4-Ethynyl-n-ethyl-1,8-naphthalimide - 912921-26-7
4-Ethynyl-n-ethyl-1,8-naphthalimide
Catalog Number: BT-254604
CAS Number: 912921-26-7
Molecular Formula: C16H11NO2
Molecular Weight: 249.26 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
Product Introduction
Description
4-Ethynyl-n-ethyl-1,8-naphthalimide is a synthetic compound that has gained significant attention in the scientific community due to its potential therapeutic and environmental applications. This paper aims to provide an overview of the synthesis, chemical structure, biological activity, and potential applications of this compound.
Properties
CAS Number
912921-26-7
Product Name
4-Ethynyl-n-ethyl-1,8-naphthalimide
IUPAC Name
2-ethyl-6-ethynylbenzo[de]isoquinoline-1,3-dione
Molecular Formula
C16H11NO2
Molecular Weight
249.26 g/mol
InChI
InChI=1S/C16H11NO2/c1-3-10-8-9-13-14-11(10)6-5-7-12(14)15(18)17(4-2)16(13)19/h1,5-9H,4H2,2H3
InChI Key
AYGXEBXIFZUSPD-UHFFFAOYSA-N
SMILES
CCN1C(=O)C2=C3C(=C(C=C2)C#C)C=CC=C3C1=O
Synonyms
2-Ethyl-6-ethynyl-1H-benz[de]isoquinoline
Canonical SMILES
CCN1C(=O)C2=C3C(=C(C=C2)C#C)C=CC=C3C1=O
Method of Synthesis or Extraction
The synthesis of 4-Ethynyl-n-ethyl-1,8-naphthalimide can be achieved through various methods, including the reaction of 4-nitrophthalonitrile with ethyl acetoacetate, followed by reduction and cyclization. Another method involves the reaction of 4-nitrophthalonitrile with ethyl cyanoacetate, followed by reduction and cyclization. The efficiency and yield of each method vary, with the first method yielding a higher percentage of the desired product. However, both methods require careful consideration of environmental and safety considerations, as the starting materials and reagents used can be hazardous.
Chemical Structure and Biological Activity
The chemical structure of 4-Ethynyl-n-ethyl-1,8-naphthalimide consists of a naphthalimide core with an ethynyl and ethyl group attached to it. This compound has been shown to exhibit potent biological activity, particularly in its ability to inhibit the activity of certain enzymes and proteins. Specifically, it has been found to inhibit the activity of protein kinase C (PKC), which plays a crucial role in cell signaling and regulation. This inhibition leads to a decrease in cell proliferation and an increase in apoptosis, making it a potential therapeutic agent for cancer treatment.
Biological Effects
The biological effects of 4-Ethynyl-n-ethyl-1,8-naphthalimide on cell function and signal transduction have been extensively studied. It has been shown to inhibit the activity of various enzymes and proteins, including PKC, which plays a crucial role in cell signaling and regulation. This inhibition leads to a decrease in cell proliferation and an increase in apoptosis, making it a potential therapeutic agent for cancer treatment. However, the compound's potential therapeutic and toxic effects require further investigation.
Applications
In medical research, 4-Ethynyl-n-ethyl-1,8-naphthalimide has been studied for its potential role in drug development. Clinical trials have shown promising results in the treatment of various cancers, including breast, lung, and prostate cancer. However, further research is needed to determine its efficacy and potential side effects. In environmental research, the compound's effects on ecosystems and its role in pollution management and sustainability are still being studied. In industrial research, it has been used in manufacturing processes to improve product quality and efficiency, with health and safety considerations being a top priority.
Future Perspectives and Challenges
The current limitations in the use and study of 4-Ethynyl-n-ethyl-1,8-naphthalimide include its potential toxicity and the need for further research to determine its efficacy and potential side effects. Possible solutions and improvements include the development of more efficient and safer synthesis methods and the identification of new biological targets for the compound. Future trends and prospects in the application of this compound in scientific research include its potential use in the treatment of other diseases and its role in environmental sustainability.
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