2564-07-0

Basic information

• Product Name: 2-CHLORO-N-(2,3-DIMETHYL-PHENYL)-ACETAMIDE
• Synonyms: CHEMBRDG-BB 3015630;ART-CHEM-BB B015630;AKOS BBS-00004041;AKOS B015630;2-CHLORO-N-(2,3-DIMETHYL-PHENYL)-ACETAMIDE;2-chloro-N-(2,3-dimethylphenyl)acetamide(SALTDATA: FREE);2-chloro-N-(2,3-dimethylphenyl)ethanamide;NSC166431
• CAS NO: 2564-07-0
• Molecular Formula: C₁₀H₁₂ClNO
• Molecular Weight: 197.66
• Mol File: 2564-07-0.mol

Chemical Properties

• Melting Point: 135-136
• Boiling Point: 333.1 °C at 760 mmHg
• Flash Point: 155.2 °C
• Appearance: /
• Density: 1.187 g/cm³
• Vapor Pressure: 0.00014mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 12.91±0.70(Predicted)
• CAS DataBase Reference: 2-CHLORO-N-(2,3-DIMETHYL-PHENYL)-ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-N-(2,3-DIMETHYL-PHENYL)-ACETAMIDE(2564-07-0)
• EPA Substance Registry System: 2-CHLORO-N-(2,3-DIMETHYL-PHENYL)-ACETAMIDE(2564-07-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 2564-07-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-N-(2,3-dimethylphenyl)-acetamide is used as a reactant for the preparation of quinoxalinyl thioether derivatives, which exhibit antibacterial and antifungal activity. This application is significant in the development of new drugs to combat bacterial and fungal infections, potentially leading to more effective treatments and addressing the growing concern of antibiotic resistance.

InChI:InChI=1/C10H12ClNO/c1-7-4-3-5-9(8(7)2)12-10(13)6-11/h3-5H,6H2,1-2H3,(H,12,13)

Upstream product

• 95-64-7 4-amino-o-xylene 
• 79-04-9 chloroacetyl chloride 
• 87-59-2 2,3-Dimethylaniline 

Downstream Products

• 109099-67-4 N,N-dimethyl-glycine-(2,3-dimethyl-anilide) 
• 142713-08-4 2-(diethylamino)-N-(2,3-dimethyl-phenyl)acetamide 
• 108086-45-9 N-(2,3-Dimethyl-phenyl)-2-(4-oxo-4H-quinazolin-3-yl)-acetamide 
• 1446270-28-5 (S)-2-((2, 3-dimethylphenyl)amino)-2-oxoethyl(2-oxotetrahydrofuran-3-yl)carbamodithioate 
• 1304771-73-0 2-(2-methylquinoxalin-3-ylthio)-N-(2,3-dimethylphenyl)acetamide 
• 1190213-55-8 2-(4-(3,4-dichlorophenyl)-1,2,3-selenadiazol-5-ylthio)-N-(2,3-dimethylphenyl)acetamide 
• 1188890-70-1 2-(4-(2,4-dibromophenyl)-1,2,3-thiadiazol-5-ylthio)-N-(2,3-dimethylphenyl)acetamide 
• 1198271-75-8 N-(2,3-dimethylphenyl)-2-(4-(naphthalen-2-yl)-1,2,3-thiadiazol-5-ylthio)acetamide 
• 1018074-61-7 C₁₈H₁₆Cl₂FN₅OS 

Relevant articles and documents

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.

Highly Potent and Selective Butyrylcholinesterase Inhibitors for Cognitive Improvement and Neuroprotection

Butyrylcholinesterase (BChE) has been considered as a potential therapeutic target for Alzheimer's disease (AD) because of its compensation capacity to hydrolyze acetylcholine (ACh) and its close association with Aβ deposit. Here, we identified S06-1011 (hBChE IC50 = 16 nM) and S06-1031 (hBChE IC50 = 25 nM) as highly effective and selective BChE inhibitors, which were proved to be safe and long-acting. Candidate compounds exhibited neuroprotective effects and the ability to improve cognition in scopolamine- and Aβ1-42 peptide-induced cognitive deficit models. The best candidate S06-1011 increased the level of ghrelin, a substrate of BChE, which can function as improving the mental mood appetite. The weight gain of the S06-1011-treated group remarkably increased. Hence, BChE inhibition not only plays a protective role against dementia but also exerts a great effect on treating and nursing care.

Ether acetamide derivative containing alpha-carbonyl amide structure and application of ether acetamide derivative

The invention discloses application of an ether acetamide derivative containing an alpha-carbonyl amide structure in an aspect of resisting plant diseases. The structure is shown in a general formulaI. Limitation of groups such as R and R is shown as the specification. A compound shown in the general formula I has a function of preventing and treating the plant diseases, and TMV, rice bacterial blight, citrus canker, ralstonia solanacearum and other plant virus diseases can be prevented and treated.

Discovery of novel AHLs as potent antiproliferative agents

Three series of novel AHL analogs were synthesized and evaluated for their in vitro cytotoxic activity against four human cancer cell lines. The SARs investigation indicated that AHLs with a terminal phenyl group, especially those with the chalcone scaffold had remarkably enhanced cytotoxicity than those with the hydrophobic side chains. Besides, some of these compounds were much more potent than 5-Fu and natural OdDHL. Through the detailed SARs discussions, we found that compounds 10a-k and 14 with the 4-amino chalcone scaffold showed excellent inhibition against all the tested cancer cell lines and were much more potent than 5-Fu and AHLs. Such scaffold may act as a template for further lead optimization. Compound 10i with a 3, 4, 5-trimethoxy group was the most potent one against all the tested cancer cell lines. Flow cytometry analysis indicated that analog 11e induced the cellular apoptosis and cell cycle arrest of MCF-7 cells at G2/M phase in a concentration-and time-dependent manner.

Design, synthesis and antibacterial evaluation of novel AHL analogues

Two series of novel AHL analogues were designed, synthesized and evaluated for antibacterial activity under cell membrane conditions in vitro. Analogues 4a-c and 4g-m presented potent activity against Gram-positive bacteria. Especially the analogue 4l exe

Synthesis and antimicrobial activity of some new thioether derivatives of quinoxaline

2-Chloro-3-methylquinoxaline was selected as nucleus around which the molecular manipulations were carried out to get new compounds expected to possess better anti microbial activity. Various quinoxaline derivatives have been synthesized by replacing the chlorine at C-2 with a thioether linkage, which in turn attached to 2-(N-(substituted phenyl)acetamides. The synthesized compounds (5) were tested for their antimicrobial activity. Compounds 5b, 5c, 5d and 5i were found most active (comparable to the standard antibacterial Ciprofloxacin) amongst them. The structure of the compounds was confirmed on the basis of their spectral data.

Synthesis and antispasmodic activity of lidocaine derivatives endowed with reduced local anesthetic action

The present structure-activity relationship (SAR) study focused on chemical modifications of the structure of the local anesthetic lidocaine, and indicated analogues having reduced anesthetic potency, but with superior potency relative to the prototype in preventing anaphylactic or histamine-evoked ileum contraction. From the SAR analysis, 2-(diethylamino)-N-(trifluoromethyl-phenyl) and 2-(diethylamino)-N-(dimethyl-phenyl) acetamides were selected as the most promising compounds. New insights into the applicability of non-anesthetic lidocaine derivatives as templates in drug discovery for allergic syndromes are provided.

Tri-substituted triazoles as potent non-nucleoside inhibitors of the HIV-1 reverse transcriptase

A new series of 1,2,4-triazoles was synthesized and tested against several NNRTI-resistant HIV-1 isolates. Several of these compounds exhibited potent antiviral activities against efavirenz- and nevirapine-resistant viruses, containing K103N and/or Y181C mutations or Y188L mutation. Triazoles were first synthesized from commercially available substituted phenylthiosemicarbazides, then from isothiocyanates, and later by condensing the desired substituted anilines with thiosemicarbazones.

Evaluation of glycolamide esters of indomethacin as potential cyclooxygenase-2 (COX-2) inhibitors

A number of novel indomethacin glycolamide esters were synthesized and tested for their cyclooxygenase (COX-1 and COX-2) inhibition properties in vitro. Many of these compounds proved to be selective COX-2 inhibitors, and subtle structural changes in the substituents on the glycolamide ester moiety altered the inhibitory properties as well as potencies significantly. Their in vitro data were rationalized through molecular modeling studies. Few of them displayed anti-inflammatory activity in vivo. Compound 32, [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid 2-morpholin-4-yl-2-oxo ethyl ester, was identified as a promising compound in this class and its good anti-inflammatory activity was demonstrated in the in vivo model.

Acetamides and benzamides that are useful in treating sexual dysfunction

The present invention relates to the use of compounds of formula (I) for the treatment of sexual dysfunction and to compositions containing compounds of formula (I) for the treatment of sexual dysfunction.