| Names | |
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| IUPAC name
[(3aR,8bS)-3,4,8b-Trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-(2-methylphenyl)carbamate
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| Other names
2-Methylphenserine
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
PubChem CID
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| Properties | |
| C21H25N3O2 | |
| Molar mass | 351.450 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tolserine (2-methylphenserine) is an inhibitor of acetylcholinesterase. It has been described as of potential interest for the treatment of myasthenia gravis (MG)[1] and Alzheimer's disease.[2]
Chemistry
[edit]Tolserine is a substituted derivative of phenserine.[3] Additionally, certain analogs of tolserine possess less selectivity between different cholinesterase enzymes.[4]
Biological activity
[edit]As an inhibitor of the AChE enzyme, tolserine slows the breakdown of acetylcholine, a neurotransmitter. Tests have described tolserine as having an average IC50 value of 8.13 nM and an estimated Ki of 4.69 nM, which represents a more potent inhibition than its parent compound phenserine.[5]
References
[edit]- ^ Yu, Qian-Sheng; Holloway, Harold W.; Luo, Weiming; Lahiri, Debomoy K.; Brossi, Arnold; Greig, Nigel H. (2010). "Long-acting anticholinesterases for myasthenia gravis: Synthesis and activities of quaternary phenylcarbamates of neostigmine, pyridostigmine and physostigmine". Bioorganic & Medicinal Chemistry. 18 (13): 4687–4693. doi:10.1016/j.bmc.2010.05.022. PMC 2989343. PMID 20627738.
- ^ Košak, Urban; Gobec, Stanislav (September 2020). "A Simple and Effective Synthesis of 3- and 4-((Phenylcarbamoyl)oxy)benzoic Acids". Acta Chimica Slovenica. 67 (3): 940–948. doi:10.17344/acsi.2020.6006. PMID 33533422.
- ^ Tolserine from PubChem
- ^ Yu, Qian-Sheng; Holloway, Harold W.; Utsuki, Tadanobu; Brossi, Arnold; Greig, Nigel H. (1999). "Synthesis of Novel Phenserine-Based-Selective Inhibitors of Butyrylcholinesterase for Alzheimer's Disease". Journal of Medicinal Chemistry. 42 (10): 1855–1861. doi:10.1021/jm980459s. PMID 10346939.
- ^ Kamal, Mohammad A.; Greig, Nigel H.; Alhomida, Abdullah S.; Al-Jafari, Abdulaziz A. (2000). "Kinetics of human acetylcholinesterase inhibition by the novel experimental alzheimer therapeutic agent, tolserine". Biochemical Pharmacology. 60 (4): 561–570. doi:10.1016/s0006-2952(00)00330-0. PMID 10874131.