835616-61-0 | 2-(2,6-Dioxopiperidin-3-yl)-5-fluoroisoindoline-1,3-dione

CAS:835616-61-0 | 2-(2,6-Dioxopiperidin-3-yl)-5-fluoroisoindoline-1,3-dione,Description

This compound is an anti-inflammatory and anti-tumor agent used in the treatment of multiple myeloma.

Synthesis Analysis

Based on 2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione as a raw material, a series of novel pomalidomide linked with diphenylcarbamide derivatives were synthesized through several step reactions of substitution, click reaction, and addition reaction. The structures of these compounds were confirmed by 1H NMR, 13C NMR, and MS.

Chemical Reactions Analysis

The compound reacted with 2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethan-1-amine and N,N-diisopropylethylamine (DIPEA) in the N,N-dimethylformamide (DMF) to form compound 2. Compound 2 reacted with 3-ethynylaniline or 4-ethynylaniline to form compound 3 or 4.

Physical And Chemical Properties Analysis

The molecular weight of the compound is 276.22 g/mol. It has a XLogP3 value of 0.4.

Scientific Research Applications

Synthesis and Biological Activity

A novel series of compounds based on 2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione were synthesized and showed the ability to suppress indoleamine pyrrole-2,3-dioxygenase-1 activities, suggesting potential in therapeutic applications (Sun et al., 2022). Similarly, derivatives of this compound have been synthesized as cereblon modulators, showing potent antiproliferative activity against certain cell lines, suggesting their utility in antitumor drug development (Liu et al., 2022).

Herbicidal Applications

Phthalimide derivatives, including variations of 2-(2,6-dioxopiperidin-3-yl)-5-fluoroisoindoline-1,3-dione, have been evaluated for their herbicidal activities. Some compounds demonstrated good herbicidal activities and efficacy comparable to commercial herbicides (Gao et al., 2019). Another study synthesized derivatives with notable herbicidal activity, showing promise for agricultural applications (Huang et al., 2005).

Anti-Inflammatory and Antipsoriatic Potential

Thalidomide derivatives, including those based on 2-(2,6-dioxopiperidin-3-yl)-5-fluoroisoindoline-1,3-dione, have been explored for anti-inflammatory and antipsoriatic potential. Certain derivatives showed improved inhibitory activities on TNF-α and IL-6 expression in cells, indicating potential as anti-psoriasis agents (Tang et al., 2018).

Diagnostic and Imaging Applications

A study focused on the synthesis of 2-(2,6-dioxopiperidin-3-yl)-4-[(18)F]fluoroisoindole-1,3-dione for in vivo studies of angiogenesis. This compound was used in positron emission tomography (PET) imaging, indicating its potential in diagnostic imaging (Kim et al., 2006).

Ion Detection and Bioimaging

A novel application of thalidomide derivatives, including 2-(2,6-dioxopiperidin-3- yl)isoindoline-1,3-dione, has been reported in ion detection and bioimaging. A fluorescent fluoride probe based on this compound was developed for detecting fluoride ions in water and living cells (Liu et al., 2020).

Tyrosinase Inhibition and Antioxidant Properties

Compounds derived from 2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione were synthesized and evaluated for their antioxidant and antityrosinase properties. One compound, in particular, showed higher tyrosinase inhibitory activity than the positive control, indicating potential in cosmetic and pharmaceutical industries (Then et al., 2018).

Future Directions

Proteolysis-targeting technology is a new emerging technique to target mutated, denatured, and misfolded proteins that accumulate in various parts of the body. The development of small-molecule inhibitors requires a different approach. Targeted protein degradation technology (PROTAC) subverts the treatment of small-molecule inhibitors in the past. It can degrade the target protein through the protein degradation pathway in vivo, which has become a hot issue in the field of medicinal chemistry.

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