Physovenine

Base Information

• Chemical Name: Physovenine
• CAS No.: 6091-05-0
• Molecular Formula: C14H18 N2 O3
• Molecular Weight: 262.309
• UNII: H67Q5553UW
• DSSTox Substance ID: DTXSID90877566
• Nikkaji Number: J1.261.114E
• Wikidata: Q27107896
• Pharos Ligand ID: W3UX1JNAQ9FZ
• Metabolomics Workbench ID: 126533
• ChEMBL ID: CHEMBL205231
• Mol file: 6091-05-0.mol

Synonyms:physovenine

Chemical Property of Physovenine

Chemical Property:

• Vapor Pressure: 1.52E-06mmHg at 25°C
• Melting Point: 124-125°
• Boiling Point: 398°C at 760 mmHg
• Flash Point: 194.5°C
• PSA: 50.80000
• Density: 1.214g/cm³
• LogP: 2.31460
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 262.13174244
• Heavy Atom Count: 19
• Complexity: 376

Purity/Quality:

99% ^*data from raw suppliers

PHYSOVENINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC12CCOC1N(C3=C2C=C(C=C3)OC(=O)NC)C
• Isomeric SMILES: C[C@@]12CCO[C@@H]1N(C3=C2C=C(C=C3)OC(=O)NC)C
• General Description: Physovenine is a naturally occurring alkaloid and acetylcholinesterase (AChE) inhibitor, structurally related to physostigmine, with potential therapeutic applications in treating neurodegenerative disorders such as Alzheimer's disease, as well as myasthenia gravis and glaucoma. Its inhibitory activity, along with its analogs, depends on structural modifications, particularly the substituent size at the quaternary carbon center, where smaller alkyl groups enhance AChE inhibition, while larger arylalkyl groups improve butyrylcholinesterase (BuChE) selectivity. These findings highlight its significance in cholinesterase-targeted drug development.

Technology Process of Physovenine

There total 1 articles about Physovenine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

eseroline (469-22-7) → (-)-physovenine (6091-05-0)

Guidance literature:

Multi-step reaction with 4 steps

1: KOH / dimethylsulfoxide / 2 h / Ambient temperature

2: 7 N NaOH / 6 h / Heating

3: 97 percent / BBr₃ / CH₂Cl₂ / 2 h / Ambient temperature

4: 1) Na / 1) AcOEt, rt, 2) rt

With potassium hydroxide; sodium hydroxide; sodium; boron tribromide; In dichloromethane; dimethyl sulfoxide;

DOI:10.1002/hlca.19910740409

upstream raw materials:

eseroline

Refernces

Novel synthesis of physovenine and physostigmine analogs

10.1016/j.tetlet.2016.06.005

The research aims to develop a versatile synthetic approach to create analogs of physovenine and physostigmine, which are known acetylcholinesterase (AChE) inhibitors used in treating conditions like myasthenia gravis, glaucoma, and Alzheimer's disease. The study's purpose is to establish structure-activity relationships (SAR) among these analogs to understand their inhibitory activities against human AChE and butyrylcholinesterase (BuChE). The synthesis process involves multiple steps, including radical cyclization to form the spiro-oxindole ring, acetylation, N-alkylation, and reductive radical cyclization. The most potent analogs identified were 21a with an IC50 value of 70 nM against hBuChE and 21g with an IC50 value of 53 nM against hAChE. The study concludes that the size of the substituent at the quaternary carbon center significantly affects the inhibitory activity against hAChE, with smaller alkyl substituents generally yielding more active compounds. Conversely, larger arylalkyl substituents were more effective against hBuChE. This work provides valuable insights into the SAR of physovenine and physostigmine analogs, guiding future drug design efforts.