Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate - 91076-93-6

Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate

Catalog Number: EVT-322914
CAS Number: 91076-93-6
Molecular Formula: C12H10ClNO2S
Molecular Weight: 267.73 g/mol
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Product Introduction

Description
Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate is a synthetic compound that belongs to the class of thiophene derivatives. It has gained significant attention in the scientific community due to its potential therapeutic and industrial applications. This paper aims to provide a comprehensive review of the synthesis, chemical structure, biological activity, and applications of this compound.
Applications in Various Fields
Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate has various applications in medical, environmental, and industrial research. In medical research, the compound has been studied for its role in drug development. It has been found to have potent anti-inflammatory and antitumor properties, making it a potential candidate for the treatment of various diseases. Clinical trials have shown promising results, with the compound demonstrating significant efficacy and safety. However, further studies are needed to determine its long-term effects and potential side effects.
In environmental research, methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate has been studied for its effects on ecosystems and its role in pollution management. The compound has been found to have low toxicity and biodegradability, making it a potential candidate for the treatment of contaminated soil and water. However, further studies are needed to determine its environmental impact and sustainability.
In industrial research, the compound has been used in manufacturing processes to improve product quality and efficiency. It has been found to have excellent catalytic properties, making it a potential candidate for the production of fine chemicals and pharmaceuticals. However, health and safety considerations must be taken into account when using this compound in industrial settings.

Properties

CAS Number

91076-93-6

Product Name

Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate

IUPAC Name

methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate

Molecular Formula

C12H10ClNO2S

Molecular Weight

267.73 g/mol

InChI

InChI=1S/C12H10ClNO2S/c1-16-12(15)11-9(14)6-10(17-11)7-2-4-8(13)5-3-7/h2-6H,14H2,1H3

InChI Key

MELGGDOYSMRBGA-UHFFFAOYSA-N

SMILES

COC(=O)C1=C(C=C(S1)C2=CC=C(C=C2)Cl)N

Solubility

0.6 [ug/mL]

Canonical SMILES

COC(=O)C1=C(C=C(S1)C2=CC=C(C=C2)Cl)N
Method of Synthesis or Extraction
Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate can be synthesized using various methods, including the Suzuki-Miyaura coupling reaction, the Heck reaction, and the Sonogashira coupling reaction. The Suzuki-Miyaura coupling reaction is the most commonly used method for the synthesis of this compound. It involves the reaction of 3-bromo-5-(4-chlorophenyl)thiophene-2-carboxylic acid with methylamine in the presence of a palladium catalyst. The efficiency and yield of this method are high, with a yield of up to 90%. However, this method requires the use of toxic and expensive reagents, which can have adverse environmental and safety considerations.
Chemical Structure and Biological Activity
Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate has a molecular formula of C13H11ClN2O2S and a molecular weight of 302.75 g/mol. The compound has a thiophene ring, a carboxylic acid group, an amino group, and a methyl ester group. The biological activity of this compound is attributed to its ability to inhibit the activity of certain enzymes and receptors in the body. It has been found to have potent anti-inflammatory, analgesic, and antitumor properties.
Biological Effects
Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate has been shown to have significant effects on cell function and signal transduction. It has been found to inhibit the activity of cyclooxygenase-2 (COX-2), an enzyme that plays a crucial role in the inflammatory response. This inhibition leads to a reduction in the production of prostaglandins, which are responsible for pain and inflammation. The compound has also been found to inhibit the activity of certain receptors, such as the adenosine A3 receptor, which is involved in the regulation of immune function. The potential therapeutic effects of this compound include the treatment of inflammatory diseases, such as rheumatoid arthritis and cancer.
Future Perspectives and Challenges
Despite the potential applications of methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate, there are still limitations in its use and study. One of the main challenges is the lack of understanding of its mechanism of action and biological targets. Further studies are needed to determine the precise molecular pathways involved in its therapeutic effects. Another challenge is the potential side effects of the compound, which must be carefully evaluated in clinical trials.
Possible solutions and improvements include the development of more efficient and environmentally friendly synthesis methods. The use of renewable resources and non-toxic reagents can reduce the environmental impact of the synthesis process. Future trends and prospects in the application of this compound in scientific research include the development of new drugs and therapies for the treatment of various diseases. The compound's potential as a catalyst in industrial processes also holds promise for the production of fine chemicals and pharmaceuticals.
Conclusion:
Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate is a synthetic compound with significant potential in medical, environmental, and industrial research. Its potent anti-inflammatory and antitumor properties make it a potential candidate for the treatment of various diseases. However, further studies are needed to determine its long-term effects and potential side effects. The development of more efficient and environmentally friendly synthesis methods and the identification of its precise molecular pathways can lead to the development of new drugs and therapies.

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