11-Azaartemisinin cocrystals with preserved lactam : acid heterosynthons
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 seve...
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| Veröffentlicht in: | CrystEngComm 2018, Vol.2 (9), p.125-1219 |
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| creator | Nisar, Madiha Sung, Herman H.-Y Puschmann, Horst Lakerveld, Richard Haynes, Richard K Williams, Ian D |
| description | 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 R
2
2
(8) heterosynthons with short OH-O&z.dbd;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.
The R
2
2
(8) lactam : acid hetero-synthon, found in several new 1 : 1 and 2 : 1 cocrystals between the anti-malarial 11-azaartemisinin and organic acids. |
| doi_str_mv | 10.1039/c7ce01875d |
| format | Article |
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2
2
(8) heterosynthons with short OH-O&z.dbd;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.
The R
2
2
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2
2
(8) heterosynthons with short OH-O&z.dbd;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.
The R
2
2
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2
2
(8) heterosynthons with short OH-O&z.dbd;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.
The R
2
2
(8) lactam : acid hetero-synthon, found in several new 1 : 1 and 2 : 1 cocrystals between the anti-malarial 11-azaartemisinin and organic acids.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/c7ce01875d</doi><tpages>15</tpages><orcidid>https://orcid.org/0000-0001-8743-401X</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1466-8033 |
| ispartof | CrystEngComm, 2018, Vol.2 (9), p.125-1219 |
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| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Acids Amides |
| title | 11-Azaartemisinin cocrystals with preserved lactam : acid heterosynthons |
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