3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione 3,4-二氢-2,2-二甲基-2H-萘并[1,2-b]吡喃-5,6-二酮
CAS 4707-32-8 MFCD01712233
化学结构图
SMILES: CC1(C)CCC2=C(O1)c1ccccc1C(=O)C2=O
化学属性
| Mol. Formula | C15 H14 O3 |
|---|---|
| Mol. Weight | 242.27 |
| Appearance | Solid powder |
| Solubility | Soluble in DMSO, not in water |
| Melting Point | >110°C (dec.) |
| Boiling Point |
别名和识别编码
| Chemical Name | 3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione |
|---|---|
| CAS Number | 4707-32-8 |
| Synonym | 3,4-Dihydro-2,2-dimethyl-2H-naphtho(1,2-b)pyran-5,6-dione 3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione ARQ 501 ARQ501, beta lapachone Beta-Lapachone (90%) b-Lapachone (90%) {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} b-Lapachone (90%) {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {TRC} SL 11001 {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {TRC} NSC 629749 {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} |
| MDL Number | MFCD01712233 |
| PubChem Substance ID | 3885 |
| Chemical Name Translation | 3,4-二氢-2,2-二甲基-2H-萘并[1,2-b]吡喃-5,6-二酮 |
| Beilstein Registry Number | 0181499 |
| LabNetwork Molecule ID | LN01109720 |
| InChI | InChI=1S/C15H14O3/c1-15(2)8-7-11-13(17)12(16)9-5-3-4-6-10(9)14(11)18-15/h3-6H,7-8H2,1-2H3 |
| Formula | C15H14O3 |
| IUPAC Name | 2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione |
| InChIKey | QZPQTZZNNJUOLS-UHFFFAOYSA-N |
| Canonical SMILES | O=C1C(CCC(C)(C)O2)=C2C3=CC=CC=C3C1=O |
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分类
- Isotope Labelled Compounds
- {SNA} Apoptosis and Cell Cycle, Bioactive Small Molecules, Biochemicals and Reagents, Cancer Research, Cell Biology, Cell Signaling and Neuroscience, Chemopreventive Agents, DNA Repair Regulators,
- {SNA} Apoptosis and Cell Cycle, Bioactive Small Molecule Alphabetical Index, DNA Repair Regulators, DNA metabolism, Enzyme Inhibitors, Enzyme Inhibitors by Enzyme, Gene Regulation, L, R to Z, Topoisomerase I, 化学预防剂, 生化试剂, 生物活性小分子, 癌症研究, 细胞信号转导和神经科学, 细胞生物学,
产品应用
- ARQ-501 is a naphthoquinone compound derived from bark of Tabebuia sp., with antitumor, antibacterial, antifungal and antitrypanosomal activities. Beta-lapachone exerts its anti-tumor effect by indirect actions of inducing p53-independent apoptosis and cell cycle arrest mediated through altered activities of cell cycle control regulatory proteins; including down-regulating retinoblastoma protein (pRB), a transcriptional repressor target at transcription factor E2F-1, as well as induces expression of cyclin dependent kinase inhibitor 1A (CDKN1A or p21). Both E2F-1 and p21 are required for G1/S-phase transition during cell cycle. This agent also inhibits DNA topoisomerase I by a mechanism distinct from that of camptothecin, and thereby blocks the formation of a cleavable complex leading to enzyme inhibition and prevent DNA repair. Furthermore, beta-lapachone could induce reactive oxygen species in vivo, and result in cytotoxicity.
相关文献及参考
- Renslo, A., et al.: Nat. Chem. Biol., 2, 701 (2006),
- Hopkins, A., et al.: Nat. Chem. Biol., 4, 682 (2008),
- Stuart, K., et al.: J. Clin. Invest., 118, 1301 (2008),
安全信息
TYPE OF TEST : Cytogenetic analysis TEST SYSTEM : Rodent - hamster Ovary DOSE/DURATION : 2 umol/L REFERENCE : MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 288,263,1993
TYPE OF TEST : Sister chromatid exchange TEST SYSTEM : Rodent - hamster Ovary DOSE/DURATION : 1 umol/L REFERENCE : MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 288,263,1993
