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

4707-32-8
SMILES: CC1(C)CCC2=C(O1)c1ccccc1C(=O)C2=O

化学属性

Mol. FormulaC15 H14 O3
Mol. Weight242.27
Appearance Solid powder
SolubilitySoluble in DMSO, not in water
Melting Point>110°C (dec.)
Boiling Point

别名和识别编码

Chemical Name3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione
CAS Number4707-32-8
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 NumberMFCD01712233
PubChem Substance ID3885
Chemical Name Translation3,4-二氢-2,2-二甲基-2H-萘并[1,2-b]吡喃-5,6-二酮
Beilstein Registry Number0181499
LabNetwork Molecule IDLN01109720
InChIInChI=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
FormulaC15H14O3
IUPAC Name2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione
InChIKeyQZPQTZZNNJUOLS-UHFFFAOYSA-N
Canonical SMILESO=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

WGK Germany3
RTECSQL6127400
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter 
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

Storage condition -20 -20°C -20℃ Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

系列性分类

  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Apoptosis and Cell Cycle - Cell Signaling and Neuroscience
  5. DNA metabolism - Apoptosis and Cell Cycle
  6. DNA Repair Regulators - DNA metabolism
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Apoptosis and Cell Cycle - Cell Signaling and Neuroscience
  5. DNA metabolism - Apoptosis and Cell Cycle
  6. DNA Repair Regulators - DNA metabolism
  1. Medical Research Areas
  2. DNA Damage
  3. Topoisomerase

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