65017-94-9

Upstream product

• 67-56-1 methanol 
• 4707-32-8 2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione 
• 64-17-5 ethanol 
• 84-79-7 Lapachol 

Relevant academic research and scientific papers

Synthesis and pharmacophore modeling of naphthoquinone derivatives with cytotoxic activity in human promyelocytic leukemia HL-60 cell line

Catalyst/HypoGen pharmacophore modeling approach and three-dimensional quantitative structure-activity relationship (3D-QSAR)/comparative molecular similarity indices analysis (CoMSIA) methods have been successfully applied to explain the cytotoxic activity of a set of 51 natural and synthesized naphthoquinone derivatives tested in human promyelocytic leukemia HL-60 cell line. The computational models have facilitated the identification of structural elements of the ligands that are key for antitumoral properties. The four most salient features of the highly active β-cycled-pyran-1,2-naphthoquinones [0.1 μM 50 0.6 μM] are the hydrogen-bond interactions of the carbonyl groups at C-1 (HBA1) and C-2 (HBA2), the hydrogen-bond interaction of the oxygen atom of the pyran ring (HBA3), and the interaction of methyl groups (HYD) at the pyran ring with a hydrophobic area at the receptor. The moderately active 1,4-naphthoquinone derivatives accurately fulfill only three of these features. The results of our study provide a valuable tool in designing new and more potent cytotoxic analogues.

Bromination with N-Bromosuccinimide : Part II - An Unusual Dibromination of β-Lapachone to 3',4'-Dibromo-β-lapachone

β-Lapachone (I), on bromination with N-bromosuccinimide, affords 3-bromo-dehydro-α-lapachone (II), dehydro-α-lapachone (III), 3'-bromo-dehydro-β-lapachone (IV) and 3'-bromo-4'-hydroxy-β-lapachone (VI).The formation of II, IV and VI via an intermediate product 3',4'-dibromo-β-lapachone (IX) has been established.IX is also easily converted to 3'-bromo-4'-methoxy-β-lapachone (XIV) and 3'-bromo-4'-ethoxy-β-lapachone (XV) by treatment with methanol and ethanol, respectively.