Tolserine

Last updated
2-Methyl Phenserine
Tolserine.svg
Names
IUPAC name
[(3aR,8bS)-3,4,8b-Trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-(2-methylphenyl)carbamate
Other names
2-Methylphenserine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C21H25N3O2/c1-14-7-5-6-8-17(14)22-20(25)26-15-9-10-18-16(13-15)21(2)11-12-23(3)19(21)24(18)4/h5-10,13,19H,11-12H2,1-4H3,(H,22,25)/t19-,21+/m1/s1
    Key: JGAGHIIOCADQOV-CTNGQTDRSA-N
  • CC1=CC=CC=C1NC(=O)OC2=CC3=C(C=C2)N([C@@H]4[C@]3(CCN4C)C)C
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).

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]

Contents

Chemistry

Tolserine is a substituted derivative of phenserine. [3] Additionally, certain analogs of tolserine possess less selectivity between different cholinesterase enzymes. [4]

Biological activity

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

  1. ↑ 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.
  2. ↑ 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.
  3. ↑ Tolserine from PubChem
  4. ↑ 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.
  5. ↑ 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.
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