21258-08-2

Upstream product

• 104-94-9 4-methoxy-aniline 
• 532-55-8 Benzoyl isothiocyanate 
• 333-20-0 potassium thioacyanate 
• 98-88-4 benzoyl chloride 
• 1147550-11-5 ammonium thiocyanate 
• 14002-51-8 4-biphenyl-carboxylic acid chloride 

Downstream Products

• 340034-03-9 4-methoxy-1-[4-methoxyanilino(phenylcarbonylimino)methylamino]benzene 
• 1334511-29-3 1-benzoyl-3-(4'-methoxyphenyl)-4-methyl-1,3-dihydroimidazol-2-thione 
• 7472-54-0 N-(p-methoxyphenyl)benzamide 
• 5310-26-9 N-(4-methoxyphenyl)benzothioamide 
• 101091-38-7 N¹-(4-Methoxy-phenyl)-N³-benzoyl-guanidin 

Relevant academic research and scientific papers

Synthesis, characterization, antimicrobial and cytotoxic activity of novel half-sandwich Ru(II) arene complexes with benzoylthiourea derivatives

Three new ruthenium(II)-arene complexes, [Ru(η6-p-cymene)(L1)Cl2] (C1) where L1 is N-((4 methoxyphenyl)carbamothioyl)benzamide; [Ru(η6-p-cymene)(L2)Cl2] (C2) where L2

1-Benzoyl-3-(4-methoxyphenyl)thiourea

In the title molecule, C15H14N2O2S, there is an intramolecular N-H...O hydrogen bond of 2.618 (4) A between an amide N atom and the benzoyl O atom, which completes a nearly planar six-membered ring in the central part of the molecule. The benzene rings of the benzoyl and methoxyphenyl groups make dihedral angles of 28.8(4) and 44.2 (4)°, respectively, with this plane. In the crystal, the molecules are packed in a centrosymmetric manner through weak N-H...S interactions.

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

Iodine-mediated multi-component reactions: Readily access to tetrazoles and guanidines

Environmentally benign syntheses of One-pot sequential reactions of benzoyl chloride with amines followed by the treatment of molecular I2 reagent under basic conditions provide benzoyl tetrazoles and guanidines in moderate to excellent yields. This one-pot synthesis has several advantages such as mild reaction conditions, short reaction time, convenient workup, high yields, using cheap and readily available reagent molecular Iodine. In addition, functional group tolerance has been explored.

THEORETICAL AND EXPERIMENTAL INVESTIGATION OF THIOUREA DERIVATIVES: SYNTHESIS, CRYSTAL STRUCTURE, IN-SILICO AND IN-VITRO BIOLOGICAL EVALUATION

In this study, five different thiourea derivatives were synthesized from aryl amines according to the reported method. 1-Benzoyl-3-(4-methoxyphenyl)thiourea (2) was confirmed with single crystal XRD analysis while 1-benzoyl-3-phenylthiourea (1), 1-benzoyl

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.

N, N′ N″-trisubstituted guanidines: Synthesis, characterization and evaluation of their leishmanicidal activity

Leishmaniasis is a group of diseases caused by protozoan parasites from the genus Leishmania. There are estimated 1.3 million new cases annually with a mortality of 20,000–30,000 per year, when patients are left untreated. Current chemotherapeutic drugs available present high toxicity and low efficacy, the latter mainly due to the emergence of drug-resistant parasites, which makes discovery of novel, safe, and efficacious antileishmanial drugs mandatory. The present work reports the synthesis, characterization by ESI-MS, 1H and 13C NMR, and FTIR techniques as well as in vitro and in vivo evaluation of leishmanicidal activity of guanidines derivatives presenting lower toxicity. Among ten investigated compounds, all being guanidines containing a benzoyl, a benzyl, and a substituted phenyl moiety, LQOF-G2 (IC50-ama 5.6 μM; SI = 131.8) and LQOF-G7 (IC50-ama 7.1 μM; SI = 87.1) were the most active against L. amazonensis intracellular amastigote, showing low cytotoxicity to the host cells according to their selectivity index. The most promising compound, LQOF-G2, was further evaluated in an in vivo model and was able to decrease 60% of the parasite load in foot lesions at a dose of 0.25 mg/kg/day. Moreover, this guanidine derivative demonstrated reduced hepatotoxicity compared to other leishmanicidal compounds and did not show nephrotoxicity, as determined by the analyses of biomarkers of hepatic damage and renal function, which make this compound a potential new hit for therapy against leishmaniasis.

Effect of N-1 arylation of monastrol on kinesin Eg5 inhibition in glioma cell lines

An original and focused library of two sets of dihydropyrimidin-2-thiones (DHPMs) substituted with N-1 aryl groups derived from monastrol was designed and synthesized in order to discover a more effective Eg5 ligand than the template. Based on molecular docking studies, four ligands were selected to perform pharmacological investigations against two glioma cell lines. The results led to the discovery of two original compounds, called 20h and 20e, with an anti-proliferative effects, achieving IC50 values of about half that of the IC50 of monastrol in both cell lines. As with monastrol, flow cytometry analyses showed that the 20e and 20h compounds induced cell cycle arrest in the G2/M phase, and immunocytochemistry essays revealed the formation of monopolar spindles due to Eg5 inhibition without any toxicity to Caenorhabditis elegans.

Benzoylguanidines as Anion-Responsive Systems

A series of benzoylguanidinium salts was prepared and the changes in UV/Vis spectra, triggered by the presence of anions, were investigated. All compounds undergo deprotonation with basic anions like dihydrogenphosphate and acetate in acetonitrile. The most pronounced spectral changes were obtained by deprotonation of N1-benzoyl-N3-(p-nitrophenyl) guanidinium chloride which shows the naked-eye visible color change from colorless to yellow. Measured pKa(BH+) in acetonitrile ranges from 12–16, which is comparable to the pyridinium cations. The proton transfer equilibria were also tested in acetonitrile/water mixture where all but the most acidic derivatives showed pKa(BH+) of 4–6 units which corresponds to apparent association constants of 104–106 dm3 mol?1. UV/Vis spectra of neutral and protonated forms were modelled by the TD-DFT approach using CAM-B3LYP and PBE0 functionals and compared to CC2 results. In the case of CAM-B3LYP, a parameter ω, defining amount of long-range exchange correction, was varied to achieve the best agreement with the experimental spectra. The optimized ω parameters are 0.10 a0?1 for neutral benzoylguanidines and 0.20 a0?1 for neutral nitrobenzoyl and protonated systems. The larger ω parameter in the latter is ascribed to more pronounced charge transfer character of the HOMO-LUMO transition – the one responsible for the lowest energy absorption band.

Fe3O4@SiO2 nanoparticle supported ionic liquid for green synthesis of antibacterially active 1-carbamoyl-1-phenylureas in water

In the present work, we have designed a novel, heterogeneous and recyclable magnetic Br?nsted acidic ionic liquid based on 5-phenyl-1H-tetrazole. The {Fe3O4@SiO2@CH2)35-phenyl-1H-tetrazole-SO3H/Cl} ([FSTet-SO3H]Cl) was prepared via the immobilization of 5-phenyl-1H-tetrazole-bonded sulfonic acid onto the surface of silica-coated magnetic nanoparticles using 3-chloropropyltriethoxysilane as a linker. The catalyst was characterized by XRD, TEM, FESEM, EDS, TG-DTA, and FT-IR. The ability and high activity of this catalyst were demonstrated in the synthesis of 1-carbamoyl-1-phenylureas with good to excellent yields via a new, simple and one-pot procedure in aqueous media under reflux conditions. This procedure has advantages such as high yields, short reaction times, a simple methodology and work-up process, green reaction conditions, high stability, catalytic activity, and easy preparation, separation and reusability of the catalyst. The synthesis of these compounds was confirmed by FT-IR, 1H NMR, 13C NMR and CHN. In addition, we investigated the biological properties of the 1-carbamoyl-1-phenylureas as newly synthesized compounds. The described catalyst could be easily separated from the reaction mixture by additional magnetic force and reused several times without a remarkable loss of its catalytic activity and any considerable changes in the product yield and the reaction time.