70706-99-9

Usage

Uses

Used in Pharmaceutical Development:
(S)-2-(benzyloxycarbonylamino)-4-methoxybutanoic acid is used as a building block for the development of new pharmaceuticals due to its unique structural features that may allow it to interact with biological targets.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (S)-2-(benzyloxycarbonylamino)-4-methoxybutanoic acid is used as a compound with potential applications in the synthesis of new drugs, given its specific arrangement of functional groups that could be harnessed for targeting biological molecules.
Used in Chemical Synthesis:
(S)-2-(benzyloxycarbonylamino)-4-methoxybutanoic acid is used as an intermediate in chemical synthesis processes, where its complex structure and functional groups can be utilized to create a variety of other compounds with different applications.

Upstream product

• 1213783-55-1 (S)-benzyl 2-(benzyloxycarbonylamino)-4-methoxybutanoate 

Downstream Products

• 1213783-60-8 (S)-benzyl 4-methoxy-1-(methylamino)-1-oxobutan-2-ylcarbamate 

Relevant academic research and scientific papers

Design and synthesis of novel P2 substituents in diol-based HIV protease inhibitors

The synthesis and SAR of HIV-1 protease inhibitors containing novel P2 structural elements are presented. The inhibitors were designed having hydrogen bond accepting P2 substituents to probe potential favorable interactions to Asp-29/Asp-30 of the HIV-1 protease backbone utilizing inhibitor 3 as a model template. Several inhibitors were synthesized from an l-Val methyl amide P2 motif by appending hydrogen bonding moieties from either the isopropyl side-chain or from the methyl amide portion. The most promising inhibitors 4a and 4e displayed Ki values of 1.0 nM and 0.7 nM respectively and EC50 values in the MT4 cell-based assay of 0.17 μM and 0.33 μM respectively, a slight loss in potency compared to lead inhibitor 3. These inhibitors were also tested against an HIV protease inhibitor resistant strain carrying the M46I, V82F, and I84V mutations. Inhibitors 4a and 4e displayed a 3 and 4 fold change respectively compared with HIV wild type, whereas lead inhibitor 3 showed a higher 9 fold change. This study further demonstrate the chemical tractability of the approach where various P2 substituents can be introduced in just one chemical step from lactone 21 enabling facile modifications of the overall properties in this inhibitor class.