53865-04-6Relevant articles and documents
Synthesis and cytotoxic activity of benzo[a]pyrano[3,2-h] and [2,3-i]xanthone analogues of psorospermine, acronycine, and benzo[a]acronycine
Sittisombut, Chavalit,Boutefnouchet, Sabrina,Trinh Van-Dufat, Hanh,Tian, Wen,Michel, Sylvie,Koch, Michel,Tillequin, Francois,Pfeiffer, Bruno,Pierre, Alain
, p. 1113 - 1118 (2006)
Condensation of 2-hydroxy-1-naphthalenecarboxylic acid with phloroglucinol afforded 9,11-dihydroxy-12H-benzo[a]xanthen-12-one (6). Construction of an additional dimethylpyran ring onto this skeleton, by alkylation with 3-chloro-3-methyl-1-butyne followed by Claisen rearrangement, gave access to 6-hydroxy-3,3-dimethyl-3H,7H-benzo[a]pyrano[3,2-h]xanthen-7-one (12) and 5-hydroxy-2,2-dimethyl-2H,6H-benzo[a]pyrano[2,3-i]xanthen-6-one (13), which were methylated into 6-methoxy-3,3-dimethyl-3H,7H-benzo[a]pyrano[3,2-h]xanthen-7-one (14) and 5-methoxy-2,2-dimethyl-2H,6H-benzo[a]pyrano[2,3-i]xanthen-6-one (15), respectively. Osmium tetroxide oxidation of 14 and 15 gave the corresponding (±)-cis-diols 16 and 17, which afforded the corresponding esters 18-21 upon acylation. Similarly, condensation of 2-hydroxy-1-naphthalenecarboxylic acid with 3,5-dimethoxyaniline gave 11-amino-9-methoxy-12H-benzo[a]xanthen-12- one (23) which was converted into 11-amino-9-hydroxy-12H-benzo[a]xanthen-12-one (24) upon treatment with hydrogen bromide in acetic acid. Alkylation with 3-chloro-3-methyl-1-butyne followed by Claisen rearrangement afforded 6-amino-3,3-dimethyl-3H,7H-benzo[a]pyrano[3,2-h]xanthen-7-one (25) and 5-amino-2,2-dimethyl-2H,6H-benzo[a]pyrano[2,3-i]xanthen-6-one (26). The new benzopyranoxanthone derivatives only displayed marginal antiproliferative activity when tested against L1210 and KB-3-1 cell lines. The only compounds found significantly active against L1210 cell line, 16 and 20, belong to the benzo[a]pyrano[3,2-h]xanthen-7-one series, which possess a pyran ring fused angularly onto the xanthone basic core.
New benzoxanthone derivatives as topoisomerase inhibitors and DNA cross-linkers
Cho, Hee-Ju,Jung, Mi-Ja,Woo, Sangwook,Kim, Jungsook,Lee, Eung-Seok,Kwon, Youngjoo,Na, Younghwa
experimental part, p. 1010 - 1017 (2010/04/26)
We synthesized 12 benzoxanthone derivatives classified as three different groups based on the tetracyclic ring shapes and evaluated their pharmacological activities to find potential anticancer agents. In the cytotoxicity test, most compounds showed effective cancer cell growth inhibition against the HT29 and DU145 cell lines. Among the compounds tested, compound 19 was the most effective in the cancer cell lines tested. Compound 9 showed dual inhibitory activities against DNA relaxation by topoisomerases I and II. The% inhibition of compound 9 on topoisomerase I was comparable to that of camptothecin. Compound 9 efficiently blocked topoisomerase II function by almost threefold than etoposide at 20 μM. Compound 19 had selective topoisomerase II inhibitory activity at 100 μM. The DNA cross-linking test revealed that only compounds 8 and 19, which possess epoxy groups, cross-linked DNA duplex, while 14 did not. From the combined pharmacological results, we proposed that the target through which compound 19 inhibits cancer cell growth may be the DNA duplex itself and/or DNA-topoisomerase II complex.
Studies in synthesis of xanthones: Part VIII
Patel G N,Trivedi K N
, p. 437 - 439 (2007/10/02)
Thermal condensation of the methyl esters of 2,6-dihydroxy-, 2,4-dihydroxy- and 2,4,6-trihydroxy-benzoic acids has been carried out with different phenols in refluxing diphenyl ether to give various xanthones in good yields.Condensation of methyl 5-bromo-2-hydroxybenzoate with hydroquinone gives 7-bromo-1,4-dihydroxyxanthone (19) and 7-bromo-2-hydroxyxanthone (20).However, condensation of methyl 5-chloro-2,6-dihydroxybenzoate with phloroglucinol gives 5-chloro-1,3,8-trihydroxyxanthone (21).The structures of these products have been established by IR, mass and PMR spectral studies.
