Browsing by Author "Jerry P. Jasinski"

Now showing 1 - 9 of 9

5-pyridine 4-yl-3H-(1,3,4) oxadiazole-2 thione hydrochloride monohydrate, (I), and 4 [5-ethylsulfanyl)-(1,3,4) thiadiazole-2-yl]-pyridinium perchlorate, (II)
(2011) Jerry P. Jasinski; M.K. Bharty; N.K. Singh; S.K. Kushwaha; Ray J. Butcher
The title compounds C7H8ClN3O 2S, (I), and C9H10ClN3O 4S2, (II), both crystallize in monoclinic space group P21/c with unit cell parameters (I) a = 7.9402(7), b = 10.6312(9), c = 11.7626(10),Å, β = 99.271(5)°, Z = 4 and (II) a = 5.1439(2), b = 9.0636(4), c = 27.1814 (7), Å, β = 95.116(2)°, Z = 4. In (I) the molecule consists of a 5-pyridine-4-yl group bonded to the carbon atom at the 5 position of (1, 3, 4) oxadiazole-2 thione hydrochloride monohydrate. The angle between the mean planes of the oxadiazole and pyridine rings is 9.6(6)°. Crystal packing in (I) is stabilized by strong N-H⋯Ohydrogen bonds in concert with a solvent water molecule and weak O-H⋯Cl, O-H⋯S, N-H⋯Cl intermolecular interactions. The crystal structure of compound (II) consists of 4 [5-ethylsulfanyl)-(1, 3, 4) thiadiazole-2-yl]- pyridinium perchlorate, (C9H10N3S 2)+(ClO4)-, cation-anion pairs, containing strong intermolecular N-H⋯O hydrogen bonds and weak C-H⋯O and N-H⋯O intermolecular interactions operating between the ionic species that form a cooperative hydrogen-bonded, infinite chain O-H⋯O-H⋯O- H network which generates a sheet motif structure in the unit cell. It is also supported by weak intermolecular Cg⋯Cg π-π and Cl-O⋯Cg π-ring interactions which gives additional support to molecular packing stability in the unit cell. Geometry optimized MOPAC AM1 computational calculations on each compound provides support to the structural features in their respective crystal structures. © Springer Science+Business Media, LLC 2010.
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.
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
N′-[Bis(benzyl-sulfan-yl)methyl-ene]-2-furohydrazide
(2007) Ray J. Butcher; Jerry P. Jasinski; Sruendra K. Kushawaha; Manoj K. Bharty; Nand K. Singh
In the title compound, C20H18N2O2S2, the dihedral angles between the 2-furoic acid group and the two benzyl groups are 72.4 (9) and 75.8 (8)°, while the angle between the mean planes of the two benzyl groups is 48.9 (2)°. The crystal packing is stabilized by inter-molecular C - H⋯O inter-actions between the extended O atom of a 2-furoic acid group and H atoms from nearby benzyl and 2-furoic acid groups in the unit cell, linking the mol-ecules into chains in a zigzag pattern, diagonally across the ac plane containing the 2-fuoric acid rings. Additional inter-molecular inter-actions occur between the π orbitals of one benzyl ring and H atoms from a nearby benzyl ring at the opposite end of the mol-ecule. Additional intra-molecular inter-actions between the hydrazide H atom and both an O atom from a nearby furoic acid group and an S atom from a close sulfanyl group provide added stability to the molecule. © International Union of Crystallography 2007.
N′-[Bis(benzylsulfanyl)methylidene]-4-methoxybenzohydrazide
(2010) Jerry P. Jasinski; Ray J. Butcher; S.K. Kushawaha; M.K. Bharty; N.K. Singh
In the title compound, C23H22N2O 2S2, the dihedral angles between the 4-methoxy-substituted phenyl ring and the other two phenyl rings are 84.4 (4) and 77.7 (1)°, respectively, while the dihedral angle between the two phenyl rings is 57.5 (2)°. The amino group is not involved in an N - H hydrogen bond. The crystal packing is established by inter-molecular C - H⋯O packing inter-actions involving a relatively rare weak three-center hydrogen bond between the keto O atom and H atoms of the two nearby phenyl rings, which link the mol-ecules into chains running along the a axis. Additional weak inter-molecular hydrogen-bond inter-actions between the 4-methoxy O atom and one of the phenyl rings and provide added stability to the crystal packing.
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, 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, 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