Exploration of synthetic approaches and pharmacological evaluation of PNU-69176E and its stereoisomer as 5-HT2C receptor allosteric modulators

ACS Chemical Neuroscience

Volumn 3, Issue 7, 2012, Pages 538-545

  Ding, Chunyong ^a   Bremer, Nicole M ^a   Smith, Thressa D ^a   Seitz, Patricia K ^a   Anastasio, Noelle C ^a   Cunningham, Kathryn A ^a   Zhou, Jia ^a  

^a University of Texas Medical Branch School of Medicine   (United States)

Author keywords

5 HT 2Creceptor; allosteric modulator; diastereomer; PNU 69176E; synthesis

Indexed keywords

[(2S,4R) N ((1S,2S) 2 CHLORO 1 ((2R,3R,4S,5R,6R) 3,4,5 TRIHYDROXY 6 (METHYLTHIO)TETRAHYDRO 2H PYRAN 2 YL)PROPYL) 4 UNDECYLPIPERIDINE 2 CARBOXAMIDE]; PICOLINIC ACID; SEROTONIN 2C AGONIST; UNCLASSIFIED DRUG;

ALLOSTERISM; ANIMAL CELL; ARTICLE; CALCIUM CELL LEVEL; CLINICAL EVALUATION; DRUG ACTIVITY; DRUG DESIGN; DRUG EFFICACY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; OVARY CELL; PRIORITY JOURNAL; STEREOISOMERISM;

ALLOSTERIC REGULATION; ANIMALS; CALCIUM; CHO CELLS; CRICETINAE; CRICETULUS; DRUG EVALUATION, PRECLINICAL; GALACTOSIDES; HUMANS; PIPERIDINES; RECEPTOR, SEROTONIN, 5-HT2C; STEREOISOMERISM;

CRICETULUS GRISEUS;

EID: 84863941986     PISSN: None     EISSN: 19487193     Source Type: Journal    
DOI: 10.1021/cn300020x     Document Type: Article

References (29)

1. Iwamoto, K., Bundo, M., and Kato, T. (2009) Serotonin receptor 2C and mental disorders: genetic, expression and RNA editing studies RNA Biol. 6, 248-253
2. 2R Pharmacotherpay in psychostimulant abuse Prog. Brain Res. 172, 319-346
3. 2C receptor function in the brain: molecular and functional implications Neuropharmacology 55, 969-976
4. Di Giovanni, G., Di Matteo, V., Pierucci, M., Benigno, A., and Esposito, E. (2006) Central serotonin 2C receptor: from physiology to pathology Curr. Top. Med. Chem. 6, 1909-1925 (Pubitemid 44524469)
5. 2C receptor levels in the rat Br. J. Pharmacol. 123, 1707-1715 (Pubitemid 28182055)
6. Leggio, G. M., Cathala, A., Moison, D., Cunningham, K. A., Piazza, P. V., and Spampinato, U. (2009) Serotonin (2C) receptors in the medial prefrontal cortex facilitate cocaine-induced dopamine release in the rat nucleus accumbens Neuropharmacology 56, 507-513
7. Nic Dhonnchadha, B. M. and Cunningham, K. A. (2008) Serotonergic mechanisms in addiction-related memories Behav. Brain Res. 195, 39-53
8. 2C coupling: a new target for treating drug addiction Prog. Brain Res. 172, 407-240
9. 2C/2B antagonist SB 206553 on hyperactivity induced by cocaine Neuropsychopharmacology 20, 556-564 (Pubitemid 29189260)
10. 2C receptor agonists: potential for the treatment of obesity Mol. Interventions 5, 282-291 (Pubitemid 41595460)
11. 2C Agonist (R)-9-Ethyl-1,3,4,10b-tetrahydro- 7-trifluoromethylpyrazino[2,1-a]isoindol-6(2 H)-one: Impact on Selectivity and Toxicological Evaluation Mol. Pharmacol. 76, 1211-1219
12. 2C receptors as a potential therapeutic target for the design antiepileptic drugs Curr. Top. Med. Chem. 5, 59-67 (Pubitemid 40202110)
13. Conn, P. J., Christopoulos, A., and Lindsley, C. W. (2009) Allosteric modulators of GPCRs: A novel approach for the treatment of CNS disorders Nat. Rev. Drug Discovery 8, 41-54
14. Kenakin, T. P. (2010) Ligand Detection in the Allosteric World J. Biomol. Screening 15, 119-130
15. 2C Receptor Mol. Pharmacol. 64, 78-84 (Pubitemid 36759820)
16. Birkenmeyer, R. D., Kroll, S. J., Lewis, C., Stern, K. F., and Zurenko, G. E. (1984) Synthesis and antimicrobial activity of Clindamycin analogues: Pirlimycin, a potent antibacterial agent J. Med. Chem. 27, 216-223 (Pubitemid 14178875)
17. van Rijt, S. H., Peacock, A. F. A., Johnstone, R. D. L., Parsons, S., and Sadler, P. J. (2009) Organometallic osmium(II) arene anticancer complexes containing picolinate derivatives Inorg. Chem. 48, 1753-1762
18. Lewis, J. G., Anandan, S. K., Odowd, H., and Gordeev, M. F. (2005) Novel lincomycin derivatives possessing antimicrovial activity. WO Patent 012320 A2.
19. Birkenmeyer, R. D. (1969) Process for preparing 7(R)- and 7(S)-Halolincomycins. U.S. Patent Nr: 3,475,407.
20. Argoudelis, A. D. (1966) Process for the preparation of methyl α-thiolincosaminide and 4-ethyl- l -hygric acid hydrazide. U.S. Patent Nr: 3,284,439.
21. Schroeder, W., Bannister, B., and Hoeksema, H. (1967) Lincomycin. III. The structure and stereochemistry of the carbohydrate moiety J. Am. Chem. Soc. 89, 2448-2452
22. Lewis, J. G., Anandan, S. K., Odowd, H., and Gordeev, M. F. (2005) Novel lincomycin derivatives possessing antimicrovial activity. U.S. Patent 0043248 A1.
23. Shuman, R. T., Ornstein, P. L., Paschal, J. W., and Gesellchen, P. D. (1990) An improved synthesis of homoproline and derivatives J. Org. Chem. 55, 738-741 (Pubitemid 20082882)
24. Berg, K. A., Harvey, J. A., Spampinato, U., and Clarke, W. P. (2008) Physiological and therapeutic relevance of constitutive activity of 5-HT 2A and 5-HT 2C receptors for the treatment of depression Prog. Brain Res. 172, 287-305
25. Hannon, J. and Hoyer, D. (2008) Molecular biology of 5-HT receptors Behav. Brain Res. 195, 198-213
26. Millan, M. J., Marin, P., Bockaert, J., and la Cour, C. M. (2008) Signaling at G-protein-coupled serotonin receptors: recent advances and future research directions Trends Pharmacol. Sci. 29, 454-64
27. 2C receptor delays agonist-stimulated calcium release Mol. Pharmacol. 58, 859-862
28. Berg, K. A., Clarke, W. P., Sailstad, C., Saltzman, A., and Maayani, S. (1994) Signal transduction differences between 5-hydroxytryptamine type 2A and type 2C receptor systems Mol. Pharmacol. 46, 477-484 (Pubitemid 24296681)
29. Keov, P., Sexton, P. M., and Christopoulos, A. (2011) Allosteric modulation of G protein-coupled receptors: a pharmacological perspective Neuropharmacology 60, 24-35