2564-05-8

Usage

Uses

Used in Chemical Synthesis:
2-Chloro-N-(3-chlorophenyl)acetamide is used as a key intermediate in the synthesis of novel substituted 2-chloroacetanalides. These compounds exhibit a wide range of chemical properties and can be further modified to create various derivatives with specific applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-chloro-N-(3-chlorophenyl)acetamide may be utilized as a building block for the development of new drugs with potential therapeutic applications. Its unique structure and reactivity can be exploited to design molecules with specific biological activities, such as antimicrobial, anti-inflammatory, or analgesic properties.
Used in Material Science:
The compound may also find applications in the field of material science, where it can be used to develop new materials with specific properties. For instance, it could be incorporated into the synthesis of polymers or other materials with tailored characteristics, such as improved mechanical strength, thermal stability, or chemical resistance.

InChI:InChI=1/C8H7Cl2NO/c9-5-8(12)11-7-3-1-2-6(10)4-7/h1-4H,5H2,(H,11,12)

Upstream product

• 108-42-9 3-chloro-aniline 
• 105-39-5 chloroacetic acid ethyl ester 
• 593-71-5 Chloroiodomethane 
• 2909-38-8 m-chlorophenyl isocyanate 
• 19103-78-7 chloroacetyl isothiocyanate 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 38367-19-0 N-(3-chloro-phenyl)-2-piperidin-1-yl-acetamide 
• 100388-40-7 N-(3-chloro-phenyl)-2-morpholin-4-yl-acetamide 
• 114794-11-5 1-[(3-chloro-phenylcarbamoyl)-methyl]-pyridinium; chloride 
• 56311-60-5 thiocyanato-acetic acid-(3-chloro-anilide) 
• 690947-13-8 2-amino-N-(3-chlorophenyl)acetamide 
• 116133-19-8 N-methyl-glycine-(3-chloro-anilide); hydrochloride 
• 60093-21-2 [3-(3-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-cyanamide 
• 128890-27-7 N-(3-Chloro-phenyl)-2-(2,2-dimethyl-4-oxo-chroman-7-yloxy)-acetamide 
• 128890-34-6 N-(3-Chloro-phenyl)-2-(2,2,5-trimethyl-4-oxo-chroman-7-yloxy)-acetamide 
• 42351-76-8 3-(m-Chlorphenyl)-hydantoin 
• 139438-02-1 N-(3-Chloro-phenyl)-2-[5-(4-{[1-(1H-indol-3-yl)-meth-(E)-ylidene]-amino}-phenyl)-4-phenyl-4H-[1,2,4]triazol-3-ylsulfanyl]-acetamide 
• 139438-13-4 N-(3-Chloro-phenyl)-2-[4-phenyl-5-(4-{[1-(2-phenyl-1H-indol-3-yl)-meth-(E)-ylidene]-amino}-phenyl)-4H-[1,2,4]triazol-3-ylsulfanyl]-acetamide 
• 20870-77-3 4-chloroindolin-2-one 
• 56341-37-8 6-chloro-2-oxindole 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation studies of novel small molecule ENPP1 inhibitors for cancer immunotherapy

Ecto-nucleotide pyrophosphatase/phosphodiesterases 1 (ENPP1 or NPP1), is an attractive therapeutic target for various diseases, primarily cancer and mineralization disorders. The ecto-enzyme is located on the cell surface and has been implicated in the control of extracellular levels of nucleotide, nucleoside and (di) phosphate. Recently, it has emerged as a critical phosphodiesterase that hydrolyzes cyclic 2′3′- cGAMP, the endogenous ligand for STING (STimulator of INterferon Genes). STING plays an important role in innate immunity by activating type I interferon in response to cytosolic 2′3′-cGAMP. ENPP1 negatively regulates the STING pathway and hence its inhibition makes it an attractive therapeutic target for cancer immunotherapy. Herein, we describe the design, optimization and biological evaluation studies of a series of novel non-nucleotidic thioguanine based small molecule inhibitors of ENPP1. The lead compound 43 has shown good in vitro potency, stability in SGF/SIF/PBS, selectivity, ADME properties and pharmacokinetic profile and finally potent anti-tumor response in vivo. These compounds are a good starting point for the development of potentially effective cancer immunotherapy agents.

Synthesis and Biological Evaluation of Dithiobisacetamides as Novel Urease Inhibitors

Thirty-eight disulfides containing N-arylacetamide were designed and synthesized in an effort to develop novel urease inhibitors. Biological evaluation revealed that some of the synthetic compounds exhibited strong inhibitory potency against both cell-free urease and urease in intact cell with low cytotoxicity to mammalian cells even at concentration up to 250 μM. Of note, 2,2′-dithiobis(N-(2-fluorophenyl)acetamide) (d7), 2,2′-dithiobis(N-(3,5-difluorophenyl)acetamide) (d24), and 2,2′-dithiobis(N-(3-fluorophenyl)acetamide) (d8) were here identified as the most active inhibitors with IC50 of 0.074, 0.44, and 0.81 μM, showing 32- to 355-fold higher potency than the positive control acetohydroxamic acid. These disulfides were confirmed to bind urease without covalent modification of the cysteine residue and to inhibit urease reversibly with a mixed inhibition mechanism. They also showed very good anti-Helicobacter pylori activities with d8 showing a comparable potency to the clinical used drug amoxicillin. The impressive in vitro biological profile indicated their immense potential as therapeutic agents to tackle H. pylori caused infections.

Discovery of a Potent Botulinum Neurotoxin A Inhibitor ZM299 with Effective Protections in Botulism Mice

Botulinum neurotoxins serotype A (BoNT/A) is the deadliest toxins known to humans and the "Category A" agent for bioterrorism. Over the past 20 years, significant efforts have been put forth to develop effective inhibitors of BoNT/A. Unfortunately, few id

Discovery of cyclic sulfonamide derivatives as potent inhibitors of SARS-CoV-2

Severe Acute Respiratory Syndrome Coronavirus-2 (SARS-CoV-2) continues to spread worldwide, with 25 million confirmed cases and 800 thousand deaths. Effective treatments to target SARS-CoV-2 are urgently needed. In the present study, we have identified a

Anti-melanogenesis and anti-tyrosinase properties of aryl-substituted acetamides of phenoxy methyl triazole conjugated with thiosemicarbazide: Design, synthesis and biological evaluations

A series of aryl phenoxy methyl triazole conjugated with thiosemicarbazides were designed, synthesized, and evaluated for their tyrosinase inhibitory activities in the presence of L-dopa and L-tyrosine as substrates. All the compounds showed tyrosinase inhibition in the sub-micromolar concentration. Among the derivatives, compound 9j bearing benzyl displayed exceptionally high potency against tyrosinase with IC50 value of 0.11 μM and 0.17 μM in the presence of L-tyrosine and L-dopa as substrates which is significantly lower than that of kojic acid as the positive control with an IC50 value of 9.28 μM for L-tyrosine and 9.30 μM for L-dopa. According to Lineweaver–Burk plot, 9j demonstrated an uncompetitive type of inhibition in the kinetic assay. Also, in vitro antioxidant activities determined by DPPH assay recorded an IC50 value of 68.43 μM for 9i. The melanin content of 9j was determined on B16F10 melanoma human cells which demonstrated a significant reduction of the melanin content. Moreover, the binding energies corresponding to the same ligand as well as computer-aided drug-likeness and pharmacokinetic studies were also carried out. Compound 9j also possessed metal chelation potential correlated to its high anti-TYR activity.

Synthesis, pharmacological evaluation, and in-silico studies of thiophene derivatives

The relevance of Retinoic acid receptor-related orphan receptors in cancer progression has sparked interest in developing multifunctional therapeutics. In the search for potentially active novel compounds with anticancer characteristics, the Gewald reaction was employed to develop different thiophene derivatives (8a–8i). Physicochemical and spectroanalytical investigations verified the molecular structures of the synthesized derivatives. Using an in vitro primary anticancer assay, NCI chose all of the synthesized molecules as prototypes and assessed their anticancer efficacy against a panel of various cancer cell lines representing nine distinct neoplasms. The compounds were found to have a wide range of anticancer activity. Following significant anticancer efficacy against all cell lines in the initial screening, compound 8e was chosen for a five-dose test. Compound 8e inhibited growth at concentrations ranging from 0.411 to 2.8 μM. The antioxidant activity of the compounds was further evaluated using the radical scavenging action of the stable DPPH free radical. In comparison to Ascorbic Acid, compounds 8e and 8i showed outstanding antioxidant activity, while the remaining compounds in the series demonstrated acceptable antioxidant activity. In a molecular docking investigation, 8e demonstrated excellent docking scores inside the binding pocket of the specified pdb-id (6q7a), complementing the results of anticancer screening. Based on our results, novel ethyl 5-acetyl-2-amino-4-methylthiophene-3-carboxylate derivatives could be useful in the development of potential anticancer treatments.

Design, synthesis, docking study and urease inhibitory activity evaluation of novel 2-((5-amino-1,3,4-thiadiazol-2-yl)thio)-N-arylacetamide derivatives

In this paper, novel 2-((5-amino-1,3,4-thiadiazol-2-yl)thio)-N-arylacetamide derivatives (7a–l) are designed, synthesized, and evaluated in vitro for their urease inhibitor activities. The compounds are synthesized efficiently in three steps in high isolated yields from amines, 2-chloroacetyl chloride, hydrazinecarbothioamide, and carbon disulfide. The molecular docking simulation were performed using AutoDock4 by docking all synthesized compound and standard inhibitors into the crystal structure of Jack bean urease. Comparison between the urease inhibitory activity of compounds 7a–l with the IC50 of (2.85–5.83 μM) and thiourea and hydroxyurea as standards inhibitors with the IC50 of (22.00 and 100.00 μM, respectively) proved the high activity of the synthesized compounds against the mentioned enzyme. Docking results were in good agreement with experimental results and indicate that synthesized compounds could interact well with the active site of the urease enzyme and among all; compound 7j shows more favorable interactions with the active site which confirm its great inhibitory activity with IC50 of 2.85 μM. Therefore, compound 7j might be a promising candidate for further evaluation.

Synthesis of novel 1,2,3-triazoles bearing 2,4 thiazolidinediones conjugates and their biological evaluation

Searching for new active molecules against M. Bovis BCG and Mycobacterium tuberculosis (MTB) H37Ra, a focused of 1,2,3-triazoles-incorporated 2,4 thiazolidinedione conjugates have been efficiently prepared via a click chemistry approach cyclocondensation of 4-amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide (4), aryl aldehyde (5a–l), and mercapto acetic acid (6) with good to promising yields. The newly synthesized compounds were tested against drug-sensitive MTB and BCG. In particular, compounds 8g, 8h, 8j and 8l are highly potent against both the strains with IC90 values in the range of 1.20–2.70 and 1.24–2.65?μg/mL, respectively. Based on the results from the antitubercular activity, SAR for the synthesized series has been developed. Most of the active compounds were non-cytotoxic against MCF-7, HCT 116 and A549 cell lines. Most active compounds were having a higher selectively index, which suggested that these compounds were highly potent.

Microwave-assisted multicomponent synthesis of benzo[f]pyrrolo[1,2-a]quinoline derivatives

We present an efficient one-pot, three component microwave-assisted synthesis of benzo[f]pyrrolo[1,2-a]quinoline derivatives starting from benzo[f]quinoline, 2-bromo-acetophenones or 2-chloro-(N-phenyl)acetamides and electron-deficient alkynes. This synthetic strategy provides a direct and easy access to a range of novel benzo[f]pyrrolo[1,2-a]quinoline derivatives. The method has the advantages of considerable shorter reaction time, reduced solvent consumption, operational simplicity and minimal impact on the environment. Nine new benzo[f]pyrrolo[1,2-a]quinoline derivatives have been synthesized with the new method and they are fully characterized.

Design, synthesis and biological evaluation of novel 5-(4-chlorophenyl)-4-phenyl-4H-1,2,4-triazole-3-thiols as an anticancer agent

Cellular tumor antigen p53 is significant for cancer prevention and its mutation is most documented genomic change in human cancers. Thus, restoration of p53 function by interruption of the p53-MDM2 interaction opens up a prospect for a nongenotoxic anticancer therapeutic strategy. A novel series of molecules comprising 1,2,4-triazole-3-thiol scaffold were successfully discovered by structure-based designing approach. In silico modules predicted that 5-(4-chlorophenyl)-4-phenyl-4H-1,2,4-triazole-3-thiol derivatives have draggability and ability to mimic critical binding residues of p53. All target compounds were assayed for their in vitro antiproliferative activity against A549, U87 and HL60 cell lines. Twelve out of sixteen compounds exhibited good in vitro inhibitory activity in micromolar range. Especially, compound 6h possessed acute antitumor activity with IC50 values 3.854, 4.151 and 17.522 μM against three tested cell lines. It represents as a promising lead for further optimization and a template for development of novel antitumor agents.