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11-Azaartemisinin cocrystals with preserved lactam: acid heterosynthons

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=C H-bonds ≤2.60Å between the 11-Aza lactam and the coformer acid groups. The new phases show enhanced aqueous solubility of 11-Aza of about 3x after 12h. 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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Publication details

The article was received on 29 Oct 2017, accepted on 02 Jan 2018 and first published on 10 Jan 2018


Article type: Paper
DOI: 10.1039/C7CE01875D
Citation: CrystEngComm, 2018, Accepted Manuscript
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    11-Azaartemisinin cocrystals with preserved lactam: acid heterosynthons

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

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