotoxicity exerted by them is mainly through perturbation of DNA structure. © 2019 Elsevier Ltd
Experimental and theoretical exploration of molecular structure and anticancer properties of two N, N′–disubstituted thiocarbamide derivatives
(Elsevier B.V., 2019) Sunil K. Pandey; Seema Pratap; Manish K. Tiwari; Gaetano Marverti; Jerry P. Jasinski
Two new compounds N-(2-chloro-4-nitrophenyl)-N’-(phenoxycarbonyl) thiocarbamide (1) and N-(2-chloro-4-nitrophenyl)-N’-(4-nitrobenzoyl) thiocarbamide (2), have been derived by the reaction of phenoxycarbonyl isothiocyanate/4-nitrobenzoyl isothiocyanate with 2-chloro-4-nitroaniline. The structures of these compounds were determined by spectroscopic (FT-IR, 1H and 13C NMR, UV–Visible) and single crystal X-ray studies. Both the crystal structures are symmetrical and planar with anti-periplanar orientation of C[dbnd]O and C[dbnd]S group. The molecular structure and vibrational properties of the compounds studied at B3LYP/6-311G ++ (d, p) level of density functional theory further concrete the experimental results. These compounds were screened for their in vitro cytotoxicity activity against seven human cancer cell lines; cervical (2008 and C13*), colorectal (HT29 and HCT116) and ovarian carcinoma (A2780, A2780/CP and IGROV-1). Compound 2 exhibited significant activity against all the cell lines whereas compound 1 demonstrated appreciable activity only against ovarian carcinoma cell lines. © 2018
Monodentate Coordination of N, N′-Disubstituted Thiocarbamide Ligands: Syntheses, Structural Analyses, In Vitro Cytotoxicity and DNA Damage Studies of Cu(I) Complexes
(Wiley-Blackwell, 2018) Sunil K. Pandey; Durga P. Singh; Gaetano Marverti; R.J. Butcher; Seema Pratap
Structural analysis of three novel substituted thiocarbamide ligands N-(naphthyl)-N′-(isobutoxycarbonyl) thiocarbamide (H2L1), N-(4-methoxyphenyl)-N′-(isobutoxycarbonyl) thiocarbamide (H2L2) & N-(2-methoxy-4-nitrophenyl)-N′-(isobutoxycarbonyl) thiocarbamide (H2L3) and their copper(I) complexes [(H2L1)2CuCl] (1), [(H2L2)2CuCl] (2) and [(H2L3)2CuCl] (3) was performed using various spectroscopic techniques (FT−IR, 1H and 13C NMR, UV-Visible),TG analysis and single crystal X-ray studies of (H2L1) and [(H2L1)2CuCl] (1). The copper(I) complexes possess trigonal planar geometry coordinating through two thione sulfur atoms from two ligand molecules and one chloride ion. Two intramolecular hydrogen bonding interactions present between (−N1H) and carbonyl oxygen (−N2H) and coordinated chlorine stabilize the trigonal planar structure of the complexes. Cyclic voltammogram of complexes 1–3 displayed quasireversible redox behaviour corresponding to CuI/CuII couple. Determination of in vitro cytotoxicity of ligands and their complexes using five human carcinoma cell lines 2008, C13* (cervical carcinoma), A2780, A2780/CP and IGROV-1 (ovarian carcinoma) revealed that copper(I) complexes were more potent inhibitors than the ligands against all the cell lines. The most effective were complexes 2 and 3. The comet assay test of complexes 2 and 3 against 2008, C13* and IGROV-1 cell lines indicated significant damage to the DNA structure. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
N-(naphthyl)-N′-(methoxy carbonyl)thiocarbamide and its Cu(I) complex: Synthesis, spectroscopic, X-ray, DFT and in vitro cytotoxicity study
(Taylor and Francis Ltd., 2015) Durga P. Singh; Seema Pratap; Sunil K. Pandey; Ray J. Butcher; Gaetano Marverti
The structural characterization of two new compounds N-naphthyl-N′-methoxycarbonyl thiocarbamide (NMCT) (1) and its Cu(I) complex, bis(N-naphthyl-N′-methoxycarbonyl thiocarbamide) copper(I) chloride [(NMCT)2CuCl] (1a) have been done by spectroscopic techniques (FT-IR, 1H NMR, 13C NMR and electronic spectroscopy) and X-ray crystallography. To get a deeper insight of vibrational frequencies and electronic transitions, DFT and TD-DFT studies have also been performed. X-ray study revealed trigonal planar geometry around copper(I). The ligand coordinates through thione sulfur only. The cytotoxicity of 1 and 1a has been assayed in five human carcinoma cell lines, 2008, C13∗ (cervical carcinoma), A2780, A2780/CP and IGROV-1 (ovarian carcinoma). Both the compounds exhibited cytotoxicity. The inhibitory activity of copper complex was better than ligand against all the cell lines. © 2014 Taylor & Francis.
Structural, Hirshfeld surface and in vitro cytotoxicity evaluation of five new N-aryl-N’-alkoxycarbonyl thiocarbamide derivatives
(Taylor and Francis Ltd., 2020) Sunil K. Pandey; Seema Pratap; Sunil K. Rai; Gaetano Marverti
Five new compounds, N-(2, 4-dichlorophenyl)-N’-(methoxycarbonyl) thiocarbamide (1), N-(2, 4-dichlorophenyl)-N’-(ethoxycarbonyl) thiocarbamide (2), N-(2, 4-dichlorophenyl)-N’-(2, 2, 2-trichloroethoxycarbonyl) thiocarbamide (3), N-(2,4-dichlrophenyl)-N’-(pentoxycarbonyl) thiocarbamide (4) and N-(4-nitrophenyl)-N’-(pentoxycarbonyl) thiocarbamide (5), have been synthesized by the reaction of various alkoxy chloroformates with 2, 4-dichloroaniline/4-nitroaniline.The molecular structures of the compounds were elucidated by using spectroscopic methods (FT-IR, 1H and 13C NMR) and single-crystal X-ray structure analysis of compounds 2 and 5. Antiperiplanar orientation of C = O and C = S group across C–N bonds of thiocarbamide core may be due to the presence of intramolecular (N–H···O–C) hydrogen bond in the crystal structure of both the compounds. The presence of intermolecular interactions (C–H···S, C–H···O and N–H···S) in the molecular structure of the compounds has been studied in detail using Hirshfeld surfaces and their associated two-dimensional fingerprint plots. In vitro cytotoxicity screening of the synthesized compounds evaluated on a panel of seven human cancer cell lines (cervical carcinoma (2008, C13*), colorectal (HT29 and HCT116) and ovarian carcinoma (A2780, A2780/CP and IGROV-1)) demonstrated significant inhibitory properties. © 2020 Taylor & Francis Group, LLC.
Synthesis, characterisation, Hirshfeld surface and in vitro cytotoxicity evaluation of new N-aryl-N′-Alkoxycarbonyl thiocarbamide derivatives
(Elsevier B.V., 2020) Sunil K. Pandey; Seema Pratap; Sunil K. Rai; Gaetano Marverti; Manpreet Kaur; Jerry P. Jasinski
Four new compounds N-(4-nitrophenyl)-N’-(isobutoxycarbonyl) thiocarbamide (1), N-(2, 4-nitrophenyl)-N’-(isobutoxycarbonyl) thiocarbamide (2), N-(4-nitrophenyl)-N’-(ethoxycarbonyl) thiocarbamide (3) and N-(2-Chloro- 4-nitrophenyl)-N’-(ethoxycarbonyl) thiocarbamide (4) were prepared and their structures confirmed by using various spectroscopic (FT-IR, UV–Visible, 1H and 13C NMR) and single crystal X-ray studies of 1 and 3. The presence of intramolecular (N–H⋯O[dbnd]C) hydrogen bond in the crystal structure of both the compounds causes planarity of carbonyl thiocarbamide unit and trans orientation of C[dbnd]O and C[dbnd]S group. The intermolecular contacts (C–H⋯S, C–H⋯O and N–H⋯S) present in crystal structures have been examined by Hirshfeld surface analysis and their associated 2D fingerprint plots. All the compounds were assessed for their in vitro cytotoxic properties against a panel of seven human cancer cells such as cervical carcinoma (2008, C13*), colorectal (HT29 and HCT116) and ovarian carcinoma (A2780, A2780/CP and IGROV-1). Among them, compounds 2 and 4 exhibited better activity than 1 and 3 against all the cell lines tested. © 2019 Elsevier B.V.
Synthesis, characterization, Hirshfeld surface, cytotoxicity, DNA damage and cell cycle arrest studies of N, N-diphenyl-N’-(biphenyl-4-carbonyl/4-chlorobenzoyl) thiocarbamides
(Elsevier B.V., 2019) Sunil K. Pandey; Seema Pratap; Sunil K. Rai; Gaetano Marverti; Manpreet Kaur; Jerry P. Jasinski
The condensation reaction of biphenyl-4-carbonyl isothiocyanate/4-chlorobenzoyl isothiocyanate with diphenylamine yielded two new compounds; N-diphenyl-N’-(biphenyl-4-carbonyl) thiocarbamide (1) and N, N-diphenyl-N’-(4-chlorobenzoyl) thiocarbamide (2). Structure of the compounds were determined by analytical, spectroscopic (UV–Visible, FT−IR, 1 H, & 13 C NMR), powder and single-crystal X-ray diffraction methods. Hirshfeld surface analysis and their associated two dimensional fingerprint plots of compounds were used as theoretical approach to assess driving force for crystal structure formation via the intermolecular interactions in their crystal lattices. The compounds were screened for their in vitro cytotoxicity activity against a panel of five human cancer cell lines namely; cervical (2008 and C13*) and ovarian carcinoma (A2780, A2780/CP and IGROV-1). Both the compounds exhibited promising activity against cervical and IGROV-1 cancer cells whereas for the other two cell lines appreciable activities were observed. The cell cycle arrest at G 0 /G 1 phase is supported by the DNA damage and apoptosis studies of the compounds against 2008, C13* and IGROV-1 cell lines. © 2019 Elsevier B.V.
Synthesis, molecular structure exploration and in vitro cytotoxicity screening of five novel N, N′- disubstituted thiocarbamide derivatives
(Taylor and Francis Ltd., 2018) Sunil K. Pandey; Seema Pratap; Gaia Gozzi; Gaetano Marverti; R.J. Butcher
The synthesis of five N,N″-substituted thiocarbamides, namely N-(naphthyl)-N″-(pentoxycarbonyl) thiocarbamide (H2L1), N-(2-Chloro-4-nitrophenyl)-N″-(pentoxycarbonyl) thiocarbamide(H2L2), N-(2-methoxy-4-nitrophenyl)-N″-(pentoxycarbonyl) thiocarbamide (H2L3), N-(3-nitrophenyl)-N″-(pentoxycarbonyl) thiocarbamide (H2L4) and N-(naphthyl)-N″-(2, 2, 2-trichloroethoxycarbonyl) thiocarbamide (H2L5) was performed by the reaction of pentoxycarbonyl chloroformate with naphthyl amine, 2-chloro-4-nitroaniline, 2-methoxy-4-nitroaniline, 3-nitroaniline, respectively, for the first four and by the reaction of 2, 2, 2-trichloroethoxycarbonyl chloroformate with naphthyl amine for the last compound. These compounds were fully characterized by using various spectroscopic (FT-IR, 1H and 13C NMR) and single crystal X-ray studies of H2L1 and H2L5. In the crystal structure of both the compounds the (C˭S) and (C˭O) groups are trans to each other across the C−N bond. The crystal packing of H2L1 shows that the molecules form centrosymmetric dimers connected by N2−H····S hydrogen bonds. In H2L5 an offset face-to-face π–π stacking is observed between two naphthalene rings of two molecules. In vitro cytotoxicity of synthesized compounds was evaluated using five human carcinoma cell lines 2008, C13* (cervical carcinoma), A2780, A2780/CP and IGROV-1 (ovarian carcinoma). The IC50 values of compounds H2L2 ─ H2L4 demonstrated them to be very promising anticancer agents. © 2018, © 2018, © 2018 Taylor & Francis Group, LLC.
Synthesis, spectroscopic, crystal structure and in vitro cytotoxicity studies of N-thiophenoyl-N′-substituted phenyl thiocarbamide derivatives
(Elsevier B.V., 2019) Sunil K. Pandey; Seema Pratap; Gaetano Marverti; Manpreet Kaur; Jerry P. Jasinski
A series of eight biologically active N, N′-disubstituted thiocarbamide compounds (1–8) have been prepared from thiophene-2-carbonyl isothiocyanate and various substituted aromatic primary amines (2,4-dichlorophenyl aniline, 4-chloro-3-nitrophenyl aniline, 4-methoxycarbonylphenyl aniline, 3-methoxycarbonylphenyl aniline, 2-methoxycarbonylphenyl aniline, 4-methoxyphenyl aniline, 2-methoxyphenyl aniline and 2-nitrophenyl aniline). Their structures were confirmed by elemental analyses, various spectroscopic techniques ((FT–IR, 1 H and 13 C NMR) and single crystal X-ray analysis of compound (1). In the molecular structure of compound (1) twisted confirmation of the carbonyl and thiocarbonyl group across C–N bond of thiocarbamide moiety and an offset face-to-face π–π stacking between two thiophene and two benzene ring of two molecules is observed. In vitro cytotoxicity assay of all the above compounds and five more (9–13) were carried out using seven human cancer cell lines; cervical (2008 and C13*), colorectal (HT29 and HCT116) and ovarian carcinoma (A2780, A2780/CP and IGROV-1). The results revealed that compounds 1, 11, 12 and 13 displayed promising inhibitory activity against all the cell lines tested. © 2018