199107-79-4

Basic information

• Product Name: N-(4-Ethylphenyl)-4-nitrobenzaMide
• Synonyms: N-(4-Ethylphenyl)-4-nitrobenzaMide
• CAS NO: 199107-79-4
• Molecular Formula: C₁₅H₁₄N₂O₃
• Molecular Weight: 270.28326
• Mol File: 199107-79-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(4-Ethylphenyl)-4-nitrobenzaMide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-Ethylphenyl)-4-nitrobenzaMide(199107-79-4)
• EPA Substance Registry System: N-(4-Ethylphenyl)-4-nitrobenzaMide(199107-79-4)

Safety Data

• Hazardous Substances Data: 199107-79-4(Hazardous Substances Data)

Upstream product

• 143063-89-2 para-ethylphenyl isocyanide 
• 62-23-7 4-nitro-benzoic acid 
• 589-16-2 4-aminoethylbenzene 

Downstream Products

• 1257874-87-5 N-(4-ethylphenyl)-4-nitrothiobenzamide 
• 1237737-87-9 4-(6-ethylbenzothiazol-2-yl)phenylamine 
• 1237737-84-6 6-ethyl-2-(4-nitrophenyl)benzothiazole 

Relevant articles and documents

Design, synthesis and antimetastatic evaluation of 1-benzothiazolylphenylbenzotriazoles for photodynamic therapy in oral cancer cells

We have designed and synthesized a new series of 1-benzothiazolylphenylbenzotriazoles 9a-p and studied their antimetastatic mechanism involved in photosensitive effects induced by UVA in oral cancer cell Ca9-22. Our results revealed that the compounds plus UVA significantly suppressed migration and invasion, as detected by wound healing assay and Boyden chamber assay. Quantitative RT-PCR assay indicated that compound 9i plus UVA induced an antimetastatic effect through up-regulation of syndecan-1 and TIMP-3 and down-regulation of heparanase, MMP-2 and MMP-9 mRNA expressions. Western blot analysis showed that Ca9-22 treated with 9i plus UVA resulted in decreased levels of p-EGFR and p-ERK, MMP-2 and MMP-9, and an increased level of TIMP-3. These results are the first to report the function of UVA-activated 1-benzothiazolylphenylbenzotriazoles in tumor metastasis and their underlying molecular mechanism, and thus suggest that compound 9i plus PDT may serve as a potential ancillary modality for the treatment of oral cancer.

Synthesis of amides by palladium-catalyzed decarbonylative coupling of carboxylic acids with isocyanides

Amides were synthesized from carboxylic acids and isocyanides under Pd II/AgI/base catalytic conditions. The reaction conditions were optimized, and the scope was studied. Various carboxylic acids and aryl isocyanides are compatible with this reaction, but alkyl isocyanides are not. A plausible mechanism, which features distinctive PdII-mediated decarbonylative coupling and unprecedented nucleophilic attack of carboxylates to PdII-ligated isocyanides, was proposed to account for this reaction. N-Arylamides are assembled in high yields from carboxylic acids and isocyanides under PdII/AgI/base catalytic conditions. The decarbonylative coupling features unprecedented nucleophilic attack of the carboxylate on the isocyanide, which acts as an electrophile as a result of its coordination to PdII, and this inverted reactivity is proposed to account for this transformation.

Synthesis of 2-(4-aminophenyl) benzothiazole derivatives and use thereof

The present invention provides a method of preparing a compound of formula 6 comprising: (a) reacting a compound of formula 1 with a compound of formula 2 to form a compound of formula 3 wherein X of formula 2 is Cl or OH; (b) treating the compound formula 3 with Lawesson's reagent to form a compound of formula 4 (c) reacting a compound of formula 4 with potassium ferricyanide to produce a compound of formula 5 and (d) performing catalytic reduction of nitro group of the compound of formula 5 with palladium on charcoal to generate the compound of formula 6, wherein R1 of formulae 1-6 is H, C1-10 alkyl, C1-10 alkoxy or C1-10 haloalkyl, and R2 of formulae 1-6 is H or C1-10 alkyl. The present invention also provides a photodynamic therapy to a patient having at least one tumor comprising the steps of: administering a compound of formula 6 (wherein R1 and R2 are defined as the above) in a pharmaceutically acceptable carrier to the patient; waiting for a sufficient time to allow the administered compound to be taken up by a target tissue having the at least one tumor; and irradiating a region of the patient containing the target tissue; wherein growth of the tumor is inhibited.

SYNTHESIS OF 2-(4-AMINOPHENYL) BENZOTHIAZOLE DERIVATIVES AND USE THEREOF

The present invention provides a method of preparing a compound of formula 6 comprising: (a) reacting a compound of formula 1 with a compound of formula 2 to form a compound of formula 3 wherein X of formula 2 is Cl or OH; (b) treating the compound formula 3 with Lawesson's reagent to form a compound of formula 4 (c) reacting a compound of formula 4 with potassium ferricyanide to produce a compound of formula 5 and (d) performing catalytic reduction of nitro group of the compound of formula 5 with palladium on charcoal to generate the compound of formula 6, wherein R1 of formulae 1-6 is H, C1-10 alkyl, C1-10 alkoxy or C1-10 haloalkyl, and R2 of formulae 1-6 is H or C1-10 alkyl. The present invention also provides a photodynamic therapy to a patient having at least one tumor comprising the steps of: administering a compound of formula 6 (wherein R1 and R2 are defined as the above) in a pharmaceutically acceptable carrier to the patient; waiting for a sufficient time to allow the administered compound to be taken up by a target tissue having the at least one tumor; and irradiating a region of the patient containing the target tissue; wherein growth of the tumor is inhibited.