22283-39-2Relevant articles and documents
Benzoylthioureas: Design, synthesis and antimycobacterial evaluation
Abreu, Lethícia O.,Bispo, Marcelle L. F.,Brito, Tiago O.,Gomes, Karen M.,Louren?o, Maria C. S.,Macedo, Fernando,Pereira, Patricia M. L.,Tisher, Cesar A.,Yamada-Ogatta, Sueli F.,de Fátima, ?ngelo
, p. 93 - 103 (2020/02/04)
Background: New drugs and strategies to treat tuberculosis (TB) are urgently needed. In this context, thiourea derivatives have a wide range of biological activities, including anti-TB. This fact can be illustrated with the structure of isoxyl, an old anti-TB drug, which has a thiourea as a pharmacophore group. Objective: The aim of this study is to describe the synthesis and the antimycobacterial activity of fifty-nine benzoylthioureas derivatives. Methods: Benzoylthiourea derivatives have been synthesized and evaluated for their activity against Mycobacterium tuberculosis using the MABA assay. After that, a structure-activity relationship study of this series of compounds has been performed. Results and Discussion: Nineteen compounds exhibited antimycobacterial activity between 423.1 and 9.6 μM. In general, we observed that the presence of bromine, chlorine and t-Bu group at the para-position in benzene ring plays an important role in the antitubercular activity of Series A. These substituents were fixed at this position in benzene ring and other groups such as Cl, Br, NO2 and OMe were introduced in the benzoyl ring, leading to the derivatives of Series B. In general, Series B was less cytotoxic than Series A, which indicates that the presence of a substituent at benzoyl ring contributes to an improvement in both antimycobacterial activity and toxicity profiles. Conclusion: Compound 4c could be considered a good prototype to be submitted to further structural modifications in the search for new anti-TB drugs, since it is 1.8 times more active than the first line anti-TB drug ethambutol and 0.65 times less active than isoxyl.
A convenient and efficient method for the synthesis of mono- and N,N-disubstituted thioureas
Kodomari, Mitsuo,Suzuki, Masato,Tanigawa, Keiko,Aoyama, Tadashi
, p. 5841 - 5843 (2007/10/03)
A convenient method for the synthesis of mono- and N,N-disubstituted thioureas by the debenzoylation of N-substituted- and N,N-disubstituted- N′-benzoylthioureas with hydrazine hydrate under solvent-free conditions has been developed. N-Substituted-N′-benzoylthioureas and hydrazine hydrate were mixed, and stirred at room temperature without a solvent to give the corresponding N-substituted thioureas in high yields.
N'-Substituted N-Acyl- and N-Imidoyl-thioureas: Preparation and Conversion of N',N'-Disubstituted Compounds into 2-(N,N-Disubstituted Amino)thiazol-5-yl Ketones
Brindley, Jocelyn C.,Caldwell, Jennifer M.,Meakins, G. Denis,Plackett, Simon J.,Price, Susan J.
, p. 1153 - 1158 (2007/10/02)
Known methods were developed to give convenient general procedures for preparing N-acyl-N'-mono- and -N',N'-disubstituted thioureas from acid chlorides, and related N-imidoyl thioureas from imidoyl chlorides.In the products from three acid chlorides and ammonium thiocyanate the acyl isothiocyanates did not appear to be accompained by the isomeric thiocyanates.Treatment of N-(anilino)benzylidene-N',N'-disubstituted thioures with chloroacetone in the presence of triethylamine leads to 5-acetyl-4-phenyl-2-(N,N-disubstituted amino)thiazoles.In contrast, the corresponding N-benzoyl thioureas form only small amounts of these compounds; the main products are the 5-benzoyl-4-methyl isomers, and this unexpected outcome requires a revision of the literature.It is thought that formation of the 5-benzoyl-4-methylthiazoles involves N-C(4) fission of a cyclic intermediate to give an open-chain intermediate in which nucleophilic attack can occur at either the acetyl or the benzoyl group.One of the latter intermediates was generated directly from 2-acetyl-2-bromoacetophenone and N-methyl-N-phenylthiourea, and found to give the 5-benzoyl-4-methyl- and 5-acetyl-4-phenyl-thiazoles as the major and minor products, respectively.
