13076-29-4Relevant articles and documents
Conversion of Alkoxy-9,10-anthraquinones to Alkoxyanthracenes
Shyamasundar, Nagaraj,Caluwe, Paul
, p. 809 - 811 (1981)
-
Syntheses and bioactivities of substituted 9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrones. Unusual reactivities with amines
Hua, Duy H.,Tamura, Masafumi,Huang, Xiaodong,Stephany, Heidi A.,Helfrich, Brian A.,Perchellet, Elisabeth M.,Sperfslage, Bonnie J.,Perchellet, Jean-Pierre,Jiang, Suping,Kyle, Dennis E.,Chiang, Peter K.
, p. 2907 - 2912 (2002)
A number of substituted 9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrones have been synthesized and their anticancer and antimalarial activities evaluated. A one-pot synthesis of 2,5,8-trimethoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4-dione (4) was achieved by heating a mixture of 1,4-dimethoxyanthracene, methoxyhydroquinone, silver oxide, and zinc iodide in toluene. Regioselective bromination of 4 and 2-methoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrone (7) with N-bromosuccinimide provided 2-bromo-3,5,8-trimethoxy-9,10-dihydro-9,10-[1,2]-benzenoanthracene-1,4-dione and 2-bromo-3-methoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrone (1), respectively. The reactions of 1 with aliphatic primary amines and secondary amines, respectively, produced different products, a result most likely attributed to the different basicities (or nucleophilicities) and steric effects of the two kinds of amines. The structure of the displacement product, 2-bromo-3- [2-(tert-butoxycarbonyl)ethylamino]-9,10-dihydro-9,10-[1,2] benzenoanthracene-1,4,5,8-tetrone, from the reaction of 1 with tert-butyl 3-aminopropanoate was unequivocally determined by a single-crystal X-ray analysis. IC50 values of triptycene bisquinones for the inhibition of L1210 leukemia cell viability are in the 0.11-0.27 μM range and for the inhibition of Plasmodium falciparum 3D7 are in the 4.7-8.0 μM range.
Clip[5]arenes: A new family of molecular clips
Shi, Bingbing,Li, Zhengtao,Liu, Yuezhou,Shangguan, Liqing,Zhu, Huangtianzhi,Ju, Huaqiang,Huang, Feihe
, p. 3477 - 3480 (2018)
Here we report the design and syntheses of two new triptycene-based rigid acyclic C-shaped hosts, clip[5]arenes C[5]OH and C[5]ME, and the strong host–guest complexation between C[5]OH and an electron-poor bipyridinium salt, paraquat G. The Ka value for the host–guest complex C[5]OH ? G was calculated to be (1.09 ± 0.36) × 105 M?1 in acetone by using a non-linear curve-fitting method based on the UV–vis absorption titration experiments. Furthermore, based on this new host–guest recognition motif, a novel pseudopolyrotaxane-like supramolecular structure was constructed with C[5]OH threaded on polyviologen polymer VP-10.
The reaction of triptycene haloquinones with alkoxides. An unusual route to pentiptycene quinones
Spyroudis, Spyros,Xanthopoulou, Nikoletta
, p. 3767 - 3770 (2007/10/03)
Triptycene haloquinones 3 react with sodium alkoxides in refluxing alcohol to afford, besides the expected substitution products, pentiptycene quinone 4. This approach to 4 is compared with a Diels-Alder strategy to the same compound.