86604-36-6

Usage

Thiophene ring with

Amino group ( \textNH2 ) at the 2-position,
Chlorophenyl group ( \textC6\textH4\textCl ) at the 4-position,
Carbonitrile group ( \textCN ) at the 3-position.

Classification

Thiophene derivative, aromatic organic compound.

Properties

Aromaticity: Possesses aromatic properties due to the presence of the thiophene ring.
Reactivity: Exhibits reactivity typical of compounds with amino, chlorophenyl, and carbonitrile groups.

Applications

Organic Synthesis: Utilized as a reagent or intermediate in organic synthesis processes.
Pharmaceutical Research: Used for investigating potential drug candidates due to its unique structure and reactivity.

Potential Applications

Medicinal Chemistry: Investigating its pharmacological properties and potential as a drug lead compound.
Material Science: Exploring its properties for applications in materials science, such as in polymers or nanomaterials.

Upstream product

• 3111-60-2 2-[1-(4-chlorophenyl)ethylidene]malononitrile 
• 99-91-2 para-chloroacetophenone 
• 109-77-3 malononitrile 

Downstream Products

• 1040392-89-9 4-amino-3-(4-chlorophenyl)-5,6,7,8-tetrahydro-thieno[2,3-b]quinoline 
• 1040392-88-8 4-amino-3-(4-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]thieno[3,2-e]pyridine 
• 1040392-91-3 4-amino-3-(4-chlorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]thieno[3,2-e]pyridine 
• 1402043-50-8 4-(4-chlorophenyl)-2-(5,5-dimethyl-3-oxocyclohex-1-enylamino)thiophene-3-carbonitrile 
• 1402043-49-5 4-(4-chlorophenyl)-2-(3-oxocyclohex-1-enylamino)thiophene-3-carbonitrile 
• 1402043-58-6 4-amino-3-(4-chlorophenyl)-7,8-dihydrothieno[2,3-b]quinolin-5(6H)-one 
• 1402043-59-7 4-amino-3-(4-chlorophenyl)-7,7-dimethyl-7,8-dihydrothieno[2,3-b]quinolin-5(6H)-one 
• 1402043-60-0 4-amino-3-(4-chlorophenyl)-7-phenyl-7,8-dihydrothieno[2,3-b]quinolin-5(6H)-one 
• 342780-86-3 5-(4-chlorophenyl)-4-(4-phenylpiperazin-1-yl)thieno[2,3-d]pyrimidine 
• 331761-46-7 4-chloro-5-(4-chlorophenyl)thieno[2,3-d]pyrimidine 

Relevant academic research and scientific papers

Synthesis, in vivo anti-inflammatory, COX-1/COX-2 and 5-LOX inhibitory activities of new 2,3,4-trisubstituted thiophene derivatives

New series of thiophene derivatives were synthesized and evaluated for their in vivo anti-inflammatory activity using carrageenan-induced paw edema model. The most active in vivo anti-inflammatory compounds 5b, 11b, 14c, 18c, 19c and 20d were further evaluated for their in vitro COX-1/COX-2 and 5-LOX inhibitory activities. The in vitro assay results revealed that the N-(4-(4-chlorophenyl)-3-cyanothiophen-2-yl)-2-morpholinoacetamide (5b) possesses the highest selectivity toward COX-2 (IC50 = 5.45 μM) with selectivity index value of 8.37 compared to celecoxib with COX-2 selectivity index value of 15.44. In addition, it showed acceptable 5-LOX inhibitory activity (IC50 = 4.33 μM) compared to NDGA (IC50 = 2.46 μM). Molecular modeling study was conducted to study the postulated binding of compound 5b into the active site of COX-2 and 5-LOX, and it revealed that 5b binds similarly to celecoxib and NDGA, respectively. Overall, the morpholinoacetamide-thiophene hybrid 5b could serve as a promising lead for further development of new potent anti-inflammatory agents that act as dual COX-2/5-LOX inhibitors.

2-aminothiophene compound preparation method

The invention discloses a 2-aminothiophene compound preparation method. The method includes the step that ketone, nitrile and sulfur in a mole ratio of 1:1:1 are used as raw materials for preparing 2-aminothiophene compounds through catalytic cyclization. By adoption of ketone, nitrile and sulfur as the raw materials, the method has advantages of simple operating steps, high product yield, low cost and the like, and a high industrial value is achieved.

Synthesis and evaluation of 4-anilinoquinazoline bioisosteres as potential anti-breast cancer agents

Based on one of the four major categories of scaffold hopping theory namely hetrocycle replacements, a series of 5-arylthieno[2,3-d]pyrimidines had been prepared and evaluated as anti-breast cancer agents. Optimization by combination of different pharmacophores with the thienopyrimidine scaffold led to discovery of biologically active compounds.

Synthesis of thieno[2,3-b]quinolinone derivatives

The Knoevenagel reactions of malononitrile with acetophenone or 4-substituted acetophenons were carried to give the corresponding 2-(1-aryle thylidene)malononitriles, which was further cyclized with sulfur using NaHCO3 as catalysts to generate

Synthesis of substituted amino-cycloalkyl[b]thieno-[3,2-e]pyridines

(Chemical Equation Presented) An efficient two respectively three steps procedure for the synthesis of cycloalkyl[b]thieno[3,2-e]-pyridine amines was developed and in general good to very good yields were obtained.