25369-78-2

Usage

Chemical Properties

white to yellowish crystalline powder

InChI:InChI=1/C7H5ClN2S/c8-4-1-2-5-6(3-4)10-7(11)9-5/h1-3H,(H2,9,10,11)

Upstream product

• 95-83-0 4-Chloro-1,2-phenylenediamine 
• 1147550-11-5 ammonium thiocyanate 
• 89-63-4 4-Chloro-2-nitroaniline 
• 103-72-0 phenyl isothiocyanate 
• 137-26-8 Thiram 
• 67-68-5 dimethyl sulfoxide 
• 1438-16-0 3-aminorhodanine 
• 75-15-0 carbon disulfide 
• 87049-66-9 2'-amino-5'-chloroacetanilide 
• 5443-33-4 N-(5-chloro-2-nitrophenyl)acetamide 
• 1635-61-6 5-chloro-2-nitroaniline 
• 140-92-1 potassium isopropylxanthate 
• 63467-57-2 potassium ethyldithiocarbamate 
• 881-51-6 N-(4-chloro-2-nitrophenyl)-acetamide 

Downstream Products

• 7154-93-0 3-(5-chloro-1(3)H-benzimidazol-2-ylmercapto)-propionic acid 
• 6963-77-5 2-(5-chloro-1(3)H-benzimidazol-2-ylmercapto)-propionic acid 
• 40279-17-2 2-benzylsulfanyl-5-chloro-1⁽³⁾H-benzoimidazole 
• 7692-57-1 5-chloro-2-(methylthio)-1H-benzimidazole 
• 91067-30-0 5-chloro-1,3-diacetylbenzimidazoline-2-thione 
• 106550-92-9 5-Chloro-1,3-bis-{[4-((E)-styryl)-phenylamino]-methyl}-1,3-dihydro-benzoimidazole-2-thione 
• 91067-21-9 5-Chloro-1,3-bis-phenylaminomethyl-1,3-dihydro-benzoimidazole-2-thione 
• 40828-56-6 5(6)-Chlorobenzimidazole-2-sulfonic acid 

Relevant academic research and scientific papers

A new series of benzoxazole-based SIRT1 modulators for targeted therapy of non-small-cell lung cancer

In an attempt to identify potential anticancer agents for non-small-cell lung cancer (NSCLC) targeting sirtuin 1 (SIRT1), the synthesis of a new series of benzoxazoles (3a – i) was carried out through a facile and versatile synthetic route. The compounds were evaluated for their cytotoxic effects on A549 human lung adenocarcinoma and NIH/3T3 mouse embryonic fibroblast cells using the MTT assay. 2-[(5-Nitro-1H-benzimidazol-2-yl)thio]-N-(2-methylbenzoxazol-5-yl)acetamide (3e) and 2-[(5-chloro-1H-benzimidazol-2-yl)thio]-N-(2-methylbenzoxazol-5-yl)acetamide (3g) were the most potent and selective anticancer agents in this series against the A549 cell line, with IC50 values of 46.66 ± 11.54 and 55.00 ± 5.00 μM, respectively. The flow cytometry-based apoptosis detection assay was performed to determine their effects on apoptosis in A549 cells. Both compounds induced apoptosis in a dose-dependent manner. The effects of compounds 3e and 3g on SIRT1 activity were determined. On the basis of in vitro studies, it was observed that compound 3g caused a significant decrease in SIRT1 levels in a dose-dependent manner, whereas compound 3e increased the SIRT1 levels. According to molecular docking studies, the substantial alteration in the type of action could be attributed to the difference between the interactions of compounds 3e and 3g with the same residues in the active site of SIRT1 (PDB code: 4IG9). On the basis of in silico ADME (absorption, distribution, metabolism, and excretion) studies, these compounds are predicted to possess favorable ADME profiles. According to the in vitro and in silico studies, compounds 3e and 3g, small-molecule SIRT1 modulators, were identified as potential orally bioavailable anticancer agents for the targeted therapy of NSCLC.

Design, synthesis, and evaluation of different scaffold derivatives against NS2B-NS3 protease of dengue virus

The number of deaths or critical health issues is a threat in the infection caused by Dengue virus, which complicates the situation, as only symptomatic treatment is the current solution. In this regard we have targeted the dengue protease NS2B-NS3 that is responsible for the replication. The series was designed with the help of molecular modeling approach using docking protocols. The series comprised of different scaffolds viz. cinnamic acid analogs (CA1–CA11), chalcone (C1–C10) and their molecular hybrids (Lik1–Lik10), analogs of benzimidazole (BZ1-BZ5), mercaptobenzimidazole (BS1-BS4), and phenylsulfanylmethylbenzimidazole (PS1-PS4). Virtual screening of various natural phytoconstituents was employed to determine the interactions of designed analogs with the residues of catalytic triad in the active site of NS2B-NS3. We have further synthesized the selected leads. The synthesized analogs were evaluated for the cytotoxicity and NS2B-NS3 protease inhibition activity and compared with known anti-dengue natural phytoconstituent quercetin as the standard. CA2, BZ1, and BS2 were found to be more potent and efficacious than the standard quercetin as evident from the protease inhibition assay.

A new strategy for the synthesis of 2-mercaptobenzazole derivatives by green chemistry metrics

A green and efficient method has been developed for the synthesis of 2-mercaptobenzazole derivatives via the reaction of commercially available aniline derivatives with low-cost and nontoxic potassium thiocyanate in water. The reactions proceeded smoothly under catalyst- and ligand-free conditions to give the corresponding products in good to excellent yields. The versatility, low cost, and environmental friendliness, in combination with high yields and easy work-up makes the procedure noteworthy.

Synthesis, state-of-the-art NMR-binding and molecular modeling study of new benzimidazole core derivatives as Pin1 inhibitors: Targeting breast cancer

New series of benzimidazole ring core conjugated with either dithiocarbamate or thiopropyl linkers, hybridized with different secondary amines were synthesized; 5–15 and 22–31; respectively. The new compounds were characterized by different spectroscopic techniques (1H, 13C 1D & 2D NMR, ESI-MS and IR). They were screened for in vitro anticancer activity against breast cancer using MCF7 cell line. The results obtained revealed that compounds 5, 12, 15 and 25 were the most active among the synthesized series exhibiting IC50 15N-labeled Pin1 enzyme was conducted using state-of-the-art 2D NMR binding experiments. Results showed promising binding between compounds 5, 12, and 25 by chemical shift perturbation (peak shifting or peak disappearance). Molecular docking study were quite valuable to explain the binding mode of active derivatives via hydrogen bonding. Additional contact preferences and surface mapping studies stated the similarity pattern between active candidates which may pave the way for more precise anti breast cancer target optimization.

HETEROCYCLIC COMPOUNDS AND THEIR USE IN THE TREATMENT OF AMYLOID-RELATED DISEASES

A compound of Formula (I) or a pharmaceutically acceptable salt thereof is described, wherein the substituents are as defined herein. Pharmaceutical compositions comprising the same and method of using the same are also described.

N-heterocycles scaffolds as quorum sensing inhibitors. Design, synthesis, biological and docking studies

Quorum sensing is a communication system among bacteria to sense the proper time to express their virulence factors. Quorum sensing inhibition is a therapeutic strategy to block bacterial mechanisms of virulence. The aim of this study was to synthesize and evaluate new bioisosteres of N-acyl homoserine lactones as Quorum sensing inhibitors in Chromobacterium violaceum CV026 by quantifying the specific production of violacein. Five series of compounds with different heterocyclic scaffolds were synthesized in good yields: thiazoles, 16a–c, thiazolines 17a–c, benzimidazoles 18a–c, pyridines 19a–c and imidazolines 32a–c. All 15 compounds showed activity as Quorum sensing inhibitors except 16a. Compounds 16b, 17a–c, 18a, 18c, 19c and 32b exhibited activity at concentrations of 10 μM and 100 μM, highlighting the activity of benzimidazole 18a (IC50 = 36.67 μM) and 32b (IC50 = 85.03 μM). Pyridine 19c displayed the best quorum sensing inhibition activity (IC50 = 9.66 μM). Molecular docking simulations were conducted for all test compounds on the Chromobacterium violaceum CviR protein to gain insight into the process of quorum sensing inhibition. The in-silico data reveal that all 15 the compounds have higher affinity for the protein than the native AHL ligand (1). A strong correlation was found between the theoretical and experimental results.

Three-Component Synthesis of 2-Alkylthiobenzoazoles in Aqueous Media

A highly efficient three-component protocol for the synthesis of the 2-alkylthiobenzoazoles is described. Tetramethylthiuram disulfide (TMTD) cyclized with o -aminothiophenols, generating the intermediate 2-mercaptobenzothiazoles, and the successive C-S coupling with halogenated alkanes afforded a series of 2-alkyl-substituted thiobenzothiazoles smoothly in a one-pot process. This procedure could also be utilized for the preparation of 2-alkyl-substituted thiobenzoxazoles and 2-alkyl-substituted thiobenzimidazoles. Inexpensive and easily available starting materials, metal catalyst-free, broad substrate scope, and water as solvent are the features of this protocol.

A catalyst-free and additive-free method for the synthesis of benzothiazolethiones from: O -iodoanilines, DMSO and potassium sulfide

Under catalyst-free and additive-free conditions, a novel, convenient, eco-friendly method for the synthesis of benzothiazolethiones has been developed. The three-component reaction of o-iodoanilines and K2S with DMSO proceeded smoothly and the corresponding benzothiazolethiones were obtained with good isolated yields. Meanwhile, this method could be used for the synthesis of thioureas from primary diamines. Furthermore, mechanism research showed that DMSO not only functioned as a carbon source, but also as a mild oxidant in this reaction.

2-substituted thioacetamide compound, and preparation method and application thereof

The invention discloses a 2-substituted thioacetamide compound, and a preparation method and an application thereof. The structure of the 2-substituted thioacetamide compound is represented by formulaI, and R in the formula I is a C1-C3 alkoxy group, halogen or NR1R2, wherein R1 and R2 are H and a C1-C3 alkyl group independently. The compound can effectively inhibit protein-arginine methyltransferase 5, and can be used as a PRMT5 inhibitor.