5680-51-3Relevant articles and documents
Synthesis of Polyfunctional Diorganomagnesium and Diorganozinc Reagents through In Situ Trapping Halogen–Lithium Exchange of Highly Functionalized (Hetero)aryl Halides in Continuous Flow
Ketels, Marthe,Ganiek, Maximilian A.,Weidmann, Niels,Knochel, Paul
supporting information, p. 12770 - 12773 (2017/09/13)
We report a halogen–lithium exchange performed in the presence of various metal salts (ZnCl2, MgCl2?LiCl) on a broad range of sensitive bromo- or iodo(hetero)arenes using BuLi or PhLi as the exchange reagent and a commercially available continuous-flow setup. The resulting diarylmagnesium or diarylzinc species were trapped with various electrophiles, resulting in the formation of polyfunctional (hetero)arenes in high yields. This method enables the functionalization of (hetero)arenes containing highly sensitive groups such as an isothiocyanate, nitro, azide, or ester. A straightforward scale-up was possible without further optimization.
PYRANONE COMPOUNDS USEFUL TO TREAT RETROVIRAL INFECTIONS
-
, (2008/06/13)
The present invention relates to compounds of formulae (I) and (II) which are pyran-2-ones, 5,6-dihydro-pyran-2-ones, 4-hydroxy-benzopyran-2-ones, 4-hydroxy-cycloalkyl[b]pyran-2-ones, and derivatives thereof, useful for inhibiting a retrovirus in a mammalian cell infected with said retrovirus, wherein R 10 and R 20 taken together are formulae (III) and (IV). STR1
Structure-based design of nonpeptidic HIV protease inhibitors: The sulfonamide-substituted cyelooctylpyranones
Skulnick, Harvey I.,Johnson, Paul D.,Aristoff, Paul A.,Morris, Jeanette K.,Lovasz, Kristine D.,Howe, W. Jeffrey,Watenpaugh, Keith D.,Janakiraman, Musiri N.,Anderson, David J.,Reischer, Robert J.,Schwartz, Theresa M.,Banitt, Lee S.,Tomich, Paul K.,Lynn, Janet C.,Horng, Miao-Miao,Chong, Kong-Teck,Hinshaw, Roger R.,Dolak, Lester A.,Seest, Eric P.,Schwende, Francis J.,Rush, Bob D.,Howard, Gina M.,Toth, Lisa N.,Wilkinson, Karen R.,Kakuk, Thomas J.,Johnson, Carol W.,Cole, Serena L.,Zaya, Renee M.,Zipp, Gail L.,Possert, Peggy L.,Dalga, Robert J.,Zhong, Wei-Zhu,Williams, Marta G.,Romines, Karen R.
, p. 1149 - 1164 (2007/10/03)
Recently, cyclooctylpyranone derivatives with m-carboxamide substituents (e.g. 2c) were identified as potent, nonpeptidic HIV protease inhibitors, but these compounds lacked significant antiviral activity in cell culture. Substitution of a sulfonamide group at the meta position, however, produces compounds with excellent HIV protease binding affinity and antiviral activity. Guided by an iterative structure-based drug design process, we have prepared and evaluated a number of these derivatives, which are readily available via a seven-step synthesis. A few of the most potent compounds were further evaluated for such characteristics as pharmacokinetics and toxicity in rats and dogs. From this work, the p-cyanophenyl sulfonamide derivative 35k emerged as a promising inhibitor, was selected for further development, and entered phase I clinical trials.