148-18-5Relevant articles and documents
Novel imidazole derivatives as antifungal agents: Synthesis, biological evaluation, ADME prediction and molecular docking studies
Alt?nda?, Firuze Diyar,Sa?l?k, Begüm Nurpelin,Acar ?evik, Ulviye,I??kda?, ?lhan,?zkay, Yusuf,Karaca Gen?er, Hülya
, p. 887 - 894 (2019)
A series of 2-(substituteddithiocarbamoyl)-N-[4-((1H-imidazol-1-yl)methyl)phenyl]acetamide derivatives was designed and synthesized to combat the increasing incidence of drug-resistant fungal infections. All synthesized compounds were characterized by IR, 1H-NMR, 13C-NMR, and HRMS spectra and elemental analyses. Antifungal activity tests were performed against four different fungal strains. Molecular docking studies were performed to investigate the mode of action towards the fungal lanosterol 14α-demethylase, a cytochrome P450-dependent enzyme. ADME studies were carried out and a connection between activities and physicochemical properties of the target compounds was determined. Most of the final compounds exhibited significant activity against Candida albicans and Candida krusei with MIC50 value 12.5 μg/mL. The results of in vitro anti-Candida activity, a docking study and ADME prediction revealed that the newly synthesized compounds have potential anti-Candida activity and evidenced the most active derivative, 5b (2-Pyrrolidinthiocarbonylthio-N-[4-((1H-imidazol-1-yl)methyl)phenyl]acetamide), which can be further optimized as a lead compound.
Dithiocarbamates: Efficient metallo-β-lactamase inhibitors with good antibacterial activity when combined with meropenem
Wang, Ming-Ming,Chu, Wen-Chao,Yang, Yi,Yang, Qian-Qian,Qin, Shang-Shang,Zhang, En
, p. 3436 - 3440 (2018)
The activity of β-lactam antibiotics is compromised by metallo-β-lactamases (MBLs). Herein, a series of dithiocarbamate derivatives were designed and synthesized. Their antibacterial activities were tested in combination with meropenem (MEM) against several MBL (NDM and IMP type)-producing clinical isolates. Clinical isolates harboring NDM-1 and IMP-4 became susceptible to MEM when it was combined with dithiocarbamate compounds 4a, 4b or 4f synthesized in this work. Compounds 4a and 4b increased the effectiveness of MEM by up to 2560 times against strains. In vitro bactericidal dynamics tests showed that bacteria died within 24 h when they were treated with compound 4f + MEM. Compounds 4a, 4b and 4f were non-hemolytic and exhibited low toxicity toward HeLa cells in vitro. These data show that compounds containing dithiocarbamate functional group may be helpful in the development of MBL inhibitors.
Molecular structure, natural bond analysis, vibrational and electronic spectra, surface enhanced Raman scattering and Mulliken atomic charges of the normal modes of [Mn(DDTC)2] complex
Téllez S., Claudio A.,Costa, Anilton C.,Mondragón,Ferreira, Glaucio B.,Versiane,Rangel,Lima, G. Müller,Martin
, p. 95 - 107 (2016)
Theoretical and experimental bands have been assigned for the Fourier Transform Infrared and Raman spectra of the bis(diethyldithiocarbamate)Mn(II) complex, [Mn(DDTC)2]. The calculations have been based on the DFT/B3LYP method, second derivative spectra and band deconvolution analysis. The UV–vis experimental spectra were measured in acetonitrile solution, and the calculated electronic spectrum was obtained using the TD/B3LYP method with 6-311G(d, p) basis set for all atoms. Charge transfer bands and those d-d spin forbidden were assigned in the UV–vis spectrum. The natural bond orbital analysis was carried out using the DFT/B3LYP method and the Mn(II) hybridization leading to the planar geometry of the framework was discussed. Surface enhanced Raman scattering (SERS) was also performed. Mulliken charges of the normal modes were obtained and related to the SERS enhanced bands.
Synthesis and dynamic NMR studies of some new symmetrical podands of dithiocarbamates formed from Bis(N-thiazol)chloroacetamides
Shockravi, Abbas,Kamali, Mahmood,Halimehjani, Azim Ziyaei,Jafari, Reza
, p. 209 - 215 (2013)
Reactions of dithiocarbamates salts (IVa-c) with bis(N-thiazol) chloroacetamides(IIa,b) in DMF furnished corresponding podands V a-fas in high to excellent yields. Two reacting ligands (II a,b) were obtained in the reaction of bis(aminothiazoles) (I a,b) with chloroacetyl chloride. Dynamic NMR spectroscopic data of two series of podands (and) are discussed and figured out their free energy of activation (ΔGc≠) at coalescence temperatures. The ΔGc≠s of these podands were attributed to conformational isomerization in the range of 14.9-16.2 kcal/mol due to rotation and resonance effect about thioamide C - N bond.
Solid-phase synthesis, crystal structure, and quantum chemical calculation of a molybdenum(II) complex with bis(diethyldithiocarbamate)
He, Guang-Yu,Bei, Feng-Li,Chen, Hai-Qun,Sun, Xiao-Qiang
, p. 481 - 486 (2006)
The complex Mo(Et2dtc)2 [Et2dtc: bis(diethyldithiocarbamate)] was synthesized by solid-phase reaction at room temperature and characterized by elemental analysis, powder XRD, IR, 1H NMR and TG/DTA. Its crystal structure was determined by X-ray single crystal diffraction. The crystals are monoclinic with space group P2 1/c, a=0.61800(12)nm; b=1.1540(2)nm; c=1.1610(2)nm; β=95.78(3)°; V=0.8238(3)nm3; D c=1.582g/cm 3; Z=2 F(000)=400; μ=1.285mm-1; R=0.0703; wR=0.2330; GOF=1.060. The coordination geometry of Mo atom, by four S anions from Et 2dtc ligand, is that of a slightly distorted planar square. Furthermore, the optimized geometry, charge distribution, and thermodynamic functions were calculated by quantum chemical method.
An experimental and theoretical approach of spectroscopic and structural properties of the bis(diethyldithiocarbamate)-cobalt(II)
Costa Júnior,Versiane,Faget Ondar,Ramos,Ferreira, Glaucio B.,Martin,Téllez Soto
, p. 119 - 134 (2012)
Theoretical and experimental bands have been assigned for the Fourier Transform Infrared spectrum (FT-IR) and FT-Raman of the bis(diethydithiocarbamate)Co(II) complex, [Co(DDTC)2]. The calculations have been based on the DFT/B3LYP method, second derivative spectrum and band deconvolution analysis. The UV-Vis experimental spectra of [Co(DDTC)2] was measured in the solid state and in an acetonitrile solution. The calculated electronic spectrum was estimated using the TD/PBE1PBE and TD/B3LYP methods 6-311G (d,p) basis set for all atoms. The Bond Orbital Analysis was carried out with the DFT:B3LYP/PBE1PBE methods, revealing electronic delocalization effects involving CoS and CN bonds and their neighboring groups. The observed valence configurations for the alpha and beta electrons of the cobalt atom were (4s)0.46(3d)7.69 (B3LYP) and (4s)0.46(3d)7,68 (PBE1PBE), as expected for the planar structure around the Co(II) cation. The calculated infrared and UV-Vis spectra, based on the proposed geometrical structure of the bis(diethyldithiocarbamate)cobalt(II) complex, showed an excellent agreement with the experimental spectra.
A 2H-MoS2/carbon cloth composite for high-performance all-solid-state supercapacitors derived from a molybdenum dithiocarbamate complex
Yan, Zhishuo,Zhao, Jixing,Gao, Qingsheng,Lei, Hao
, p. 11954 - 11964 (2021)
A molecular complex Mo2O2(μ-S)2(Et2dtc)2(dtc = dithiocarbamate) is prepared and loaded onto carbon cloth (CC) through facile solvothermal treatment, followed by subsequent single-source pyrolysis. This results in a highly porous 2H-MoS2/CC composite with a sponge-like stacked lamellar morphology. Due to its high porosity and unique nano/microstructure, the MoS2/CC composite exhibits a specific capacitance of 550.0 F g?1at 1 A g?1, outperforming some 1T-MoS2based electrodes. The composite is further assembled into a symmetric all-solid-state supercapacitor, which can be operated stably at a wide potential window and shows a specific capacitance of 127.5 F g?1at 1 A g?1. In addition, the device delivers a high energy density of 70.8 W h kg?1at 1 kW kg?1, which still remains 15.0 W h kg?1at 18.0 kW kg?1. 75% of the performance of the device can be retained after 8000 cycles. Such remarkable electrochemical performance is attributed to its novel nano/microstructures with a large surface area, convenient ion transport pathways, enhanced conductivity, and improved structural stability. Thus, this work demonstrates a highly promising dithiocarbamate-based single-precursor pyrolysis route towards the fabrication of metal sulfides/carbon composites for energy storage applications.
Structure Elucidation of an Yttrium Diethyldithiocarbamato-Phenanthroline Complex by X-ray Crystallography, Solid-State NMR, and ab-initio Quantum Chemical Calculations
Gowda, Vasantha,Sarma, Bipul,?berg, Sven,Telkki, Ville-Veikko,Larsson, Anna-Carin,Lantto, Perttu,Antzutkin, Oleg N.
, p. 3278 - 3291 (2016)
We present a structural analysis method for molecular and electronic structure of yttrium diethyldithiocarbamato-phenanthroline complex {[Y(S2CNR2)3PHEN] with R = C2H5and PHEN = 1,10-phenanthroline} combining solid-state NMR spectroscopy, XRD, and first principles DFT calculations. Replacing the Nd3+ion with Y3+in the reported crystal structure of [Nd(S2CNR2)3PHEN] complex generated an approximate 3D structure of the title complex. The structure was then subjected to first principles quantum chemical geometry optimisation using periodic DFT method. The quality of the method is discussed by comparing predicted and experimental powder XRD patterns. Full assignment of13C and15N solid-state CP-MAS NMR spectra as well as analyses of the principal values of the chemical shift tensors were carried out using periodic scalar relativistic DFT modelling. Spin-orbit relativistic effects, estimated by SO-ZORA formalism for one molecular unit, were evaluated. Finally, the X-ray structure of the title complex was determined, which proved that the former procedure is appropriate. The most important orbital interactions were investigated by Natural Bond Orbital analysis. The isotropic shielding values for S2CN-carbons were analysed by Natural Localised Molecular Orbital analysis. The present approach can be further extended to study other rare earth metal complexes, particularly those having similar but not yet solved crystal structures.
Single-crystal structure and intracellular localization of Zn(II)-thiosemicarbazone complex targeting mitochondrial apoptosis pathways
Chen, Qiu,Fan, Weiwei,Gao, Huashan,Qi, Jinxu,Wang, Fu-An,Wang, Ruiya,Xia, Xichao,Zhao, Wei,Zheng, Yunyun
supporting information, (2020/06/22)
Tracking of drugs in cancer cells is important for basic biology research and therapeutic applications. Therefore, we designed and synthesised a Zn(II)-thiosemicarbazone complex with photoluminescent property for organelle-specific imaging and anti-cancer proliferation. The Zn(AP44eT)(NO3)2 coordination ratio of metal to ligand was 1:1, which was remarkably superior to 2-((3-aminopyridin-2-yl) methylene)-N, N-diethylhydrazinecarbothioamide (AP44eT·HCl) in many aspects, such as fluorescence and anti-tumour activity. Confocal fluorescence imaging showed that the Zn(AP44eT)(NO3)2 was aggregated in mitochondria. Moreover, Zn(AP44eT)(NO3)2 was more effective than the metal-free AP44eT·HCl in shortening the G2 phase in the MCF-7 cell cycle and promoting apoptosis of cancer cells. Supposedly, the effects of these complexes might be located mainly in the mitochondria and activated caspase-3 and 9 proteins.
Substituted carbamothioic amine-1-carbothioic thioanhydrides as novel trichomonicidal fungicides: Design, synthesis, and biology
Mandalapu, Dhanaraju,Kushwaha, Bhavana,Gupta, Sonal,Krishna, Shagun,Srivastava, Nidhi,Shukla, Mahendra,Singh, Pratiksha,Chauhan, Bhavana S.,Goyani, Ravi,Maikhuri, Jagdamba P.,Sashidhara, Koneni V.,Kumar, Brijesh,Tripathi, Renu,Shukla, Praveen K.,Siddiqi, Mohammad I.,Lal, Jawahar,Gupta, Gopal,Sharma, Vishnu L.
, p. 632 - 645 (2017/12/08)
Sexually transmitted diseases like trichomoniasis along with opportunistic fungal infections like candidiasis are major global health burden in female reproductive health. In this context a novel non-nitroimidazole class of substituted carbamothioic amine-1-carbothioic thioanhydride series was designed, synthesized, evaluated for trichomonacidal and fungicidal activities, and was found to be more active than the standard drug Metronidazole (MTZ). Compounds were trichomonicidal in the MIC ranges of 4.77–294.1 μM and 32.46–735.20 μM against MTZ-susceptible and -resistant strains, respectively. Further, compounds inhibited the growth of at least two out of ten fungal strains tested at MIC of 7.50–240.38 μM. The most active compound (20) of this series was 3.8 and 9.5 fold more active than the MTZ against the two Trichomonas strains tested. Compound 20 also significantly inhibited the sulfhydryl groups present over Trichomonas vaginalis and was found to be more active than the MTZ in vivo. Further, a docking analysis carried out with cysteine proteases supported their thiol inhibiting ability and preliminary pharmacokinetic study has shown good distribution and systemic clearance.
