- New N-(1,3,4-thiadiazol-2-yl)furan-2-carboxamide derivatives as potential inhibitors of the VEGFR-2
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The present study reports the synthesis and biological evaluation of a new series of novel N-(1,3,4-thiadiazol-2-yl)furan-2-carboxamide derivatives. The reactions were executed under both conventional and microwave irradiation conditions. An enhancement i
- Hekal, Mohamed H.,Farag, Paula S.,Hemdan, Magdy M.,El-Sayed, Wael M.
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- Nano nickel [1,2,4]-triazole-3-thiones complex: Design, sonochemical synthesis, and antimicrobial evaluation
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A series of new 1,2,4-triazole-3-thiones were synthesized by calm, benign, no risk, eco-friendly, and energy efficient sequential reaction methodology like grinding and ultrasonic (US). In addition, 1,2,4-triazoles were prepared under conventional method and comparative study was done. The synthesized 1,2,4-triazoles were complexed with Ni(II) to produce nanoparticles complexes (NPC's) with average particle size vary from 55 to 100 nm (using scanning electron microscope technique) with good yields via both US and conventional techniques. X-ray diffraction technique and spectra analysis techniques were used to confirm the square planer geometry of the synthesized NPC's. Antimicrobial activity of the prepared 1,2,4-triazoles and their nickel complexes were studied which evaluated a high activity with complexes instead their triazoles.
- El-Sayed, Amira A.,Farag, Paula S.,Hemdan, Magdy M.
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- Tunable Anticancer Activity of Furoylthiourea-Based RuII–Arene Complexes and Their Mechanism of Action
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Fourteen new RuII–arene (p-cymene/benzene) complexes (C1–C14) have been synthesized by varying the N-terminal substituent in the furoylthiourea ligand and satisfactorily characterized by using analytical and spectroscopic techniques. Electrosta
- Swaminathan, Srividya,Haribabu, Jebiti,Kalagatur, Naveen Kumar,Nikhil, Maroli,Balakrishnan, Nithya,Bhuvanesh, Nattamai S. P.,Kadirvelu, Krishna,Kolandaivel, Ponmalai,Karvembu, Ramasamy
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- Synthesis of photoactive 5-aroyl-4-furyl-2-(morpholin-4-yl)thiazoles
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5-Aroyl-4-furyl-2-(morpholin-4-yl)thiazoles were synthesized by the reaction of (morpholin-4-ylthiocarbonyl)furan-2-carboxamide with α-bromoketones.
- Chudov,Levchenko,Yarovenko,Krayushkin,Barachevskii,Baryshnikova,Grebennikov
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- O-benzyl-N-(2-furoyl)thiocarbamate
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The O-benzyl-N-(2-furoyl)thiocarbamate (1) was obtained by direct reaction between furoyl isothiocyanate and benzyl alcohol. The X-ray diffraction analysis of 1 showed an orthorhombic system, with a = 7.811(4) A, b = 9.685(4) A, c = 33.562(15) A, and spac
- Montiel-Ortega, Luis Alberto,Rojas-Lima, Susana,Otazo-Sanchez, Elena,Villagomez-Ibarra, Roberto
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- Three practical approaches for the synthesis of novel 4,7- dihetarylpyrazolo[1,5-a][1,3,5]triazines
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Novel 4,7-dihetarylpyrazolo[1,5-a][1,3,5]triazines were synthesized from three different approaches. The first one, involved a one-step reaction between 5-amino-3-hetaryl-1H-pyrazoles and O,S-diethyl hetaroylimidothiocarbonates or S,S-diethyl hetaroylimidodithiocarbonates under solvent-free conditions employing microwave irradiation as the energy source. In the second approach, conventional heating under reflux in DMF as solvent was used instead of the microwave irradiation; and the third one was achieved from a two-step sequence through the treatment of 5-amino-3-hetaryl-1H-pyrazoles with hetaroyl isothiocyanates and the subsequent S-alkylation and cyclization process in DMF as solvent. Some intermediates were isolated and characterized to support the regiochemistry of the studied reactions. The structures of the new compounds were unambiguously established by spectroscopic and analytical techniques.
- Insuasty, Henry,Insuasty, Braulio,Castro, Edison,Quiroga, Jairo,Abonia, Rodrigo,Nogueras, Manuel,Cobo, Justo
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- Highly active copper(i) complexes of aroylthiourea ligands against cancer cells-synthetic and biological studies
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The reaction of copper(i) bromide with aroylthiourea ligands (L) in the molar ratio 1?:?3 resulted in the formation of [CuBr(L)3]. The complexes were well characterized by analytical and spectroscopic (UV-visible, FT-IR, NMR and mass) technique
- Jeyalakshmi, Kumaramangalam,Haribabu, Jebiti,Balachandran, Chandrasekar,Narmatha, Eswaramoorthi,Bhuvanesh, Nattamai S. P.,Aoki, Shin,Awale, Suresh,Karvembu, Ramasamy
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- Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution
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1-Acyl thioureas [R1C(O)NHC(S)NR2R3] are shown to display conformational flexibility depending on the degree of substitution at the nitrogen atom. The conformational landscape and structural features for two closely related thioureas having R1?=?2-furoyl have been studied. The un-substituted 2-furoyl thiourea (I) and its dimethyl analogue, i.e. 1-(2-furoyl)-3,3-dimethyl thiourea (II), have been synthesized and fully characterized by spectroscopic (FT-IR, 1H and 13C NMR) and elemental analysis. According to single crystal X-ray diffraction analysis, compounds I and II crystallize in the monoclinic space group P21/c. In the compound I, the trans–cis geometry of the almost planar thiourea unit is stabilized by intramolecular N[sbnd]H???O[dbnd]C hydrogen bond between the H atom of the cis thioamide and the carbonyl O atom. In compound II, however, the acyl thiourea group is non-planar, in good agreement with the potential energy curve computed at the B3LYP/6-31?+?G(d,p) level of approximation. Centrosymmetric dimers generated by intermolecular N[sbnd]H???S[dbnd]C hydrogen bond forming R22(8) motif are present in the crystals. Intermolecular interactions have been rationalized in terms of topological partitions of the electron distributions and Hirshfeld surface analysis, which showed the occurrence of S???H, O???H and H???H contacts that display an important role to crystal packing stabilization of both thiourea derivatives.
- Cairo, Raúl Ramos,Stevens, Ana María Plutín,de Oliveira, Tamires Donizeth,Batista, Alzir A.,Castellano, Eduardo E.,Duque, Julio,Soria, Delia B.,Fantoni, Adolfo C.,Corrêa, Rodrigo S.,Erben, Mauricio F.
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- Electrochemical sensing of doxepin using acylthiourea-modified glassy carbon electrode
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Acylthiourea (ATU) compounds 4-(3-(furan-2-carbonyl)thioureido)benzoic acid (1), 4-(3-(thiophene-2-carbonyl)thioureido)benzoic acid (2), and 4-(3-(benzoyl)thioureido)benzoic acid (3) were synthesized and characterized by NMR (1H and 13/su
- Bhuvanesh, N. S. P.,Biju, V. M.,Kalaiyarasi, A.,Karvembu, R.
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- Substituted 4-phenylthiazoles: Development of potent and selective A1, A3 and dual A1/A3 adenosine receptor antagonists
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Adenosine acts as a powerful signaling molecule via four distinct G protein-coupled receptors, designated A1, A2A, A2B and A3 adenosine receptors (ARs). A2A and A2B ARs are Gs-coupled, while A1 and A3 ARs inhibit cAMP production via Gi proteins. Antagonists for A1 and A3 ARs may be useful for the treatment of (neuro)inflammatory diseases including acute kidney injury and kidney failure, pulmonary diseases, and Alzheimer's disease. In the present study, we optimized the versatile 2-amino-4-phenylthiazole scaffold by introducing substituents at N2 and C5 to obtain A1 and A3 AR antagonists including dual-target compounds. Selective A1 antagonists with (sub)nanomolar potency were produced, e.g. 11 and 13. These compounds showed species differences being significantly more potent at the rat as compared to the human A1 AR, and were characterized as inverse agonists. Several potent and selective A3 AR antagonists, e.g. 7, 8, 17 and 22 (Ki values of 5–9 nM at the human A3 AR) were prepared, which were much less potent at the rat orthologue. Moreover, dual A1/A3 antagonists (10, 18) were developed showing Ki values between 8 and 42 nM. Docking and molecule dynamic simulation studies using the crystal structure of the A1 AR and a homology model of the A3 AR were performed to rationalize the observed structure-activity relationships.
- Abdelrahman, Aliaa,Yerande, Swapnil G.,Namasivayam, Vigneshwaran,Klapschinski, Tim A.,Alnouri, Mohamad Wessam,El-Tayeb, Ali,Müller, Christa E.
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supporting information
(2019/12/24)
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- Water soluble Ru (II)–p-cymene complexes of chiral aroylthiourea ligands derived from unprotected D/L-alanine as proficient catalysts for asymmetric transfer hydrogenation of ketones
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The newfangled chiral aroylthiourea ligands (L1-L6) were produced from unprotected D/L-alanine and their water soluble Ru (II) organometallic catalysts (1–6) were designed from their reaction with [RuCl2(η6-p-cymene)]2. The analytical and spectral methods were used to confirm the structure of the ligands and complexes. The solid state structure of L1, 5 and 6 was confirmed by single crystal XRD. The organometallic compounds (1–6) catalyzed the asymmetric transfer hydrogenation of aromatic, heteroaromatic and bulky ketones to yield respective enantiopure secondary alcohols with admirable conversions (up to 99%) and attractive enantiomeric excesses (ee up to 98%), in presence of formic acid and triethylamine in water medium under non-inert atmospheric conditions.
- Sheeba, Mani Mary,Tamizh, Manoharan Muthu,Bhuvanesh, Nattamai S.P.,Karvembu, Ramasamy
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- Chemosensing, molecular docking and antioxidant studies of 8-aminoquinoline appended acylthiourea derivatives
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Acylthiourea derivatives, 1-benzoyl-3-(quinolin-8-yl)thiourea (1), 1-(furan-2-carbonyl)-3-(quinolin-8-yl)thiourea (2) and 1-(thiophene-2-carbonyl)-3-(quinolin-8-yl)thiourea (3) were synthesized and well characterized by using NMR (1H and 1
- Kalaiyarasi,Haribabu,Gayathri,Gomathi,Bhuvanesh,Karvembu,Biju
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p. 450 - 460
(2019/03/14)
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- Catalytic Assessment of Copper(I) Complexes and a Polymer Analog towards the One-Pot Synthesis of Imines and Quinoxalines
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Three copper(I) complexes, [CuCl(L)(PPh3)2] [L = FL (1), BL (2) or TL (3)] were prepared from [(PPh3)2Cu(μ-Cl)2Cu(PPh3)] and N-carbamothioylfuran-2-carboxamide (FL), N-carbamothioylbenzamide (BL) or N-carbamothioylthiophene-2-carboxamide (TL) ligands in benzene and four-coordinated tetrahedral copper complexes were well characterized by various spectroscopic techniques (UV/Vis, FT-IR, 1H NMR, 13C NMR and 31P NMR). The molecular structure of the ligands (FL and BL) and complexes was established from single-crystal X-ray diffraction studies. Copper complexes have been shown to catalyse the one-pot synthesis of imines and quinoxalines. Heterogenized catalyst (4) was prepared by reacting more active complex 3 with polystyrene supported triphenylphosphane, and characterized by elemental analyses, and DRS-UV, FT-IR, ICP-OES, and solid-state NMR techniques. Catalytic activity of the complexes (3 and 4) was tested in the formation of imines from alcohols and amines, and quinoxalines from hydroxy ketones and diamines. Heterogeneity and reusability of catalyst 4 were evaluated, and the catalyst can be reused for four runs without any loss in activity.
- Sindhuja, Dharmalingam,Vasanthakumar, Punitharaj,Bhuvanesh, Nattamai,Karvembu, Ramasamy
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p. 3588 - 3596
(2019/08/20)
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- Novel inhibitors of Staphylococcus aureus RnpA that synergize with mupirocin
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We recently discovered RnpA as a promising new drug discovery target for methicillin-resistant S. aureus (MRSA). RnpA is an essential protein that is thought to perform two required cellular processes. As part of the RNA degrasome Rnpa mediates RNA degradation. In combination with rnpB it forms RNase P haloenzymes which are required for tRNA maturation. A high throughput screen identified RNPA2000 as an inhibitor of both RnpA-associated activities that displayed antibacterial activity against clinically relevant strains of S. aureus, including MRSA. Structure-activity studies aimed at improving potency and replacing the potentially metabotoxic furan moiety led to the identification of a number of more potent analogs. Many of these new analogs possessed overt cellular toxicity that precluded their use as antibiotics but two derivatives, including compound 5o, displayed an impressive synergy with mupirocin, an antibiotic used for decolonizing MSRA whose effectiveness has recently been jeopardized by bacterial resistance. Based on our results, compounds like 5o may ultimately find use in resensitizing mupirocin-resistant bacteria to mupirocin.
- Lounsbury, Nicole,Eidem, Tess,Colquhoun, Jennifer,Mateo, George,Abou-Gharbia, Magid,Dunman, Paul M.,Childers, Wayne E.
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supporting information
p. 1127 - 1131
(2018/02/21)
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- Chemoselective transfer hydrogenation of nitroarenes, ketones and aldehydes using acylthiourea based Ru(II)(p-cymene) complexes as precatalysts
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A new series of Ru(II)(η6-p-cymene) complexes (1–5) was synthesized from pyridine based acylthiourea ligands (L1-L5) and [Ru(η6-p-cymene)Cl2]2. All the ligands and complexes were well characterized by UV-Visible, FT-IR, mass and 1H & 13C NMR spectroscopic techniques. The molecular structures of the ligands (L1, L2, L4 and L5) and complex 1 were confirmed using single crystal X-ray diffraction study. The Ru(II)(η6-p-cymene) complexes (1–5) were proved to be efficient precatalysts for the transfer hydrogenation of carbonyl compounds and nitroarenes in the presence of 2-propanol as a hydrogen donor and KOH as a base. The catalytic transfer hydrogenation reactions were chemoselective towards the nitro group in presence of carbonyl group, which is a rare scenario in homogeneous catalysis. The catalyst was compatible with broad range of substrates which include furfural, quinone and many heterocycles. The catalytic reactions exhibited very high conversions (upto 100%) and excellent yields (upto 99%). Turn Over Number (TON) was found upto 990.
- Sathishkumar, Pushpanathan N.,Raveendran, Neethi,Bhuvanesh, Nattamai S.P.,Karvembu, Ramasamy
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- Synthesis, characterization, molecular docking, thermal degradation studies and biological screening of N-{[2-(pyridin-4-ylcarbonyl)hydrazinyl]carbonothioyl}furan-2-carboxamide and its Mn(II), Ni(II), Co(II), Cu(II) and Zn(II) complexes
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N-{[2-(Pyridin-4-ylcarbonyl)hydrazinyl]carbonothioyl}furan-2-carboxamide and its complexes with Ni(II), Co(II), Cu(II), Zn(II) and Mn(II) ions have been synthesized. The structure of the synthesized compounds was elucidated by elemental analysis, conductivity measurements, UV-visible, FT-IR, 1H NMR, powder XRD and thermal analysis studies. Most of metal complexes have exhibit thermal degradation between 80-750 °C and the powder X-rays diffraction data suggest that all the synthesized metal complexes were in nano crystalline phase. The computational molecular docking has been studied using Hex molecular modeling package version 8.2. The three dimensional structure of E. coli MurBenzyme (PDB code 2MBR) was used in microbial activity. The metal complexes showed comparable E total values with the standard drug tetracycline. The antioxidant and antimicrobial activity of prepared compounds indicate agreeable results versus bacterial strains three Gram-positive bacteria; S. aureus, S. pyogenes and P. acnes and three Gram-negative bacteria; E. coli, K. terrigena and K. pneumonia. The antifungal activity gave good results against fungal strains C. albicans, C. neoformans and Trichosporon.
- Yuvaraj,Parameshwara Naik,Krishnamurthy,Venkatesh,Mohammed Shafeeulla,Manjuraj,Venugopal
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p. 2177 - 2183
(2017/10/05)
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- Palladium(II)/N,N-disubstituted-N′-acylthioureas complexes as anti-Mycobacterium tuberculosis and anti-Trypanosoma cruzi agents
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The new complexes of Pd(II) with N,N-disubstituted-N′-acylthioureas:[(1) [Pd(dppf)(N,N-dimethyl-N′-benzoylthioureato-k2O,S)]PF6, (2) [Pd(dppf)(N,N-diethyl-N′-benzoylthioureato-k2O,S)]PF6, (3) [Pd(dppf)(N,N-dibut
- Plutín, Ana M.,Alvarez, Anislay,Mocelo, Raúl,Ramos, Raúl,Castellano, Eduardo E.,da Silva, Monize M.,Villarreal, Wilmer,Pavan, Fernando R.,Meira, Cássio Santana,Filho, José Sim?o Rodrigues,Moreira, Diogo Rodrigo M.,Soares, Milena Botelho P.,Batista, Alzir A.
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- Half sandwich Ru(II)-acylthiourea complexes: DNA/HSA-binding, anti-migration and cell death in a human breast tumor cell line
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Organometallic ruthenium complexes as potential anticancer agents have been explored due to their suitable properties, such as stability in the solid state and in solution, water solubility and low toxicity. In this study, eight metal complexes of this cl
- Colina-Vegas, Legna,Luna-Dulcey, Liany,Plutín, Ana M.,Castellano, Eduardo E.,Cominetti, Marcia R.,Batista, Alzir A.
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p. 12865 - 12875
(2017/10/13)
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- Organosilatranes with Acylthiourea Derivatives – Metal-Ion Binding, Substituent-Dependent Sensitivity, and Prospects for the Fabrication of Magnetic Hybrids
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A variety of topologically interesting acylthiourea-tethered organosilatranes (AcTu-OS) were prepared, and their function as metal-ion binding sites was investigated. The prepared compounds have been characterized by elemental analysis; FTIR, UV/Vis and NMR (1H and13C) spectroscopy; and mass spectrometry. The organosilicon complexes 4a–4e possess diverse coordination abilities for the surveyed metal ions (Cu2+, Cd2+, Hg2+and Pb2+), as was appraised by the corresponding absorption shifts in the UV/Vis spectra. In addition, a facile preparatory route for the covalent grafting of the most efficient receptor 4e onto a silica-encrusted magnetic nanosupport was implemented. The resultant organic–inorganic hybrid nanoparticles (H-NPs) were characterized by physicochemical techniques such as FTIR spectroscopy, XRD, thermogravimetric analysis (TGA), TEM, field-emission SEM (FE-SEM) and energy-dispersive X-ray spectroscopy (EDX). The grafting of the sensory module afforded active sites for the adsorption of metal ions from the aqueous solution which is outlined using the Langmuir adsorption isotherm. The potential in sensing, sorbent properties and facile magnetic recovery of the hybrid evinces the separation process practical to undertake environmental issues.
- Singh, Gurjaspreet,Rani, Sunita
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p. 3000 - 3011
(2016/07/12)
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- Anti-Mycobacterium tuberculosis activity of platinum(II)/N,N-disubstituted-N′-acyl thiourea complexes
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Synthesis, characterization and anti-Mycobacterium tuberculosis assays of new platinum(II)/dppf/N,N-disubstituted-N′-acyl thiourea complexes with general formulae [Pt(dppf)(L)]PF6, [dppf = 1,1′-bis(diphenylphosphino)ferrocene; L = N,N-disubstit
- Plutín, Ana M.,Alvarez, Anislay,Mocelo, Raúl,Ramos, Raúl,Castellano, Eduardo E.,Da Silva, Monize M.,Colina-Vegas, Legna,Pavan, Fernando R.,Batista, Alzir A.
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- Ru(II)-p-cymene complexes containing esters of chiral D/L-phenylalanine derived aroylthiourea ligands for enantioselective reduction of pro-chiral ketones
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A series of new chiral aroylthiourea ligands was derived from unprotected d/l-phenylalanine: (R)/(S)-2-(3-benzoylthioureido)-3-phenylpropanoic acid (L1/L2), (R)/(S)-2-(3-(thiophene-2-carbonyl)thioureido)-3-phenylpropanoic acid (L3/L4) and (R)/(S)-2-(3-(furan-2-carbonyl)thioureido)-3-phenylpropanoic acid (L5/L6). Chiral Ru(ii) complexes (1-6) were obtained from the reactions between the chiral ligands (L1-L6) and [RuCl2(p-cymene)2]2 through in situ catalytic esterification of the ligand in the presence of methanol solvent. The ligands and complexes were characterized by analytical and spectral (1H NMR, 13C NMR, Mass, FT-IR, electronic) techniques. The molecular structure of the ligand L1 showed the presence of an unprotected acid group and that of the representative complexes confirmed the conversion of acid to ester. The X-ray structure of two of the complexes (3 and 6) revealed the sulfur only monodentate coordination of the aroylthiourea ligands. All the chiral complexes turned out to be efficient catalysts for the enantioselective reduction of aromatic pro-chiral ketones in the presence of 2-propanol and NaOH to produce chiral alcohols in excellent conversions (up to 99%) and enantiomeric excesses (up to 99%) within 10-12 h.
- Sheeba, Mani Mary,Tamizh, Manoharan Muthu,Babu, Sundaram Ganesh,Bhuvanesh, Nattamai S. P.,Karvembu, Ramasamy
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p. 68494 - 68503
(2016/08/02)
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- Identification of acylthiourea derivatives as potent Plk1 PBD inhibitors
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Thiourea derivatives have drawn much attention for their latent capacities of biological activities. In this study, we designed acylthiourea compounds as polo-like kinase 1 (Plk1) polo-box domain (PBD) inhibitors. A series of acylthiourea derivatives without pan assay interference structure (PAINS) were synthesized. Four compounds with halogen substituents exhibited binding affinities to Plk1 PBD in low micromole range. The most potent compound (3v) showed selectivity over other subtypes of Plk PBDs and inhibited the kinase activity of full-length Plk1.
- Yun, Taikangxiang,Qin, Tan,Liu, Ying,Lai, Luhua
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p. 229 - 236
(2016/09/09)
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- Synthesis, biological evaluation and docking study of 3-aroyl-1-(4- sulfamoylphenyl)thiourea derivatives as 15-lipoxygenase inhibitors
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A series of 3-aroyl-1-(4-sulfamoylphenyl)thiourea derivatives containing sulfonamide moiety were designed and synthesized as 15-lipoxygenase (15-LOX) inhibitors. Most synthesized compounds showed potent activity against soybean 15-LOX with IC50
- Mahdavi, Mohammad,Shirazi, Maryam Shahzad,Taherkhani, Raana,Saeedi, Mina,Alipour, Eskandar,Moghadam, Farshad Homayouni,Moradi, Alireza,Nadri, Hamid,Emami, Saeed,Firoozpour, Loghman,Shafiee, Abbas,Foroumadi, Alireza
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p. 308 - 313
(2014/06/24)
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- Chiral (η6-p-cymene)ruthenium(II) complexes containing monodentate acylthiourea ligands for efficient asymmetric transfer hydrogenation of ketones
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The new chiral ligands (R)-/(S)-N-((1-phenylethyl)carbamothioyl)benzamide (L1/L2), (R)-/(S)-N-((1-phenylethyl)carbamothioyl)thiophene-2-carboxamide (L3/L4), and (R)-/(S)-N-((1-phenylethyl)carbamothioyl)furan-2-carboxamide (L5/L6) were synthesized, characterized, and used to prepare novel chiral Ru(II) complexes. The chiral Ru(II) complexes 1-6 were obtained from reactions between the chiral ligands L1-L6 and [RuCl2(p-cymene)2] 2. The complexes were characterized by analytical and spectroscopic (NMR, FT-IR, electronic) techniques. The solid-state structures of the ligands L1 and L3 and complexes 1, 4, and 6 were determined by single-crystal X-ray diffraction methods. In all of the complexes, the ligand is bound to the Ru(II) center only via the sulfur donor atom. This monodentate coordination of the acylthiourea ligands was observed for the first time with ruthenium. The Ru(II) complexes 1-6 all act as efficient catalysts for the asymmetric transfer hydrogenation of aromatic ketones in the presence of 2-propanol and KOH to produce chiral alcohols. All of the catalysts showed excellent conversions of up to 99% and enantiomeric excesses of up to 99%.
- Sheeba, Mani Mary,Muthu Tamizh, Manoharan,Farrugia, Louis J.,Endo, Akira,Karvembu, Ramasamy
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p. 540 - 550
(2014/02/14)
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- New aminobenzenesulfonamide-thiourea conjugates: Synthesis and carbonic anhydrase inhibition and docking studies
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A variety of 1-substituted-3-(3-aminosulfonylphenyl)thioureas (3a-k) and two new 1-aroyl-3-(4-aminosulfonylphenyl)thiourea derivatives (5a and 5b) were synthesized by reaction of 3-aminobenzenesulfonamide and 4- aminobenzenesulfonamide respectively with f
- Zaib, Sumera,Saeed, Aamer,Stolte, Karin,Fl?rke, Ulrich,Shahid, Mohammad,Iqbal, Jamshed
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p. 140 - 150
(2014/04/17)
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- Discovery of N-(4-sulfamoylphenyl)thioureas as Trypanosoma brucei leucyl-tRNA synthetase inhibitors
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Human African trypanosomiasis (HAT) is one of the most neglected diseases in the tropic regions, which is fatal if not treated in time. There is an urgent need for new therapeutics, especially those in new chemical classes. Leucyl-tRNA synthetase (LeuRS) has been paid much attention as a recently clinically validated antimicrobial target. Our group has previously reported T. brucei LeuRS (TbLeuRS) inhibitors, including benzoxaboroles targeting the editing site and pyrrolinones targeting the synthetic site. Here we report the discovery of N-(4-sulfamoylphenyl)thioureas as a new class of TbLeuRS inhibitors. The R1 and R2 groups, reminiscent of the leucyl and adenyl regions of aa-AMP and aa-AMS, were optimized to result in a significant 13-fold increase of inhibitory activity (compound 19, IC 50 = 13.7 μM). Aided by ligand-protein docking, the 1,3-substitution at the central phenyl ring was predicted and proved to give significantly improved activity (59, IC50 = 1.1 μM). This work provided a new scaffold for the exploration of novel inhibitors against TbLeuRS, which may become potential therapeutics for the treatment of HAT.
- Zhang, Fenglong,Du, Jin,Wang, Qing,Hu, Qinghua,Zhang, Jiong,Ding, Dazhong,Zhao, Yaxue,Yang, Fei,Wang, Enduo,Zhou, Huchen
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p. 5310 - 5324
(2013/08/23)
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- Synthesis, spectroscopic characterization, crystal structure, antimicrobial and in vitro hemolytic studies of some novel substituted thiourea derivatives
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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) A, b = 11.7766(4) A, c = 8.1059(3) A, 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) A, b = 11.3895(9) A, c = 24.121(2) A, 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.]
- Singh, Durga Prasad,Gangwar, Mayank,Kumar, Dharmendra,Nath, Gopal,Pratap, Seema
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p. 610 - 621
(2013/12/04)
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- New insight into adenosine receptors selectivity derived from a novel series of [5-substituted-4-phenyl-1,3-thiazol-2-yl] benzamides and furamides
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A series of [5-substituted-4-phenyl-1,3-thiazol-2-yl] benzamide and furamide analogues were investigated in radioligand binding studies at adenosine receptor subtypes with an aim to obtain potent and selective adenosine receptor ligands. Benzamide and furamide linked to thiazole was found to be crucial for high adenosine receptor affinity. The most potent compound indentified in this study was 5d with low nanomolar affinity for all four adenosine receptor subtypes. Compounds 5a and 5g showed moderate selectivity for A2A adenosine receptors. Molecular docking versus all four human adenosine receptors combined with membrane molecular dynamics studies were performed to rationalise the peculiar selectivity profile of 5d antagonist.
- Inamdar, Gajanan S.,Pandya, Amit N.,Thakar, Hardik M.,Sudarsanam, Vasudevan,Kachler, Sonja,Sabbadin, Davide,Moro, Stefano,Klotz, Karl-Norbert,Vasu, Kamala K.
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p. 924 - 934
(2013/07/27)
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- Novel and efficient cyclization procedure for the synthesis of 2,5-disubstituted-1,3,4-thiadiazoles without using any ring-closing reagents
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A novel method for the synthesis of 2,5-disubstituted-1,3,4-thiadiazoles via direct ring closure of 1,6-disubstituted-2,5-dithioureas in dimethylformanide without using any ring-closing reagents has been accidentally discovered. Repeated and extended experiments confirmed that this is a very simple and efficient way to synthesize these kinds of fine chemicals. A series of novel 2,5-disubstituted-1,3,4-thiadiazoles have been synthesized via this method in good yields.
- Lin, Qi,Zhang, You-Ming,Li, Man-Lin,Wei, Tai-Bao
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p. 3251 - 3260
(2012/09/10)
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- Synthesis and structural characterization of cobalt(II) and copper(II) complexes with N,N-disubstituted-N′-acylthioureas
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A new complexes of Co(II) and Cu(II) with N,N-disubstituted-N′- acylthioureas have been prepared and characterized by elemental analysis, and spectroscopic techniques. The structure of N,N-diethyl-N′-furoylthiourea and Co(II) complexes with N,N-diethyl-N′
- O'Reilly, Beatriz,Plutin, Ana M.,Perez, Hiram,Calderon, Osmar,Ramos, Raul,Martinez, Roberto,Toscano, Ruben A.,Duque, Julio,Rodriguez-Solla, Humberto,Martinez-Alvarez, Roberto,Suarez, Margarita,Martin, Nazario
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experimental part
p. 133 - 140
(2012/05/20)
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- Synthesis and antimicrobial activities of some heterocyclic systems from 2-furoyl isothiocyanate
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2-Furoyl isothiocyanate (1) is used as a building block in synthesizing different heterocyclic systems of anticipated biological activities. Thus, isothiocyanate 1 was reacted with different nucleophilic reagents to produce five- and six-membered heterocyclic systems such as 1,2,4-triazoline, thiadiazolidine, quinazoline, benzothiazole, benzoxazole, benzimidazole, thiazolidine, and imidazolidine. The structures of all the synthesized compounds were confirmed by microanalytical and spectral data. The antimicrobial activity of some of the synthesized compounds was tested. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
- Hemdan, Magdy M.
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experimental part
p. 620 - 627
(2010/06/15)
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- Design and synthesis of indole, 2,3-dihydro-indole, and 3,4-dihydro-2H-quinoline-1-carbothioic acid amide derivatives as novel HCV inhibitors
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An efficient synthetic methodology to provide indole, 2,3-dihydro-indole, and 3,4-dihydro-2H-quinoline-1-carbothioic acid amide derivatives is described. These conformationally restricted heterobicyclic scaffolds were evaluated as a novel class of HCV inhibitors. Introduction of an acyl group at the NH2 of the thiourea moiety has been found to enhance inhibitory activity. The chain length and the position of the alkyl group on the indoline aromatic ring markedly influenced anti-HCV activity. The indoline scaffold was more potent than the corresponding indole and tetrahydroquinoline scaffolds and analogue 31 displayed excellent activity (EC50 = 510 nM) against HCV without significant cytotoxicity (CC50 >50 μM).
- Kang, Iou-Jiun,Wang, Li-Wen,Hsu, Sheng-Ju,Lee, Chung-Chi,Lee, Yen-Chun,Wu, Yen-Shian,Hsu, Tsu-An,Yueh, Andrew,Chao, Yu-Sheng,Chern, Jyh-Haur
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scheme or table
p. 4134 - 4138
(2010/04/26)
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- 1-Phenacylmethyl-2-(acylaminothiocarbonylamino)pyridinium bromides as protectors of steel acid corrosion
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Inhibiting effect of 1-phenacylmethylpyridinium bromides containing acylthiourea substituents in the pyridine ring on corrosion of mild steel in sulfuric acid (3 M) was studied.
- Yurchenko,Pogrebova,Pilipenko
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p. 675 - 677
(2008/03/12)
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- Synthesis of new acyl, furoyl, and benzoylthiocarbamates as polydentate systems. Structural study of isopropyl N-(2-furoyl)thiocarbamate
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Synthesis of new acylthiocarbamates has been carried out. To establish the preferential conformation and to explain the behaviour chemically, the structure of isopropyl N-(2-furoyl)thiocarbamate 3m has been determined by single-crystal X-ray analysis. The most stable conformation E,Z′ established by X-ray analysis was corroborated by semiempirical theoretical calculations.
- Plutín, Ana M.,Suárez, Margarita,Ochoa, Estael,Machado, Teresita,Mocelo, Raúl,Concellón, José M.,Rodríguez-Solla, Humberto
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p. 5812 - 5817
(2007/10/03)
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- An efficient synthesis of polymethylene-bis-aroyl thiourea derivatives under the condition of phase-transfer catalysis
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Reaction of polymethylene diamine with aroyl chloride and ammonium thiocyanate under the condition of solid-liquid phase-transfer catalysis using polyethylene glycol-400 (PEG-400) as the catalyst yielded polymethylene-bis- aroyl thiourea derivatives 3a-q
- Zhang, You-Ming,Wei, Tai-Bao,Xian, Liang,Gao, Li-Ming
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p. 2007 - 2013
(2007/10/03)
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- Phase transfer catalyzed synthesis of arene-bis-aroyl thiourea derivatives
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Reaction of arene diamines with aroyl chloride and ammonium thiocyanate under the condition of solid-liquid phase transfer catalysis using polyethylene-glycol-600 (PEG-600) as the catalyst furnishes arene-bis-aroyl thioureas 3a-I in good to excellent yiel
- Zhang,Wei,Gao
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p. 700 - 702
(2007/10/03)
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- Preparation and immunosuppressive activity of 32-(O)-acylated and 32- (O)-thioacylated analogues of ascomycin
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A series of 32-(O)-acylated and 32-(O)-thioacylated derivatives of the antibiotic ascomycin (1) have been synthesized. These readily accessible analogues exhibit potent immunosuppressive activity in vitro, as measured by an interleukin-2 reporter gene assay and the mixed lymphocyte reaction. Such molecules are expected to have a therapeutic potential in chronic inflammatory diseases of the airways such as asthma.
- Hersperger, Rene,Schuler, Walter,Zenke, Gerhard
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p. 227 - 232
(2007/10/03)
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- Phase transfer catalyzed synthesis of 1,6- diaroyldithiohydrazodicarbonamide derivatives
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Reaction of hydrazine hydrate with aroyl chloride and ammonium thiocyanate under the condition of solid-liquid phase transfer catalysis using polyethylene glycol-600 (PEG-600) as the catalyst yielded 1,5- diaroyldithiohydrazodicarbonamides 3a - 3h in good to excellent yield.
- Zhang, Youming,Wei, Taibao,Lu, Jinren
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p. 3243 - 3248
(2007/10/03)
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- Synthesis of n-aroyl-n'-hydroxyethyl (hydroxyphenyl)thiourea derivatives under the condition of phase transfer catalysis
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Reaction of aminoethanol or aminophenol with aroyl chloride and ammonium thiocyanate under the condition of solid-liquid phase transfer catalysis using polyethylene glycol-600 (PEG-600) as the catalyst yielded N-aroyl-N'- hydroxyethyl(hydroxy phenyl)thiou
- Wei, Taibao,Zhang, Youming
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p. 2851 - 2859
(2007/10/03)
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- Phase transfer catalyzed synthesis of N-aryl-N′-(2-furoyl) thiourea derivatives
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A series of N-aryl-N′-(2-furoyl)thiourea derivatives have been prepared in good to excellent yield under the conditions of solid-liquid phase transfer catalysis using polyethylene glycol-400 (PEG-400) as the catalyst.
- Zhang, You-Ming,Wei, Tai-Bao
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p. 1088 - 1090
(2007/10/03)
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- Phase-transfer-catalysed Synthesis of 1-Aryloxyacetyl-4-(2-furoyl)thiosemicarbazide Derivatives
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Eleven new 1-aryloxyacetyl-4-(2-furoyl)thiosemicarbazides were prepared in good to excellent yield under the condition of solid-liquid phase-transfer catalysis using poly(ethylene glycol)-400 (PEG-400) as the catalyst.
- Wei, Tai-Bao,Chen, Ji-Chou,Wang, Xi-Cun,Zhang, You-Ming
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p. 138 - 139
(2007/10/03)
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- Synthesis of N-acyl-1,3-oxathiol-2-imines
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A facile synthesis of N-acyl-1,3-oxathiol-2-imines, 7, is reported.It comprises the reaction of O-alkyl acylcarbamothioates, 4, with 2-chloroketones in the presence of alcoholic sodium alkoxide.The resulting O-alkyl-S-substituted-N-acylcarbonimidothiates, 6, undergo cyclization with elimination of alcohol, spontaneously, or upon heating in boiling toluene to form 7.
- Kulka, Marshall
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p. 1557 - 1559
(2007/10/02)
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- 2,3-Bis-(3-acyl-2-thioureido)-pyridines
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New 2,3-bis(3-acyl-2-thioureido)-pyridines having anthelmintic activity are prepared by reacting a diaminopyridine with acylthiocyanates.
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