Literature DB >> 24900430

Identification of amides as carboxylic Acid surrogates for quinolizidinone-based m1 positive allosteric modulators.

Scott D Kuduk1, Ronald K Chang1, Thomas J Greshock1, William J Ray1, Lei Ma1, Marion Wittmann1, Matthew A Seager1, Kenneth A Koeplinger1, Charles D Thompson1, George D Hartman1, Mark T Bilodeau1.   

Abstract

Selective activation of the M1 muscarinic receptor via positive allosteric modulation represents an approach to treat the cognitive decline in patients with Alzheimer's disease. A series of amides were examined as a replacement for the carboxylic acid moiety in a class of quinolizidinone carboxylic acid M1 muscarinic receptor positive allosteric modulators, and leading pyran 4o and cyclohexane 5c were found to possess good potency and in vivo efficacy.

Entities:  

Keywords:  carboxylic acid surrogates; positive allosteric modulators; quinolizidinone

Year:  2012        PMID： 24900430      PMCID： PMC4025801          DOI： 10.1021/ml300280g

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


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

Authors:  Scott D Kuduk; Ronald K Chang; Christina N Di Marco; William J Ray; Lei Ma; Marion Wittmann; Matthew A Seager; Kenneth A Koeplinger; Charles D Thompson; George D Hartman; Mark T Bilodeau
Journal:  ACS Med Chem Lett       Date:  2010-06-04       Impact factor: 4.345

Review 6.  Muscarinic agonists and antagonists in the treatment of Alzheimer's disease.

Authors:  W Greenlee; J Clader; T Asberom; S McCombie; J Ford; H Guzik; J Kozlowski; S Li; C Liu; D Lowe; S Vice; H Zhao; G Zhou; W Billard; H Binch; R Crosby; R Duffy; J Lachowicz; V Coffin; R Watkins; V Ruperto; C Strader; L Taylor; K Cox
Journal:  Farmaco       Date:  2001-04

7.  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

8.  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 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
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  10 in total

1.  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

2.  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 3.  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

4.  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

Review 5.  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

6.  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

Review 7.  Recent Advances in the Synthesis of Marine-Derived Alkaloids via Enzymatic Reactions.

Authors:  Bi-Shuang Chen; Di Zhang; Fayene Zeferino Ribeiro de Souza; Lan Liu
Journal:  Mar Drugs       Date:  2022-05-30       Impact factor: 6.085

Review 8.  Drug Design Targeting the Muscarinic Receptors and the Implications in Central Nervous System Disorders.

Authors:  Chad R Johnson; Brian D Kangas; Emily M Jutkiewicz; Jack Bergman; Andrew Coop
Journal:  Biomedicines       Date:  2022-02-07

Review 9.  Allosteric Modulation of Class A GPCRs: Targets, Agents, and Emerging Concepts.

Authors:  Eric A Wold; Jianping Chen; Kathryn A Cunningham; Jia Zhou
Journal:  J Med Chem       Date:  2018-08-28       Impact factor: 7.446

10.  Enzymatic synthesis of 2-hydroxy-4H-quinolizin-4-one scaffolds by integrating coenzyme a ligases and a type III PKS from Huperzia serrata.

Authors:  Juan Wang; Ning Ding; Yun Wu; Xiaoping Shi; Bowen Qi; Xiao Liu; Xiaohui Wang; Jun Li; Pengfei Tu; Shepo Shi
Journal:  RSC Adv       Date:  2020-06-22       Impact factor: 4.036
  10 in total

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