7442-11-7Relevant articles and documents
Photocatalytic synthesis of unsymmetrical thiourea derivativesviavisible-light irradiation using nitrogen-doped ZnO nanorods
Koohgard, Mehdi,Sarvestani, Abdollah Masoudi,Hosseini-Sarvari, Mona
supporting information, p. 14505 - 14512 (2020/09/21)
An efficient, mild, and environmentally friendly route has been developed for the synthesis of unsymmetrical thiourea derivatives in moderate yields by the reaction of tertiary aromatic and aliphatic amines with phenyl-iso-thiocyanate in the presence of N-ZnO as a photocatalyst under visible-light irradiation. This method provides a pathway to activate the tertiary aromatic and aliphatic aminesviaC-N bond cleavage.
Synthesis and antiplatelet activity of antithrombotic thiourea compounds: Biological and structure-activity relationship studies
Louren?o, André Luiz,Saito, Max Seidy,Dorneles, Luís Eduardo Gomes,Viana, Gil Mendes,Sathler, Plínio Cunha,De Aguiar, Lúcia Cruz Sequeira,De Pádula, Marcelo,Domingos, Thaisa Francielle Souza,Fraga, Aline Guerra Manssour,Rodrigues, Carlos Rangel,DeSousa, Valeria Pereira,Castro, Helena Carla,Cabral, Lucio Mendes
, p. 7174 - 7200 (2015/05/06)
The incidence of hematological disorders has increased steadily in Western countries despite the advances in drug development. The high expression of the multi-resistance protein 4 in patients with transitory aspirin resistance, points to the importance of finding new molecules, including those that are not affected by these proteins. In this work, we describe the synthesis and biological evaluation of a series of N,N′-disubstituted thioureas derivatives using in vitro and in silico approaches. New designed compounds inhibit the arachidonic acid pathway in human platelets. The most active thioureas (compounds 3d, 3i, 3m and 3p) displayed IC50 values ranging from 29 to 84 μM with direct influence over in vitro PGE2 and TXA2 formation. In silico evaluation of these compounds suggests that direct blockage of the tyrosyl-radical at the COX-1 active site is achieved by strong hydrophobic contacts as well as electrostatic interactions. A low toxicity profile of this series was observed through hemolytic, genotoxic and mutagenic assays. The most active thioureas were able to reduce both PGE2 and TXB2 production in human platelets, suggesting a direct inhibition of COX-1. These results reinforce their promising profile as lead antiplatelet agents for further in vivo experimental investigations.
Actinide-Mediated Catalytic Addition of E-H Bonds (E=N, P, S) to Carbodiimides, Isocyanates, and Isothiocyanates
Karmel, Isabell S.R.,Tamm, Matthias,Eisen, Moris S.
supporting information, p. 12422 - 12425 (2015/10/12)
Unprecedented catalytic reactivity of actinide coordination complexes toward heterocumulenes, such as carbodiimides, isocyanates, and isothiocyanates is reported. The mono(imidazolin-2-iminato) thorium(IV) complex [Th(ImDippN){N(SiMe3)2}3] (1) was applied as a precatalyst for the addition of E-H (E=N, P, S) bonds to the Y≡C≡X core (Y=R2N; X=NR2, O, S) of carbodiimides, isocyanates, and isothiocyanates. The respective insertion products were obtained in high yields under mild reaction conditions, with complex 1 displaying high tolerance toward functional groups and heteroatoms. New reactivity: The mono(imidazolin-2-iminato) thorium complex [Th(ImDippN){N(SiMe3)2}3] was successfully applied as an active catalyst for the addition of E-H (E=N, P, S) bonds across the central Y≡N≡C≡X linkage of carbodiimides, isocyanates and isothiocyanates, yielding the respective insertion products in high yields and under mild reaction conditions.
A highly efficient one-pot method for the synthesis of thioureas and 2-imino-4-thiazolidinones under microwave conditions
Chau, Chi-Min,Chuan, Tzu-Jung,Liu, Kuan-Miao
, p. 1276 - 1282 (2014/01/06)
A one-pot synthesis of symmetrical and unsymmetrical substituted thioureas and 2-imino-4-thiazolidinones from simple starting materials under microwave irradiation and solventless conditions without base additives is presented. Various di- and trisubstituted thioureas are obtained in good yields in a few minutes. The sequential, three-component, one-pot synthesis of 2-imino-4-thiazolidinone derivatives is also studied, with satisfactory results obtained.
Insertion of arynes into thioureas: A new amidine synthesis
Biswas, Kallolmay,Greaney, Michael F.
supporting information; experimental part, p. 4946 - 4949 (2011/11/06)
Arynes, generated from trimethylsilyl phenyltriflate precursors, have been found to react with thioureas via a formal π-insertion into the C=S bond. The reaction contrasts with that of ureas, which proceeds via benzyne σ-insertion into the C-N bond, and r
A Concise and Convenient Method for the Synthesis of Pure Substituted Thioureas
Ramadas, K.,Janarthanan, N.
, p. 1101 - 1108 (2007/10/03)
Zinc dialkyldithiocarbamates offer excellent substrates for pure thioureas required for the ntifungal and X-ray crystallographic studies.
A facile conversion of symmetrical to unsymmetrical thioureas
Ramadas,Srinivasan,Janarthanan
, p. 6447 - 6450 (2007/10/02)
A convenient route for quantitative conversion of symmetrical thioureas into unsymmetrical thioureas is described. The method circumvents the use of toxic isothiocyanates and a case study is reported using 1,3-diphenylthiourea.
Estimation of Charge Transfer Parameters of Complexes of Substituted Thioureas with Iodine
Seal, B. K.,Banerjee, B.,Mukherjee, D. C.
, p. 799 - 802 (2007/10/02)
A biquadratic equation in the variable b/a has been derived from Mulliken's theory of charge transfer(CT) complexes.The equation gives b/a values close to those obtained from the dipole moments of CT complexes.The solution of the equation makes use of the values of the frequency (νCT) of the CT band, the enthalpy (ΔH) of formation, obtained spectrophotometrically, for the complexes and assumed values for the overlap integral (S01).The energies of the no-bond and dative states, the resonance energies in the ground and excited states, the degree of CT in the ground state, the donor-acceptor distances in a series of complexes of thioureas with iodine and dipole moments of some of these complexes have been calculated from the values of a, b, a*, b*, S01, hνCT and ΔH with the help of the equations derived from Mulliken's theory by applying variational principle.The calculated values of the energy parameters correlate well with the strength of the complex as measured by the values of their equilibrium constants.The ionization potentials of the thioureas have also been determined.
Cycloaddition Reactions of Heterocumulenes, XXVI. Cycloadducts from Aryl Isothiocyanates and 2,2-Disubstituted Enamines
Schaumann, Ernst,Baeuch, Hans-Guenther,Sieveking, Stefan,Adiwidjaja, Gunadi
, p. 55 - 65 (2007/10/02)
Aryl isothiocyanates 1 react with enamines 2 to give two types of 2:1 cycloadducts.Below 50 deg C, 1a - g and 2 give rise to 6-imino-1,3-thiazine-2-thiones 5, the constitutions of which are proved by an X-ray analysis of 5c.Above 50 deg C or starting from 4-nitrophenyl isothiocyanate (1h), 2,4-dithiouracils 6 are formed. 1:1 cycloadducts of the reactants are detected spectroscopically; on workup, they hydrolyze to give 2-formylthiopropionanilides 9.
