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Variations of the P...
Variations of the P2 Group in HIV-1 Protease Inhibitors Containing a Tertiary Alcohol in the Transition-State Mimicking Scaffold
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- Ekegren, Jenny (author)
- Uppsala universitet,Institutionen för läkemedelskemi
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- Gising, Johan (author)
- Uppsala universitet,Institutionen för läkemedelskemi
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Wallberg, Hans (author)
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- Larhed, Mats (author)
- Uppsala universitet,Institutionen för läkemedelskemi
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Samuelsson, Bertil (author)
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- Hallberg, Anders (author)
- Uppsala universitet,Institutionen för läkemedelskemi
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(creator_code:org_t)
- Royal Society of Chemistry (RSC), 2006
- 2006
- English.
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In: Organic and biomolecular chemistry. - : Royal Society of Chemistry (RSC). - 1477-0520 .- 1477-0539. ; 4:16, s. 3040-3043
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Subject headings
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- The development of synthetic protocol leading to HIV-1 protease inhibitors with a tertiary alcohol based transition-state mimicking unit and different P2 side chains was investigated. (2S)-2-benztloxirane-2-carboxylic acid ((S)-5) was used as a key intermediate in the synthesis of the new HIV-1 protease inhibitors. (S)-5 was coupled with different amines using EDC, NMM, and HOBT, resulting in the corresponding amides at low to moderate yields. The observation supports the hypothesis that intramolecular hydrogen bonding to the tertiary alcohol in the transition-state mimic is present in these molecules. Purification by reverse-phase LC-MS resulted in moderate to good yields of most target compounds. The HIV-1 protease inhibition data suggest that the size and polarity of the P2 substituent are crucial to allow proper accommodation in the S2 sub-site.
Subject headings
- MEDICIN OCH HÄLSOVETENSKAP -- Medicinska och farmaceutiska grundvetenskaper -- Farmaceutiska vetenskaper (hsv//swe)
- MEDICAL AND HEALTH SCIENCES -- Basic Medicine -- Pharmaceutical Sciences (hsv//eng)
Keyword
- PHARMACY
- FARMACI
Publication and Content Type
- ref (subject category)
- art (subject category)
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