{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,20]],"date-time":"2026-01-20T11:22:56Z","timestamp":1768908176851,"version":"3.49.0"},"reference-count":44,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2015,1,8]],"date-time":"2015-01-08T00:00:00Z","timestamp":1420675200000},"content-version":"vor","delay-in-days":7,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"name":"Indian Council of Medical Research (ICMR) New Delhi","award":["58\/11\/2006 July 2009"],"award-info":[{"award-number":["58\/11\/2006 July 2009"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Archiv der Pharmazie"],"published-print":{"date-parts":[[2015,1]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:sec><jats:label\/><jats:p>Series of piperazine analogs of naphthyridine\u20103\u2010carboxamides and indole\u20102\u2010carboxamides were designed using a ligand\u2010based approach with consideration of the pharmacophoric requirements for 5\u2010HT<jats:sub>3<\/jats:sub> receptor antagonists. The title carboxamides were synthesized using appropriate synthetic routes. Initially, the 5\u2010HT<jats:sub>3<\/jats:sub> receptor antagonistic activity of all the compounds was determined on isolated guinea pig ileum tissue against the 5\u2010HT<jats:sub>3<\/jats:sub> agonist, 2\u2010methyl\u20105\u2010hydroxytryptamine, which was denoted in the form of p<jats:italic>A<\/jats:italic><jats:sub>2<\/jats:sub> values. The structure\u2013activity relationship regarding the influence of the aromatic part and basic moiety as features in the 5\u2010HT<jats:sub>3<\/jats:sub> pharmacophore was derived. Among all the compounds screened, the piperazine derivatives of indole\u20102\u2010carboxamide <jats:bold>13i<\/jats:bold> and naphthyridine\u20103\u2010carboxamide <jats:bold>8h<\/jats:bold> exhibited prominent 5\u2010HT<jats:sub>3<\/jats:sub> receptor antagonism with p<jats:italic>A<\/jats:italic><jats:sub>2<\/jats:sub> values of 7.5 and 7.3, respectively. Subsequent investigation of the antidepressant activities of selected compounds in the mouse forced swim test (FST) led to the identification of the piperazine analogs of indole\u20102\u2010carboxamide <jats:bold>13i<\/jats:bold> and naphthyridine\u20103\u2010carboxamide <jats:bold>8h<\/jats:bold> as the most promising compounds. Both <jats:bold>13i<\/jats:bold> and <jats:bold>8h<\/jats:bold> demonstrated significant reduction in the duration of immobility as compared to the control. Importantly, none of the tested compounds affected the baseline locomotion of mice at the tested dose levels.<\/jats:p><\/jats:sec>","DOI":"10.1002\/ardp.201400293","type":"journal-article","created":{"date-parts":[[2015,1,8]],"date-time":"2015-01-08T10:53:11Z","timestamp":1420714391000},"page":"34-45","source":"Crossref","is-referenced-by-count":13,"title":["Piperazine Analogs of Naphthyridine\u20103\u2010carboxamides and Indole\u20102\u2010carboxamides: Novel 5\u2010HT<sub>3<\/sub> Receptor Antagonists with Antidepressant\u2010Like Activity"],"prefix":"10.1002","volume":"348","author":[{"given":"Arghya K.","family":"Dhar","sequence":"first","affiliation":[{"name":"Department of Pharmacy FD\u2010III Birla Institute of Technology &amp; Science Pilani Rajasthan India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Radhakrishnan","family":"Mahesh","sequence":"additional","affiliation":[{"name":"Department of Pharmacy FD\u2010III Birla Institute of Technology &amp; Science Pilani Rajasthan India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ankur","family":"Jindal","sequence":"additional","affiliation":[{"name":"School of Medicine University of New Mexico Albuquerque USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shvetank","family":"Bhatt","sequence":"additional","affiliation":[{"name":"Department of Pharmacy FD\u2010III Birla Institute of Technology &amp; Science Pilani Rajasthan India"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2015,1,8]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1056\/NEJMra073096"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.4088\/JCP.v61n0405"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.288.5463.39"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0140-6736(99)03121-9"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.pharmthera.2006.07.002"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1097\/01.yic.0000137184.64610.c8"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/med.2610130304"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.3109\/09540269009028285"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0165-6147(02)02017-5"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0028-3908(99)00010-6"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1080\/030097400446625"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1097\/MJT.0b013e3181ea7821"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1080\/030097400446625"},{"key":"e_1_2_6_15_1","first-page":"171","volume":"1","author":"Israili Z. H.","year":"2001","journal-title":"Curr. Med. Chem. \u2013 CNS Agents"},{"key":"e_1_2_6_16_1","first-page":"411","volume":"30","author":"Srivastava S. K.","year":"1998","journal-title":"Indian J. Pharmacol."},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/0014-2999(92)90074-E"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1600-0773.1992.tb00448.x"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0091-3057(01)00566-4"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1734-1140(10)70263-2"},{"key":"e_1_2_6_21_1","first-page":"919","volume":"62","author":"Mahesh R.","year":"2007","journal-title":"Pharmazie."},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1097\/FBP.0b013e3282f3cfd4"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.pbb.2013.05.006"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1177\/0269881109348161"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm00168a011"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm300801u"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.2174\/1568026023393813"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201200038"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2010.543419"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2010.08.128"},{"key":"e_1_2_6_31_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2010.12.064"},{"key":"e_1_2_6_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm00105a021"},{"key":"e_1_2_6_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm00075a026"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm00169a017"},{"key":"e_1_2_6_35_1","first-page":"212","volume":"158","author":"Boissier J. R.","year":"1965","journal-title":"Arch. Int. Pharmacodyn. Ther."},{"key":"e_1_2_6_36_1","doi-asserted-by":"publisher","DOI":"10.1038\/266730a0"},{"key":"e_1_2_6_37_1","first-page":"327","volume":"229","author":"Porsolt R. D.","year":"1977","journal-title":"Arch. Int. Pharmacodyn. Ther."},{"key":"e_1_2_6_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00919a033"},{"key":"e_1_2_6_39_1","unstructured":"Y.Xiao X.Chen S. R.Karra B. R.Huck A. E.Sutton A.Goutopoulos Patent. WO2010\/002779 A2."},{"key":"e_1_2_6_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm049944f"},{"key":"e_1_2_6_41_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2006.02.006"},{"key":"e_1_2_6_42_1","doi-asserted-by":"publisher","DOI":"10.1248\/bpb.27.1403"},{"key":"e_1_2_6_43_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.2042-7158.1978.tb13237.x"},{"key":"e_1_2_6_44_1","doi-asserted-by":"publisher","DOI":"10.1113\/jphysiol.1968.sp008392"},{"key":"e_1_2_6_45_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbrc.2011.05.075"}],"container-title":["Archiv der Pharmazie"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fardp.201400293","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ardp.201400293","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,6]],"date-time":"2023-10-06T23:46:54Z","timestamp":1696636014000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/ardp.201400293"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,1]]},"references-count":44,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2015,1]]}},"alternative-id":["10.1002\/ardp.201400293"],"URL":"https:\/\/doi.org\/10.1002\/ardp.201400293","archive":["Portico"],"relation":{},"ISSN":["0365-6233","1521-4184"],"issn-type":[{"value":"0365-6233","type":"print"},{"value":"1521-4184","type":"electronic"}],"subject":[],"published":{"date-parts":[[2015,1]]}}}