{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,15]],"date-time":"2026-09-15T20:40:58Z","timestamp":1789504858990,"version":"build-2803163510"},"reference-count":44,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2024,11,21]],"date-time":"2024-11-21T00:00:00Z","timestamp":1732147200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemMedChem"],"published-print":{"date-parts":[[2025,3,3]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A facile multicomponent synthesis of new indole\u2010based phenylthiazolyl\u2010dihydropyrazolone hybrids, their structural characterization, biological evaluation, and <jats:italic>in silico<\/jats:italic> investigations as anticancer agents are reported. Lead molecule <jats:bold>5\u2009i<\/jats:bold> of the series showed potent activity against MCF\u20107 breast cancer cells with an IC<jats:sub>50<\/jats:sub> of 3.92\u00b10.01\u2005<jats:italic>\u03bc<\/jats:italic>M while showing minimal toxicity to normal human lung cells (IC<jats:sub>50<\/jats:sub>=69.85\u00b13.95\u2005<jats:italic>\u03bc<\/jats:italic>M). Further studies show that the compound exhibits antiproliferative activity by inducing apoptosis in MCF\u20107 cancer cells. The wound healing assay indicated impaired cell migration under the concentration\u2010dependent dosage. The lead molecule <jats:bold>5\u2009i<\/jats:bold> also successfully inhibited the tubulin polymerase enzyme with an IC<jats:sub>50<\/jats:sub> of 4.16\u00b10.18\u2005<jats:italic>\u03bc<\/jats:italic>M. A flow cytometric assay indicated compound <jats:bold>5\u2009i<\/jats:bold> induced apoptosis through G0 phase cell cycle arrest. The binding mode and interactions of the compound with the tubulin were predicted by molecular modelling and calculating binding free energies. These findings explain the current series as a new class of microtubule polymerization inhibitors with anticancer activity suitable for developing anticancer agents targeting tubulin.<\/jats:p>","DOI":"10.1002\/cmdc.202400817","type":"journal-article","created":{"date-parts":[[2024,11,10]],"date-time":"2024-11-10T23:55:24Z","timestamp":1731282924000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["New Indole\u2010Based Phenylthiazolyl\u20102,4\u2010dihydropyrazolones as Tubulin polymerization inhibitors: Multicomponent Synthesis, Cytotoxicity Evaluation, and <i>in silico<\/i> Studies"],"prefix":"10.1002","volume":"20","author":[{"given":"Bulti","family":"Bakchi","sequence":"first","affiliation":[{"name":"Department of Chemical Sciences National Institute of Pharmaceutical Education and Research (NIPER)  Balanagar Hyderabad 500037 Telangana India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Geetanjali","family":"Devabattula","sequence":"additional","affiliation":[{"name":"Department of Biological Sciences National Institute of Pharmaceutical Education and Research (NIPER)  Balanagar Hyderabad 500037 Telangana India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sarvan","family":"Maddipatla","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences National Institute of Pharmaceutical Education and Research (NIPER)  Balanagar Hyderabad 500037 Telangana India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anuradha","family":"Singampalli","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences National Institute of Pharmaceutical Education and Research (NIPER)  Balanagar Hyderabad 500037 Telangana India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dileep","family":"Kumar Porna","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences National Institute of Pharmaceutical Education and Research (NIPER)  Balanagar Hyderabad 500037 Telangana India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Srinivas","family":"Nanduri","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences National Institute of Pharmaceutical Education and Research (NIPER)  Balanagar Hyderabad 500037 Telangana India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anamika","family":"Sharma","sequence":"additional","affiliation":[{"name":"Department of Biological Sciences National Institute of Pharmaceutical Education and Research (NIPER)  Balanagar Hyderabad 500037 Telangana India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chandraiah","family":"Godugu","sequence":"additional","affiliation":[{"name":"Department of Biological Sciences National Institute of Pharmaceutical Education and Research (NIPER)  Balanagar Hyderabad 500037 Telangana India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9813-8694","authenticated-orcid":false,"given":"Venkata Madhavi","family":"Yaddanapudi","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences National Institute of Pharmaceutical Education and Research (NIPER)  Balanagar Hyderabad 500037 Telangana India"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,11,21]]},"reference":[{"key":"e_1_2_9_1_1","doi-asserted-by":"publisher","DOI":"10.7554\/eLife.34574"},{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.3322\/caac.21708"},{"key":"e_1_2_9_3_1","unstructured":"\u201cCancer Statistics \u2013 NCI \u201d can be found underhttps:\/\/www.cancer.gov\/about-cancer\/understanding\/statistics 2015."},{"key":"e_1_2_9_4_1","unstructured":"\u201c2024 Cancer Facts & Figures Cancer | 2024\u2013First Year the US Expects More than 2\u2005M New Cases of Cancer \u201d can be found underhttps:\/\/www.cancer.org\/research\/acs-research-news\/facts-and-figures-2024.html n.d."},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.200700178"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.1c00100"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2014.09.051"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0960-894X(03)00301-9"},{"key":"e_1_2_9_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2016.12.046"},{"key":"e_1_2_9_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cclet.2015.03.015"},{"key":"e_1_2_9_11_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2015.1024673"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm900060s"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2014.02.028"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6MD00179C"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm801449a"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2014.10.054"},{"key":"e_1_2_9_17_1","author":"El-Zahar M. I.","year":"2009","journal-title":"S. Afr. J. Chem."},{"key":"e_1_2_9_18_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00044-012-0071-5"},{"key":"e_1_2_9_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2019.103035"},{"key":"e_1_2_9_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm501123r"},{"key":"e_1_2_9_21_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules22020260"},{"key":"e_1_2_9_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2014.03.072"},{"key":"e_1_2_9_23_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00044-012-0191-y"},{"key":"e_1_2_9_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2011.07.010"},{"key":"e_1_2_9_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2012.11.020"},{"key":"e_1_2_9_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2014.11.029"},{"key":"e_1_2_9_27_1","doi-asserted-by":"publisher","DOI":"10.3184\/174751912X13501278349974"},{"key":"e_1_2_9_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm900016t"},{"key":"e_1_2_9_29_1","first-page":"1843","volume":"12","author":"Hawash M.","year":"2022","journal-title":"Biomol. Eng."},{"key":"e_1_2_9_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2020.104447"},{"key":"e_1_2_9_31_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11418-012-0722-3"},{"key":"e_1_2_9_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/med.21568"},{"key":"e_1_2_9_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2006.02.001"},{"key":"e_1_2_9_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2015.04.015"},{"key":"e_1_2_9_35_1","author":"Bakchi B.","journal-title":"Arch. Pharm."},{"key":"e_1_2_9_36_1","doi-asserted-by":"publisher","DOI":"10.1080\/10426507.2010.505593"},{"key":"e_1_2_9_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.201800402"},{"key":"e_1_2_9_38_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2022.105706"},{"key":"e_1_2_9_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2020.103983"},{"key":"e_1_2_9_40_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2019.103188"},{"key":"e_1_2_9_41_1","unstructured":"R.\u2005P.\u2005D. Bank \u201cRCSB PDB \u2013 3UT5: Tubulin-Colchicine-Ustiloxin: Stathmin-like domain complex \u201d can be found underhttps:\/\/www.rcsb.org\/structure\/3UT5 n.d."},{"key":"e_1_2_9_42_1","unstructured":"\u201cSchrodinger \u201c Release 2023\u20131: Maestro Schrodinger \u201d LLC New York NY 2023."},{"key":"e_1_2_9_43_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2022.132712"},{"key":"e_1_2_9_44_1","unstructured":"\u201cSwissADME \u201d can be found underhttp:\/\/www.swissadme.ch\/ n.d."}],"container-title":["ChemMedChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cmdc.202400817","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T10:36:25Z","timestamp":1760265385000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cmdc.202400817"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,11,21]]},"references-count":44,"journal-issue":{"issue":"5","published-print":{"date-parts":[[2025,3,3]]}},"alternative-id":["10.1002\/cmdc.202400817"],"URL":"https:\/\/doi.org\/10.1002\/cmdc.202400817","archive":["Portico"],"relation":{},"ISSN":["1860-7179","1860-7187"],"issn-type":[{"value":"1860-7179","type":"print"},{"value":"1860-7187","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,11,21]]},"assertion":[{"value":"2024-10-17","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-11-21","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202400817"}}