- Anti HIV-1 agents 7. Discovery of 1-hydroxy-4-chloro-9,10-anthraquinone derivatives as New HIV-1 Inhibitors in Vitro
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In continuation of our program aimed at the discovery and development of anti-HIV-1 agents, six 1-hydroxy-4- chloro-9, 10-anthraquinone derivatives (3-8) were prepared and preliminarily evaluated as HIV-1 inhibitors in vitro for the first time. Compounds 4 and 6 exhibited the potent anti-HIV-1 activities with EC50 values of 9.81 and 17.90 μg/mL, and TI values of >13.58 and >11.17, respectively. It demonstrated that introduction of the alkylacyloxy or alkylsulfonyloxy group at the 1-position of 1-hydroxy-4-chloro-9,10- anthraquinone could afford the more promising and potent compound than that having arylacyloxy or arylsulfonyloxy one.
- Huang, Ning,Wang, Qin,Yang, Liu-Meng,Xu, Hui,Zheng, Yong-Tang
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experimental part
p. 602 - 605
(2012/05/05)
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- Halophenol rearrangement in Lewis acid-catalyzed Friedel-Crafts conditions: Evidence of competitive initial protonation and acylation
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Halogen rearrangement was observed during the Lewis acid-catalyzed Friedel-Crafts reaction of phthalic anhydride with bromophenols or bromoanisole. Further investigation revealed that 2-, 3-, and 4-bromophenols undergo rearrangement into other isomers under these reaction conditions. Product distribution from these reactions suggested that halogen rearrangement takes place during the s-complex intermediate of the condensation step. Furthermore, iodophenol undergoes hydrodeiodination rapidly rather than rearrangement, whereas chlorophenol does not undergo rearrangement at all. CSIRO 2008.
- Saha, Koushik,Lajis, Nordin H.,Abas, Faridah,Naji, Nabil Ali,Hamzah, A. Sazali,Shaari, Khozirah
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p. 821 - 825
(2008/12/22)
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- Reactions of 1-Halo-4-nitroanthraquinones with C-nucleophiles
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1-Fluoro-4-nitroanthraquinone reacts with C-nucleophiles, yielding the corresponding fluorine replacement products. Reactions of 1-chloro-4-nitroanthraquinone with the same nucleophiles result in formation of mixtures of dechlorination and denitration pro
- Tabatskaya,Beregovaya
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p. 410 - 415
(2007/10/03)
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- Sodium trimethyl silanoate. A hydroxyl synthon for fluoride S(n)Ar type displacements from anthracene-9,10-diones, benz[g]isoquinoline-5-10-diones and nitrobenzenes
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Treatment of fluoroanthracene-9,10-diones, fluorobenz[g]isoquinoline- 5,10-diones and 1- or 4-fluoronitrobenzenes with sodium trimethylsilanoate in THF followed by acidification readily yields the corresponding hydroxyl analogues.
- Krapcho, A. Paul,Waterhouse, David
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p. 3415 - 3422
(2007/10/03)
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- PHOTO-NUCLEOPHILIC SUBSTITUTION REACTION OF HALOGENOANTHRAQUINONE IN CONCENTRATED SULFURIC ACID. PHOTO-HYDROXYDEHALOGENATION
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The photo-reaction of halogen-substituted anthraquinones in sulfuric acid was studied with near UV or visible light. α-Chloro-substituted anthraquinones were photo-hydroxylated mainly to form α-hydroxyanthraquinones in fairly good yields.However, β-halogenoanthraquinones gave no dehalogenated products under the same conditions.
- Seguchi, Kazuyoshi,Ikeyama, Hiromi
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p. 1493 - 1494
(2007/10/02)
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