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Present communication aimed at total synthesis of indanocine and its close analogues. Total synthesis was improved by double yields than previously reported yields. Some of the benzylidene and 2\u2010benzyl derivatives with free rotation at C2 position exhibited potential cytotoxicities against various human cancer cell lines. Five such analogues exhibited potential antiproliferative effect against HCT\u2010116 and MIA PACA\u20102 cell lines. Benzylindanocine <jats:bold>12i<\/jats:bold> induced microtubule destabilization by occupying colchicine binding pocket of \u03b2\u2010tubulin. It also exhibited anti\u2010inflammatory activity by down\u2010regulating IL\u20106 and TNF\u2010\u03b1. In Ehrlich ascites carcinoma model, <jats:bold>12i<\/jats:bold> reduced 78.4% of EAC tumour in Swiss albino mice at 90\u00a0mg\/kg (i.p.) dose. Further, in in vivo safety studies, <jats:bold>12i<\/jats:bold> was found to be safe to rodents up to 1,000\u00a0mg\/kg dose. Concomitant anticancer and anti\u2010inflammatory activity of benzylindanocine is distinctive, which suggests its further optimization for better efficacy and druggability.<\/jats:p>","DOI":"10.1111\/cbdd.13857","type":"journal-article","created":{"date-parts":[[2021,5,10]],"date-time":"2021-05-10T05:31:30Z","timestamp":1620624690000},"page":"127-143","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["An improved synthesis of indanocine and antiproliferative activity of 2\u2010benzylindanocine via microtubule destabilization"],"prefix":"10.1111","volume":"98","author":[{"given":"Sadiya","family":"Khwaja","sequence":"first","affiliation":[{"name":"CSIR\u2010Central Institute of Medicinal and Aromatic Plants (CSIR\u2010CIMAP) P.O. 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