5177-35-5

Usage

Uses

Used in Pharmaceutical Industry:
2-CHLORO-N-(2,5-DIMETHYLPHENYL)ACETAMIDE is used as an intermediate in the synthesis of impurities for Lidocaine (L397800), which is a local anesthetic and antiarrhythmic class IB agent. Its role in the synthesis process is crucial for the development and production of Lidocaine, a widely used medication for local anesthesia and the management of certain types of abnormal heart rhythms.
In the pharmaceutical industry, 2-CHLORO-N-(2,5-DIMETHYLPHENYL)ACETAMIDE serves as a key component in the synthesis of Lidocaine-related compounds, contributing to the development of anesthetic and antiarrhythmic medications. Its structural properties and reactivity make it a valuable intermediate for further chemical modifications and improvements in drug design.

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

Upstream product

• 95-78-3 2,5-Dimethylaniline 
• 79-11-8 chloroacetic acid 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 111589-39-0 1-[(2,5-dimethyl-phenylcarbamoyl)-methyl]-pyridinium; chloride 
• 84489-79-2 (3-Chloro-2-chloromethyl-5,8-dimethyl-quinolin-4-yl)-(2,5-dimethyl-phenyl)-amine 
• 26958-84-9 2.5-Dimethyl-α-iodo-acetanilid 
• 10533-09-2 (2,5-dimethyl-phenyl)-carbamonitrile 
• 57264-71-8 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-[N-(2,5-xylyl)carbamoylmethyl]imidazolium chloride 
• 1374400-28-8 2-{[3-(benzenesulfonyl)-7-hydroxy-5-oxo-4H,5H-thieno[3,2-b]pyridin-2-yl]sulfanyl}-N-(2,5-dimethylphenyl)acetamide 
• 857570-37-7 2-(diethylamino)-N-(2,5-dimethyl-phenyl)acetamide 
• 87165-31-9 cyano-acetic acid-(2,5-dimethyl-anilide) 
• 87169-09-3 cyanomercapto-acetic acid-(2,5-dimethyl-anilide) 

Relevant academic research and scientific papers

New Ag(I) and Pd(II) complexes derived from symmetrical and asymmetrical NHC precursors: Synthesis, Characterization, Antibacterial activity, and Theoretical calculations

New symmetric and asymmetric imidazolium salts namely 1-methyl-3-(2,5-dimethylphenyl)-acetamideimidazolium chloride (2), 1-benzyl-3-(2,5-dimethylphenyl)-acetamideimidazolium chloride (3) and 1,3-bis-(2,5-dimethylphenyl)-acetamideimidazolium chloride (4) w

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.

Design and synthesis of 2,4-dioxochroman-pyridinium-phenylacetamide derivatives as new anti-Alzheimer agents: in vitro and in silico studies

2,4-Dioxochroman-pyridinium-phenylacetamide derivatives 7a–n were synthesized and evaluated for their in vitro cholinesterase (ChE) inhibitory activities against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). Obtained results demonstrated that, among the synthesized compounds, two compounds, 7j and 7k, were more potent than the standard drug donepezil against BuChE and did not show cytotoxicity and carcinogenicity. Furthermore, through molecular modeling and molecular dynamic studies. we showed that these compounds can be located deep in the gorge cavity of BuChE and that they interacted with catalytic residues, acyl, and cholin-binding pockets of this enzyme. Support information.

Anti-proliferative activity, molecular modeling studies and interaction with calf thymus DNA of novel ciprofloxacin analogues

Abstract: In our pursuit to expand new potential anticancer leads, a series of eighteen novel 1-cyclopropyl-6-fluoro-4-oxo-7-(4-substituted piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid analogues have been synthesized, characterized and evaluated anti-proliferative activity against five human cancer cell lines such as A549 (lung cancer), Mia Paca (pancreatic cancer), HeLa (cervical cancer), MDA MB-231 (breast cancer), MCF-7 (breast cancer) and normal embryonic kidney?cell line (HEK) were carried out using MTT assay. Few of the synthesized analogues exhibited potent anticancer activity against the cancer cell lines at a lower concentration. The synthesized compounds showed the less toxic effect on normal human embryonic kidney?cell line (HEK) compared with doxorubicin. Noticeably, compound 3o exhibited potent activity against all five cancer cell lines compared with ciprofloxacin. Further study exposed that compound 3o could competently intercalate into calf thymus DNA to form 3o-DNA complex which might block DNA replication to apply anti-proliferative activity. Docking simulation studies supported by molecular interactions with DNA type II topoisomerase. These derivates can become lead structures for the development of potential anticancer drugs. Graphical Abstract: Eighteen CP analogues were synthesized and evaluated for anti-proliferative activity. The interactions with DNA topoisomerase II were supported by molecular docking studies. 3o showed promising anticancer activity than CP against MCF7 cell line and interaction with calf thymus DNA was studied by fluorescence spectroscopy.[Figure not available: see fulltext.].

Biology-Oriented Drug Synthesis (BIODS) Approach towards Synthesis of Ciprofloxacin-Dithiocarbamate Hybrids and Their Antibacterial Potential both in Vitro and in Silico

A novel series of ciprofloxacin-dithiocarbamate hybrids 7a?–?7l were designed, synthesized, and evaluated against Gram-positive and Gram-negative bacteria. A significant part of the title compounds showed considerable antibacterial activity against Gram-positive species. The most potent compound against Gram-positive bacteria was 2-chloro derivative 7h and the most potent derivative against Gram-negative bacteria was 3-chloro compound 7i. In?vitro antibacterial evaluation of compound 7h against clinically isolated bacteria methicillin-resistant Staphylococcus aureus (MRSA) and methicillin-sensitive Staphylococcus aureus (MSSA) showed that this compound acted better than ciprofloxacin against the latter bacteria. Docking study of compound 7h in the active site of S.?aureus DNA gyrase revealed that this ciprofloxacin-dithiocarbamate derivative interacted with the main components of the active site of the enzyme.

Synthesis, biological evaluation, in silico docking, and virtual ADME studies of 2-[2-Oxo-3-(arylimino)indolin-1-yl]-N-arylacetamides as potent anti-breast cancer agents

A series of ten novel isatin analogs have been synthesized and screened for their in vitro anti-breast cancer activity against MCF-7 cell line using sulforhodamine-B assay method. All the tested compounds showed highly potent activity against MCF-7 cell line with especially four compounds exhibited demonstrative antiproliferative effects on MCF-7 breast cancer cell line compared to reference adramycin (doxorubicin) and GI 50 0.02 μM. Docking the synthesized compounds into the epidermal growth factor receptor, which is highly expressed in breast cancer, was employed to explore the possible interactions of these compounds with the receptor. Structure activity relationship as well as virtual ADME studies were carried out and a connection between activities, electronic and physicochemical properties of the target compounds was determined.

Synthesis of Novel 6-Mercapto-12-phenethyl-quinazolino[3,4-a]quinazolinones

Novel 6-mercapto-12-phenethyl-quinazolino[3,4-a]quinazolinone derivatives were synthesized through a user-friendly five-step reaction starting from isatoic anhydride. All products were characterized by IR,1H-NMR,13C-NMR spectroscopy, and chemical analysis. All of them were evaluated for their in vitro cytotoxic activity against two cell lines namely MOLT-4 (human lymphoblastic leukemia) and MCF-7 (human breast adenocarcinoma).

MOLECULES HAVING CERTAIN PESTICIDAL UTILITIES, AND INTERMEDIATES, COMPOSITIONS, AND PROCESSES RELATED THERETO

This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Nematoda, Arthropoda, and/or Mollusca, processes to produce such molecules and intermediates used in such processes, compositions containing such molecules,

Design and development of novel Mycobacterium tuberculosis l-alanine dehydrogenase inhibitors

In the present study, we used crystal structure of MTB L-AlaDH protein complex with N6-methyl adenosine for structure based virtual screening of in house database to identify new small molecule inhibitors for MTB-L-AlaDH. Two molecules identified as better leads and were modified synthetically to obtain thirty novel analogues belonging to 2-iminothiazolidine-4-ones and 4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamides. Among the screened compounds four (4n, 4o, 12 and 14) emerged as potent inhibitors displaying IC50 values ranging from 0.58 ± 0.02 to 1.74 ± 0.03 μM against MTB-L-AlaDH and were non-cytotoxic at 50 μM. Some of these synthesized compounds also exhibited good activity against nutrient starved dormant MTB cells. The most potent inhibitors were found to stabilize the protein which was confirmed biophysically through differential scanning fluorimetry.

Design, synthesis and SAR exploration of tri-substituted 1,2,4-triazoles as inhibitors of the annexin A2-S100A10 protein interaction

Recent target validation studies have shown that inhibition of the protein interaction between annexin A2 and the S100A10 protein may have potential therapeutic benefits in cancer. Virtual screening identified certain 3,4,5-trisubstituted 4H-1,2,4-triazoles as moderately potent inhibitors of this interaction. A series of analogues were synthesized based on the 1,2,4-triazole scaffold and were evaluated for inhibition of the annexin A2-S100A10 protein interaction in competitive binding assays. 2-[(5-{[(4,6-Dimethylpyrimidin-2-yl)sulfanyl]methyl}-4-(furan-2-ylmethyl)-4H-1,2,4-triazol-3-yl)sulfanyl]-N-[4-(propan-2-yl)phenyl]acetamide (36) showed improved potency and was shown to disrupt the native complex between annexin A2 and S100A10.