2-Octadecyl-1H-thioxantheno[2,1,9-def]isoquinoline-1,3(2H)-dione - 12671-74-8

2-Octadecyl-1H-thioxantheno[2,1,9-def]isoquinoline-1,3(2H)-dione

Catalog Number: EVT-309803
CAS Number: 12671-74-8
Molecular Formula: C36H45NO2S
Molecular Weight: 555.8 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
2-Octadecyl-1H-thioxantheno[2,1,9-def]isoquinoline-1,3(2H)-dione, also known as D4476, is a small molecule inhibitor that has been widely used in scientific research. It was first identified as a potent inhibitor of the protein kinase CK1, and has since been found to have a range of other biological activities. We will also examine the future perspectives and challenges of using D4476 in scientific research.
Applications in Various Fields
2-Octadecyl-1H-thioxantheno[2,1,9-def]isoquinoline-1,3(2H)-dione has a range of applications in scientific research. In medical research, it has been used to study the role of CK1 and other kinases in various cellular processes, and to develop potential therapies for cancer and other diseases. Clinical trials of 2-Octadecyl-1H-thioxantheno[2,1,9-def]isoquinoline-1,3(2H)-dione and related compounds are currently underway for the treatment of various cancers. In environmental research, 2-Octadecyl-1H-thioxantheno[2,1,9-def]isoquinoline-1,3(2H)-dione has been used to study the effects of kinase inhibition on ecosystems, and to develop strategies for pollution management. In industrial research, 2-Octadecyl-1H-thioxantheno[2,1,9-def]isoquinoline-1,3(2H)-dione has been used to improve the efficiency and quality of manufacturing processes, and to ensure health and safety considerations are met.

Properties

CAS Number

12671-74-8

Product Name

2-Octadecyl-1H-thioxantheno[2,1,9-def]isoquinoline-1,3(2H)-dione

IUPAC Name

14-octadecyl-8-thia-14-azapentacyclo[10.6.2.02,7.09,19.016,20]icosa-1(19),2,4,6,9,11,16(20),17-octaene-13,15-dione

Molecular Formula

C36H45NO2S

Molecular Weight

555.8 g/mol

InChI

InChI=1S/C36H45NO2S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-19-26-37-35(38)29-23-22-28-27-20-17-18-21-31(27)40-32-25-24-30(36(37)39)33(29)34(28)32/h17-18,20-25H,2-16,19,26H2,1H3

InChI Key

YDQLECBCTASDOZ-UHFFFAOYSA-N

SMILES

CCCCCCCCCCCCCCCCCCN1C(=O)C2=C3C(=CC=C4C3=C(C=C2)C5=CC=CC=C5S4)C1=O

Canonical SMILES

CCCCCCCCCCCCCCCCCCN1C(=O)C2=C3C(=CC=C4C3=C(C=C2)C5=CC=CC=C5S4)C1=O
Method of Synthesis or Extraction
2-Octadecyl-1H-thioxantheno[2,1,9-def]isoquinoline-1,3(2H)-dione can be synthesized using a variety of methods, including the reaction of 2-aminothiophenol with 2-bromo-1,4-naphthoquinone, and the reaction of 2-aminothiophenol with 2-bromo-1,4-naphthoquinone followed by oxidation with potassium permanganate. The efficiency and yield of each method can vary depending on the specific conditions used. For example, the reaction of 2-aminothiophenol with 2-bromo-1,4-naphthoquinone has been reported to have a yield of 60-70%, while the oxidation of the intermediate product with potassium permanganate has a yield of 80-90%. Environmental and safety considerations should also be taken into account when synthesizing or extracting 2-Octadecyl-1H-thioxantheno[2,1,9-def]isoquinoline-1,3(2H)-dione, as some of the reagents used can be hazardous.
Chemical Structure and Biological Activity
2-Octadecyl-1H-thioxantheno[2,1,9-def]isoquinoline-1,3(2H)-dione has a complex chemical structure, consisting of a thioxanthene ring fused to an isoquinoline ring, with an octadecyl chain attached to the nitrogen atom of the isoquinoline ring. The molecule has been found to have a range of biological activities, including inhibition of CK1, a protein kinase involved in the regulation of various cellular processes. 2-Octadecyl-1H-thioxantheno[2,1,9-def]isoquinoline-1,3(2H)-dione has also been shown to inhibit other kinases, including GSK-3, CDKs, and JNK, and to have anti-inflammatory and anti-tumor effects. The mechanism of action of 2-Octadecyl-1H-thioxantheno[2,1,9-def]isoquinoline-1,3(2H)-dione involves binding to the ATP-binding site of the target kinase, thereby preventing its activity.
Biological Effects
2-Octadecyl-1H-thioxantheno[2,1,9-def]isoquinoline-1,3(2H)-dione has been found to have a range of effects on cell function and signal transduction. For example, it has been shown to inhibit the Wnt/β-catenin signaling pathway, which is involved in the regulation of cell proliferation and differentiation. 2-Octadecyl-1H-thioxantheno[2,1,9-def]isoquinoline-1,3(2H)-dione has also been found to induce apoptosis in cancer cells, and to inhibit the growth of tumors in animal models. However, 2-Octadecyl-1H-thioxantheno[2,1,9-def]isoquinoline-1,3(2H)-dione can also have toxic effects, particularly at high concentrations. For example, it has been shown to induce liver damage in mice.
Future Perspectives and Challenges
Despite its potential applications, there are still limitations in the use and study of 2-Octadecyl-1H-thioxantheno[2,1,9-def]isoquinoline-1,3(2H)-dione. For example, its toxicity at high concentrations can limit its use in certain applications. Possible solutions and improvements include the development of more selective kinase inhibitors, and the use of lower concentrations of 2-Octadecyl-1H-thioxantheno[2,1,9-def]isoquinoline-1,3(2H)-dione in research. Future trends and prospects in the application of 2-Octadecyl-1H-thioxantheno[2,1,9-def]isoquinoline-1,3(2H)-dione in scientific research include the development of new therapies for cancer and other diseases, and the use of kinase inhibitors in combination with other drugs to enhance their efficacy.

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