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Several restrictions limit the use of Friedel–Crafts reactions. First, the halogen in the alkyl halide must be attached to an sp3-hybridized carbon for the Friedel–Crafts reactions to occur. Vinyl or aryl halides do not react since the carbocations formed are unstable under the reaction conditions. Second, Friedel–Crafts alkylation is susceptible to carbocation rearrangement, and the major products obtained have a rearranged carbon skeleton. In contrast, the acylium ion is...
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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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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
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Modular synthesis of functional libraries by accelerated SuFEx click chemistry.

Joshua A Homer1, Rebecca A Koelln1, Andrew S Barrow2

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|March 15, 2024
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Accelerated SuFEx Click Chemistry (ASCC) enables efficient synthesis of functional molecules. This method is valuable for drug discovery, including the creation of potent anticancer agents.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Chemical Biology

Background:

  • SuFEx (Sulfur(VI) Fluoride Exchange) click chemistry offers a robust platform for molecular construction.
  • Accelerated SuFEx Click Chemistry (ASCC) enhances reaction kinetics and product yields.
  • Efficient synthetic methods are crucial for discovering novel functional molecules and drug candidates.

Purpose of the Study:

  • To demonstrate the utility of Accelerated SuFEx Click Chemistry (ASCC) for synthesizing functional molecules.
  • To showcase ASCC as a tool for late-stage derivatization of bioactive compounds.
  • To explore the application of ASCC in the synthesis of novel anticancer agents.

Main Methods:

  • Utilized ASCC for coupling aryl and alkyl alcohols with SuFEx-compatible functional groups.
  • Applied ASCC for late-stage derivatization of bioactive molecules.
  • Performed array synthesis of sulfonate-linked microtubule targeting agents (MTAs) using ASCC.

Main Results:

  • ASCC demonstrated favorable kinetics and high product yields.
  • The ASCC reaction proved versatile for late-stage functionalization.
  • Synthesized MTAs exhibited potent nanomolar anticancer activity against multidrug-resistant cancer cell lines.

Conclusions:

  • ASCC is a powerful and efficient method for molecular synthesis and functionalization.
  • ASCC is a practical tool for drug discovery, particularly for developing novel anticancer therapeutics.
  • The developed MTAs show significant promise for treating multidrug-resistant cancers.