74693-34-8Relevant academic research and scientific papers
Synthesis and pharmacophore modeling of naphthoquinone derivatives with cytotoxic activity in human promyelocytic leukemia HL-60 cell line
Pérez-Sacau, Elisa,Díaz-Peńate, Raquel G.,Estévez-Braun, Ana,Ravelo, Angel G.,García-Castellano, Jose M.,Pardo, Leonardo,Campillo, Mercedes
, p. 696 - 706 (2008/02/01)
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.
Radermachera xylocarpa: The highly efficient source of lapachol and synthesis of its derivatives
Shetgiri,Kokitkar,Sawant
, p. 133 - 135 (2007/10/03)
Isolation and characterization of the major chemical constituents from the stem bark of Radermachera xylocarpa. Chloroform extract of the powdered stem bark contains mainly two components: one is lapachol (91.2%) and second is α-lapachone (5.0%), which are reported herewith first time from this plant, in good quantity and purity.
Bromination with N-Bromosuccinimide : Part III - Formation of 3'-Bromo-β-lapachone, Dehydro-iso-β-lapachone and 4'-Bromo-iso-β-lapachone from Lapachol
Gupta, R. B.,Khanna, R. N.
, p. 17 - 19 (2007/10/02)
Lapachol (I), on bromination with N-bromosuccinimide, affords three ortho-naphthoquinone derivatives which have been characterized to be 3'-bromo-β-lapachone (IV), dehydro-iso-β-lapachone (V) and 4'-bromo-iso-β-lapachone (X) on the basis of spectral and chemical studies.
