- The Reaction of Imidazolidine-2-thione with Carbon Disulphide
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The reaction of imidazolidine-2-thione (ethylenethiourea) with carbon disulphide in the presence of strong bases was investigated.The use of sodium hydride as base afforded 1,2-bis-ethane (6) and 2,3,6,7-tetrahydrodi-imidazothiadiazine-5-thione (8).On the other hand, reaction using n-butyl-lithium, followed by methylation, gave a dimethylated compound, methyl 2-methylthio-4,5-dihydroimidazole-1-carbodithioate (11).
- Yokoyama, Masataka,Motozawa, Kosei,Kawamura, Ei-ichi,Imamoto, Tsuneo
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- Metal derivatives of N-substituted imidazolidine-2-thiones with d10 metal ions (Zn-Hg): Synthesis, spectroscopy, ESI-mass and structures
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N-substituted 1,3-imidazolidine-2-thiones (LI-NMe; LII-NEt; LIII-NPrn) on reacting with Zn(II), Cd(II) and Hg(II) halides in methanol have yielded the mononuclear complexes [ZnCl2(LII-NEt-S)2] 1, [ZnI2(LI-NMe-S)2] 2, [CdBr2(LI-NMe-S)2] 3, [CdBr2(LII-NEt-S)2] 4, [CdI2(LI-NMe-S)2] 5, [HgCl2(LI-NMe-S)2] 6, [HgCl2(LIII-NPrn-S)2] 7 and [HgI2(LI-NMe-S)2] 8. All these complexes have been characterized by elemental analysis, spectroscopy (IR, 1H NMR), ESI-mass and X-ray crystallography. Complexes 1-6 and 8 crystallized in the monoclinic system, with each having the space group P21/c except for complex 4 which has the space group C2/c, and complex 7 crystallized in the trigonal system with the space group R-3c. Interestingly, the complex molecules adopt four types of conformations which give rise to different patterns of intermolecular interactions and hence 2D (1-6, 8) or 1D (7) polymeric networks are obtained. ESI mass data support the formation of [M-X]+ ions (X = halogen) in complexes 1-7.
- Lobana, Tarlok S.,Sandhu, Amanpreet K.,Jassal, Amanpreet K.,Hundal, Geeta,Mahajan,Jasinski, Jerry P.,Butcher, Ray J.
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- Synthesis, spectroscopic characterization and in vitro anticancer activity of new platinum(II) complexes with some thione ligands?in the presence of triethylphosphine
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Seven new platinum(II) complexes (1–7) of triethylphosphine (Et3P) and thiones (L) with general formula, cis-[Pt(Et3P)2(L)2]Cl2 were prepared and characterized by elemental analysis, FTIR and NMR (1H, 13C & 31P) measurements. The analytical and spectroscopic data suggested the formation of the desired complexes. The complexes were tested for in vitro cytotoxicity against four cell lines: Hela (human cervical adenocarcinoma), MCF-7 (human breast carcinoma), A549 (human lung carcinoma), and HTC15 (human colon carcinoma). The anticancer activity values of compounds 1–6 are much better than cisplatin and carboplatin as indicated by their IC50 values.
- Jomaa, Mohammed Yagoub,Altaf, Muhammed,Ahmad, Saeed,Bhatia, Gaurav,Singh, Jatinder,Altuwaijri, Saleh,Isab, Anvarhusein A.
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- Evidence for the involvement of N-methylthiourea, a ring cleavage metabolite, in the hepatotoxicity of methimazole in glutathione-depleted mice: Structure-toxicity and metabolic studies
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In mice depleted of GSH by treatment with buthionine sulfoximine (BSO), methimazole (2-mercapto-1-methylimidazole, MMI) causes liver injury characterized by centrilobular necrosis of hepatocytes and an increase in serum alanine transaminase (SALT) activity. MMI requires metabolic activation by both P450 monooxygenase and flavin-containing monooxygenase (FMO) before it produces the hepatotoxicity. MMI and its analogues were examined for the ability to increase SALT activity in GSH-depleted mice. Saturation of the C- 4,5 double bond in MMI resulted in a complete loss of hepatotoxicity. Similarly, ring fusion of a benzene nucleus to the C-4,5 double bond, forming 2-mercapto-1-methylbenzimidazole, abolished the toxic potency. As for MMI, 2- mercapto-1,4,5-trimethylimidazole, and 2-mercapto-1-methyl-4,5-di-n- propylimidazole, the toxic potency decreased with the increasing bulk of the 4- and 5-alkyl substituents. Furthermore, methylation of the thiol group of MMI totally reduced its toxicity. These structural requirements and the known toxicity of thiono-sulfur compounds led us to the hypothesis that MMI would undergo epoxidation of the C-4,5 double bond by P450 enzymes and, after being hydrolyzed, the resulting epoxide would be then decomposed to form N- methylthiourea, a proximate toxicant. Before N-methylthiourea would produce toxicity, it would be further biotransformed to its S-oxidized metabolites mainly by FMO. Evidence for this hypothesis was provided by the facts that N- methylthiourea and glyoxal as the accompanying fragment were identified as urinary metabolites in mice treated with MMI and that N-methylthiourea caused a marked increase in SALT activity when administered to mice in combination with BSO.
- Mizutani, Tamio,Yoshida, Kaoru,Murakami, Mihoko,Shirai, Mutsuko,Kawazoe, Sadahiro
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- Tetrakis(thione)platinum(II) complexes: Synthesis, spectroscopic characterization, crystal structures, and in vitro cytotoxicity
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A new series of platinum(II) complexes based on thione ligands with general formula [Pt(thione)4]X2 (X- = Cl-, NO3-) has been synthesized and characterized using CHNS elemental analysis, infrared, 1H and 13C solution-state NMR as well as 13C and 15N solid-state NMR spectroscopy, and X-ray crystallography. The spectroscopic methods confirm the coordination of Pt(II) with thiocarbonyl groups via sulfur of the thione ligands. The X-ray structures showed a distorted square planar geometry for 1, [Pt(MeImt)4]Cl2 (MeImt = N-Methylimidazolidine-2-thione) while the hydrogen bonding interactions in 7, [Pt(iPrImt)4](NO3)2·0.6(H2O) induce a bent see-saw distortion relative to the ideal square planar geometry. The in vitro cytotoxicity studies showed that 2, [Pt(EtImt)4]Cl2 is generally the most effective, a two-fold better cytotoxic agent than cisplatin and carboplatin against MCF7 (human breast cancer).
- Mustafa, A. Zainelabdeen A.,Monim-ul-Mehboob,Jomaa,Altaf,Fettouhi,Isab,Wazeer,Stoeckli-Evans,Bhatia,Dhuna
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- Synthesis, Spectroscopy, and Structures of Mono- and Dinuclear Copper(I) Halide Complexes with 1,3-Imidazolidine-2-thiones
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Copper(I) halides with triphenyl phosphine and imidaozlidine-2-thiones (L-NMe, L-NEt, and L-NPh) in acetonitrile/methanol (or dichloromethane) yielded copper(I) mixed-ligand complexes: mononuclear, namely, [CuCl(κ1-S-L-NMe)(PPh3)2] (1), [CuBr(κ1-S-L-NMe)(PPh3)2] (2), [CuBr(κ1-S-L-NEt)(PPh3)2] (5), [CuI(κ1-S-L-NEt)(PPh3)2] (6), [CuCl(κ1-S-L-NPh)(PPh3)2] (7), and [CuBr(κ1-S-L-NPh)(PPh3)2] (8), and dinuclear, [Cu2(κ1-I)2(μ-S-L-NMe)2(PPh3)2] (3) and [Cu2(μ-Cl)2(κ1-S-L-NEt)2(PPh3)2] (4). All complexes were characterized with analytical data, IR and NMR spectroscopy, and X-ray crystallography. Complexes 2-4, 7, and 8 each formed crystals in the triclinic system with Pβar{1}$ space group, whereas complexes 1, 5, and 6 crystallized in the monoclinic crystal system with space groups P21/c, C2/c, and P21/n, respectively. Complex 2 has shown two independent molecules, [(CuBr(κ1-S-L-NMe)(PPh3)2] and [CuBr(PPh3)2] in the unit cell. For X = Cl, the thio-ligand bonded to metal as terminal in complex 4, whereas for X = I it is sulfur-bridged in complex 3.
- Walia, Simran,Kaur, Supreet,Kaur, Jaspreet,Sandhu, Amanpreet K.,Lobana, Tarlok S.,Hundal, Geeta,Jasinski, Jerry P.
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- Cyclopalladation of azobenzenes and their reactivity towards N-substituted imidazolidine-2-thiones and allied ligands: Synthesis, structures, spectroscopy and ESI-mass studies
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Reactions of palladium(II) chloride with azobenzene (azbH), p-methoxyazobenzene (mazbH) and 4, 4′-diethoxyazobenzene (deazbH) in methanol yielded halogen bridged dinuclear precursors [Pd2(κ2:C,N-L)2(μ-Cl)2] (here L = azb?, mazb? and deazb?). These precursors were further reacted with a series of N, S- donor thio-ligands, namely, 1,3-imidazolidine-2-thiones (imdzSH-NR; R = H, Me, Et, Prn, Bun, Ph), N-methyl-imidazoline-2-thione (imzSH-NMe), 1,3-benzimidazoline-2-thione (bzimSH-NH) and 1, 3- thiazolidine-2-thione (tzdSH). Nineteen dinuclear organometallic compounds synthesized are listed as follows: (a) [Pd2(κ2:C, N-azb)2(μ-N, S-imdzS-NR)2] (R = H, 1; Me, 2; Et 3; Prn 4; Bun 5; Ph 6), (b) [Pd2(κ2:C, N-mazb)2(N, S-imdzS-NR)2] (R = Me, 7; Et, 8; Prn 9; Bun 10), (c) [Pd2(κ2:C, N-deazb)2(N, S-imdzS-NR)2] (R = Et, 11; Prn 12; Bun 13; Ph 14), (d) [Pd2(κ2:C, N-azb)2(μ-N, S-L)2] (L = bzimS-NH 15; imzS-NMe 16; tzdS 17), and (e) [Pd2(κ2:C, N-deazb)2(N, S-L)2] (L = bzimS-NH 18; imzS-NMe 19). All these compounds have been characterized with the help of analytical data, electron absorption, NMR and fluoresecence spectroscopy, ESI-mass spectrometry and single crystal X-ray crystallography. The loss of one C-H proton of an azobenzene and one N-H proton of a thio-ligand occurred per palladium metal center in dinuclear complexes synthesized, which have C, N-chelating azobenzenes and N, S-bridging heterocyclic thiolates.
- Sandhu, Amanpreet K.,Lobana, Tarlok S.,Sran, Balkaran S.,Hundal, Geeta,Jasinski, Jerry P.
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- Precursor reaction kinetics control compositional grading and size of CdSe1-: XSx nanocrystal heterostructures
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We report a method to control the composition and microstructure of CdSe1-xSx nanocrystals by the simultaneous injection of sulfide and selenide precursors into a solution of cadmium oleate and oleic acid at 240 °C. Pairs of substituted thio- and selenoureas were selected from a library of compounds with conversion reaction reactivity exponents (kE) spanning 1.3 × 10-5 s-1 to 2.0 × 10-1 s-1. Depending on the relative reactivity (kSe/kS), core/shell and alloyed architectures were obtained. Growth of a thick outer CdS shell using a syringe pump method provides gram quantities of brightly photoluminescent quantum dots (PLQY = 67 to 90%) in a single reaction vessel. Kinetics simulations predict that relative precursor reactivity ratios of less than 10 result in alloyed compositions, while larger reactivity differences lead to abrupt interfaces. CdSe1-xSx alloys (kSe/kS = 2.4) display two longitudinal optical phonon modes with composition dependent frequencies characteristic of the alloy microstructure. When one precursor is more reactive than the other, its conversion reactivity and mole fraction control the number of nuclei, the final nanocrystal size at full conversion, and the elemental composition. The utility of controlled reactivity for adjusting alloy microstructure is discussed.
- Hamachi, Leslie S.,Yang, Haoran,Jen-La Plante, Ilan,Saenz, Natalie,Qian, Kevin,Campos, Michael P.,Cleveland, Gregory T.,Rreza, Iva,Oza, Aisha,Walravens, Willem,Chan, Emory M.,Hens, Zeger,Crowther, Andrew C.,Owen, Jonathan S.
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p. 6539 - 6552
(2019/07/10)
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- Bis-(triethylphosphine)platinum(II) complexes with thiones as anti cancer agents
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Platinum(II) complexes having mixed ligands as anticancer agents. The central platinum atom is coordinated by two phosphine ligands and two heterocyclic thione ligands. Each heterocyclic thione ligand has a five-, six- or seven-membered heterocyclic ring with two nitrogen atoms at positions 1 and 3 of the ring and a thiocarbonyl group at position 2. Pharmaceutical compositions incorporated the platinum(II) complexes, methods of synthesizing the complexes and methods of treating cancers with the complexes or pharmaceutical compositions thereof are also described.
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- Platinum(II) complexes with thione ligands and methods thereof
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Platinum(II) complexes having thione-based heterocyclic ligands as anticancer agents. The central platinum atom is coordinated by four of the ligands, each having a five-, six- or seven-membered heterocyclic ring with two nitrogen atoms at positions 1 and 3 of the ring and a thiocarbonyl group at position 2. Pharmaceutical compositions incorporated the platinum(II) complexes, methods of synthesizing the complexes and methods of treating cancers with the complexes or pharmaceutical compositions thereof are also described.
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(2016/11/21)
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- Heterocyclic-2-thione derivatives of silver(I): Synthesis, spectroscopy and structures of mono- and di-nuclear silver(I) halide complexes
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The scarcely known chemistry of silver(I) halides with a series of heterocyclic thiones in acetonitrile (or methanol-acetonitrile) is described. Silver(I) chloride with a series of imidazolidine-2-thiones [C3H 5NS(N-R)] in the presence of one equivalent of PPh3 with respect to the thione ligand has yielded chloro-bridged dinuclear complexes, [Ag2(μ-Cl)2(κ1-S-C3H 5NS(N-R))2(PPh3)2] (1, R = H; 2, R = Me; 3, R = Et), and in the presence of two equivalents of PPh3, it has yielded mononuclear complexes, [Ag(κ1-Cl) (κ1-S-C3H5NS(N-R))(PPh3) 2] (4, R = Me; 5, R = Et). The n-propyl-imidazolidine-2-thione with silver(I) chloride formed only a mononuclear complex, [Ag(κ1- Cl)(κ1-S-C3H5NS(N-Prn)) (PPh3)2] (6), in the presence of one or two equivalents of PPh3. In contrast, silver(I) bromide with C3H 5NS(N-R) in the presence of one or two equivalents of PPh3 with respect to the thione ligand has yielded bromide-bridged dinuclear complexes, [Ag2(μ-Br)2(κ1-S-C 3H5NS(N-R))2(PPh3)2] (7, R = Me; 8, R = Et; 9, R = Prn). The related thio-ligands, namely, 1-methyl-imidazoline-2-thione and thiazolidine-2-thione with silver(I) bromide in the presence of one or two equivalents of PPh3 have formed bromide bridged dimeric [Ag2(μ-Br)2(κ1-S- C3H3NS(N-Me))2(PPh3)2] (10) or mononuclear Ag(κ1-Br)(κ1-S-C 3H5NS2)(PPh3)2] (11) complexes respectively. The 2,4-dithiouracil (C4H4N 2S2) with silver(I) chloride/bromide and PPh3 has yielded hetero-bridged dinuclear complexes, [Ag2(μ-S,S-C 4H3N2S2)(μ-X)(PPh 3)4] (X = Cl, 12; Br, 13) involving rupture of Ag-X bonds directly with a thio-ligand, a rare case of such rupture in metal-heterocyclic thione chemistry.
- Lobana, Tarlok S.,Sultana, Razia,Butcher, Ray J.,Jasinski, Jerry P.,Golen, James A.,Castineiras, Alfonso,Pr?pper, Kevin,Fernandez, Francisco J.,Vega, M. Cristina
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supporting information
p. 460 - 469
(2013/10/01)
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- HEPATITIS C VIRUS INHIBITORS
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The present disclosure relates to (4-4' -diimidazolyl) biphenyls compositions and methods for the treatment of hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.
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Page/Page column 223
(2009/10/09)
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- Hepatitis C Virus Inhibitors
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The present disclosure relates to compounds, compositions and methods for the treatment of hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.
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Page/Page column 137
(2008/06/13)
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- Hepatitis C Virus Inhibitors
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The present disclosure relates to compounds, compositions and methods for the treatment of hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.
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Page/Page column 135-136
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- Process for preparation of enantiomerically pure polysubstituted 1,4-dihydropyridines
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A process for the optical resolution of racemic 1,4-dihydropyridines, containing isothioureido groups. Salification of racemic isothioureas with optically active acids produces diasteroisomeric mixtures of isothiouronium salts, that, using conventional techniques, are separated in the individual components to give optically pure isothioureides of 1,4-dihydropyridines and salts thereof with conventional acids. Said optically pure 1,4-dihydropyridines can then be subjected to desulphuration and to different transformations to give to other enantiomerically pure and therapeutically useful 1,4-dihydropyridines.
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- 7-Alkylation and 7-Sulphonylation of 5,6-Dihydroimidazolo-thiazoles
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Reinvestigation of the alkylation of 3-phenyl-5,6-dihydroimidazolothiazole has shown that methylation occurs exclusively at the 7-position, and that the free base is readily solvolysed to a mixture of 1-methylimidazolidin-2-one, 1-methylimidazolidine-2-thione, and diphenacyl sulphide and disulphide. 3-Methyl-5,6-dihydroimidazolothiazole with methane- and arene-sulphonyl chlorides gave the corresponding 7-sulphonylthiazolium chlorides.On heating, these rearranged to 3-(2-chloroethyl)-4-methyl-3-aryl (or alkyl)sulphonylimido-2,3-dihydrothiazoles.The 7-(4-chlorophenylsulphonyl) derivative lost this substituent with aqueous base while concentrated aqueous ammonia attacked the 7a-position leading to a 3--2-imino-4-methyl-2,3-dihydrothiazole.
- Acheson, R. Morrin,Cooper, Martin W.,Cox, Ian R.
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p. 1773 - 1778
(2007/10/02)
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