11-Azaartemisinin cocrystals with preserved lactam : acid heterosynthons

Madiha Nisar; Herman H.-Y. Sung; Horst Puschmann; Richard Lakerveld; Richard K. Haynes; Ian D. Williams

doi:10.1039/C7CE01875D

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11-Azaartemisinin cocrystals with preserved lactam : acid heterosynthons†

Madiha Nisar,^a Herman H.-Y. Sung,^a Horst Puschmann,^b Richard Lakerveld,^c Richard K. Haynes*^ad and Ian D. Williams

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
E-mail: chwill@ust.hk

^b OlexSys, University of Durham, Durham, UK

^c Department of Chemical and Biological Engineering, Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China

^d Centre of Excellence for Pharmaceutical Sciences, Faculty of Health Science, North-West University, Potchefstroom, South Africa
E-mail: Richard.haynes@nwu.ac.za
Fax: +852 2358 1594
Tel: +852 2358 7384

Abstract

11-Azaartemisinin (11-Aza) is a potent anti-malarial drug more readily able to form cocrystals than its parent compound. 13 new 1 : 1 and 2 : 1 cocrystal phases from 25 mono- and bi-functional acids are reported here in excellent yield and purity by liquid assisted grinding. X-ray structures of several of these cocrystals reveal R²₂(8) heterosynthons with short OH–O [double bond, length as m-dash] C H-bonds ≤2.60 Å between the 11-Aza lactam and the coformer acid groups. The new phases can show enhanced aqueous solubility of 11-Aza of 3× after 12 h. Notably diastereospecific cocrystal formation can occur, with the DL-mandelic acid system yielding solely the 11-Azaart : D-mandelic acid 1 : 1 product.

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Article information

DOI: https://doi.org/10.1039/C7CE01875D
Article type: Paper
Submitted: 29 Oct 2017
Accepted: 02 Jan 2018
First published: 10 Jan 2018

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CrystEngComm, 2018,20, 1205-1219

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11-Azaartemisinin cocrystals with preserved lactam : acid heterosynthons

M. Nisar, H. H.-Y. Sung, H. Puschmann, R. Lakerveld, R. K. Haynes and I. D. Williams, CrystEngComm, 2018, 20, 1205 DOI: 10.1039/C7CE01875D

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