Browsing by Author "Seema Pratap"

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1-(2-Furoyl)-3-(2-methoxy-4-nitrophenyl)thiourea
(2013) Seema Pratap; Durga P. Singh; Sushil K. Gupta; Sema Öztürk Yildirim; Ray J. Butcher
The asymmetric unit of the title compound, C13H11N3O5S, contains two independent molecules, which are linked by a pair of intermolecular N - H⋯S hydrogen bonds, forming an R 2 2(8) ring motif. The central thiourea core forms dihedral angles of 3.02 (12) and 14.00 (10)° with the essentially planar furoyl groups [maximum deviations = 0.030 (2) and 0.057 (2) Å] in the two molecules and dihedral angles of 2.43 (13) and 8.03 (12)° with the benzene rings. The dihedral angles between the furoyl and benzene rings in the two molecules are 3.97 (10) and 5.98 (9)°. The trans-cis geometry of the thiourea group is stabilized by three intramolecular N - H⋯O hydrogen bonds involving carbonyl and methoxy O atoms with the H atom of the cis-thioamide group and between furan O atom and the other thioamide H atom. There is also a weak intramolecular C - H⋯S interaction in each molecule. © 2013 Pratap et al.
1-(Naphthalen-1-yl)-3-[(thiophen-2-yl)-carbonyl]thiourea
(2012) Durga P. Singh; Seema Pratap; Sushil K. Gupta; Ray J. Butcher
In the title compound, C16H12N2OS 2, the dihedral angles between the mean planes of the central thiourea core and the thiophene ring and the naphthalene ring system are 1.8 (2) and 6.45 (18)°, respectively. The molecule adopts a trans-cis conformation with respect to the position of thiophenoyl and naphthyl groups relative to the S atom across the thiourea C - N bonds. Both the thiophene ring and the sulfanylidene S atom are disordered over two sets of sites with occupancies of 0.862 (3):0.138 (3) and 0.977 (3):0.023 (3), respectively. An intramolecular N - H···O hydrogen bond is observed. The crystal packing features two N - H···S hydrogen bonds.
3-[(Furan-2-yl)carbonyl]-1-(pyrimidin-2-yl)thiourea
(2012) Durga P. Singh; Seema Pratap; Sushil K. Gupta; Ray J. Butcher
The title compound, C10H8N4O2S, was synthesized from furoyl isothiocynate and 2-aminopyrimidine in dry acetone. The two N-H groups are in an anti conformation with respect to each other and one N-H group is anti to the C=S group while the other is syn. The amide C=S and the C=O groups are syn to each other. The mean plane of the central thiourea fragment forms dihedral angles of 13.50 (14) and 5.03 (11)°with the furan and pyrimidine rings, respectively. The dihedral angle between the furan and pyrimidine rings is 18.43 (10)°. The molecular conformation is stabilized by an intramolecular N-H⋯N hydrogen bond generating an S(6) ring motif. In the crystal, molecules are linked by pairs of N-H⋯N and weak C-H⋯S hydrogen bonds to form inversion dimers.
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
Methyl 2-(thiophene-2-carboxamido)-benzoate
(2012) Durga Prasad Singh; Seema Pratap; Ray J. Butcher; Sushil K. Gupta
The title compound, C13H11NO3S, was synthesized from methyl anthranilate, triethylamine and 2-thiophenoyl chloride in benzene. The molecular conformation is stabilized by an intramolecular N - H⋯O hydrogen bond. The dihedral angle between the rings is 2.74 (12)°. In the crystal, C - H⋯O interactions link neighbouring molecules into a three-dimensional network.
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-(1,3-Thiazol-2-yl)-N′-[(thiophen-2-yl)carbonyl]thiourea hemihydrate
(2012) Durga Prasad Singh; Seema Pratap; Sema Öztürk Yildirim; Ray J. Butcher
The title compound, C9H7N3OS3·0.5H2O, crystallizes with two independent but similar molecules in the asymmetric unit, both of which are linked by a water molecule through O-H⋯N hydrogen bonds. In addition the water O atom is further linked by N-H⋯O hydrogen bonds to two additional main molecules, forming a tetrameric unit. These tetrameric units then form infinite ribbons parallel to the ac plane.The dihedral angle between the thiophenoyl and thiazolyl rings is 12.15 (10) and 21.69 (11)°in molecules A and B, respectively. The central thiourea core makes dihedral angles of 5.77 (11) and 8.61 (9)°, respectively, with the thiophenoyl and thiazolyl rings in molecule A and 8.41 (10) and 13.43 (12)°in molecule B. Each molecule adopts a trans-cis geometry with respect to the position of thiophenoyl and thiazole groups relative to the S atom across the thiourea C-N bonds. This geometry is stabilized by intramolecular N-H⋯O hydrogen bonds.
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.
Solvent induced geometry transformation of trigonal planar Cu(I) complexes of N-((2/4-methyoxy carbonyl) phenyl)-N′-(ethoxy/methoxy carbonyl) thiocarbamides to square-planar Cu(II) complexes: Synthesis, spectral, single crystal, DFT and in vitro cytotoxic study
(Elsevier S.A., 2014) Durga P. Singh; Seema Pratap; Madhulata Shukla
Complexation between copper(II) chloride and three newly synthesized ligands, (N-((2/4-methyoxy carbonyl) phenyl)-N′-(ethoxy carbonyl) thiocarbamides (2/4-MCPET)(1, 2) and (N-(2-methyoxy carbonyl phenyl)-N′-(methoxy carbonyl) thiocarbamide (2-MCPMT)(3) afforded Cu(I) complexes bis(N-((2/4-methoxycarbonyl) phenyl)-N'-(ethoxycarbonyl) thiocarbamide) copper(I) chloride (2/4-MCPET)2CuCl(1a, 2a) and bis(N-((2-methoxycarbonyl) phenyl)-N'-(methoxycarbonyl) thiocarbamide) copper(I) chloride (2-MCPMT)2CuCl(3a). The geometry transformation reaction of above copper(I) complexes in DCM-DMSO (3:1, v/v) mixture of solvents resulted in dark green Cu(II) complexes bis(N-((2/4-methoxycarbonyl) phenyl)-N'-(ethoxycarbonyl) thiocarbamide) copper(II) (2/4-MCPET)2Cu(1a′, 2a′) and bis(N-((2-methoxycarbonyl) phenyl)-N'-(methoxycarbonyl) thiocarbamide) copper(II) (2-MCPMT)2Cu(3a′). Spectroscopic studies together with single crystal analysis of (2-MCPMT)2CuCl revealed trigonal planar structure for Cu(I) complexes in which ligand coordinates to the metal ion in neutral monodentate fashion through sulfur only. The physico-chemical studies of Cu(II) complexes together with single crystal data of (2/4-MCPET)2Cu(1a′) support their distorted square-planar geometry, with formation of 1,3-N,S four-membered chelate ring. The N, S coordination observed for the first time in Cu(II) complexes is stabilized by the intramolecular hydrogen bonding present in them. Complex 1a shows quasi-reversible redox behavior assignable to Cu(I)/Cu(II) one electron transfer. Theoretical study on (2-MCPET)2Cu(1a′) was performed to concrete the spectral study and structure of the complexes. Ligands and their Cu(I) complexes have been screened for their in vitro cytotoxicity against five human cancer cell lines. © 2014 Elsevier B.V. All rights reserved.
Structural and spectral speciation on methyl 2-(3-(furan-2-carbonyl) thioureido)benzoate: A comparative experimental and theoretical study
(Elsevier B.V., 2013) Durga P. Singh; Seema Pratap; Sushil K. Gupta; Ray J. Butcher
A new thiourea derivative, methyl 2-(3-(furan-2-carbonyl)thioureido) benzoate (MFCTB) is synthesized and characterized by elemental analysis, FT-IR, FT-Raman, electronic, NMR and single crystal X-ray diffraction study. The compound crystallizes in the orthorhombic space group Pbca with Z = 8. The molecular geometry was also optimized using density functional theory (DFT) employing B3LYP exchange correlation with the 6-311G(d, p) basis set. The theoretically calculated bond parameters are in good agreement with the experimentally obtained results as reflected by C=S 1.673 (1.668), C=O 1.221 (1.228) Å, bond distances. The infrared spectra of the compound showed four significant vibrations δ(N-H) (I), ν(C-N) (II and III) and ν(C=S) (IV) around 1500, 1300, 1100 and 750 cm-1 and matched well with DFT calculated values. The 1H NMR spectrum of the compound shows mainly three peaks S=C-NH, O=C-NH and O=C-OCH3 at 13.25 (12.94); 9.25 (8.99) and 3.94 (3.81) ppm, respectively and displayed good correlation while its 13C NMR spectrum showed some differences with its theoretical counterpart. -lso electronic spectrum of the compound which comprises mainly two bands around 289 and 325 was compared with the theoretical spectrum obtained from time-dependent (TD) DFT and a good agreement is observed. The molecular electrostatic potential (MEP) map shows the negative potential sites are on oxygen, sulphur and nitrogen atoms and the positive potential sites are around the hydrogen atoms. © 2013 Elsevier B.V. All rights reserved.
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 of N,N-Bis-Sulfonylated and N-Alkyl-N-Sulfonylated G1 Dendrimers via Click Reaction: Application of Thiocarbamide based CuI Catalysts
(Wiley-Blackwell, 2017) Shaziya Khanam; Sunil K. Pandey; Sunil K. Rai; Deepshikha Verma; Jerry P. Jasinski; Seema Pratap; Ashish K. Tewari
This manuscript deals with the design of thiocarbamide based CuI catalysts C1, C2 and C3 and their application in synthesis of 1,2,3-triazole based N,N-bis-sulfonylated and N-alkyl-N-sulfonylated G1 dendrimers. Since thermal stability of N−S bonds of persulfone moiety is poor, therefore, CuAAC reactions were performed at ambient conditions using catalysts C1, C2 and C3, and solvents water/t-BuOH, DCM, DMSO. It was observed that product yield was satisfactory in DCM however it was very poor in DMSO. However, liquid assisted grinding (LAG) approach improved the yield from good to excellent and lowers the reaction time. Among all the three catalysts, C3 showed the better catalytic activity under LAG approach. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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 and crystal structure of thiadiazoles derived from aroylthiourea
(2014) Durga P. Singh; Seema Pratap; Ray J. Butcher; Sushil K. Gupta
Three thiadiazole derivatives, (Z)-N-(2H-[1,2,4]thiadiazolo[2,3-a]pyridine- 2-ylidine)benzamide (I), (Z)-N-(2H-thiazolo[3,2-b] [1,2,4] thiadiazolo-2- ylidine)thiophene-2-carboxamide(II) and (Z)-N-(2H-[1,2,4] thiadiazolo[2,3-a] pyridine-2-ylidine)thiophene-2-carboxamide(III), have been synthesized and examined by X-ray crystallography and NMR spectroscopy. I, C13H 9N3OS, is monoclinic with space group P21/n and cell constants a = 6.2699(11) Å, b = 18.025(4) Å, c = 10.207(2) Å, β = 95.088(19), V = 1149.0(4) Å3 and Z = 4. II, C9H5N3OS3, is orthorhombic with space group Pbca and cell constants a = 12.52148(17) Å, b = 11.27270(18) Å, c = 14.9154(3) Å, V = 1370.3(7) Å3 and Z = 8. III, C11H7N3OS2, is monoclinic with space group P21/c, and cell constants a = 10.9171(15) Å, b = 18.227(2) Å, c = 11.8019(16) Å, β = 108.955(14), V = 1370.3(7) Å3, Z = 8. In III, two independent molecules crystallize in the asymmetric unit (Z = 2). The pyridothiadiazole fused ring in I and III, and thiazolothiadiazole fused ring in II, are planar with a maximum deviation of 0.012(3) (I), 0.011(2) and 0.006(3) (III) and 0.029(1) (II) Å, respectively. The dihedral angle between mean planes of the pyridothiadiazole ring and benzamide and thiocarboxamide rings are 3.48(13) (I), 0.97(25) and 3.68(31) (III) while in between thiazolothiadiazole ring and thiocarboxamide ring in II is, 5.27(12). The thiophene rings in II and III are disordered over two sets of site in a 0.5028(19): 0.4972(19) (II) and 0.624(4):0.376(4) (molecule A) and 0.710:0.290(4) (molecule B) ratio (III). Weak C-H⋯O, C-H⋯N (I and II) and C-H⋯O (III) intermolecular hydrogen bond interactions help to stabilize crystal packing in each of their unit cells. It is also supported by weak intermolecular Cg⋯Cg π⋯π and C-H⋯Cg π-ring interactions which gives additional support to molecular packing stability leading to supramolecular layers. Graphical Abstract: Synthesis, spectroscopic studies and crystal structures of three thiadiazole derivatives. [Figure not available: see fulltext.] © 2014 Springer Science+Business Media New York.
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 characterization, crystal structure, antimicrobial and in vitro hemolytic studies of some novel substituted thiourea derivatives
(2013) Durga Prasad Singh; Mayank Gangwar; Dharmendra Kumar; Gopal Nath; Seema Pratap
A series of N,N′-disubstituted thioureas, [R-CONHCSNH-R′] where (R = thiophenyl, furonyl, phenyl and R′ = 4-sulphonamido phenyl, pyrimidine-2yl, thiazole-2yl, 3-nitro phenyl, 2-nitro-4-chloro phenyl, 2-chloro-4-nitro phenyl, 2-methoxy-4-nitro phenyl, and 6-phenyl-1,3,5-triazinyl were synthesized, characterized and screened for their antimicrobial activities. The structures of synthesized compounds were established by elemental analysis and spectroscopic techniques (FT-IR, 1H NMR, and 13C NMR). Single crystal study on compounds 1a and 1c have been done. The compound 1a crystallizes in monoclinic space group Cc, with a = 15.2974(5) Å, b = 11.7766(4) Å, c = 8.1059(3) Å, α = 90, β = 106.31(3), γ = 90 and Z = 4 molecules per unit cell, where as compound 1c crystallizes in orthorhombic space group Pbca, with a = 7.6307(6) Å, b = 11.3895(9) Å, c = 24.121(2) Å, α = β = γ = 90 and Z = 8 molecules per unit cell. All the compounds were tested for their inhibitory activities against four human pathogen bacteria and three fungal strains. The screening data revealed that five compounds showed moderate to good activity whereas one of the compound 1k displayed excellent activity. In vitro hemolytic activity of the compounds has shown them to be nontoxic in nature. Graphical Abstract: Eleven disubstituted thiourea compounds have been synthesized and characterized by elemental analysis, spectroscopic techniques (FT-IR, 1H NMR, and 13C NMR) and single crystal study on two of compounds has been done to understand the proper structural features of the compounds. All the compounds have been screened for their antimicrobial activity; out of them two have shown promising activity against the bacteria and fungi used.[Figure not available: see fulltext.] © 2013 Springer Science+Business Media New York.
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