Literature DB >> 21344069

Structure-Activity Relationships at the Monoamine Transporters for a Novel Series of Modafinil (2-[(diphenylmethyl)sulfinyl]acetamide) Analogues.

Jianjing Cao1, Thomas E Prisinzano, Oluyomi M Okunola, Theresa Kopajtic, Matthew Shook, Jonathan L Katz, Amy Hauck Newman.   

Abstract

A series of modafinil (1) analogues was synthesized wherein 1) para-halo-substitutents were added to the aryl rings, 2) the sulfoxide function was removed, and 3) the primary amide group was replaced with secondary and tertiary amides and amines to investigate the effects of these chemical modifications on DAT, SERT and NET binding. In addition, the locomotor-stimulant effects in mice of (±)-modafinil (1), its R- and S-enantiomers and its para-chloro sulfinylacetamide analogue (5c) were compared to those of cocaine.

Entities:  

Year:  2010        PMID： 21344069      PMCID： PMC3041981          DOI： 10.1021/ml1002025

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


  28 in total

1.  Efficient synthesis and biological evaluation of two modafinil analogues.

Authors:  Carmela De Risi; Luca Ferraro; Gian P Pollini; Sergio Tanganelli; Filippo Valente; Augusto C Veronese
Journal:  Bioorg Med Chem       Date:  2008-10-17       Impact factor: 3.641

2.  Novel 3alpha-diphenylmethoxytropane analogs: selective dopamine uptake inhibitors with behavioral effects distinct from those of cocaine.

Authors:  J L Katz; S Izenwasser; R H Kline; A C Allen; A H Newman
Journal:  J Pharmacol Exp Ther       Date:  1999-01       Impact factor: 4.030

3.  Novel 4'-substituted and 4',4"-disubstituted 3 alpha-(diphenylmethoxy)tropane analogs as potent and selective dopamine uptake inhibitors.

Authors:  A H Newman; R H Kline; A C Allen; S Izenwasser; C George; J L Katz
Journal:  J Med Chem       Date:  1995-09-29       Impact factor: 7.446

4.  Novel 3 alpha-(diphenylmethoxy)tropane analogs: potent dopamine uptake inhibitors without cocaine-like behavioral profiles.

Authors:  A H Newman; A C Allen; S Izenwasser; J L Katz
Journal:  J Med Chem       Date:  1994-07-22       Impact factor: 7.446

5.  Modafinil binds to the dopamine uptake carrier site with low affinity.

Authors:  E Mignot; S Nishino; C Guilleminault; W C Dement
Journal:  Sleep       Date:  1994-08       Impact factor: 5.849

Review 6.  Clinical pharmacokinetic profile of modafinil.

Authors:  Philmore Robertson; Edward T Hellriegel
Journal:  Clin Pharmacokinet       Date:  2003       Impact factor: 6.447

7.  Modafinil does not serve as a reinforcer in cocaine abusers.

Authors:  Suzanne K Vosburg; Carl L Hart; Margaret Haney; Eric Rubin; Richard W Foltin
Journal:  Drug Alcohol Depend       Date:  2009-09-23       Impact factor: 4.492

8.  Structure-activity relationships at monoamine transporters for a series of N-substituted 3alpha-(bis[4-fluorophenyl]methoxy)tropanes: comparative molecular field analysis, synthesis, and pharmacological evaluation.

Authors:  Santosh S Kulkarni; Peter Grundt; Theresa Kopajtic; Jonathan L Katz; Amy Hauck Newman
Journal:  J Med Chem       Date:  2004-06-17       Impact factor: 7.446

Review 9.  Armodafinil.

Authors:  Karly P Garnock-Jones; Sohita Dhillon; Lesley J Scott
Journal:  CNS Drugs       Date:  2009-09       Impact factor: 5.749

10.  Chiral analysis of d- and l-modafinil in human serum: application to human pharmacokinetic studies.

Authors:  Jennifer L Donovan; Robert J Malcolm; John S Markowitz; C Lindsay DeVane
Journal:  Ther Drug Monit       Date:  2003-04       Impact factor: 3.681
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  22 in total

1.  The Novel Modafinil Analog, JJC8-016, as a Potential Cocaine Abuse Pharmacotherapeutic.

Authors:  Hai-Ying Zhang; Guo-Hua Bi; Hong-Ju Yang; Yi He; Gilbert Xue; Jiajing Cao; Gianluigi Tanda; Eliot L Gardner; Amy Hauck Newman; Zheng-Xiong Xi
Journal:  Neuropsychopharmacology       Date:  2017-03-07       Impact factor: 7.853

2.  R-modafinil (armodafinil): a unique dopamine uptake inhibitor and potential medication for psychostimulant abuse.

Authors:  Claus J Loland; Maddalena Mereu; Oluyomi M Okunola; Jianjing Cao; Thomas E Prisinzano; Sonia Mazier; Theresa Kopajtic; Lei Shi; Jonathan L Katz; Gianluigi Tanda; Amy Hauck Newman
Journal:  Biol Psychiatry       Date:  2012-04-25       Impact factor: 13.382

3.  Atypical dopamine transporter inhibitors R-modafinil and JHW 007 differentially affect D2 autoreceptor neurotransmission and the firing rate of midbrain dopamine neurons.

Authors:  Alicia J Avelar; Jianjing Cao; Amy Hauck Newman; Michael J Beckstead
Journal:  Neuropharmacology       Date:  2017-06-15       Impact factor: 5.250

4.  Modafinil potentiates cocaine self-administration by a dopamine-independent mechanism: possible involvement of gap junctions.

Authors:  Maddalena Mereu; Takato Hiranita; Chloe J Jordan; Lauren E Chun; Jessica P Lopez; Mark A Coggiano; Juliana C Quarterman; Guo-Hua Bi; Jacqueline D Keighron; Zheng-Xiong Xi; Amy Hauck Newman; Jonathan L Katz; Gianluigi Tanda
Journal:  Neuropsychopharmacology       Date:  2020-04-27       Impact factor: 7.853

5.  Modafinil attenuates reinstatement of cocaine seeking: role for cystine-glutamate exchange and metabotropic glutamate receptors.

Authors:  Stephen V Mahler; Megan Hensley-Simon; Pouya Tahsili-Fahadan; Ryan T LaLumiere; Charles Thomas; Rebecca V Fallon; Peter W Kalivas; Gary Aston-Jones
Journal:  Addict Biol       Date:  2012-09-27       Impact factor: 4.280

Review 6.  Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter.

Authors:  Maarten E A Reith; Bruce E Blough; Weimin C Hong; Kymry T Jones; Kyle C Schmitt; Michael H Baumann; John S Partilla; Richard B Rothman; Jonathan L Katz
Journal:  Drug Alcohol Depend       Date:  2014-12-18       Impact factor: 4.492

7.  Effects of ( R)-Modafinil and Modafinil Analogues on Dopamine Dynamics Assessed by Voltammetry and Microdialysis in the Mouse Nucleus Accumbens Shell.

Authors:  Jacqueline D Keighron; Juliana C Quarterman; Jianjing Cao; Emily M DeMarco; Mark A Coggiano; Apre Gleaves; Rachel D Slack; Claudio Zanettini; Amy Hauck Newman; Gianluigi Tanda
Journal:  ACS Chem Neurosci       Date:  2019-01-31       Impact factor: 4.418

8.  The unique psychostimulant profile of (±)-modafinil: investigation of behavioral and neurochemical effects in mice.

Authors:  Maddalena Mereu; Lauren E Chun; Thomas E Prisinzano; Amy H Newman; Jonathan L Katz; Gianluigi Tanda
Journal:  Eur J Neurosci       Date:  2016-09-11       Impact factor: 3.386

9.  Novel and High Affinity 2-[(Diphenylmethyl)sulfinyl]acetamide (Modafinil) Analogues as Atypical Dopamine Transporter Inhibitors.

Authors:  Jianjing Cao; Rachel D Slack; Oluyomi M Bakare; Caitlin Burzynski; Rana Rais; Barbara S Slusher; Theresa Kopajtic; Alessandro Bonifazi; Michael P Ellenberger; Hideaki Yano; Yi He; Guo-Hua Bi; Zheng-Xiong Xi; Claus J Loland; Amy Hauck Newman
Journal:  J Med Chem       Date:  2016-11-28       Impact factor: 7.446

Review 10.  The neurobiology of modafinil as an enhancer of cognitive performance and a potential treatment for substance use disorders.

Authors:  Maddalena Mereu; Antonello Bonci; Amy Hauck Newman; Gianluigi Tanda
Journal:  Psychopharmacology (Berl)       Date:  2013-08-10       Impact factor: 4.530
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