4921-86-2

Usage

Uses

Used in Pharmaceutical Research:
1-BENZOYL-3-(2-PYRIDYL)-2-THIOUREA is used as a research compound for its potential anti-inflammatory and anti-tumor properties. Its ability to modulate inflammatory responses and inhibit tumor growth makes it a valuable tool in the development of new therapeutic agents.
Used in Neurodegenerative Disease Treatment:
1-BENZOYL-3-(2-PYRIDYL)-2-THIOUREA is used as a potential therapeutic agent for treating neurodegenerative diseases. Its neuroprotective properties and ability to target specific pathways involved in neurodegeneration make it a promising candidate for further research and development.
Used as a Chelating Agent for Heavy Metal Ions:
1-BENZOYL-3-(2-PYRIDYL)-2-THIOUREA is used as a chelating agent for heavy metal ions. Its ability to bind and remove toxic heavy metals from the body makes it a valuable compound in environmental and medical applications, such as detoxification therapies.

InChI:InChI=1/C13H11N3OS/c17-12(10-6-2-1-3-7-10)16-13(18)15-11-8-4-5-9-14-11/h1-9H,(H2,14,15,16,17,18)

Upstream product

• 504-29-0 2-aminopyridine 
• 532-55-8 Benzoyl isothiocyanate 
• 1147550-11-5 ammonium thiocyanate 
• 98-88-4 benzoyl chloride 
• 333-20-0 potassium thioacyanate 

Downstream Products

• 36273-99-1 2-benzoylamino-[1,2,4]thiadiazolo[2,3-a]pyridinylium; chloride 
• 439579-07-4 3-[2-(pyridin-2-ylamino)-thiazol-5-ylsulfanyl]-benzoic acid 
• 125859-79-2 N-benzoyl-N'-(pyrid-2-yl)-thiocarbamide cobalt(II) complex 
• 125859-75-8 N-benzoyl-N'-(pyrid-2-yl)-thiocarbamide copper(II) complex 
• 125859-76-9 N-benzoyl-N'-(pyrid-2-yl)-thiocarbamide copper(II) complex 
• 125891-10-3 N-benzoyl-N'-(pyrid-2-yl)-thiocarbamide cobalt(II) complex 
• 125859-80-5 N-benzoyl-N'-(pyrid-2-yl)-thiocarbamide cobalt(II) complex 
• 125859-83-8 N-benzoyl-N'-(pyrid-2-yl)-thiocarbamide cobalt(II) complex 
• 125859-78-1 N-benzoyl-N'-(pyrid-2-yl)-thiocarbamide cobalt(II) complex 
• 125859-74-7 N-benzoyl-N'-(pyrid-2-yl)-thiocarbamide copper(II) complex 
• 125859-82-7 N-benzoyl-N'-(pyrid-2-yl)-thiocarbamide cobalt(II) complex 
• 125859-77-0 N-benzoyl-N'-(pyrid-2-yl)-thiocarbamide cobalt(II) complex 
• 125859-73-6 N-benzoyl-N'-(pyrid-2-yl)-thiocarbamide copper(II) complex 
• 125859-81-6 N-benzoyl-N'-(pyrid-2-yl)-thiocarbamide cobalt(II) complex 

Relevant academic research and scientific papers

A chemosensor for micro- to nano-molar detection of Ag+ and Hg2+ ions in pure aqueous media and its applications in cell imaging

The pyridine substituted thiourea derivative PTB-1 was synthesized and characterized by spectroscopic techniques as well as by single crystal X-ray crystallography. The metal ion sensing ability of PTB-1 was explored by various experimental (naked-eye, UV

SO2F2-Mediated N-Alkylation of Imino-Thiazolidinones

The N-alkylation of ambident and weakly nucleophilic imino-thiazolidinones has been developed via substitution with alkyl fluorosulfonates. These reactive electrophiles are obtained through the transformation of nontoxic, economic, and commercially availa

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.

COMPOUNDS AND METHODS FOR MODULATING INTERLEUKIN-2-INDUCIBLE T-CELL KINASE

Provided herein, inter alia, are methods and compounds for modulating Interleukin-2-inducible T-cell kinase.

Synthesis and antitumor evaluation of 5-(benzo[: D] [1,3]dioxol-5-ylmethyl)-4-(tert -butyl)- N -arylthiazol-2-amines

A series of novel N-aryl-5-(benzo[d][1,3]dioxol-5-ylmethyl)-4-(tert-butyl)thiazol-2-amines (C1-C31) were synthesized and evaluated for their antitumor activities against HeLa, A549 and MCF-7 cell lines. Some tested compounds showed potent growth inhibition properties with IC50 values generally below 5 μM against the three human cancer cells lines. Compound C27 showed potent activities against HeLa and A549 cell lines with IC50 values of 2.07 ± 0.88 μM and 3.52 ± 0.49 μM, respectively. Compound C7 (IC50 = 2.06 ± 0.09 μM) was the most active compound against A549 cell line, while compound C16 (IC50 = 2.55 ± 0.34 μM) showed the best inhibitory activity against the MCF-7 cell line. The preliminary mechanism of the inhibitory effect was investigated via further experiments, such as morphological analysis by dual AO/EB staining and Hoechst 33342 staining, and cell apoptosis and cycle assessment by FACS analysis. The results illustrated that compound C27 could induce apoptosis and cause both S-phase and G2/M-phase arrests in HeLa cell line. Therefore, compound C27 could be developed as a potential antitumor agent.

Synthesis, Spectroscopic and Molecular Studies of Half-Sandwich η6-Arene Ruthenium, Cp Rhodium and Cp Iridium Metal Complexes with Bidentate Ligands

The bidentate ligand benzoyl(2-pyridyl)thiourea (L1) was prepared by reaction of benzoyl isothiocyanate with primary amine (2-aminopyridine) but the reaction with secondary amine bis(2-pyridyl)amine, yielded the unexpected product bis(2-pyridyl)benzoylami

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.

Synthesis, crystal structure, and cytotoxic activity of novel cyclic systems in [1,2,4]thiadiazolo[2,3-a]pyridine benzamide derivatives and their copper(ii) complexes

Three N-(pyridine-2-ylcarbamothioyl)benzamide derivatives were synthesized by the reaction of potassium thiocyanate, benzoyl chloride, and 2-amino pyridine derivatives in one pot. The obtained derivatives were oxidized using copper(ii) chloride. During the oxidation, two hydrogen atoms were removed, cyclization of the derivatives occurred, and finally, three new N-(2H-[1,2,4]thiadiazolo[2,3- a]pyridine-2-ylidene)benzamide derivatives were produced. Coordination of these three new derivative ligands to the copper(ii) ion resulted in the formation of three new complexes: dichlorobis(N-(2H-[1,2,4]thiadiazolo[2,3-a]pyridine-2- ylidene)benzamide)copper(ii), dichlorobis(N-(7-methyl-2H-[1,2,4]thiadiazolo[2,3- a]pyridine-2ylidene)benzamide)copper(ii), and dichlorobis(N-(5-methyl-2H-[1,2,4] thiadiazolo[2,3-a]pyridine-2-ylidene)benzamide)copper(ii). All the synthesized products were characterized by IR, 1H NMR, and 13C NMR spectroscopies. Crystal structures of the obtained N-(pyridine-2- ylcarbamothioyl)benzamide derivatives, N-(2H-[1,2,4]thiadiazolo[2,3-a]pyridine- 2-ylidene)benzamide derivatives, and complexes were determined using X-ray single-crystal diffraction; the positions of atoms, bond lengths, bond angles, and dihedral angles were also determined. In all complexes, the coordination of two large monodentate ligands and two chloride anions to the copper(ii) ion resulted in the formation of a stable planar geometry around the central ion. Three N-(pyridine-2-ylcarbamothioyl)benzamide derivatives, three N-(2H-[1,2,4]thiadiazolo[2,3-a]pyridine-2-ylidene)benzamide derivatives, and three complexes were evaluated for their cytotoxicity against five human cancer cell lines (breast cancer cell line MDA-MB-231, neuroblastoma cell line SK-N-MC, prostate adenocarcinoma cell line LNCap, nasopharyngeal epidermoid carcinoma cell line KB, and liver cancer cell line HEPG-2) using an in vitro analysis. The N-(pyridine-2-ylcarbamothioyl)benzamide derivatives showed no cytotoxic activity, whereas the N-(2H-[1,2,4]thiadiazolo[2,3-a]pyridine-2-ylidene) benzamide derivatives and their complexes showed significant cytotoxicity, especially against MDA-MB-231 and LNCap cell lines. The complexes demonstrated smaller IC50 values than N-(2H-[1,2,4]thiadiazolo[2,3-a]pyridine-2- ylidene)benzamide derivatives. This journal is the Partner Organisations 2014.

Structure-activity relationships of 2-aminothiazoles effective against Mycobacterium tuberculosis

A series of 2-aminothiazoles was synthesized based on a HTS scaffold from a whole-cell screen against Mycobacterium tuberculosis (Mtb). The SAR shows the central thiazole moiety and the 2-pyridyl moiety at C-4 of the thiazole are intolerant to modification. However, the N-2 position of the aminothiazole exhibits high flexibility and we successfully improved the antitubercular activity of the initial hit by more than 128-fold through introduction of substituted benzoyl groups at this position. N-(3-Chlorobenzoyl)-4-(2-pyridinyl) -1,3-thiazol-2-amine (55) emerged as one of the most promising analogues with a MIC of 0.024 μM or 0.008 μg/mL in 7H9 media and therapeutic index of nearly ～300. However, 55 is rapidly metabolized by human liver microsomes (t1/2 = 28 min) with metabolism occurring at the invariant aminothiazole moiety and Mtb develops spontaneous low-level resistance with a frequency of ～10-5.

Design, synthesis, and evaluation of unsymmetrical difluoro-boron complexes with imidazoline as potential fungicides

A series of unsymmetrical difluoroboron (BF2) complexes with pyridine and imidazoline were synthesized by reaction of new chelating ligands (arylmethyl-imidazolidinylidene)-pyridin-2-yl-amine with boron trifluoride diethyl etherate. All the ligands and BF2 complexes were structurally characterized by IR, HRMS, 1H, 13C, 11B, and 19F NMR,indicating the bidentate complexation of imidazoline nitrogen and the pyridine nitrogen to the boron center. Evaluation of agricultural bioactivities showed that some of the BF2 complexes exhibited moderate fungicidal activities, and most of the BF2 complexes exhibited higher activities than the none-BF2 complexed substrates.