Literature DB >> 24900878

Design, Synthesis, and Optimization of Balanced Dual NK1/NK3 Receptor Antagonists.

Stephen Hanessian1, Thomas Jennequin1, Nicolas Boyer1, Vincent Babonneau1, Udaykumar Soma1, Clotilde Mannoury la Cour2, Mark J Millan2, Guillaume De Nanteuil3.   

Abstract

In connection with a program directed at potent and balanced dual NK1/NK3 receptor ligands, a focused exploration of an original class of peptidomimetic derivatives was performed. The rational design and molecular hybridization of a novel phenylalanine core series was achieved to maximize the in vitro affinity and antagonism at both human NK1 and NK3 receptors. This study led to the identification of a new potent dual NK1/NK3 antagonist with pK i values of 8.6 and 8.1, respectively.

Entities:  

Keywords:  Schizophrenia; dual NK1/NK3 receptor antagonists; molecular hybridization; peptidomimetic

Year:  2014        PMID： 24900878      PMCID： PMC4027792          DOI： 10.1021/ml400528y

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


  31 in total

1.  Antagonists of the human CCR5 receptor as anti-HIV-1 agents. part 1: discovery and initial structure-activity relationships for 1 -amino-2-phenyl-4-(piperidin-1-yl)butanes.

Authors:  C P Dorn; P E Finke; B Oates; R J Budhu; S G Mills; M MacCoss; L Malkowitz; M S Springer; B L Daugherty; S L Gould; J A DeMartino; S J Siciliano; A Carella; G Carver; K Holmes; R Danzeisen; D Hazuda; J Kessler; J Lineberger; M Miller; W A Schleif; E A Emini
Journal:  Bioorg Med Chem Lett       Date:  2001-01-22       Impact factor: 2.823

2.  The design and discovery of novel amide CCR5 antagonists.

Authors:  David C Pryde; Martin Corless; David R Fenwick; Helen J Mason; Blanda C Stammen; Peter T Stephenson; David Ellis; David Bachelor; David Gordon; Christopher G Barber; Anthony Wood; Donald S Middleton; David C Blakemore; Gemma C Parsons; Rachel Eastwood; Michelle Y Platts; Keith Statham; Kerry A Paradowski; Catherine Burt; Wolfgang Klute
Journal:  Bioorg Med Chem Lett       Date:  2009-01-10       Impact factor: 2.823

Review 3.  Opinion: NK3 receptor antagonists: the next generation of antipsychotics?

Authors:  Will Spooren; Claus Riemer; Herbert Meltzer
Journal:  Nat Rev Drug Discov       Date:  2005-12       Impact factor: 84.694

4.  Synthesis and antihypertensive activity of 4'-substituted spiro[4H-3,1-benzoxazine-4,4'-piperidin]-2(1H)-ones.

Authors:  R D Clark; J M Caroon; A F Kluge; D B Repke; A P Roszkowski; A M Strosberg; S Baker; S M Bitter; M D Okada
Journal:  J Med Chem       Date:  1983-05       Impact factor: 7.446

5.  Asymmetric alkyl-alkyl cross-couplings of unactivated secondary alkyl electrophiles: stereoconvergent Suzuki reactions of racemic acylated halohydrins.

Authors:  Nathan A Owston; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2010-09-01       Impact factor: 15.419

6.  Enantioselective α-arylation of N-acyloxazolidinones with copper(II)-bisoxazoline catalysts and diaryliodonium salts.

Authors:  Aurélien Bigot; Alice E Williamson; Matthew J Gaunt
Journal:  J Am Chem Soc       Date:  2011-08-17       Impact factor: 15.419

7.  Nickel-BINAP catalyzed enantioselective alpha-arylation of alpha-substituted gamma-butyrolactones.

Authors:  Dirk J Spielvogel; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2002-04-10       Impact factor: 15.419

8.  Asymmetric Suzuki cross-couplings of activated secondary alkyl electrophiles: arylations of racemic alpha-chloroamides.

Authors:  Pamela M Lundin; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

Review 9.  Dual- and triple-acting agents for treating core and co-morbid symptoms of major depression: novel concepts, new drugs.

Authors:  Mark J Millan
Journal:  Neurotherapeutics       Date:  2009-01       Impact factor: 7.620

10.  Design and synthesis of potential dual NK(1)/NK(3) receptor antagonists.

Authors:  Stephen Hanessian; Vincent Babonneau; Nicolas Boyer; Clotilde Mannoury la Cour; Mark J Millan; Guillaume De Nanteuil
Journal:  Bioorg Med Chem Lett       Date:  2013-12-15       Impact factor: 2.823
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  3 in total

1.  CuH-Catalyzed Regio- and Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers.

Authors:  Sheng Feng; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2021-03-24       Impact factor: 15.419

2.  Synthesis and Fungicidal Activity of 1-(Carbamoylmethyl)-2-aryl-3,1-benzoxazines.

Authors:  Zi-Long Tang; Lian Wang; Jing-Zhao Tan; Yi-Chao Wan; Yin-Chun Jiao
Journal:  Molecules       Date:  2017-07-06       Impact factor: 4.411

3.  From receptor binding kinetics to signal transduction; a missing link in predicting in vivo drug-action.

Authors:  Indira Nederpelt; Maria Kuzikov; Wilbert E A de Witte; Patrick Schnider; Bruno Tuijt; Sheraz Gul; Adriaan P IJzerman; Elizabeth C M de Lange; Laura H Heitman
Journal:  Sci Rep       Date:  2017-10-26       Impact factor: 4.379
  3 in total

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