66090-36-6

Usage

Uses

Used in Organic Synthesis:
3-Chlorobenzoyl isothiocyanate is used as a reagent in organic synthesis for its ability to form thioamide derivatives with amines and amino acids, which are essential in creating a variety of bioactive molecules.
Used in Biochemical and Pharmaceutical Research:
In the realm of biochemical and pharmaceutical research, 3-Chlorobenzoyl isothiocyanate is utilized as a reagent to explore its interactions with biological molecules and its potential in developing new therapeutic agents.
Used in Pesticide Development:
3-Chlorobenzoyl isothiocyanate is used as an active ingredient in the development of pesticides due to its potent insecticidal properties, making it a crucial component in controlling insect pests.
Used in Herbicide Formulation:
3-CHLOROBENZOYL ISOTHIOCYANATE is also used in the formulation of herbicides, leveraging its strong fungicidal properties to manage and eliminate unwanted fungal growth in agricultural settings.
Used in Medicinal Chemistry:
3-Chlorobenzoyl isothiocyanate is applied in medicinal chemistry for its potential role in the discovery and synthesis of new pharmaceuticals, particularly those involving thioamide-based drug candidates.
Used in Agrochemical Development:
In agrochemical development, 3-CHLOROBENZOYL ISOTHIOCYANATE is used to enhance crop protection products, contributing to the creation of effective insecticides and fungicides that safeguard crops from various threats.

InChI:InChI=1/C8H4ClNOS/c9-7-3-1-2-6(4-7)8(11)10-5-12/h1-4H

Upstream product

• 535-80-8 3-chlorobenzoate 
• 333-20-0 potassium thioacyanate 
• 540-72-7 sodium thiocyanide 
• 618-46-2 m-Chlorobenzoyl chloride 
• 1147550-11-5 ammonium thiocyanate 
• 345647-21-4 C₁₃H₁₉ClO₂Si 

Downstream Products

• 958449-46-2 C₂₂H₁₈Cl₂N₈O₄S₅ 
• 56437-96-8 1-(m-chlorobenzoyl)-3-phenylthiourea 
• 1278585-96-8 4β-[3-(3-chlorobenzoyl)thioureido]-4'-O-demethyl-4-desoxypodophyllotoxin 
• 1251950-07-8 C₂₀H₁₅ClN₄O₂S₂ 
• 1606167-37-6 1-(3-chlorobenzoyl)-3-(3-aminosulfonylphenyl)thiourea 
• 347325-84-2 1-(3-chlorobenzoyl)-3-(4-methylphenyl)thiourea 
• 945136-44-7 1-(3-chlorobenzoyl)-3-(3-bromophenyl)thiourea 
• 347325-21-7 1-(3-chlorobenzoyl)-3-(2-nitrophenyl)thiourea 
• 347326-49-2 1-(3-chlorobenzoyl)-3-(2-methoxyphenyl)thiourea 
• 378217-48-2 1-(3-chlorobenzoyl)-3-(3-methoxyphenyl)thiourea 
• 347326-26-5 1-(3-chlorobenzoyl)-3-(2-trifluoromethylphenyl)thiourea 

Relevant academic research and scientific papers

Staphylococcus aureus rnpa inhibitors: Computational-guided design, synthesis and initial biological evaluation

Antibiotic resistance is spreading worldwide and it has become one of the most important issues in modern medicine. In this context, the bacterial RNA degradation and processing machinery are essential processes for bacterial viability that may be exploited for antimicrobial therapy. In Staphylococcus aureus, RnpA has been hypothesized to be one of the main players in these mech-anisms. S. aureus RnpA is able to modulate mRNA degradation and complex with a ribozyme (rnpB), facilitating ptRNA maturation. Corresponding small molecule screening campaigns have recently identified a few classes of RnpA inhibitors, and their structure activity relationship (SAR) has only been partially explored. Accordingly, in the present work, using computational modeling of S. aureus RnpA we identified putative crucial interactions of known RnpA inhibitors, and we used this information to design, synthesize, and biologically assess new potential RnpA inhibitors. The present results may be beneficial for the overall knowledge about RnpA inhibitors belonging to both RNPA2000-like thiosemicarbazides and JC-like piperidine carboxamides molecular classes. We evaluated the importance of the different key moieties, such as the dichlorophenyl and the piperidine of JC2, and the semithiocarbazide, the furan, and the i-propylphenyl ring of RNPA2000. Our efforts could provide a foundation for further computational-guided investigations.

Mononuclear copper(i) complexes of triphenylphosphine and: N, N ′-disubstituted thioureas as potential DNA binding chemotherapeutics

In this work, nine new mixed-ligand complexes with the general formula [CuBr(TPP)2Tu1-9] were synthesized. The copper(i) complexes of triphenylphosphine (TPP) and different N,N′-disubstituted thioureas (Tu) were characterized via spectroscopic techniques including Fourier transform infrared spectroscopy (FTIR), nuclear magnetic resonance spectroscopy (1H, 13C, and 31P NMR), and single-crystal X-ray diffraction (SC-XRD). The complexes were synthesized via the direct reaction of bromo(tris(triphenylphosphine)copper(i)) [BrCu(PPh3)3] precursor and thiourea ligand solution under ambient conditions. Complexes 1, 2 and 3 crystallized in a triclinic system with the P1 space group. Each complex is mononuclear, and the copper atom is tetrahedrally attached to two TPP groups through the phosphorous atom, one thiourea molecule through the sulfur atom and one bromine atom. The synthesized compounds were docked with a DNA macromolecule to predict their binding site and it was found that all molecules showed favorable binding to the DNA minor grooves. The DNA interaction studies of the representative complexes demonstrated their efficient DNA binding affinities. Based on the docking and DNA interaction results, complex 7 was found to be the best binder with a docking affinity of 382.2 kJ mol-1 and binding constant of 3.96 × 104 M-1. This compound tends to interact with the minor groove through the bromine atom positioning the side triphenylphosphine rings along the X-axis of the groove while keeping the 1-(2-chlorobenzyl)-3-(3-(trifluoromethyl)phenyl)thiourea ring on the outside.

Synthesis of Novel Tris-1,2,4-triazole Derivatives and Their Antibacterial Activity

Abstract: A series of novel 3,3′,3″-[1,3,5-triazine-2,4,6-triyltris(azanediyl)]tris(5-aryl-1H-1,2,4-triazole-1-carbothioamide) derivatives were designed and synthesized through reaction of new tris-thiourea derivatives with thiosemicarbazide and sodium hy

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.

Synthesis, characterization and biological activity of some dithiourea derivatives

Novel dithiourea derivatives have been designed as HIV-1 protease inhibitors using Autodock 4.2, synthesized and characterized by spectroscopic methods and microanalysis. 1-(3-Bromobenzoyl)-3-[2-({[(3-bromophenyl)formami-do]methanethioyl}amino)phenyl]thio

Synthesis and computational study of new meta- and para-substituted ferrocenyl thioureas as potent protein kinase inhibitors and cytotoxic agents

The present study describes the synthesis, characterization, DNA binding and in vitro biological evaluation of ferrocene-enhanced thioureas. The new complexes (N1–N6) were prepared by reacting ferrocenyl anilines (A-B) with freshly prepared isothiocyanates in dry acetone. A crystallographic study of N3 revealed a supramolecular structure involving secondary non-covalent interactions (π?H and π?π). The nature and extent of the binding of these complexes with the salmon sperm DNA (SS-DNA) were examined by cyclic voltammetry and UV–Vis spectroscopy. The complexes have strong binding to DNA with binding constants ranging from 9.83 × 103 to 5.76 × 104 M?1. The shifts in the cathodic peak potentials with the addition of DNA in the electrochemical studies of the new complexes are attributed to electrostatic interactions. This observation is an indicator of the oxidizable behavior of the complexes in the presence of DNA. The theoretically calculated energies of the frontier molecular orbitals (EHOMO and ELUMO) and the Mulliken charge distributions for the optimized structures determined by the DFT/B3LYP method correlate well with the electrochemically determined redox potentials (correlation coefficient, 0.986). The computational measurements also led to a close agreement between the calculated and observed vibrational frequencies. The new complexes proved to be good candidates for protein kinase inhibition and cytotoxicity studies.

Synthesis, carbonic anhydrase inhibitory activity and antioxidant activity of some 1,3-oxazine derivatives

(Table presented.). A series of 1-(6-methyl-2-substituted phenyl-4-thioxo-4H-1,3-oxazin-5-yl)ethanones (3a-n) were synthesized by the reaction of benzoyl isothiocyanates with active methylene compound acetylacetone in the presence of triethyl amine in a one-pot process. The structures of the products were elucidated by elemental analyses, FT-IR, 1H NMR, 13C NMR, and mass spectroscopy. These new 1,3-oxazine derivatives were evaluated for their inhibitory activity against carbonic anhydrase II. Results for in vitro assay revealed that compound 3b having 4-methoxy phenyl moiety was the most potent inhibitor with IC50 value of 0.144 ± 0.008 μM. It exhibited higher enzyme inhibitory activity as compared to the standard acetazolamide (IC50 = 0.997 ± 0.061 μM). The compounds 3c, 3h, and 3n also displayed superior inhibitory activities compared to the rest of the synthesized oxazine derivatives. The radical scavenging activity of oxazine derivatives was also performed and it was found that compounds showed moderate antioxidant activity. Lipinski rule confirmed the therapeutic potential of the synthesized compounds. Molecular docking studies were also performed to further understand the binding affinity of these compounds with PDBID 1V9E which confirmed that the synthesized derivatives bind in the active binding site of the target protein. Based upon our results, it is proposed that compound 3b may serve as a lead structure to design more potent carbonic anhydrase inhibitors.

Biologically active: Halo -substituted ferrocenyl thioureas: Synthesis, spectroscopic characterization, and DFT calculations

In our search for new therapeutic agents, ferrocene-based thioureas (M1-M9) were successively synthesized and characterized by various analytical techniques like FT-IR, Raman, CHNS, AAS, and multinuclear (1H and 13C) NMR. The interac

Synthesis and antitumor activity of novel N-benzoyl-N'-substituted pyrimidinyl (thio)semicarbazide derivatives

A series of substituted pyrimidinyl (thio)semicarbazide derivatives were designed and synthesized. The antitumor results showed that the activity of thiosemicarbazide compounds (series II) was generally higher than that of the corresponding semicarbazide derivatives (series I). Among them, IIk displayed higher cytotoxicity against HL-60, BGC-823 and Bel-7402 than that of adriamycin and exhibited broad in vitro cytotoxicity against 13 human tumor cell lines. Meanwhile, the cytotoxic selectivity and anti-multidrug resistance were evaluated, and IIk exhibited selective cytotoxicity against cancer cells in comparison to human normal cells and had significant anti-multidrug resistance capability. The bioassay results showed that IIk showed great promise as a potent lead compound for further antitumor discovery.

Solution-phase microwave assisted parallel synthesis, biological evaluation and in silico docking studies of N,N′-disubstituted thioureas derived from 3-chlorobenzoic acid

A facile and robust microwave-assisted solution phase parallel synthesis protocol was exercised for the development of a 38-member library of N,N′-disubstituted thiourea analogues (1–38) by using an identical set of conditions. The reaction time for synthesis of N,N′-disubstituted thiourea analogues was drastically reduced from a reported duration of 8–12 h for conventional methods to only 1.5–2.0 min. All the derivatives (1–38) were characterized by physico-analytical techniques such as elemental analysis in combination with FT-IR,1H,13C NMR and by single crystal XRD analysis have also been performed. These compounds were screened for their in vitro urease inhibition activities. Majority of compounds exhibited potent urease inhibition activities, however, the most significant activity was found for 16, with an IC50value of 1.23 ± 0.1 μM. Furthermore, the synthesized compounds were screened for their cytotoxic potential against lungs cancer cell lines. Cell culture studies demonstrated significant toxicity of the compounds on the cell lines, and the levels of toxicity were altered in the presence of various side groups. The molecular docking studies of the most potent inhibitors were performed to identify the probable binding modes in the active site of the urease enzymes. These compounds have a great potential and significance for further investigations.