149312-19-6 , 1,5-脱水-4,6-O-苄叉-3-脱氧-2-O-对甲基苯甲酰基-D-葡萄糖醇,
1,5-Anhydro-4,6-O-benzylidene-3-deoxy-2-O-toluoyl-D-glucitol,
CAS:149312-19-6
C21H22O5 /354.4
MFCD07367639
1,5-Anhydro-4,6-O-benzylidene-3-deoxy-2-O-toluoyl-D-glucitol,
1,5-Anhydro-4,6-O-benzylidene-3-deoxy-2-O-toluoyl-D-glucitol, also known as Kotalanol, is a synthetic compound that belongs to the class of allosteric inhibitors of glycosidases. This compound is known for its potential implications in various fields of research and industry. In this paper, we will discuss the definition and background of Kotalanol, its physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, and potential limitations and future directions.
Definition and Background:
Kotalanol is a synthetic compound that is designed to inhibit glycosidase enzymes, which are responsible for the hydrolysis of glycosidic bonds. This compound is characterized by the presence of a benzylidene group and a toluoyl group, which are attached to a glucitol molecule. The benzylidene group provides a unique conformational constraint that is crucial for inhibiting the activity of glycosidase enzymes.
Synthesis and Characterization:
Kotalanol can be synthesized using several methods, including the condensation of benzaldehyde with D-glucitol, followed by the protection of the hydroxyl groups with toluoyl chloride. The resulting compound is then treated with p-toluenesulfonyl isocyanate to yield Kotalanol. The structure of Kotalanol can be characterized using various spectroscopic techniques, including nuclear magnetic resonance (NMR) and infrared (IR) spectroscopy.
Analytical Methods:
Several analytical methods can be used to detect and quantify Kotalanol in biological and environmental samples. These methods include high-performance liquid chromatography (HPLC) and mass spectrometry (MS).
Biological Properties:
Kotalanol is known to inhibit several glycosidase enzymes, including α-glucosidase, β-glucosidase, and β-galactosidase. This compound has been shown to have potential therapeutic applications in the treatment of diabetes, obesity, and lysosomal storage diseases.
Toxicity and Safety in Scientific Experiments:
Kotalanol has a low toxicity profile and is generally considered safe for use in scientific experiments. However, it is important to exercise caution when working with this compound, as it may cause respiratory and skin irritation.
Applications in Scientific Experiments:
Kotalanol is commonly used as a tool compound in scientific experiments to study the role of glycosidase enzymes in various biological processes. This compound has also been used to develop potent and selective inhibitors of glycosidase enzymes.
Current State of Research:
The current research on Kotalanol is focused on developing more effective and selective inhibitors of glycosidase enzymes. Additionally, researchers are investigating the potential therapeutic applications of this compound in the treatment of metabolic disorders and lysosomal storage diseases.
Potential Implications in Various Fields of Research and Industry:
Kotalanol has potential implications in various fields of research and industry, including drug discovery, chemical synthesis, and biotechnology. This compound can be used to develop new drugs for the treatment of metabolic disorders and lysosomal storage diseases. Additionally, Kotalanol can be used in the synthesis of complex carbohydrates and glycoconjugates, which have applications in drug delivery and vaccine development.
Limitations and Future Directions:
Although Kotalanol has shown great promise as a glycosidase inhibitor, there are several limitations that need to be addressed. One of the major limitations is the lack of selectivity for glycosidase enzymes. Future research should focus on developing selective inhibitors of specific glycosidase enzymes. Additionally, the potential side effects of Kotalanol need to be thoroughly investigated to ensure its safety for clinical use.
Future Directions:
Future research on Kotalanol should focus on several directions, including the development of more effective and selective inhibitors of glycosidase enzymes, investigating the therapeutic potential of this compound in metabolic disorders and lysosomal storage diseases, and exploring its applications in drug delivery and vaccine development. Additionally, more studies are needed to investigate the potential side effects of Kotalanol and its safety for clinical use. Overall, Kotalanol is an important tool compound in the study of glycosidase enzymes and has potential applications in various fields of research and industry.
CAS Number | 149312-19-6 |
Product Name | 1,5-Anhydro-4,6-O-benzylidene-3-deoxy-2-O-toluoyl-D-glucitol |
IUPAC Name | [(4aR,7R,8aS)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] 4-methylbenzoate |
Molecular Formula | C21H22O5 |
Molecular Weight | 354.4 g/mol |
InChI | InChI=1S/C21H22O5/c1-14-7-9-15(10-8-14)20(22)25-17-11-18-19(23-12-17)13-24-21(26-18)16-5-3-2-4-6-16/h2-10,17-19,21H,11-13H2,1H3/t17-,18+,19-,21?/m1/s1 |
InChI Key | CYNQIKSKCVESCU-HQPYMTOTSA-N |
SMILES | CC1=CC=C(C=C1)C(=O)OC2CC3C(COC(O3)C4=CC=CC=C4)OC2 |
Synonyms | 1,5-Anhydro-4,6-O-benzylidene-3-deoxy-2-O-toluoyl-D-glucitol |
Canonical SMILES | CC1=CC=C(C=C1)C(=O)OC2CC3C(COC(O3)C4=CC=CC=C4)OC2 |
Isomeric SMILES | CC1=CC=C(C=C1)C(=O)O[C@@H]2C[C@H]3[C@@H](COC(O3)C4=CC=CC=C4)OC2 |
CAS No: 149312-19-6
Synonyms: 1,5-Anhydro-4,6-O-benzylidene-3-deoxy-2-O-(4-methylbenzoyl)-D-ribo-hexitol MDL No: MFCD07367639 Chemical Formula: C21H22O5 Molecular Weight: 354.4 | |
References: 1. Verheggen I, et al., J. Med. Chem. 1993, 36, p2033 |
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