Synthesis, Crystal Structure, and Cytotoxicity Studies of titanacalix[4 and 8]arene Complexes

Miller-Shakesby, David M.; Nigam, Shubhanchi; Hughes, David L.; Lopez-Estelles, Enrique; Elsegood, Mark R.J.; Cawthorne, Christopher J.; Archibald, Stephen J.; Redshaw, Carl

Abstract

© 2018 The Royal Society of Chemistry. Reaction of 5,11,17,23-tetra-tert-butyl-dihydroxy-26,28-bis(2-pentoxy)calix[4]arene (L(OH)2(Opentyl)2) with [TiCl4] afforded the dichlorotitanoacalix[4]arene complex [TiCl2L(O)2(Opentyl)2] (1) in good yield. Hydrolysis of 1 led to the isolation of the complex {[TiL(O)3(Opentyl)]2(μ-OH)(μ-Cl)} (2). Reaction of 5,11,17,23,29,35,41,47-p-tert-butyl-49,50,51,52,53,54,55,56-octapropoxycalix[8]arene (L′(Opropyl)8) with [TiCl4] in refluxing toluene afforded, following work-up, a 35:65 mixture (3) of the complex [Ti(NCMe)Cl]2[TiCl(μ-O)]2L′ and the silicone grease derived complex [Ti(NCMe)Cl]2[Ti(μ-O)]2[OSi(CH3)2OSi(CH3)2O]L′ in which the grease replaces two chloride ligands. The molecular structures of 1·2MeCN, 2·7MeCN, and 3·10MeCN have been determined. The complexes were studied using in vitro cell assays and were found to have CC50values in the range 111-186 μM, i.e. they have low toxicity.

Citation

Miller-Shakesby, D. M., Nigam, S., Hughes, D. L., Lopez-Estelles, E., Elsegood, M. R., Cawthorne, C. J., …Redshaw, C. (2018). Synthesis, Crystal Structure, and Cytotoxicity Studies of titanacalix[4 and 8]arene Complexes. Dalton Transactions : an international journal of inorganic chemistry, 47(27), 8992-8999. https://doi.org/10.1039/c8dt01992d

• Journal Article Type: Article
• Acceptance Date: Jun 11, 2018
• Online Publication Date: Jun 12, 2018
• Publication Date: Jun 12, 2018
• Deposit Date: Jun 12, 2018
• Publicly Available Date: Jun 13, 2019
• Journal: Dalton Transactions
• Print ISSN: 1477-9226
• Electronic ISSN: 1477-9234
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 47
• Issue: 27
• Pages: 8992-8999
• DOI: https://doi.org/10.1039/c8dt01992d
• Public URL: https://hull-repository.worktribe.com/output/873096
• Publisher URL: http://pubs.rsc.org/en/Content/ArticleLanding/2018/DT/C8DT01992D#!divAbstract
• Additional Information: : This document is Similarity Check deposited; : Single-blind; : Received 17 May 2018; Accepted 11 June 2018; Accepted Manuscript published 12 June 2018