- Development of a Scalable Synthesis of an Azaindolyl-Pyrimidine Inhibitor of Influenza Virus Replication
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A scalable, asymmetric route for the synthesis of the influenza virus replication inhibitor 2 is presented. The key steps include an enzymatic desymmetrization of cis-1,3-cyclohexanediester in 99% yield and 96% ee, SNAr displacement of a methanesulfinylpyrimidine, and a Curtius rearrangement to form a morpholinyl urea. This high-yielding route allowed us to rapidly synthesize hundreds of grams of 2 in 99% purity to support in vivo studies.
- Liang, Jianglin,Cochran, John E.,Dorsch, Warren A.,Davies, Ioana,Clark, Michael P.
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p. 965 - 969
(2016/06/09)
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- Synthesis of potent and selective inhibitors of Candida albicans N-myristoyltransferase based on the benzothiazole structure
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Two parallel synthetic methods using solid-supported reagents were established to examine the rapid optimization of weak hit compound 1. Several compounds showed high potency in the low nanomolar range against N-myristoyltransferase. The structure-activity relationship (SAR) and antifungal activities of a series of novel 2-aminobenzothiazole N-myristoyltransferase inhibitors are presented.
- Yamazaki, Kazuo,Kaneko, Yasushi,Suwa, Kie,Ebara, Shinji,Nakazawa, Kyoko,Yasuno, Kazuhiro
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p. 2509 - 2522
(2007/10/03)
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- Stereoselective process for preparing cylcohexyl amine derivatives
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A process for preparing (1R,3S)-3-(9-chloro-3-methyl-4-oxo-5H-(isoxazoloquinolin-5-yl))cyclohexanecarboxylic acid and esters thereof, as represented by formulas II and III, wherein R is a lower alkyl groups, and A and B are N or O, provided that when A is N, B is O, or when A is O, B is N: Formula (III) and Formula (II).
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- STEREOSELECTIVE PROCESS FOR PREPARING CYCLOHEXYL AMINE DERIVATIVES
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A process for preparing (1R,3S)-3-(9-chloro-3-methyl-4-oxo-5H-(isoxazoloquinolin-5-yl))cyclohexanecarboxylic acid and esters thereof, as represented by formulas II and III, wherein R is a lower alkyl groups, and A and B are N or O, provided that when A is
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- Enzymatic desymmetrization of cis-1,3-cyclohexanedicarboxylic acid diesters
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cis-1,3-Cyclohexanedicarboxylic acid (1,3-CHDA) monoesters were prepared in high overall yield and high enantiomeric purity using a three step process from cis/trans-1,3-CHDA. The asymmetry is induced by an enzymatic hydrolytic desymmetrization of a meso
- Boaz, Neil W.
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p. 813 - 816
(2007/10/03)
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