![2-(5-nitro-1H-indol-3-yl)-2-oxo-N-[(1R)-1-phenylethyl]acetamide - 355022-97-8](/images/structure/BT-254445.png)
2-(5-nitro-1H-indol-3-yl)-2-oxo-N-[(1R)-1-phenylethyl]acetamide
Catalog Number: BT-254445
CAS Number: 355022-97-8
Molecular Formula: C18H15N3O4
Molecular Weight: 337.3 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
Product Introduction
Description
2-(5-nitro-1H-indol-3-yl)-2-oxo-N-[(1R)-1-phenylethyl]acetamide is a chemical compound that has gained significant attention in the scientific community due to its potential therapeutic and environmental applications. This paper aims to provide a comprehensive overview of the synthesis, chemical structure, biological activity, and potential applications of this compound.
Properties
CAS Number
355022-97-8
Product Name
2-(5-nitro-1H-indol-3-yl)-2-oxo-N-[(1R)-1-phenylethyl]acetamide
IUPAC Name
2-(5-nitro-1H-indol-3-yl)-2-oxo-N-[(1R)-1-phenylethyl]acetamide
Molecular Formula
C18H15N3O4
Molecular Weight
337.3 g/mol
InChI
InChI=1S/C18H15N3O4/c1-11(12-5-3-2-4-6-12)20-18(23)17(22)15-10-19-16-8-7-13(21(24)25)9-14(15)16/h2-11,19H,1H3,(H,20,23)/t11-/m1/s1
InChI Key
VCKKJKQZHHPPDR-LLVKDONJSA-N
SMILES
CC(C1=CC=CC=C1)NC(=O)C(=O)C2=CNC3=C2C=C(C=C3)[N+](=O)[O-]
Synonyms
5-Nitro-α-oxo-N-(1R)-phenylethyl]-1H-indole-3-acetamide
Canonical SMILES
CC(C1=CC=CC=C1)NC(=O)C(=O)C2=CNC3=C2C=C(C=C3)[N+](=O)[O-]
Isomeric SMILES
C[C@H](C1=CC=CC=C1)NC(=O)C(=O)C2=CNC3=C2C=C(C=C3)[N+](=O)[O-]
Method of Synthesis or Extraction
The synthesis of 2-(5-nitro-1H-indol-3-yl)-2-oxo-N-[(1R)-1-phenylethyl]acetamide can be achieved through various methods, including the reaction of 5-nitroindole-3-carboxylic acid with N-[(1R)-1-phenylethyl]glycine in the presence of a coupling agent such as N,N'-dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP). Another method involves the reaction of 5-nitroindole-3-carboxylic acid with N-[(1R)-1-phenylethyl]glycine methyl ester in the presence of DCC and DMAP, followed by hydrolysis of the ester group. The efficiency and yield of each method depend on various factors such as reaction conditions, reagent purity, and the skill of the chemist. Environmental and safety considerations must also be taken into account during the synthesis process to minimize the production of hazardous waste and ensure the safety of the chemist.
Chemical Structure and Biological Activity
2-(5-nitro-1H-indol-3-yl)-2-oxo-N-[(1R)-1-phenylethyl]acetamide has a complex chemical structure consisting of an indole ring, a carbonyl group, and a phenylethyl group. The compound has been shown to exhibit potent inhibitory activity against various enzymes such as human leukocyte elastase and cathepsin G, which are involved in inflammatory processes. It also exhibits antiproliferative activity against cancer cells by inducing apoptosis and inhibiting cell cycle progression. The mechanism of action of the compound involves the inhibition of enzyme activity and the disruption of cellular signaling pathways.
Biological Effects
The biological effects of 2-(5-nitro-1H-indol-3-yl)-2-oxo-N-[(1R)-1-phenylethyl]acetamide on cell function and signal transduction have been extensively studied. The compound has been shown to modulate the expression of various genes involved in inflammation, apoptosis, and cell cycle regulation. It also affects the activity of various signaling pathways such as the mitogen-activated protein kinase (MAPK) pathway and the nuclear factor-kappa B (NF-κB) pathway. The potential therapeutic and toxic effects of the compound depend on the dose, duration of exposure, and the specific biological target.
Applications
2-(5-nitro-1H-indol-3-yl)-2-oxo-N-[(1R)-1-phenylethyl]acetamide has potential applications in medical research, environmental research, and industrial research. In medical research, the compound has been investigated for its role in drug development, particularly in the treatment of inflammatory diseases and cancer. Clinical trials have shown promising results in the treatment of various cancers, including breast cancer and leukemia. However, the compound's potential side effects, such as hepatotoxicity and nephrotoxicity, must be carefully monitored. In environmental research, the compound's effects on ecosystems and its role in pollution management have been studied. The compound has been shown to have potential as a bioremediation agent for the removal of pollutants from contaminated soil and water. In industrial research, the compound's use in manufacturing processes and its potential to improve product quality and efficiency have been investigated. Health and safety considerations must be taken into account during the industrial use of the compound.
Future Perspectives and Challenges
Despite the potential applications of 2-(5-nitro-1H-indol-3-yl)-2-oxo-N-[(1R)-1-phenylethyl]acetamide, there are current limitations in its use and study. The compound's low solubility and stability in aqueous solutions pose challenges for its formulation and delivery. Possible solutions and improvements include the development of novel drug delivery systems and the synthesis of analogs with improved solubility and stability. Future trends and prospects in the application of the compound in scientific research include the investigation of its potential as a therapeutic agent for other diseases and the exploration of its mechanism of action at the molecular level.
Conclusion:
In conclusion, 2-(5-nitro-1H-indol-3-yl)-2-oxo-N-[(1R)-1-phenylethyl]acetamide is a complex chemical compound with potential applications in medical research, environmental research, and industrial research. The synthesis of the compound can be achieved through various methods, and its chemical structure and biological activity have been extensively studied. The compound's potential therapeutic and toxic effects, as well as its effects on cell function and signal transduction, have been investigated. Future perspectives and challenges in the use and study of the compound include the development of novel drug delivery systems and the exploration of its mechanism of action at the molecular level.
Conclusion:
In conclusion, 2-(5-nitro-1H-indol-3-yl)-2-oxo-N-[(1R)-1-phenylethyl]acetamide is a complex chemical compound with potential applications in medical research, environmental research, and industrial research. The synthesis of the compound can be achieved through various methods, and its chemical structure and biological activity have been extensively studied. The compound's potential therapeutic and toxic effects, as well as its effects on cell function and signal transduction, have been investigated. Future perspectives and challenges in the use and study of the compound include the development of novel drug delivery systems and the exploration of its mechanism of action at the molecular level.
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