6009-31-0Relevant academic research and scientific papers
Discovery of N-(3-((7H-purin-6-yl)thio)-4-hydroxynaphthalen-1-yl)- sulfonamide derivatives as novel protein kinase and angiogenesis inhibitors for the treatment of cancer: Synthesis and biological evaluation. Part III
Xu, Fuming,Xu, Hao,Wang, Xuejian,Zhang, Lei,Wen, Qingli,Zhang, Yingjie,Xu, Wenfang
, p. 1487 - 1495 (2014/03/21)
A novel series of N-(3-((7H-purin-6-yl)thio)-4-hydroxynaphthalen-1-yl)- sulfonamides were designed and synthesized. Biological characterization revealed that several compounds exerted enhanced anti-proliferative activity against human umbilical vein endothelial cells (HUVECs) and several cancer cell lines and high specific protein kinase and angiogenesis inhibitory activities. Compared with our previously synthesized compounds, the substitution of sulfonamide structure for amide fragment played an essential role for the advance of inhibitory activities. In addition, the replacement of 1H-1,2,4-triazole ring by 7H-purine did not result in obvious decrease of inhibition efficacy, indicating that the sulfonamide structure contributes even more to the inhibition efficacy than the 1H-1,2,4-triazole ring. Among these compounds, compound 9n demonstrated comparable in vitro antiangiogenic activities to pazopanib in both HUVEC tube formation assay and the rat thoracic aorta rings (TARs) test. Meanwhile, compound 9n was identified to inhibit Akt1 (IC50 = 1.73 μM) and Abl tyrosine kinase (IC50 = 1.53 μM) effectively.
Synthesis of 5-substituted 2,3-dihydrobenzofurans in a one-pot oxidation/cyclization reaction
Baragona, Fabien,Lomberget, Thierry,Duchamp, Christian,Henriques, Natali,Lo Piccolo, Eugenio,Diana, Patrizia,Montalbano, Alessandra,Barret, Roland
experimental part, p. 8731 - 8739 (2011/12/02)
Variously substituted 2,3-dihydrobenzofurans have been synthesized according to a sequential one-pot oxidation/cyclization procedure between para-aminophenol derivatives and an azadiene.
BROMINATION OF 4-ARENESULFONAMIDOPHENOLS (OR 1-NAPHTHOLS) AND N-ARYLSULFONYL-1,4-BENZO(NAPHTHO)QUINON-4-IMINES
Avdeenko, A. P.,Velichko, N. V.
, p. 1687 - 1692 (2007/10/02)
2,3,6-Tribromo-N-phenylsulfonyl-1,4-benzoquinon-4-imines are formed on bromination of 4-arenesulfonamidophenols and N-aryl-sulfonyl-1,4-benzoquinon-4-imines but 2-bromo-N-arylsulfonyl-1,4-naphthoquinon-4-imines are formed from 4-arenesulfonamido-1-naphthols and N-arylsulfonyl-1,4-naphthoquinon-4-imines.
1,4-Addition of Triazolium Thiolates to Quinones.
Altland, Henry W.,Briffa, Barry F.
, p. 433 - 437 (2007/10/02)
In the presence of aprotic acid, 1,2,4-triazolium-3-thiolates 1 undergo 1,4-Michael additions to quinones to fortm the corresponding thioether-substituted hydroquinones salts 2.When, however, tetrafluoroboric acid is added to a stirred aqueous suspension of triazolium thiolate 1a and p-benzoquinone, the 2,5-bis(triazolium thiolate) adduct 6, rather than the expected monoadduct 5, is isolated.Since o-quinones are extremely reactive and often difficult to isolate, they can be generated in situ by oxidation of the corresponding catechols with hydrogen peroxide in the presence of a protic acid and then trapped by a triazolium thiolate to form thioether hydroquinone salts 8.Triazolium thiolate 1a adds to a 1,4-naphtoquinone imine to give the (triazoliothio)-4-(benzenesulfonamido)-1-naphtolsalt 11.Triazoliotioquinone tetrafluoroborates 16, which can be isolated as crystalline yellow salts, are rapidly formed by oxidation of the corresponding hydroquinone salts 2 with nitrosonium tetrafluoroborate in acetonitrile.
