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Literature DB >> 24900206

Quinolizidinone carboxylic acids as CNS penetrant, selective m1 allosteric muscarinic receptor modulators.

Scott D Kuduk¹, Ronald K Chang¹, Christina N Di Marco¹, William J Ray², Lei Ma², Marion Wittmann², Matthew A Seager², Kenneth A Koeplinger³, Charles D Thompson³, George D Hartman¹, Mark T Bilodeau¹.

Abstract

Positive allosteric modulation of the M1 muscarinic receptor represents an approach to treat the cognitive decline in patients with Alzheimer's disease. Replacement of a quinolone ring system in a quinolone carboxylic acid series of M1 modulators with a quinolizidinone bearing a basic amine linkage led to a series of compounds with higher free fraction, enhanced CNS exposure, and improved efficacy in rodent in vivo models of cognition.

Entities: Chemical Disease Species

Keywords: Alzheimer’s; M1 muscarinic receptor; Quinolizidinone; allosteric modulator; cognition

Year: 2010 PMID： 24900206 PMCID： PMC4007972 DOI： 10.1021/ml100095k

Source DB: PubMed Journal: ACS Med Chem Lett ISSN： 1948-5875 Impact factor: 4.345

17 in total

1. Hydroxy cycloalkyl fused pyridone carboxylic acid M(1) positive allosteric modulators.

Authors: Scott D Kuduk; Robert M DiPardo; Douglas C Beshore; William J Ray; Lei Ma; Marion Wittmann; Matthew A Seager; Kenneth A Koeplinger; Charles D Thompson; George D Hartman; Mark T Bilodeau
Journal: Bioorg Med Chem Lett Date: 2010-03-10 Impact factor: 2.823

Review 2. The molecular basis of muscarinic receptor diversity.

Authors: T I Bonner
Journal: Trends Neurosci Date: 1989-04 Impact factor: 13.837

3. Effects of xanomeline, a selective muscarinic receptor agonist, on cognitive function and behavioral symptoms in Alzheimer disease.

Authors: N C Bodick; W W Offen; A I Levey; N R Cutler; S G Gauthier; A Satlin; H E Shannon; G D Tollefson; K Rasmussen; F P Bymaster; D J Hurley; W Z Potter; S M Paul
Journal: Arch Neurol Date: 1997-04

Review 4. New subtypes of muscarinic acetylcholine receptors.

Authors: T I Bonner
Journal: Trends Pharmacol Sci Date: 1989-12 Impact factor: 14.819

5. A selective allosteric potentiator of the M1 muscarinic acetylcholine receptor increases activity of medial prefrontal cortical neurons and restores impairments in reversal learning.

Authors: Jana K Shirey; Ashley E Brady; Paulianda J Jones; Albert A Davis; Thomas M Bridges; J Phillip Kennedy; Satyawan B Jadhav; Usha N Menon; Zixiu Xiang; Mona L Watson; Edward P Christian; James J Doherty; Michael C Quirk; Dean H Snyder; James J Lah; Allan I Levey; Michelle M Nicolle; Craig W Lindsley; P Jeffrey Conn
Journal: J Neurosci Date: 2009-11-11 Impact factor: 6.167

6. Pyridine containing M(1) positive allosteric modulators with reduced plasma protein binding.

Authors: Scott D Kuduk; Christina N Di Marco; Victoria Cofre; Daniel R Pitts; William J Ray; Lei Ma; Marion Wittmann; Matthew A Seager; Matthew Seager; Kenneth Koeplinger; Chuck D Thompson; George D Hartman; Mark T Bilodeau
Journal: Bioorg Med Chem Lett Date: 2009-12-02 Impact factor: 2.823

7. Selective activation of the M1 muscarinic acetylcholine receptor achieved by allosteric potentiation.

Authors: Lei Ma; Matthew A Seager; Matthew Seager; Marion Wittmann; Marlene Jacobson; Denise Bickel; Maryann Burno; Keith Jones; Valerie Kuzmick Graufelds; Guangping Xu; Michelle Pearson; Alexander McCampbell; Renee Gaspar; Paul Shughrue; Andrew Danziger; Christopher Regan; Rose Flick; Danette Pascarella; Susan Garson; Scott Doran; Constantine Kreatsoulas; Lone Veng; Craig W Lindsley; William Shipe; Scott Kuduk; Cyrille Sur; Gene Kinney; Guy R Seabrook; William J Ray
Journal: Proc Natl Acad Sci U S A Date: 2009-08-26 Impact factor: 11.205

Review 8. Subtype-selective allosteric modulators of muscarinic receptors for the treatment of CNS disorders.

Authors: P Jeffrey Conn; Carrie K Jones; Craig W Lindsley
Journal: Trends Pharmacol Sci Date: 2009-02-07 Impact factor: 14.819

Review 9. Allosteric modulators of GPCRs: a novel approach for the treatment of CNS disorders.

Authors: P Jeffrey Conn; Arthur Christopoulos; Craig W Lindsley
Journal: Nat Rev Drug Discov Date: 2009-01 Impact factor: 84.694

Review 10. Muscarinic acetylcholine receptors as CNS drug targets.

Authors: Christopher J Langmead; Jeannette Watson; Charlie Reavill
Journal: Pharmacol Ther Date: 2007-12-20 Impact factor: 12.310

22 in total

1. Development of a highly selective, orally bioavailable and CNS penetrant M1 agonist derived from the MLPCN probe ML071.

Authors: Evan P Lebois; Gregory J Digby; Douglas J Sheffler; Bruce J Melancon; James C Tarr; Hyekyung P Cho; Nicole R Miller; Ryan Morrison; Thomas M Bridges; Zixiu Xiang; J Scott Daniels; Michael R Wood; P Jeffrey Conn; Craig W Lindsley
Journal: Bioorg Med Chem Lett Date: 2011-08-24 Impact factor: 2.823

2. Discovery and SAR of muscarinic receptor subtype 1 (M1) allosteric activators from a molecular libraries high throughput screen. Part 1: 2,5-dibenzyl-2H-pyrazolo[4,3-c]quinolin-3(5H)-ones as positive allosteric modulators.

Authors: Changho Han; Arindam Chatterjee; Meredith J Noetzel; Joseph D Panarese; Emery Smith; Peter Chase; Peter Hodder; Colleen Niswender; P Jeffrey Conn; Craig W Lindsley; Shaun R Stauffer
Journal: Bioorg Med Chem Lett Date: 2014-11-18 Impact factor: 2.823

3. MK-7622: A First-in-Class M₁ Positive Allosteric Modulator Development Candidate.

Authors: Douglas C Beshore; Christina N Di Marco; Ronald K Chang; Thomas J Greshock; Lei Ma; Marion Wittmann; Matthew A Seager; Kenneth A Koeplinger; Charles D Thompson; Joy Fuerst; George D Hartman; Mark T Bilodeau; William J Ray; Scott D Kuduk
Journal: ACS Med Chem Lett Date: 2018-04-30 Impact factor: 4.345

Review 4. Development of M1 mAChR allosteric and bitopic ligands: prospective therapeutics for the treatment of cognitive deficits.

Authors: Briana J Davie; Arthur Christopoulos; Peter J Scammells
Journal: ACS Chem Neurosci Date: 2013-05-23 Impact factor: 4.418

5. Discovery of naphthyl-fused 5-membered lactams as a new class of m1 positive allosteric modulators.

Authors: Zhi-Qiang Yang; Youheng Shu; Lei Ma; Marion Wittmann; William J Ray; Matthew A Seager; Kenneth A Koeplinger; Charles D Thompson; George D Hartman; Mark T Bilodeau; Scott D Kuduk
Journal: ACS Med Chem Lett Date: 2014-02-20 Impact factor: 4.345

6. Development of novel M1 antagonist scaffolds through the continued optimization of the MLPCN probe ML012.

Authors: Bruce J Melancon; Thomas J Utley; Christian Sevel; Margrith E Mattmann; Yiu-Yin Cheung; Thomas M Bridges; Ryan D Morrison; Douglas J Sheffler; Colleen M Niswender; J Scott Daniels; P Jeffrey Conn; Craig W Lindsley; Michael R Wood
Journal: Bioorg Med Chem Lett Date: 2012-06-15 Impact factor: 2.823

7. Drug Design Strategies for GPCR Allosteric Modulators.

Authors: P Jeffrey Conn; Scott D Kuduk; Darío Doller
Journal: Annu Rep Med Chem Date: 2012 Impact factor: 1.059

Review 8. Allosteric modulation of the M1 muscarinic acetylcholine receptor: improving cognition and a potential treatment for schizophrenia and Alzheimer's disease.

Authors: Bruce J Melancon; James C Tarr; Joseph D Panarese; Michael R Wood; Craig W Lindsley
Journal: Drug Discov Today Date: 2013-09-17 Impact factor: 7.851

9. Diverse Effects on M₁ Signaling and Adverse Effect Liability within a Series of M₁ Ago-PAMs.

Authors: Jerri M Rook; Masahito Abe; Hyekyung P Cho; Kellie D Nance; Vincent B Luscombe; Jeffrey J Adams; Jonathan W Dickerson; Daniel H Remke; Pedro M Garcia-Barrantes; Darren W Engers; Julie L Engers; Sichen Chang; Jarrett J Foster; Anna L Blobaum; Colleen M Niswender; Carrie K Jones; P Jeffrey Conn; Craig W Lindsley
Journal: ACS Chem Neurosci Date: 2017-01-10 Impact factor: 4.418

10. Further exploration of M₁ allosteric agonists: subtle structural changes abolish M₁ allosteric agonism and result in pan-mAChR orthosteric antagonism.

Authors: Douglas J Sheffler; Christian Sevel; Uyen Le; Kimberly M Lovell; James C Tarr; Sheridan J S Carrington; Hyekyung P Cho; Gregory J Digby; Colleen M Niswender; P Jeffrey Conn; Corey R Hopkins; Michael R Wood; Craig W Lindsley
Journal: Bioorg Med Chem Lett Date: 2012-11-09 Impact factor: 2.823