20330-46-5

Usage

Uses

Used in Organic Synthesis:
N1-[4-(TERT-BUTYL)PHENYL]-2-CHLOROACETAMIDE is used as a reagent in organic synthesis for its ability to facilitate the creation of a wide range of organic compounds. Its unique structure allows it to participate in various chemical reactions, contributing to the formation of complex molecules.
Used in Pharmaceutical Research and Development:
In the pharmaceutical industry, N1-[4-(TERT-BUTYL)PHENYL]-2-CHLOROACETAMIDE is utilized as a key intermediate in the development of new drugs and pharmaceuticals. Its structural features make it a promising candidate for the synthesis of potential therapeutic agents, particularly in the areas of medicinal chemistry where its properties can be harnessed to create novel molecules with desired pharmacological effects.
Used in Chemical Research:
N1-[4-(TERT-BUTYL)PHENYL]-2-CHLOROACETAMIDE also serves as a valuable compound in chemical research, where its properties and reactivity are studied to understand and advance the field of chemistry. Its use in research helps in exploring new reaction pathways and mechanisms, contributing to the broader knowledge base of chemical science.

InChI:InChI=1/C12H16ClNO/c1-12(2,3)9-4-6-10(7-5-9)14-11(15)8-13/h4-7H,8H2,1-3H3,(H,14,15)

Upstream product

• 769-92-6 4-tert-Butylaniline 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 307338-19-8 N-(4-tert-butylphenyl)-2-(4-nitrophenoxy)acetamide 
• 1239174-49-2 C₂₄H₂₉F₂N₅O₂ 
• 1016843-97-2 C₁₃H₂₀N₂O 
• 1412405-85-6 018TY 
• 1385049-58-0 2-(3-acetamido-6-methoxy-2-oxo-2H-chromen-7-yloxy)-N-[4-(tert-butyl)phenyl]acetamide 
• 1386999-98-9 N-[4-(tert-butyl)phenyl]-2-(6-methoxy-2-oxo-2H-chromen-7-yloxy)acetamide 
• 1365939-03-2 C₁₂H₁₆INO 
• 936632-76-7 1-deoxy-1-(6-{4-[(4-tert-butylphenylcarbamoyl)methoxy]phenylamino}-9H-purin-9-yl)-N-ethyl-2,3-O-(1-methylethylidene)-β-D-ribofuranuronamide 
• 936633-13-5 2-(4-aminophenoxy)-N-(4-tert-butylphenyl)acetamide 

Relevant academic research and scientific papers

Synthesis, biological evaluation, and structure-activity relationships of new tubulin polymerization inhibitors based on 5-amino-1,2,4-triazole scaffold

Based on our previous research, thirty new 5-amino-1H-1,2,4-triazoles possessing 3,4,5-trimethoxyphenyl moiety were synthesized, and evaluated for antiproliferative activities. Among them, compounds IIa, IIIh, and IIIm demonstrated significant antiproliferative activities against a panel of tumor cell lines, and the promising compound IIIm dose-dependently caused G2/M phase arrest in HeLa cells. Furthermore, analogue IIa exhibited the most potent tubulin polymerization inhibitory activity with an IC50 value of 9.4 μM, and molecular modeling studies revealed that IIa formed stable interactions in the colchicine-binding site of tubulin, suggesting that 5-amino-1H-1,2,4-triazole scaffold has potential for further investigation to develop novel tubulin polymerization inhibitors with anticancer activity.

Discovery and optimization of 3,4,5-trimethoxyphenyl substituted triazolylthioacetamides as potent tubulin polymerization inhibitors

Based on our previous research, three series of new triazolylthioacetamides possessing 3,4,5-trimethoxyphenyl moiety were synthesized, and evaluated for antiproliferative activities and inhibition of tubulin polymerization. The most promising compounds 8b and 8j demonstrated more significant antiproliferative activities against MCF-7, HeLa, and HT-29 cell lines than our lead compound 6. Moreover, analogues 8f, 8j, and 8o manifested more potent antiproliferative activities against HeLa cell line with IC50 values of 0.04, 0.05 and 0.16 μM, respectively, representing 100-, 82-, and 25-fold improvements of the activity compared to compound 6. Furthermore, the representative compound, 8j, was found to induce significant cell cycle arrest at the G2/M phase in HeLa cell lines via a concentration-dependent manner. Meanwhile, compound 8b exhibited the most potent tubulin polymerization inhibitory activity with an IC50 value of 5.9 μM, which was almost as active as that of CA-4 (IC50 = 4.2 μM). Additionally, molecular docking analysis suggested that 8b formed stable interactions in the colchicine-binding site of tubulin.

Narrow SAR in odorant sensing Orco receptor agonists

The systematic exploration of a series of triazole-based agonists of the cation channel insect odorant receptor is reported. The structure-activity relationships of independent sections of the molecules are examined. Very small changes to the compound structure were found to exert a large impact on compound activity. Optimal substitutions were combined using a 'mix-and-match' strategy to produce best-in-class compounds that are capable of potently agonizing odorant receptor activity and may form the basis for the identification of a new mode of insect behavior modification.

Narrow SAR in odorant sensing Orco receptor agonists

The systematic exploration of a series of triazole-based agonists of the cation channel insect odorant receptor is reported. The structure-activity relationships of independent sections of the molecules are examined. Very small changes to the compound structure were found to exert a large impact on compound activity. Optimal substitutions were combined using a 'mix-and-match' strategy to produce best-in-class compounds that are capable of potently agonizing odorant receptor activity and may form the basis for the identification of a new mode of insect behavior modification.

Synthesis and in vitro antitumor activity of novel scopoletin derivatives

Twenty scopoletin derivatives were developed by a systematic combinatorial chemical approach and their chemical structures were confirmed by MS, IR, 1H NMR spectra and elemental analysis. Primary screening against mammary (MCF-7 and MDA-MB 231) and colon (HT-29) carcinoma cells indicated that five compounds (8d, 8g, 8j, 11b and 11g) displayed high antitumor potencies with IC50 values below 20 μM whereas scopoletin showed IC50 values above 100 μM. Moreover, the most promising compound 11g was more active than 5-fluorouracil. These results clearly indicated that the modification of the scopoletin structure could greatly increase its antitumor activity in vitro.

Structure-Based Design, Synthesis, and Antifungal Activity of New Triazole Derivatives

A series of new antifungal triazole derivatives with phenylacetamide side chain were rational designed and synthesized on the basis of the structural information of lanosterol 14-demethylase (CYP51). In vitro antifungal activity assay indicated that several compounds showed higher activity than fluconazole. Especially, compound 8h showed excellent inhibitory activity against Candida albicans and Cryptococcus neoformans (MIC=0.0156μg/mL), suggesting that it is a promising lead for the development of novel antifungal agents. The binding mode of compound 8h was investigated by flexible molecular docking. It interacted with CACYP51 through hydrophobic and van der Waals interactions. A series of phenylacetamide-containing new azoles with good in vitro antifungal activity were rationally designed and synthesized.

Synthesis, antiproliferative activity evaluation and structure-activity relationships of novel aromatic urea and amide analogues of N-phenyl-N′- (2-chloroethyl)ureas

Seven subsets of aromatic urea and amide analogues of N-phenyl-N′-(2- chloroethyl)ureas (CEU) have been synthesized by nucleophilic addition of 3-chloropropylisocyanate, 2-chloroacetylisocyanate, ethylisocyanate, 2-chloroacetyl chloride, 3-chloropropanoyl

N6-[(Hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro)-5′-N-ethylcarboxamido-adenosines: The first example of adenosine-related structures with potent agonist activity at the human A2B adenosine receptor

A new series of N6-[(hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro)-5′-N-ethylcarboxamido-adenosines (24-43) has been synthesised and tested in binding assays at hA1, hA2A and hA3 adenosine receptors, and in a functional assay at the hA2B subtype. The examined compounds displayed high potency in activating A2B receptors with good selectivity versus A2A subtypes. The introduction of an unsubstituted 4-[(phenylcarbamoyl)-methoxy]-phenyl chain at the N6 position of 5′-N-ethylcarboxamido-adenosine led us to the recognition of compound 24 as a full agonist displaying the highest efficacy of the series (EC50 hA2B = 7.3 nM). These compounds represent the first report about adenosine-related structures capable of activating hA2B subtype in the low nanomolar range.