59146-85-9

Upstream product

• 1147550-11-5 ammonium thiocyanate 
• 98-88-4 benzoyl chloride 
• 64-04-0 phenethylamine 
• 532-55-8 Benzoyl isothiocyanate 

Downstream Products

• 6815-00-5 N-(2-phenylethyl)thiourea 
• 145012-92-6 C₁₄H₂₀N₂O₂S 
• 145231-26-1 S-<2-(4(5)-imidazolyl)ethyl>-N-(2-phenylethyl)isothiourea dihydrobromide 
• 145231-32-9 S-<3-(4(5)-imidazolyl)propyl>-N-(2-phenylethyl)isothiourea dihydrobromide 

Relevant academic research and scientific papers

In vitro evaluation of antitrypanosomal activity and molecular docking of benzoylthioureas

A series of sixteen benzoylthioureas derivatives were initially evaluated in vitro against the epimastigote form of Trypanosoma cruzi. All of the tested compounds inhibited the growth of this form of the parasite, and due to the promising anti-epimastigot

Benzoylthioureas: Design, synthesis and antimycobacterial evaluation

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.

ANTIVIRAL COMPOUNDS AND USE THEREOF

The present invention relates to compounds of formula (I), their use as medicaments, in particular as broad spectrum antiviral agents, their combination with a further antiviral agent and relative pharmaceutical compositions. In particular, the compounds of the invention are useful in the treatment of a disease caused by an enveloped virus.

Novel broad spectrum virucidal molecules against enveloped viruses

Viral infections are an important cause of death worldwide. Unfortunately, there is still a lack of antiviral drugs or vaccines for a large number of viruses, and this represents a remarkable challenge particularly for emerging and re-emerging viruses. For this reason, the identification of broad spectrum antiviral compounds provides a valuable opportunity for developing efficient antiviral therapies. Here we report on a class of rhodanine and thiobarbituric derivatives displaying a broad spectrum antiviral activity against seven different enveloped viruses including an HSV-2 acyclovir resistant strain with favorable selectivity indexes. Due to their selective action on enveloped viruses and to their lipid oxidation ability, we hypothesize a mechanism on the viral envelope that affects the fluidity of the lipid bilayer, thus compromising the efficiency of virus-cell fusion and preventing viral entry.

Design, syntheses and evaluation of benzoylthioureas as urease inhibitors of agricultural interest

Urea is one of the most used nitrogen fertilizers worldwide. However, occurrence of urea hydrolysis to ammonia and carbon dioxide on soil surface, catalyzed by soil ureases, considerably reduces nitrogen availability to crops. In this study, we describe the design, synthesis and screening of sixty five benzoylthioureas (BTUs) for their ability to inhibit purified jack bean and soil ureases. BTUs were readily obtained in one pot, two steps synthesis with no need of cumbersome procedures for product purification. In vitro assays revealed BTUs 11, 12, 14, 19-22 and 37 as the most active jack bean urease inhibitors. Such BTUs were found to be able to bind to both catalytic and allosteric sites of urease, acting therefore as mixed-type inhibitors. Out of 28 compounds that effectively inhibited soil ureases activity, BTUs 3, 6, 10, 12, 16, 19 and 22 were determined to be more potent than the reference inhibitor N-(butyl) thiophosphoric triamide (NBPT; 40%). The other 22 BTUs were as potent as NBPT on soil ureases. The temperature-tolerance of BTUs, along with their ability to inhibit soil ureases, makes of this class of compounds potential additive for urea-based fertilizers.

Histone deacetylase activators: N-acetylthioureas serve as highly potent and isozyme selective activators for human histone deacetylase-8 on a fluorescent substrate

We report, for the first time, that certain N-acetylthiourea derivatives serve as highly potent and isozyme selective activators for the recombinant form of human histone deacetylase-8 in the assay system containing Fluor-de-Lys as a fluorescent substrate. The experimental data reveals that such activating feature is manifested via decrease in the Km value of the enzyme's substrate and increase in the catalytic turnover rate of the enzyme.

Structural requirement(s) of N-phenylthioureas and benzaldehyde thiosemicarbazones as inhibitors of melanogenesis in melanoma B 16 cells

In order to define the structural requirements of phenylthiourea (PTU), a series of thiourea and thiosemicarbazone analogs were prepared and evaluated as inhibitors of melanogenesis in melanoma B16 cells. The most potent analog was 2-(4-tert-butylbenzylidene)hydrazinecarbothioamide (1u) with an IC50 value of 2.7 μM in inhibition of melanogenesis. The structure for potent inhibitory activity of these derivatives are required with the direct connection of π-planar structure to thiourea without steric hinderance in PTU derivatives and the hydrophobic substituent at para position in case of semicarbazones.

Clobenpropit analogs as dual activity ligands for the histamine H3 and H4 receptors: Synthesis, pharmacological evaluation, and cross-target QSAR studies

Previous studies have demonstrated that clobenpropit (N-(4-chlorobenzyl)-S-[3-(4(5)-imidazolyl)propyl]isothiourea) binds to both the human histamine H3 receptor (H3R) and H4 receptor (H4R). In this paper, we describe the synthesis and pharmacological characterization of a series of clobenpropit analogs, which vary in the functional group adjacent to the isothiourea moiety in order to study structural requirements for H3R and H4R ligands. The compounds show moderate to high affinity for both the human H3R and H4R. Furthermore, the changes in the functional group attached to the isothiourea moiety modulate the intrinsic activity of the ligands at the H4R, ranging from neutral antagonism to full agonism. QSAR models have been generated in order to explain the H3R and H4R affinities.

Bismuth chloride mediated synthesis, antimicrobial, and anti-inflammatory activities of new 4-aryl-2-amino thiazoles

Synthesis of 4-aryl-2-Amino thiazoles (3a-u), (4a-c), and (5a-c) was achieved from the reaction of 4-butyl phenacyl chlorides (2a-c) with N-substituted thioureas, in the presence of Bismuth Chloride. The antimicrobial and anti-inflammatory activities of the final products were also studied. Copyright Taylor & Francis Group, LLC.

Isothiourea analogues of histamine as potent agonists or antagonists of the histamine H3-receptor

The synthesis and H3-activity of a series of isothiourea analogues of histamine have been described. It has been shown that S-[2-(4(5)-imidazolyl)ethylisothiourea (VUF 8325) is a potent H3-agonist measured as the electrically evoked contraction of the guinea-pig ileum. Upon methylation of the imidazole system or the isothiourea moiety a decrease in affinity was observed leading to either weak agonists or weak antagonists. Introduction of N-(phenylalkyl) substituents at the isothiourea part gives rise to highly potent H3-antagonists. Particularly the 4-chlorobenzyl group appeared to be favourable in the series described resulting in a histamine H3-antagonist with a pA2-value of 9.9.