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Preparation and Reactions of Sulfides

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.

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Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay

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Sphaerococcenol A Derivatives: Design, Synthesis, and Cytotoxicity.

Dídia Sousa¹, Milene A G Fortunato², Joana Silva¹

¹MARE-Marine and Environmental Sciences Centre/ARNET-Aquatic Research Network, ESTM, Politécnico de Leiria, 2520-614 Peniche, Portugal.

|September 27, 2024

Summary

Researchers synthesized novel analogues of Sphaerococcenol A, a compound from red algae. Some analogues showed promising cytotoxic activity against cancer cell lines, particularly compound 1 and 3, indicating potential for new drug development.

Keywords:

algae anticancer apoptosis hemi-synthesis marine natural products reactive oxygen species

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Published on: February 7, 2019

Area of Science:

Marine Natural Products Chemistry
Medicinal Chemistry
Cancer Biology

Background:

Sphaerococcenol A is a cytotoxic bromoditerpene isolated from the red alga *Sphaerococcus coronopifolius*.
Exploring natural products for novel therapeutic agents is crucial in drug discovery.

Purpose of the Study:

To design and synthesize novel analogues of Sphaerococcenol A.
To evaluate the cytotoxic potential of these analogues against human cancer cell lines.

Main Methods:

Semi-synthesis of six Sphaerococcenol A analogues using thiol-Michael additions and enone reduction.
Structural characterization of analogues via spectroscopic methods.
Cytotoxic assays performed on A549, DU-145, and MCF-7 cell lines at concentrations of 1-100 µM over 24 hours.

Main Results:

The synthesized analogues (1-6) exhibited IC50 values ranging from 14.31 to 70.11 µM against the tested cancer cell lines.
Compound 1 showed the lowest IC50 values against A549 (18.70 µM) and DU-145 (15.82 µM) cells.
Compound 3 displayed the lowest IC50 value against MCF-7 cells (14.31 µM).
Compound 4, with benzylthiol addition, showed reduced cytotoxic activity.
Analogue 1 impacted A549 cell viability by affecting mitochondrial function, increasing ROS levels, activating Caspase-3, and inducing DNA fragmentation.

Conclusions:

Novel Sphaerococcenol A analogues were successfully synthesized and characterized.
Compounds 1 and 3 demonstrate significant cytotoxic potential, warranting further investigation.
Sphaerococcenol A serves as a valuable scaffold for developing new anti-cancer agents.