184174-80-9

Usage

Uses

Used in Textile Industry:
2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER is used as an intermediate in the synthesis of azo thiophene disperse dyes for the textile industry. Its role in creating vibrant and long-lasting colors in fabrics is essential, contributing to the aesthetic appeal and durability of textile products.
Used in Plastics and Polymer Industry:
In the plastics and polymer industry, 2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER is used as an intermediate for the development of azo thiophene disperse dyes that can be applied to plastics and polymers. These dyes enhance the visual appeal and colorfastness of the final products, making them more attractive and resistant to fading.
Used in Printing and Packaging Industry:
2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER is also utilized in the printing and packaging industry as an intermediate for azo thiophene disperse dyes. These dyes are crucial for producing high-quality, vibrant, and long-lasting prints on various packaging materials, ensuring that the final products are visually appealing and resistant to color degradation.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER, due to its unique chemical structure, may also have potential applications in the pharmaceutical industry. It could be used as a building block for the development of new drugs or as an intermediate in the synthesis of various pharmaceutical compounds. Further research and development would be required to explore these possibilities.

InChI:InChI=1/C9H11NO2S/c1-12-9(11)7-5-3-2-4-6(5)13-8(7)10/h2-4,10H2,1H3

Upstream product

• 67-56-1 methanol 
• 372-09-8 cyanoacetic acid 
• 120-92-3 cyclopentanone 
• 105-34-0 methyl 2-cyanoacetate 

Downstream Products

• 1268706-70-2 C₁₆H₁₈N₂O₃S 
• 1268706-83-7 C₁₉H₁₈N₂O₅S 
• 1268706-96-2 C₂₅H₂₂FN₃O₄S 
• 1268707-07-8 C₁₇H₁₄FN₃O₃S 
• 1240504-50-0 methyl 2-[(1-benzyl-5-oxo-4-trifluoromethyl-2-phenyl-4,5-dihydroimidazol-4-yl)amino]-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate 

Relevant academic research and scientific papers

Microwave-assisted synthesis of 2-aminothiophene derivatives via improved gewald reactions

In this paper, a new and efficient method was developed to prepare 2-aminothiophene derivatives through improved Gewald reaction. Thirty-one final products were synthesized under microwave radiation for 30 min with 57%-95% isolated yields. All the product

Design, Synthesis, and Structure-Activity Relationship of N-Aryl- N′-(thiophen-2-yl)thiourea Derivatives as Novel and Specific Human TLR1/2 Agonists for Potential Cancer Immunotherapy

The previous virtual screening of ten million compounds yielded two novel nonlipopeptide-like chemotypes as TLR2 agonists. Herein, we present the chemical optimization of our initial hit, 1-phenyl-3-(thiophen-2-yl)urea, which resulted in the identification of SMU-C80 (EC50 = 31.02 ± 1.01 nM) as a TLR2-specific agonist with a 370-fold improvement in bioactivity. Mechanistic studies revealed that SMU-C80, through TLR1/2, recruits the adaptor protein MyD88 and triggers the NF-κB pathway to release cytokines such as TNF-α and IL-1β from human, but not murine, cells. To the best of our knowledge, it is the first species-specific TLR1/2 agonist reported until now. Moreover, SMU-C80 increased the percentage of T, B, and NK cells ex vivo and activated the immune cells, which suppressed cancer cell growth in vitro. In summary, we obtained a highly efficient and specific human TLR1/2 agonist that acts through the MyD88 and NF-κB pathway, facilitating cytokine release and the simultaneous activation of immune cells that in turn affects the apoptosis of cancer cells.

SULFONYLUREA DERIVATIVES AND USES THEREOF

The present disclosure relates to compounds of Formula (I) and to their prodrugs, pharmaceutically acceptable salts, pharmaceutical compositions, methods of use, and methods for their preparation. The compounds disclosed herein are useful for inhibiting the maturation of cytokines of the IL-1 family by inhibiting inflammasomes and may be used in the treatment of disorders in which inflammasome activity is implicated, such as inflammatory, autoinflammatory and autoimmune diseases and cancers.

Synthesis of urea analogues bearing N-alkyl-N’-(thiophen-2-yl) scaffold and evaluation of their innate immune response to toll-like receptors

Previous high throughput virtual screening of 10 million-compound and following cell based validation led to the discovery of a novel, nonlipopeptide-like chemotype ZINC 6662436, as toll-like receptor 2 (TLR2) agonists. In this report, compounds belonging

Reactions of some anellated 2-aminothiophenes with electron poor acetylenes

The reactivity of 2-aminothiophenes in two different anellations: (a) [b]-anellation to a saturated carbocycle and (b) [3,4-c]-anellation to benzopyrans, towards typical acetylenic dienophiles has been investigated. Because of the absence of conjugation, the thiophenes of type (a) do not undergo [4+2]-cycloaddition with acetylenic dienophiles. Instead, the N-vinylated products 2 and 3 were obtained with dimethyl acetylene dicarboxylate (DMAD). Electron poor alkynes react with the thiophenes of type (b) in three main ways: DMAD reacts in a [4+2]-mode in dioxane to give the products 7, 8 and 14; a Michael addition type reaction also takes place at the doubly vinylene homologous carbon atoms (C-1 in the starting materials 4, 9 and 10) in dioxane, methanol or ethanol. Methyl propiolate reacts in a similar way. The doubly N-vinylated product 26 was obtained from 10 in toluene and the C-1 vinylated products 24B and 27 were obtained from 9 in dioxane and 10 in methanol. The reaction of 10 with phenyl ethyl propiolate in dimethylformamide gave no addition product, instead a dimer of the acetylenic reagent was the isolated product. The accuracy of the assigned structures 5, 12 and 13a could be achieved on the basis of a single-crystal X-ray structure analysis of compound 13a. The reaction mechanism and the nature of the isolated products are dependent on the nature of the solvent. No addition reaction was observed between 17 and DMAD. The influence of the N-substitution on the nature of the addition (Michael or Diels-Alder) could be settled through the reactions of 18 and 21 with DMAD, which gave 19 and 14 (via 22), respectively as the only isolable products.

Gewald synthesis of 2-aminothiophenes on a soluble polymer-support

A variety of polysubstituted thiophenes have been prepared via a solvent-free one-pot microwave assisted Gewald reaction using poly (ethylene glycol) as a soluble polymer support.