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Synthesis and in vivo biological activity of large-ringed calixarenes against Mycobacterium tuberculosis |
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| Authors: | Kerry J GoodworthAnne-Cécile Hervé Evangelos StavropoulosGwénaelle Hervé Isabel Casades Alison M HillGordon G Weingarten Ricardo E TasconM Joseph Colston Helen C Hailes |
| Institution: | a Department of Chemistry, University College London, 20 Gordon Street, London, WC1H OAJ, UK b The National Institute for Medical Research, The Ridgeway, Mill Hill, NW7 1AA, UK c School of Biosciences, Hatherly Laboratories, Prince of Wales Road, University of Exeter, Exeter, EX4 4PS, UK d GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, SG1 2NY, UK |
| Abstract: | A series of large-ringed calix6,7,8]arene analogues have been synthesised and their affect against Mycobacterium tuberculosis in vivo established. In general, when p-phenylcalixarenes and tert-butylcalixarenes were not functionalised at the lower rim, low biological activities were observed. However on going from partially to fully lower rim pegylated calixarenes the anti-mycobacterial properties improved. The addition of cyanopropoxy groups at the lower rim gave rise to low activities, whereas the addition of acetate moieties interestingly had pro-TB effects. Two upper rim sulfonated calixarenes showed promising properties. In the course of this work, a high yielding procedure to synthesise p-phenylcalix7]arene was also established. |
| Keywords: | Calixarenes Tuberculosis Anti-mycobacterial p-Phenylcalixarene Calixarene alkylation Pegylation |
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