20007-87-8

Basic information

• Product Name: cyclopenin
• Synonyms: cyclopenin
• CAS NO: 20007-87-8
• Molecular Formula: C₁₇H₁₄N₂O₃
• Molecular Weight: 294.3047
• Mol File: 20007-87-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 572.5°Cat760mmHg
• Flash Point: 300.1°C
• Appearance: /
• Density: 1.4g/cm³
• CAS DataBase Reference: cyclopenin(CAS DataBase Reference)
• NIST Chemistry Reference: cyclopenin(20007-87-8)
• EPA Substance Registry System: cyclopenin(20007-87-8)

Safety Data

• Hazardous Substances Data: 20007-87-8(Hazardous Substances Data)

Usage

Description

Cyclopenin is an acetylcholinesterase inhibitor produced by Penicillium, which demonstrates a significant selectivity for human recombinant acetylcholinesterase over equine butyrylcholinesterase. It also possesses antibacterial properties against E. coli and M. pyogenes.

Uses

Used in Pharmaceutical Applications:
Cyclopenin is used as an inhibitor for acetylcholinesterase (AChE) due to its high selectivity and potency, with an IC50 value of 2.04 μM for human recombinant AChE. This makes it a potential candidate for the treatment of conditions related to AChE dysregulation.
Used in Antibacterial Applications:
Cyclopenin is used as an antibacterial agent against E. coli and M. pyogenes, providing a potential therapeutic option for treating infections caused by these bacteria.
Used in Research and Development:
Cyclopenin's selectivity and activity against specific targets make it a valuable compound for research and development in the fields of neuroscience and microbiology, where understanding the mechanisms of AChE inhibition and bacterial growth inhibition can lead to the development of new therapeutic strategies.

Upstream product

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Downstream Products

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Relevant articles and documents

Harnessing the Substrate Promiscuity of Dioxygenase AsqJ and Developing Efficient Chemoenzymatic Synthesis for Quinolones

Nature has developed complexity-generating reactions within natural product biosynthetic pathways. However, direct utilization of these pathways to prepare compound libraries remains challenging because of limited substrate scopes, involvement of multiple-step reactions, and moderate robustness of these sophisticated enzymatic transformations. Synthetic chemistry offers an alternative approach to prepare natural product analogues. However, because of complex and diverse functional groups appended on the targeted molecules, dedicated design and development of synthetic strategies are typically required. Herein, by leveraging the power of chemoenzymatic synthesis, we report an approach to bridge the gap between biological and synthetic strategies in the preparation of quinolone alkaloid analogues. Leading byin silicoanalysis, the predicted substrate analogues were chemically synthesized. The AsqJ-catalyzed asymmetric epoxidation of these substrate analogues was followed by a Lewis acid-triggered ring contraction to complete the viridicatin formation. We evaluated the robustness of this method in gram-scale reactions. Lastly, through chemoenzymatic cascades, a library of quinolone alkaloids is effectively prepared.

Insights into the Desaturation of Cyclopeptin and its C3 Epimer Catalyzed by a non-Heme Iron Enzyme: Structural Characterization and Mechanism Elucidation

AsqJ, an iron(II)- and 2-oxoglutarate-dependent enzyme found in viridicatin-type alkaloid biosynthetic pathways, catalyzes sequential desaturation and epoxidation to produce cyclopenins. Crystal structures of AsqJ bound to cyclopeptin and its C3 epimer ar

Synthesis of (±) Cyclopenin derivatives

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