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Updated: Jun 1, 2026

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
Published on: May 27, 2015
Methyl 5,6-dimeth-oxy-1H-indole-2-carboxyl-ate
Thomas Blake Monroe1, Yasamin Moazami, Daniel S Jones
1Department of Chemistry, The University of North Carolina at Charlotte, 9201 University City Blvd, Charlotte, NC 28223, USA.
This study details a novel indole derivative precursor with potential anti-mitotic properties. Structural analysis reveals a nearly planar molecule with significant intermolecular hydrogen bonding and pi-stacking interactions.
Area of Science:
- Organic Chemistry
- Crystallography
- Medicinal Chemistry
Background:
- Indole derivatives are recognized for their diverse biological activities.
- Anti-mitotic agents are crucial in cancer therapy.
- Understanding molecular structure aids in drug design.
Purpose of the Study:
- To synthesize and characterize a novel indole derivative precursor.
- To investigate the structural and intermolecular properties of the compound.
- To explore its potential as a precursor for anti-mitotic agents.
Main Methods:
- X-ray crystallography was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, angles, and deviations from planarity.
- Identification of intermolecular interactions, including hydrogen bonding and pi-stacking.
Main Results:
- The title compound, C(12)H(13)NO(4), was successfully synthesized.
- The molecule exhibits near planarity, with methoxy carbons deviating minimally from the indole ring plane.
- Symmetry-equivalent molecules form N-H⋯O hydrogen bonds and engage in pi-stacking interactions with an inter-planar separation of 3.39 Å.
Conclusions:
- The determined structure provides a foundation for further development of indole-based anti-mitotic drugs.
- Intermolecular interactions play a significant role in the crystal packing and stability of the compound.
- The compound serves as a valuable precursor for exploring novel therapeutic agents.
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