ChemInform Abstract: Efficient Synthesis of 2(S)‐[1(S)‐Azido‐2‐phenylethyl]oxirane.

Park, Sang-Woo; Lee, Sangmi; Kang, Ho‐Jung

doi:10.1002/chin.200841099

ChemInform

2008

DOI: 10.1002/chin.200841099

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ChemInform Abstract: Efficient Synthesis of 2(S)‐[1(S)‐Azido‐2‐phenylethyl]oxirane.

Sang-Woo Park

Sangmi Lee

Ho‐Jung Kang

Abstract: Oxirane derivatives R 0030 Efficient Synthesis of 2(S)-[1(S)-Azido-2-phenylethyl]oxirane. -The approach to title compound (VI), an educt for the preparation of the antiviral substance amprenavir, is suitable for large-scale preparation. -(PARK, S.; LEE, S.; KANG*, H.-J.; Bull.

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2012

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“…18 The enantiomeric purity of the azidodiol was confirmed by optical rotation (+31.2), which compared favorably with reported values for this compound. 19,20 Tosylation of the primary alcohol followed by protection of the secondary alcohol as the corresponding THP ether gave 3 in good overall yield. Displacement of the tosyl group proceeded smoothly with benzylamine to give the intermediate 4.…”

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Nonpeptidic Lysosomal Modulators Derived from Z-Phe-Ala-Diazomethylketone for Treating Protein Accumulation Diseases

Viswanathan

Hoover

Hwang

et al. 2012

ACS Med. Chem. Lett.

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Lysosomes are involved in protein turnover and removing misfolded species, and their enzymes have the potential to offset the defect in proteolytic clearance that contributes to the age-related dementia Alzheimer's disease (AD). The weak cathepsin B and L inhibitor Z-Phe-Ala-diazomethylketone (PADK) enhances lysosomal cathepsin levels at low concentrations, thereby eliciting protective clearance of PHF-τ and Aβ42 in the hippocampus and other brain regions. Here, a class of positive modulators is established with compounds decoupled from the cathepsin inhibitory properties. We utilized PADK as a departure point to develop nonpeptidic structures with the hydroxyethyl isostere. The first-in-class modulators SD1002 and SD1003 exhibit improved levels of cathepsin up-regulation but almost complete removal of cathepsin inhibitory properties as compared to PADK. Isomers of the lead compound SD1002 were synthesized, and the modulatory activity was determined to be stereoselective. In addition, the lead compound was tested in transgenic mice with results indicating protection against AD-type protein accumulation pathology.

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confidence: 99%

Nonpeptidic Lysosomal Modulators Derived from Z-Phe-Ala-Diazomethylketone for Treating Protein Accumulation Diseases

Viswanathan

Hoover

Hwang

et al. 2012

ACS Med. Chem. Lett.

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ChemInform Abstract: Efficient Synthesis of 2(S)‐[1(S)‐Azido‐2‐phenylethyl]oxirane.

Abstract: Oxirane derivatives R 0030 Efficient Synthesis of 2(S)-[1(S)-Azido-2-phenylethyl]oxirane. -The approach to title compound (VI), an educt for the preparation of the antiviral substance amprenavir, is suitable for large-scale preparation. -(PARK, S.; LEE, S.; KANG*, H.-J.; Bull.

Cited by 1 publication

References 1 publication

Nonpeptidic Lysosomal Modulators Derived from Z-Phe-Ala-Diazomethylketone for Treating Protein Accumulation Diseases

Nonpeptidic Lysosomal Modulators Derived from Z-Phe-Ala-Diazomethylketone for Treating Protein Accumulation Diseases

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