{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,6]],"date-time":"2025-10-06T18:41:33Z","timestamp":1759776093888},"reference-count":17,"publisher":"Springer Science and Business Media LLC","issue":"1","license":[{"start":{"date-parts":[[2013,12,1]],"date-time":"2013-12-01T00:00:00Z","timestamp":1385856000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0"}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["DARU J Pharm Sci"],"published-print":{"date-parts":[[2013,12]]},"abstract":"<jats:title>Abstract<\/jats:title>\n          <jats:sec>\n            <jats:title>Background and the purpose of the study<\/jats:title>\n            <jats:p>Modafinil, a novel wake-promoting agent with low potential for abuse and dependence, has a reliable structure to find some novel derivatives with better activity and lower potential for abuse and risk of dependency. This study was designed to evaluate psychobiological activity of some novel <jats:italic>N<\/jats:italic>-aryl modafinil derivatives.<\/jats:p>\n          <\/jats:sec>\n          <jats:sec>\n            <jats:title>Methods<\/jats:title>\n            <jats:p>Seven novel <jats:italic>N<\/jats:italic>-aryl modafinil derivatives were synthesized through three reactions: a) preparation of benzhydrylsulfanyl acetic acid through reaction of benzhydrol with thioglycolic acid, b) formation of desired amide by adding the substituted aniline to activated acid with EDC (1-ethyl-3-(3-dimethyl amino propyl) carbodiimide). This reaction was catalyzed by HOBt (<jats:italic>N<\/jats:italic>- hydroxylbenzotriazole), and c) oxidation of sulfur to sulfoxide group with H<jats:sub>2<\/jats:sub>O<jats:sub>2<\/jats:sub>. Then, their psychobiological effect on the performance of male albino mice were compared to that of modafinil as following: wakefulness by determining the effects of derivatives on phenobarbital-induced loss of the righting reflex (LOPR); exploratory activity by measuring activity in the open field test (OFT); depression by measuring immobility time (IT) during forced swimming test (FST) and the anxiogenic and anxiolytic like effects by using elevated plus-maze test (EPM). All tests were videotaped and analyzed for the frequency and duration of the behaviors during the procedures.<\/jats:p>\n          <\/jats:sec>\n          <jats:sec>\n            <jats:title>Conclusions<\/jats:title>\n            <jats:p>2-(Benzhydrylsulfonyl)-<jats:italic>N<\/jats:italic>-(4-chlorophenyl)acetamide (<jats:bold>4c<\/jats:bold>) showed comparable result in LOPR test. However, all analogs were found to be stimulant except 2-(benzhydrylsulfinyl)-<jats:italic>N<\/jats:italic>-phenylacetamide (<jats:bold>4a<\/jats:bold>). Also <jats:bold>4c<\/jats:bold> led the most exploratory activity in mice among derivatives. FST results showed that 4a had the longest IT while modafinil, 2-(benzhydrylsulfinyl)-<jats:italic>N<\/jats:italic>-(3-chlorophenyl) acetamide (<jats:bold>4b<\/jats:bold>) and 2-(benzhydrylsulfinyl)-<jats:italic>N<\/jats:italic>-(4-ethylphenyl) acetamide (<jats:bold>4d<\/jats:bold>) had the shortest IT. In EPM, all derivatives showed anxiogenic-like behavior since they decreased open arms time and open arms entries and simultaneously increased close arms time.<\/jats:p>\n          <\/jats:sec>","DOI":"10.1186\/2008-2231-21-67","type":"journal-article","created":{"date-parts":[[2013,12,19]],"date-time":"2013-12-19T14:01:22Z","timestamp":1387461682000},"update-policy":"http:\/\/dx.doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Synthesis and psychobiological evaluation of modafinil analogs in mice"],"prefix":"10.1186","volume":"21","author":[{"given":"Arezou","family":"Lari","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Isaac","family":"Karimi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hadi","family":"Adibi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alireza","family":"Aliabadi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Loghman","family":"Firoozpour","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alireza","family":"Foroumadi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"297","published-online":{"date-parts":[[2013,12,19]]},"reference":[{"key":"182_CR1","doi-asserted-by":"publisher","first-page":"426","DOI":"10.2165\/00023210-199605060-00003","volume":"5","author":"C Hublin","year":"1996","unstructured":"Hublin C: Narcolepsy: current drug treatment options. CNS Drugs. 1996, 5: 426-436. 10.2165\/00023210-199605060-00003.","journal-title":"CNS Drugs"},{"key":"182_CR2","doi-asserted-by":"publisher","first-page":"1166","DOI":"10.1212\/WNL.54.5.1166","volume":"54","author":"U.S. Modafinil in Narcolepsy Multicenter Study Group","year":"2000","unstructured":"U.S. Modafinil in Narcolepsy Multicenter Study Group: Randomized trial of modafinil as a treatment for excessive daytime somnolence of narcolepsy. Neurology. 2000, 54: 1166-1175.","journal-title":"Neurology"},{"key":"182_CR3","doi-asserted-by":"publisher","first-page":"427","DOI":"10.1016\/j.sleep.2007.03.004","volume":"8","author":"M Thorpy","year":"2007","unstructured":"Thorpy M: Therapeutic advances in narcolepsy. Sleep Med. 2007, 8: 427-440. 10.1016\/j.sleep.2007.03.004.","journal-title":"Sleep Med"},{"key":"182_CR4","doi-asserted-by":"publisher","first-page":"231","DOI":"10.1016\/S1389-9457(00)00031-9","volume":"1","author":"MM Mitler","year":"2000","unstructured":"Mitler MM, Harsh J, Hirshkowitz M, Guilleminaultd C: Long-term efficacy and safety of modafinil (PROVIGIL) for the treatment of excessive daytime sleepiness associated with narcolepsy. Sleep Med. 2000, 1: 231-243. 10.1016\/S1389-9457(00)00031-9.","journal-title":"Sleep Med"},{"key":"182_CR5","doi-asserted-by":"publisher","first-page":"983","DOI":"10.1016\/j.neuroscience.2004.10.005","volume":"130","author":"JT Willie","year":"2005","unstructured":"Willie JT, Renthal W, Chemelli RM, Miller MS, Scammell TE, Yanagisawa M: Modafinil more effectively induces wakefulness in orexin-null mice than in wild-type littermates. Neuroscience. 2005, 130: 983-995. 10.1016\/j.neuroscience.2004.10.005.","journal-title":"Neuroscience"},{"key":"182_CR6","first-page":"21","volume":"15","author":"ZA Mehrjerdi","year":"2013","unstructured":"Mehrjerdi ZA: Crystal in Iran: methamphetamine or heroin kerack. Daru. 2013, 15: 21-22.","journal-title":"Daru"},{"key":"182_CR7","doi-asserted-by":"publisher","first-page":"9904","DOI":"10.1016\/j.bmc.2008.10.027","volume":"16","author":"C De Risi","year":"2008","unstructured":"De Risi C, Ferraro L, Pollini GP, Tanganelli S, Valente F, Veronese AC: Efficient synthesis and biological evaluation of two modafinil analogs. Bioorg Med Chem. 2008, 16: 9904-9910. 10.1016\/j.bmc.2008.10.027.","journal-title":"Bioorg Med Chem"},{"key":"182_CR8","doi-asserted-by":"publisher","first-page":"1053","DOI":"10.1016\/j.tetasy.2004.01.039","volume":"15","author":"T Prisinzano","year":"2004","unstructured":"Prisinzano T, Podobinski J, Tidgewell K, Luo M, Swenson D: Synthesis and determination of the absolute configuration of the enantiomers of modafinil. Tetrahedron. 2004, 15: 1053-1058.","journal-title":"Tetrahedron"},{"key":"182_CR9","doi-asserted-by":"publisher","first-page":"5384","DOI":"10.1016\/j.ejmech.2010.08.063","volume":"11","author":"A Aliabadi","year":"2010","unstructured":"Aliabadi A, Shamsa F, Ostad SN, Emami S, Shafiee A, Davoodi J: Synthesis and biological evaluation of 2-Phenylthiazole-4-carboxamide derivatives as anticancer agents. Eur J Med Chem. 2010, 11: 5384-5389.","journal-title":"Eur J Med Chem"},{"key":"182_CR10","doi-asserted-by":"publisher","first-page":"1481","DOI":"10.1023\/B:NERE.0000029559.20581.1a","volume":"29","author":"N Chatterjie","year":"2004","unstructured":"Chatterjie N, Stables JP, Wang H, Alexander GJ: Anti-narcoleptic agent modafinil and its sulfone: a novel facile synthesis and potential anti-epileptic activity. Neurochem Res. 2004, 29: 1481-1486.","journal-title":"Neurochem Res"},{"key":"182_CR11","doi-asserted-by":"publisher","first-page":"48","DOI":"10.1021\/ml1002025","volume":"2","author":"J Cao","year":"2011","unstructured":"Cao J, Prisinzano TE, Okunola OM, Kopajtic T, Shook M: SARs at the monoamine transporters for a novel series of modafinil analogues. ACS Med Chem Lett. 2011, 2: 48-52. 10.1021\/ml1002025.","journal-title":"ACS Med Chem Lett"},{"key":"182_CR12","doi-asserted-by":"publisher","first-page":"221","DOI":"10.4103\/0253-7613.40485","volume":"40","author":"AV Yadav","year":"2008","unstructured":"Yadav AV, Nade VS: Anti-dopaminergic effect of the methanolic extract of Morus alba L. leaves. Indian J Pharmacol. 2008, 40: 221-226. 10.4103\/0253-7613.44154.","journal-title":"Indian J Pharmacol"},{"key":"182_CR13","doi-asserted-by":"publisher","first-page":"413","DOI":"10.1016\/S0091-3057(00)00210-0","volume":"66","author":"CF Wu","year":"2000","unstructured":"Wu CF, Zhang HL, Liu W: Potentiation of ethanol-induced loss of the righting reflex by ascorbic acid in mice: interaction with dopamine antagonists. Pharmacol Biochem Behav. 2000, 66: 413-418. 10.1016\/S0091-3057(00)00210-0.","journal-title":"Pharmacol Biochem Behav"},{"key":"182_CR14","doi-asserted-by":"publisher","first-page":"722","DOI":"10.1016\/j.neuropharm.2009.07.010","volume":"57","author":"R Lalonde","year":"2009","unstructured":"Lalonde R, Strazielle C: The relation between open-field and emergence tests in a hyperactive mouse model. Neuropharmacology. 2009, 57: 722-724. 10.1016\/j.neuropharm.2009.07.010.","journal-title":"Neuropharmacology"},{"key":"182_CR15","doi-asserted-by":"publisher","first-page":"431","DOI":"10.1016\/S0091-3057(98)00011-2","volume":"60","author":"M Ferigolo","year":"1998","unstructured":"Ferigolo M, Barros H, Marquadt A, Tannhauser M: Comparison of behavioral effects of moclobemide and deprenyl during forced swimming. Pharmacol Biochem Behav. 1998, 60: 431-437. 10.1016\/S0091-3057(98)00011-2.","journal-title":"Pharmacol Biochem Behav"},{"key":"182_CR16","doi-asserted-by":"publisher","first-page":"501","DOI":"10.1016\/j.physbeh.2008.03.004","volume":"94","author":"A Enr\u00edquez-Castillo","year":"2008","unstructured":"Enr\u00edquez-Castillo A, Alamilla J, Barral J, Gourbi\u00e8re S, Flores-Serrano AG: Differential effects of caffeine on the antidepressant-like effect of amitriptyline in female rat subpopulations with low and high immobility in the forced swimming test. Physiol Behav. 2008, 94: 501-509. 10.1016\/j.physbeh.2008.03.004.","journal-title":"Physiol Behav"},{"key":"182_CR17","first-page":"45","volume":"5","author":"S Miraghaee","year":"2011","unstructured":"Miraghaee S, Karimi I, Becker LA: Psychobiological assessment of smoke of agarwood (Aquilaria spp.) in male rats. J Appl Biol Sci. 2011, 5: 45-53.","journal-title":"J Appl Biol Sci"}],"container-title":["DARU Journal of Pharmaceutical Sciences"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/link.springer.com\/content\/pdf\/10.1186\/2008-2231-21-67.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/link.springer.com\/article\/10.1186\/2008-2231-21-67\/fulltext.html","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/link.springer.com\/content\/pdf\/10.1186\/2008-2231-21-67.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,9,2]],"date-time":"2021-09-02T02:47:12Z","timestamp":1630550832000},"score":1,"resource":{"primary":{"URL":"https:\/\/link.springer.com\/10.1186\/2008-2231-21-67"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,12]]},"references-count":17,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2013,12]]}},"alternative-id":["182"],"URL":"https:\/\/doi.org\/10.1186\/2008-2231-21-67","relation":{},"ISSN":["2008-2231"],"issn-type":[{"value":"2008-2231","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,12]]},"assertion":[{"value":"17 May 2013","order":1,"name":"received","label":"Received","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"7 August 2013","order":2,"name":"accepted","label":"Accepted","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"19 December 2013","order":3,"name":"first_online","label":"First Online","group":{"name":"ArticleHistory","label":"Article History"}}],"article-number":"67"}}