- Novel imidazole derivatives as antifungal agents: Synthesis, biological evaluation, ADME prediction and molecular docking studies
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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.
- Alt?nda?, Firuze Diyar,Sa?l?k, Begüm Nurpelin,Acar ?evik, Ulviye,I??kda?, ?lhan,?zkay, Yusuf,Karaca Gen?er, Hülya
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- Dithiocarbamates: Efficient metallo-β-lactamase inhibitors with good antibacterial activity when combined with meropenem
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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.
- Wang, Ming-Ming,Chu, Wen-Chao,Yang, Yi,Yang, Qian-Qian,Qin, Shang-Shang,Zhang, En
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- 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
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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.
- Téllez S., Claudio A.,Costa, Anilton C.,Mondragón,Ferreira, Glaucio B.,Versiane,Rangel,Lima, G. Müller,Martin
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- Synthesis and dynamic NMR studies of some new symmetrical podands of dithiocarbamates formed from Bis(N-thiazol)chloroacetamides
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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.
- Shockravi, Abbas,Kamali, Mahmood,Halimehjani, Azim Ziyaei,Jafari, Reza
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- Solid-phase synthesis, crystal structure, and quantum chemical calculation of a molybdenum(II) complex with bis(diethyldithiocarbamate)
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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.
- He, Guang-Yu,Bei, Feng-Li,Chen, Hai-Qun,Sun, Xiao-Qiang
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- An experimental and theoretical approach of spectroscopic and structural properties of the bis(diethyldithiocarbamate)-cobalt(II)
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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.
- Costa Júnior,Versiane,Faget Ondar,Ramos,Ferreira, Glaucio B.,Martin,Téllez Soto
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- A 2H-MoS2/carbon cloth composite for high-performance all-solid-state supercapacitors derived from a molybdenum dithiocarbamate complex
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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.
- Yan, Zhishuo,Zhao, Jixing,Gao, Qingsheng,Lei, Hao
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- Structure Elucidation of an Yttrium Diethyldithiocarbamato-Phenanthroline Complex by X-ray Crystallography, Solid-State NMR, and ab-initio Quantum Chemical Calculations
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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.
- Gowda, Vasantha,Sarma, Bipul,?berg, Sven,Telkki, Ville-Veikko,Larsson, Anna-Carin,Lantto, Perttu,Antzutkin, Oleg N.
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- Single-crystal structure and intracellular localization of Zn(II)-thiosemicarbazone complex targeting mitochondrial apoptosis pathways
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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.
- Chen, Qiu,Fan, Weiwei,Gao, Huashan,Qi, Jinxu,Wang, Fu-An,Wang, Ruiya,Xia, Xichao,Zhao, Wei,Zheng, Yunyun
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supporting information
(2020/06/22)
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- Substituted carbamothioic amine-1-carbothioic thioanhydrides as novel trichomonicidal fungicides: Design, synthesis, and biology
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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.
- 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.
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p. 632 - 645
(2017/12/08)
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- Preparation method of TDEC (Tellurium Diethyl Dithiocarbamate)
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The invention provides a preparation method of TDEC (Tellurium Diethyl Dithiocarbamate), and relates to the technical field of rubber ingredients. The preparation method of the TDEC comprises the steps of adding sulfuric acid into a mixed solution of sodium tellurate and DDTC (Sodium diethyldithiocarbamate trihydrate), reacting, carrying out solid-liquid separation after finishing reacting, and obtaining the solid TDEC. The technical problems of large wastewater discharge and severe environmental pollution in the prior art are relieved, the method is simple in process and less in wastewater output, full-closed production and concentrative discharge of wastewater and waste gas can be carried out, the environmental pollution is reduced, the product yield reaches 98 percent or above, and theproduct purity is 99 percent or above.
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Paragraph 0073
(2018/07/06)
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- Synthesis, toxicities and bio-activities of manganese complexes with CO and H2S dual donors
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A series of H2S–CO dual-donors [Mn(CO)4CS2NR1R2] was synthesized, and evaluated from toxicity and bioactivity. The CO–H2S measuring test showed all the complexes not only released CO, but released H2S. The resulting data of cytotoxicity showed all the complexes had activities against the cell proliferation; among them, complexes 1, 2 and 7 displayed higher activities than the others, and their potencies were close to cis-platinum (DDP); whereas the precursors A1-A22 had almost no activities against all five tumor cell lines and W138 cell line proliferation. It is worth noting that complex 1 displayed the highest activity to MCF-7, complex 2 displayed the highest activity to HePG2, and complex 7 showed selectivity inhibition to both A549 and HeLa. The developmental toxicities of the complex were assessed using zebrafish embryos. The results showed complexes 1 and 2 had effect on the mortality and hatching rate of zebrafish embryos in dose-dependent manner. They caused zebrafish malformations when they were over 10 μM. Meanwhile, they displayed dose-dependent toxicities to larval zebrafish. In the test of bio-activities, complexes 1 and 2 had strong anti-inflammatory activities; they not only down-regulated the expression levels of iNOS and TNF-α up-regulated the expression of HO-1 and IL-10, but also up-regulated COX-2 levels. In contrast, the precursor compound (A1 or A2) displayed lower anti-inflammatory activity than the corresponding complex, which suggests both the CO and H2S from the complex took synergistic effects in the process of anti-inflammation. In addition, the complex showed antihypertensive effect and myocardial protection. This effect also possibly resulted from this synergistic effect. All these suggest the complexes have potential to be candidate medicines.
- Bai, Zhongjie,Zhang, Jinlong,Zhang, Qiuping,Zhang, Taofeng,Li, Jili,Zhao, Quanyi,Wang, Zhen,He, Dian,Cheng, Jie,Zhang, Jingke,Liu, Bin
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p. 339 - 356
(2018/10/20)
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- Thiuram disulfide intercalated hybrid materials of layered lead and cadmium iodides
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Thiuram disulfide intercalates of lead(II) and cadmium(II) were prepared by the reaction of binary layered metal iodides with five dithiocarbamates in air. The intercalates were characterized by elemental analysis, Powder X-ray diffraction (XRD), infrared (IR), ultraviolet-visible spectroscopy, diffuse reflectance spectroscopy, scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy, high-resolution transmission electron microscopy (HRTEM), and atomic force microscopy (AFM) techniques. IR showed increased contribution of the thioureide bond and the presence of weak disulfide stretching frequency. Powder XRD showed the characteristic intermediate 2θ signal confirming the intercalation. Powder XRD clearly differentiated intercalates from the iodinated product of dithiocarbamate. As the bulkiness of substituents on disulfide increased, "d" also increased. The higher thermal stability associated with intercalates clearly suggests a strong ionic interaction and a difficult de-intercalation. SEM images of lead intercalates indicated crystalline nature. The intercalates appeared as rods or spheres. The diallyl-intercalate, [PbI2](H5C3)2NCSS-SSCN(C3H5)2(where (H5C3)2NCSS-SSCN(C3H5)2is diallylthiuram disulfide), shows "net like structures." Intercalation of oxidized dithiocarbamates in the "galleries" of layered PbI2/CdI2is observed. HRTEM and AFM analysis of intercalates showed the particles to be nano-rods.
- Ramalingam,Ilakkiya
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p. 734 - 739
(2016/05/09)
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- Masked thiol sugars: Chemical behavior and synthetic applications of S-glycopyranosyl-N-monoalkyl dithiocarbamates
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The chemical behavior of S-glycopyranosyl-N-monoalkyl dithiocarbamates (DTCs) as masked 1-glycosyl thiols, easily prepared by the nucleophilic displacement of 1-halo sugars with dithiocarbamate salts of primary amines, has been studied and synthetically exploited. This behavior relies on the abstraction of the proton of the carbamate functionality that allows controlled access to thiolate sugar intermediates. The basic character of the DTC salts used as reagents leads to thiolates that evolve in situ to symmetrical diglycosyldisulfides (DGDSs) when long reaction times are allowed. Alternatively, controlled unmasking of the thiolate function can be efficiently attained by treatment with an external base of isolated anomeric glycosyl DTCs, the formation of which is prevalent when using short reaction times. In this manner, a second methodology for the preparation of symmetrical DGDSs and a chemical protocol for the S-glycosylation of any electrophilic substrate are established. The applications of this last strategy for the preparation of thioglycosyl vinyl sulfones, thiodisaccharides, and S-linked homo- and heterodivalent neoglycoconjugates are described as a proof-of-concept of the great potential of the sugar DTCs in any chemical scenario in which the covalent attachment of a thiol sugar is required. The evaluation of the biological functionality of some divalent sulfurated sugar systems is also described. Copyright
- Megia-Fernandez, Alicia,De La Torre-Gonzalez, Diego,Parada-Aliste, Jose,Lopez-Jaramillo, Francisco Javier,Hernandez-Mateo, Fernando,Santoyo-Gonzalez, Francisco
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p. 620 - 631
(2014/02/14)
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- DFT: B3LYP/6-311G (d, p) vibrational analysis of bis- (diethyldithiocarbamate)zinc (II) and natural bond orbitals
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Theoretical and experimental bands have been assigned for the Fourier Transform Infrared (FT-IR) and Fourier Transform Raman (FT-Raman) spectra of the bis-(diethydithiocarbamate)Zn(II) complex, [Zn(DDTC)2]. The calculations and spectra interpretation have been based on the DFT/B3LYP method, infrared and Raman second derivative spectra as well as band deconvolution analysis. To assign the metal-ligand normal modes the deviation percentage of the geometrical parameters was used. Results confirms a pseudo tetrahedral structure around the Zn(II) cation. The calculated infrared and Raman spectra has an excellent agreement with the experimental spectra. The Natural Bond Orbital analysis (NBO) was carried out as a way to study the Zn(II) hybridization leading to the pseudo tetrahedral geometry of the framework of the [Zn(DDTC)2] complex, and to study also which are the donor NBO and the acceptor NBO in meaningful charge transfer through the Second Order Perturbation Theory Analysis of Fox Matrix in NBO basis.
- Costa Jr.,Ondar,Versiane,Ramos,Santos,Martin,Raniero,Bussi,Tellez Soto
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p. 251 - 258
(2013/03/28)
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- Synthesis of S- and N-functionalized dithiocarbamates from cyclic sulfates
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A novel methodology for the synthesis of S- and N-functionalized dithiocarbamates starting from cyclic sulfates, amines and carbon disulfide by using different protocols, including microwave assistance and a multicomponent variant, has been developed. The procedure is highly versatile, simple and efficient. As an efficient route to dithiocarbamates, a simple and versatile method for preparing S- and N-functionalized dithiocarbamates starting for readily available cyclic sulfates and commercial amines under environmentally friendly conditions is reported. Copyright
- Parada-Aliste, Jose,Megia-Fernandez, Alicia,De La Torre-Gonzalez, Diego,Hernandez-Mateo, Fernando,Santoyo-Gonzalez, Francisco
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p. 3758 - 3763
(2013/07/19)
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- Vat dye and sulfur dye compositions
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Specific vatting accelerators according to claims 1 and 2 are described. These can be added to a vat dye or sulfur dye composition, or to a dye bath or printing paste containing a vat dye or sulfur dye, by virtue of which an improvement of dye yield, particularly on cellulose materials, is obtained.
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- Preparation and Characterization of Bis-Dithiocarbamato di-p-Tolyl Tin(IV)
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Bis-Dithiocarbamato di-p-tolyltin(IV), i.e., (p-CH3C6H4)2Sn(S2CNRR')2 (where R=R'=CH3, C2H5, i-C3H7; R=CH3, C2H5, i-C3H7 and R'=C6H5, CH2C6H5 or RR'=morpholine, 4-methylpiperidine and N-piperazine), were prepared by the reaction of di-p-tolyltin(IV) dichloride with the sodium salt of respective dithiocarbamate acid in acetone medium in the stoichiometric ratio of 1:2.The compounds have been duly characterized on the basis of infrared and nmr spectroscopic data.Anisobidentate nature of dithiocarbamate moiety has been suggested in these compounds.
- Wadhwa, Sangeeta,Garg, B. S.,Sharma, C. P.,Kumar, N.
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p. 247 - 250
(2007/10/02)
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- Reduction Potentials of Thiuram Disulfide/Dithiocarbamate Couples in Acetone/Water
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Reduction potentials relative to the saturated calomel electrode, Eo, of a series of thiuram disulfide/dithiocarbamate couples have been measured in 30percent v/v water in acetone and at μ 0.2 mol l-1 (NaNO3) by a combination of potentiometric measurements and equilibrium constant determinations for thiolate/disulfide interchange reactions.Eo values lie in the range -250 to -340 mV which place dithiocarbamates as intermediate between thiophenolate (Eo -540 mV) and ethylxanthate (Eo -206 mV) in reducing properties.The significant effect on Eo of varying the substituents on the nitrogen in the dithiocarbamates correlates with the substituent effects on the acid dissociation constants of the parent dithiocarbamic acid and with trends in the half-wave potentials for metal-based oxidation and reduction of transition metal dithiocarbamate complexes.
- Nichols, Peter J.,Grant, Michael W.
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p. 2455 - 2463
(2007/10/02)
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- Reactions of Hydrazidoyl Chlorides with Sodium N,N-Dialkyldithiocarbamates
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The reaction of N-arylbenzhydrazidoyl chlorides (1) with sodium N,N-dialkyldithiocarbamates yields the hydrazone derivatives 2, which react further to form 4 unless the reaction sites are sterically crowded.
- Kaugars, Girts,Rizzo, Victor L.
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p. 411 - 412
(2007/10/02)
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- REACTION OF DITHIOCARBAMIC ACID SALTS WITH 4-SUBSTITUTED 2-THIOLENE- AND 3,4-DISUBSTITUTED THIOLANE 1,1-DIOXIDES. STRUCTURAL STUDIES OF N-PHENYLTHIOLANOTHIAZOLIDINE-2-THIONE 5,5-DIOXIDE
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The reaction of monoalkyl(aryl)dithiocarbamic acid salts with 4-substituted 2-thiolene and 3,4-disubstituted thiolane 1,1-dioxides gave N-alkyl(aryl)thiolanothiazolidine-2-thione 5,5-dioxides, the structure of which was proved by X-ray diffraction studies. 1,1-Dioxothiol-3-en-3-yl esters were obtained with salts of dialkyl(heteryl)dithiocarbamic acids.
- Bezmenova, T. E.,Khaskin, G. I.,Slutskii, V. I.,Dul'nev, P. G.,Zakharov, L. N.,et al.
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p. 668 - 672
(2007/10/02)
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- Water-soluble azo dyestuffs containing triazine and 3-azo-2,6-dihydroxypyrid-6-one radicals
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A new class of cellulose reactive dyes have a sulphonated benzene, naphthalene or naphthalene azobenzene diazo component coupled on to a class of coupling components of the formula: SPC1 In which T1 is H, monocyclic aryl, OH, CO2 H, aminocarbonyl, lower alkyl, lower alkoxy and lower alkoxycarbonyl, T2 is H, CO2 H, lower alkyl, lower alkoxy, monocyclic aryl, benzyl, aminocarbonyl and lower alkoxycarbonyl, the diazo component carrying a cellulose-reactive group. Also included are dyes in which two moles of such a monoazo dye are linked through a diamine radical. Cr and Co complexes of dyes in which the diazo component is a o-aminophenol or o-aminonaphthol are included. These dyes are usefully employed to color cellulose, wool or polyamide textile materials. These dyes impart to the textile materials deep shades having excellent fastness to light and to the wet treatments which are commonly applied to cellulose textile materials.
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