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

11-Azaartemisinin cocrystals with preserved lactam: Acid heterosynthons

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

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

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–OC 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.

Original language	English
Pages (from-to)	1205-1219
Number of pages	15
Journal	CrystEngComm
Volume	20
Issue number	9
Early online date	Jan 2018
DOIs	https://doi.org/10.1039/c7ce01875d
Publication status	Published - Mar 2018

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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–OC H-bonds ≤2.60 {\AA} 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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T1 - 11-Azaartemisinin cocrystals with preserved lactam

T2 - Acid heterosynthons

AU - Nisar, Madiha

AU - Sung, Herman H.Y.

AU - Puschmann, Horst

AU - Lakerveld, Richard

AU - Haynes, Richard K.

AU - Williams, Ian D.

PY - 2018/3

Y1 - 2018/3

N2 - 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–OC 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.

AB - 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–OC 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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11-Azaartemisinin cocrystals with preserved lactam: Acid heterosynthons

Abstract

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