15458-48-7

Usage

Uses

Used in Chemical Industry:
N-(2-HYDROXYETHYL)-1,2,3,6-TETRAHYDROPHTHALIMIDE is used as a chemical intermediate for the synthesis of various compounds. Its specific applications and reactivity are typically outlined in more detailed chemical safety and usage documentation, which provides guidance on its handling and potential hazards.
Used in Research and Development:
In the field of research and development, N-(2-HYDROXYETHYL)-1,2,3,6-TETRAHYDROPHTHALIMIDE serves as a valuable compound for studying its properties and exploring its potential uses in different chemical reactions and processes. Its stability under normal conditions makes it a suitable candidate for various experimental setups.

InChI:InChI=1/C10H13NO3/c12-6-5-11-9(13)7-3-1-2-4-8(7)10(11)14/h1-2,7-8,12H,3-6H2

Upstream product

• 141-43-5 ethanolamine 
• 935-79-5 cis-1,2,3,6-tetrahydrophthalic anhydride 

Relevant academic research and scientific papers

Structure-based design, parallel synthesis, structure - Activity relationship, and molecular modeling studies of thiocarbamates, new potent non-nucleoside HIV-1 reverse transcriptase inhibitor isosteres of phenethylthiazolylthiourea derivatives

In this paper we describe our structure-based ligand design, synthetic strategy, and structure-activity relationship (SAR) studies that led to the identification of thiocarbamates (TCs), a novel class of non-nucleoside reverse transcriptase inhibitors (NNRTIs), isosteres of phenethylthiazolylthiourea (PETT) derivatives. Assuming as a lead compound O-[2-(phthalimido)ethyl] phenylthiocarbamate 12, one of the precursors of the previously described acylthiocarbamates (Ranise, A.; et al. J. Med. Chem. 2003, 46, 768-781), two targeted solution-phase TC libraries were prepared by parallel synthesis. The lead optimization strategy led to para-substituted TCs 31, 33, 34, 39, 40, 41, 44, 45, and 50, which were active against wild-type HIV-1 in MT-4-based assays at nanomolar concentrations (EC50 range: 0.04-0.01 μM). The most potent congener 50 (EC50 = 0.01 μM) bears a methyl group at position 4 of the phthalimide moiety and a nitro group at the para position of the N-phenyl ring. Most of the TCs showed good selectivity indices, since no cytotoxic effect was detected at concentrations as high as 100 μM. TCs 31, 37, 39, 40, and 44 significantly reduced the multiplication of the Y181C mutant, but they were inactive against K103R and K103N + Y181C mutants. Nevertheless, the fold increase in resistance of 41 was not greater than that of efavirenz against the K103R mutant in enzyme assays. The docking model predictions were consistent with in vitro biological assays of the anti-HIV-1 activity of the TCs and related compounds synthesized.

First total synthesis of concavine

The synthesis of the unusual alkaloid concavine, isolated from Clitocybe concava (Basidiomycetae), has been accomplished. The synthetic route features regio- and stereoselective manipulation of polycyclic imide intermediates via enolate substitution and Grignard addition, along with a key bridge-forming step involving a new method for sulfenylative radical cyclisation. The NMR data for synthetic concavine demonstrate that the original data reported for the natural product refer to the derived acetic acid salt, probably formed as an artefact of isolation or purification.