18486-69-6Relevant articles and documents
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Suga,T. et al.
, p. 545 - 548 (1972)
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Hydroxylation by Cytochrome P-450 and Metalloporphyrin Models. Evidence for Allylic Rearrangement
Groves, John T.,Subramanian, Durga V.
, p. 2177 - 2181 (1984)
The allylic hydroxylation of 3,3,6,6-tetradeuteriocyclohexene, methylenecyclohexane, and β-pinene has been examined with phenobarbital-induced liver microsomal cytochrome P-450 (P-450LM2) and with iron porphyrin and chromium porphyrin model systems.Aerobic and peroxide dependent enzymic regimes were investigated with purified P-450LM2 and with microsomal suspensions.Epoxidation and allylic hydroxylation were primary reactions with all substrates.With 3,3,6,6-tetradeuteriocyclohexene, the major hydroxylation product (60-80percent) was the result of hydroxylation at the deuterated allylic site.In all cases, a significant amount (20-40percent) of hydroxylation occurred with allylic rearrangement.The iron porphyrin/iodosylbenzene model system also showed preferential hydroxylation of the deuterated allylic site (70percent) with significant allylic rearrangement (30percent).By contrast, the chromium porphyrin/iodosylbenzene model system showed complete scrambling of the allylic system.Extensive rearrangement accompanied the hydroxylation of methylenecyclohexane and β-pinene by both the enzymic and metalloporphyrin systems whereas the selenium dioxide oxidation of these substrates gave selective allylic hydroxylation without rearrangement.A mechanism is suggested for allylic hydroxylation by cytochrome P-450 and by the metalloporhyrin model systems involving initial hydrogen atom abstraction from the allylic site and geminate, cage recombination of the incipient, allylic free radical.
Monoterpene-containing substituted coumarins as inhibitors of respiratory syncytial virus (Rsv) replication
Borisevich, Sophia S.,Galochkina, Anastasia V.,Khomenko, Tatyana M.,Korchagina, Dina V.,Nikolaeva, Yulia V.,Petukhova, Galina D.,Salakhutdinov, Nariman F.,Shtro, Anna A.,Volcho, Konstantin P.
, (2021/12/24)
Respiratory syncytial virus (RSV) is a critical cause of infant mortality. However, there are no vaccines and adequate drugs for its treatment. We showed, for the first time, that O-linked coumarin–monoterpene conjugates are effective RSV inhibitors. The most potent compounds are active against both RSV serotypes, A and B. According to the results of the time-of-addition experiment, the conjugates act at the early stages of virus cycle. Based on molecular modelling data, RSV F protein may be considered as a possible target.
A Simple, Mild and General Oxidation of Alcohols to Aldehydes or Ketones by SO2F2/K2CO3 Using DMSO as Solvent and Oxidant
Zha, Gao-Feng,Fang, Wan-Yin,Leng, Jing,Qin, Hua-Li
supporting information, p. 2262 - 2267 (2019/04/17)
A practical, general and mild oxidation of primary and secondary alcohols to carbonyl compounds proceeds in yields of up to 99% using SO2F2 as electrophile in DMSO as both the oxidant and the solvent at ambient temperature. No moisture- and oxygen-free conditions are required. Stoichiometric amount of inexpensive K2CO3, which generates easy to separate by-products, is used as the base. Thus, 5-gram scale runs proceeded in nearly quantitative yields by a simple filtration as the work-up. The use of a polar solvent such as DMSO, which usually promotes competing Pummerer rearrangement, is also noteworthy. This protocol is compatible with a variety of common N-, O-, and S-functional groups on (hetero)arene, alkene and alkyne substrates (68 examples). The protocol was applied (99% yield) to a formal synthesis of the important cholesterol-lowering drug Rosuvastatin. (Figure presented.).
The Taiji and Eight Trigrams chemistry philosophy of chiral iridium(III) complexes with triplex stereogenic centers
Yan, Zhi-Ping,Luo, Xu-Feng,Liao, Kang,Lin, Zi-Xuan,Wu, Zheng-Guang,Zhou, Yong-Hui,Zheng, You-Xuan
supporting information, p. 4045 - 4048 (2018/03/26)
Four novel chiral iridium(iii) complexes with triplex stereogenic centers were synthesized by introducing chiral carbon atoms into cyclometalated and ancillary ligands, and separated into eight isomers, which coincide with the old Chinese philosophy Eight Trigrams. The electron circular dichroism and circularly polarized luminescence spectra of four pairs of isomers show perfect mirror images with a dissymmetry factor (glum factor) of around 0.003.