13156-95-1

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Chloro-N-phenethylacetamide is used as a key reagent in the synthesis of praziquantel, an anthelmintic drug used to treat various parasitic worm infections. It is involved in a tandem amidoalkylation and N-acyliminium ion cyclization process, which contributes to the formation of the desired active pharmaceutical ingredient.

InChI:InChI=1/C10H12ClNO/c11-8-10(13)12-7-6-9-4-2-1-3-5-9/h1-5H,6-8H2,(H,12,13)

Upstream product

• 64-04-0 phenethylamine 
• 79-04-9 chloroacetyl chloride 
• 75-36-5 acetyl chloride 

Downstream Products

• 132700-38-0 piperidino-acetic acid phenethylamide 
• 36177-79-4 1-chloromethyl-3,4-dihydro-isoquinoline 
• 102950-25-4 N-phenethyl-2-(phenethylamino)acetamide 
• 100861-56-1 2-(diethylamino)-N-phenylethylacetamide 
• 41910-57-0 2-chloro-1-(1,2,3,4-tetrahydroisoquinolin-2-yl)ethan-1-one 
• 125698-10-4 2-<(1-naphthaleneylmethyl)thio>-N-(2-phenylethyl)acetamide 
• 125698-11-5 2-<<(4-methoxyphenyl)methyl>thio>-N-(2-phenylethyl)acetamide 
• 125728-57-6 2-<<(4-chlorophenyl)methyl>thio>-N-(2-phenylethyl)acetamide 
• 503544-96-5 N-phenethyl-2-(toluene-4-sulfonyl)-acetamide 
• 596808-11-6 2-(2-bromopyridin-3-yloxy)-N-phenethylacetamide 
• 140406-27-5 (1-Methyl-1H-tetrazol-5-yl)-phenethyl-amine 
• 71108-88-8 N,N-diethyl-N'-phenethyl-ethylenediamine 
• 810672-01-6 ethyl (2S)-2-ethoxy-3-(4-{2-oxo-2-[(2-phenylethyl)amino]-ethoxy}phenyl)propanoate 

Relevant academic research and scientific papers

A practical and efficient preparation of key intermediates in the synthesis of praziquantel

Praziquantel is the first drug of choice for all worldwide people infected by schistosomiasis. Many tons of praziquantel are needed each year. In this paper, an improved process for preparation of important intermediates to manufacture the praziquantel wa

A concise and highly efficient synthesis of praziquantel as an anthelmintic drug

A concise and practical synthesis of praziquantel as anthelmintic drug is described. The key steps include a monoalkylation of ethanolamine for the preparation of 2-(2-hydroxyethylamino)-N-phenethylacetamide and a mild oxidation protocol with SO3-Py/DMSO as oxidant to transform alcohol into the corresponding aza-acetal. The telescoped synthesis is composed of five steps without purification of the intermediates, providing an overall yield of 80% with 99.8% purity after crystallization.

Synthesis, antiproliferative evaluation, and structure–activity relationships of novel triazole–isoindoline hybrids bearing 3,4,5-trimethoxyphenyl moiety

As an aspect of our ongoing research on developing novel antiproliferative agents, 31 new triazole–isoindoline hybrids bearing 3,4,5-trimethoxyphenyl moiety were synthesized and evaluated for their antiproliferative activity against four cancer cell lines (HepG2, HeLa, PC-3, and HCT116). Some compounds showed excellent potency, and compared to fluorouracil, the most promising compound 6s exhibited 5.8-, 4.3-, and 1.3- fold increase in activities against HeLa, HepG2, and PC-3 cell lines with IC50 values of 9.7, 10.7, and 16.8?μM, respectively. Moreover, structure–activity relationship studies indicated that a much shorter amide linkage and electron-withdrawing groups at phenyl ring of the acetamide fragment contribute to the antitumour activity.

One-pot palladium-catalyzed racemization of (S)-praziquanamine: A key intermediate for the anthelmintic agent (R)-praziquantel

An one-pot palladium-catalyzed procedure for racemization of (S)-praziquanamine, which is the undesired enantiomer and produced during the resolution step for preparing the anthelmintic drug (R)-praziquantel, has been developed through dehydrogenation of

Novel Rhodamine B and 2H-benzo[b][1,4]oxazin-3(4H)-one-derived Fluorescent Sensor for Low pH Value Detection

A new fluorescent probe L fusing the rhodamine B scaffold with 2H-benzo[b][1,4]oxazin-3(4H)-one moiety has been developed and applied as an acidic pH sensor. The ultraviolet (UV) and fluorescence spectra of the probe at different pH values were investigat

Synthesis and biological evaluation of 1,2,3,4-tetrahydroisoquinolines derivatives as monoamine oxidase inhibitors for treatment of Alzheimer's and Parkinson's diseases

A series of 1,2,3,4-tetrahydroisoquinolines derivatives were synthesized and evaluated their inhibition effect on monoamine oxidase (MAO). The results of pharmacological test revealed that all the five compounds had certain monoamine oxidase inhibitory ac

Design, synthesis and biological evaluation of novel 3-alkylsulfanyl-4-amino-1,2,4-triazole derivatives

Based on our previous work, a series of novel 3-alkylsulfanyl-4-amino-1,2,4-triazole derivatives were designed, synthesized and evaluated for their antiproliferative activities. The results indicated that some compounds possessed significant antiproliferative activities against four cancer cell lines, HepG2, HCT116, PC-3, and Hela. Particularly, the most promising compound 8d displayed 184-, 18-, and 17-fold improvement compared to fluorouracil in inhibiting HCT116, Hela and PC-3 cell proliferation with IC50values of 0.37, 2.94, and 31.31 μM, respectively. Most interestingly, the compound did not affect the normal human embryonic kidney cells, HEK-293. Moreover, mechanistic investigation showed that the representative compound 8d induced apoptosis and blocked cell cycle in G2/M phase in Hela cells in a dose-dependent manner. These findings suggest that compound 8d may have potential to be developed as a promising lead for the design of novel anticancer small-molecule drugs.

Novel molecular targeting anti-tumor aza-steroid derivative based on lipid toxicity and preparation and application thereof

The invention provides a novel molecular targeting anti-tumor aza-steroid derivative based on lipid toxicity and a preparation method and application thereof, and belongs to the field of chemical medicines. The derivative is a compound as shown in a formula I, or a salt thereof, or a stereoisomer thereof. The compound is low in toxicity or basically non-toxic to normal cells, has an obvious inhibition effect to tumor cell lines, particularly has good lipid toxicity selectivity to tumor cells such as liver cancer, lung cancer and the like in vivo, and has an obvious inhibition effect; meanwhile, the compound can effectively activate SREBP1 and PPAR gamma, inhibit lipid transport MTTP, cause lipid aggregation in tumor cells and cause lipid toxicity of the tumor cells. The compound can be used for treating liver cancer, lung cancer and the like in a molecular targeting manner, is low in toxicity or even non-toxic, and has a good application prospect.

Novel chromenyl-based 2-iminothiazolidin-4-one derivatives as tubulin polymerization inhibitors: Design, synthesis, biological evaluation and molecular modelling studies

Here-in, we present molecular design, chemical synthesis and evaluation of novel chromenyl-based 2-iminothiazolidin-4-one derivatives as tubulin polymerization inhibitors. The newly synthesized compounds were evaluated for their in vitro cytotoxicities against A549 (lung cancer), MDA-MB-231 and BT-471 (breast cancer), HepG2 (liver cancer) and HCT-116 (colon cancer) cell lines by MTT assay. Among the synthesized compounds, compound 12b showed excellent anticancer activity on MDA-MB-231 cell line with IC50 value of 0.95 ± 1.88 μM and was verified to be safe in normal human bronchial epithelial cells (Beas-2B). Apoptosis induced by the lead 12b was observed using morphological observations, AO/EB and DAPI staining procedures. Further, dose-dependent increase in the depolarization of mitochondrial membrane was also observed through JC-1 staining. Annexin V-FITC/PI assay confirmed that 12b induced early apoptosis. Additionally, cell cycle analysis indicated that the MDA-MB-231 cells were arrested at sub-G2/M phase and also inhibited tubulin polymerization with IC50 value of 3.54 ± 0.2 μM. Molecular docking simulations were employed to identify the important binding modes responsible for the tubulin inhibitory activity, thus supporting their effective anticancer potential.

Tetrazanbigen Derivatives as Peroxisome Proliferator-Activated Receptor Gamma (PPARγ) Partial Agonists: Design, Synthesis, Structure-Activity Relationship, and Anticancer Activities

Tetrazanbigen (TNBG) is a novel sterol isoquinoline derivative with poor water solubility and moderate inhibitory effects on human cancer cell lines via lipoapoptosis induction. Herein, we developed a series of novel TNBG analogues with improved water sol