21582-44-5

Basic information

• Product Name: (2-Amino-3-thienyl)(phenyl)methanone
• Synonyms: Ketone,2-amino-3-thienyl phenyl (8CI); 2-Amino-3-benzoylthiophene
• CAS NO: 21582-44-5
• Molecular Formula: C₁₁H₉NOS
• Molecular Weight: 203.26
• Mol File: 21582-44-5.mol
• Article Data: 14

Chemical Properties

• Melting Point: 149-151°
• Boiling Point: 397°Cat760mmHg
• Flash Point: 193.9°C
• Appearance: /
• Density: 1.275g/cm³
• Vapor Pressure: 1.64E-06mmHg at 25°C
• Refractive Index: 1.657
• PKA: -1.39±0.10(Predicted)
• CAS DataBase Reference: (2-Amino-3-thienyl)(phenyl)methanone(CAS DataBase Reference)
• NIST Chemistry Reference: (2-Amino-3-thienyl)(phenyl)methanone(21582-44-5)
• EPA Substance Registry System: (2-Amino-3-thienyl)(phenyl)methanone(21582-44-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 21582-44-5(Hazardous Substances Data)

Usage

General Description

(2-Amino-3-thienyl)(phenyl)methanone is a chemical compound that possesses two different functional groups, namely, the amino group and the carbonyl group. It essentially consists of a thiophene ring, which is a 5-membered aromatic ring with a sulfur atom, linked to an amino group. It also includes a phenyl group attached to a methanone moiety. The diverse nature of these functional groups might make it a versatile compound for a variety of chemical reactions. However, as of now, there is relatively limited information available about its specific applications, properties, or safety measures.

InChI:InChI=1/C11H9NOS/c12-11-9(6-7-14-11)10(13)8-4-2-1-3-5-8/h1-7H,12H2

Upstream product

• 614-16-4 Benzoylacetonitrile 
• 75-07-0 acetaldehyde 
• 40018-26-6 1,4-dithiane-2,5-diol 
• 70-11-1 α-bromoacetophenone 
• 93-58-3 benzoic acid methyl ester 
• 56387-08-7 2-aminothiophene-3-carboxylic acid 
• 71-43-2 benzene 

Downstream Products

• 21582-50-3 4-phenyl-1,2-dihydrothieno(2,3-d)-pyrimidin-2-one 
• 52824-89-2 N-(3-benzoylthiophen-2-yl)-2-bromoacetamide 
• 6453-99-2 3-benzoylthiophene 
• 1300090-32-7 C₂₇H₂₁N₅O₄S 
• 53252-11-2 (2-acetylamino-thiophen-3-yl)-phenyl-methanone 

Relevant articles and documents

Design, synthesis and biological evaluation of 7-substituted 4-phenyl-6H-imidazo[1,5-a]thieno[3,2-f] [1,4]diazepines as safe anxiolytic agents

A series of 4-phenyl-6H-imidazo[1,5-a]thieno[3,2-f][1,4]diazepine-7-carboxylate esters were synthesized and tested as central benzodiazepine receptor (CBR) ligands by the ability to displace [3H]flumazenil from rat cortical membranes. All the compounds showed high affinity with IC50 values ranging from 5.19 to 16.22 nM. In particular, compounds 12b (IC50 = 8.66 nM) and 12d (IC50 = 5.19 nM) appeared as the most effective ligands being their affinity values significantly lower than that of diazepam (IC50 = 18.52 nM). Compounds 12a-f were examined in vivo for their pharmacological effects in mice and five potential benzodiazepine (BDZ) actions were thus taken into consideration: anxiolytic, anticonvulsant, anti-amnesic, hypnotic, and locomotor activities. All the new synthesized compounds were able to induce a significant antianxiety effect and, among them, compound 12f protected pentylenetetrazole (PTZ)-induced convulsions in a dose-dependent manner reaching a 40% effect at 30 mg/kg. In addition, all the compounds were able to significantly prevent the memory impairment evoked by scopolamine, while none of them was able to interfere with pentobarbital-evoked sleep and influence motor coordination. Moreover, title compounds did not affect locomotor and exploratory activity at the same time and doses at which the anti-anxiety effect was observed. Finally, molecular docking simulations were carried out in order to assess the binding mode for compounds 12a-f. The obtained results demonstrated that these compounds bind the BDZ binding site in a similar fashion to flumazenil.

Thiazole formation through a modified Gewald reaction

The synthesis of thiazoles and thiophenes starting from nitriles, via a modified Gewald reaction has been studied for a number of different substrates. 1,4-Dithiane-2,5-diol was used as the aldehyde precursor to give either 2-substituted thiazoles or 2-substituted aminothiophenes depending on the substitution of the α-carbon to the cyano group.

Effects of conformational restriction of 2-amino-3-benzoylthiophenes on A1 adenosine receptor modulation

2-Amino-3-benzoylthiophenes (2A3BTs) have been widely reported to act as allosteric enhancers (AEs) at the A1 adenosine receptor (A 1AR). Herein we describe the synthesis of a series of 1-aminoindeno[1,2-c]thiophen-8-ones and a series of (2-aminoindeno[2,1-b] thiophen-3-yl)(phenyl)methanones as conformationally rigid analogues of the 2A3BTs. These compounds were screened using a functional assay of A 1AR-mediated phosphorylation of extracellular signal-regulated kinases 1 and 2 (ERK1/2) in intact Chinese hamster ovary (CHO) cells to identify both potential agonistic effects as well as the ability to allosterically modulate the activity of the orthosteric agonist, N6-(R- phenylisopropyl)adenosine (R-PIA). All of the 1-aminoindeno[1,2-c]thiophen-8- ones (14a-c and 17a-f) proved either to be inactive or behaved as antagonists in the functional assay. However, the (2-aminoindeno[2,1-b]thiophen-3-yl)(phenyl) methanones with para-chloro substitution (compounds 25b, 25d, and 25f) did significantly augment the R-PIA response, indicating a positive allosteric effect.