79839-49-9Relevant articles and documents
Efficient Synthesis of Bis(dibromomethyl)arenes as Important Precursors of Synthetically Useful Dialdehydes
Bodzioch, Agnieszka,Owsianik, Krzysztof,Skalik, Joanna,Kowalska, Emilia,Stasiak, Anna,Ró?ycka-Soko?owska, Ewa,Marciniak, Bernard,Ba?czewski, Piotr
, p. 3509 - 3514 (2016/10/17)
This work presents an efficient synthesis of bis(dibromomethyl)benzenes and a bis(dibromomethyl)thiophene as precursors of aromatic dialdehydes by bromination of dimethyl-substituted arenes under various reaction conditions (yields up to 99%). Several new variants of this reaction, including the use of N-bromosuccinimide (NBS) and bromine, and various solvents to replace carbon tetrachloride, benzene and carbon disulfide, were also tested. In the optimised protocols, the inconvenient solvents were replaced by 1,2-dichloroethane (DCE) and/or acetonitrile. In the DCE protocols, we reduced reaction times 24-32-fold, reduced the amount of NBS a fewfold and lowered power consumption relative to the literature protocols. The procedures also allowed elimination of long-lasting incandescent irradiation (100-500 W). The replacement of NBS by bromine led to a further reduction in the amount of brominating agent. The obtained bromo derivatives were efficiently converted into the corresponding dialdehydes (90-96%), which in turn are useful in materials chemistry.
Synthesis of an alkylthio-substituted dibenz[a,j]anthracene with improved solubility via the oxidative photocyclization of 1,3-distyrylbenzene derivatives
Toyoshima, Takuya,Yoshida, Satoshi,Watanabe, Soichiro
, p. 1904 - 1911 (2013/04/10)
A series of 1,3-distyrylbenzene compounds bearing different substituents at the 2-position have been synthesized and subjected to an oxidative photocyclization process. The 1,3-distyrylbenzene compounds substituted with chloro, alkylthio, and diphenylphosphino groups at the 2-position afforded dibenz[a,j]anthracene derivatives, whereas those bearing methyl, trimethylsilyl, dimethylamino, butoxy, and fluoro groups gave benzo[c]chrysene derivatives. The solubility of dibenz[a,j]anthracene in organic solvents was improved by the introduction of alkylthio groups.
Design and synthesis of de novo cytotoxic alkaloids by mimicking the bioactive conformation of paclitaxel
Sun, Liang,Veith, Jean M.,Pera, Paula,Bernacki, Ralph J.,Ojima, Iwao
supporting information; experimental part, p. 7101 - 7112 (2010/10/19)
Novel paclitaxel-mimicking alkaloids were designed and synthesized based on a bioactive conformation of paclitaxel, that is, REDOR-Taxol. The alkaloid 2 bearing a 5-7-6 tricyclic scaffold mimics REDOR-Taxol best among the compounds designed and was found to be the most potent compound against several drug-sensitive and drug-resistant human cancer cell lines. MD simulation study on the paclitaxel mimics 1 and 2 as well as REDOR-Taxol bound to the 1JFF tubulin structure was quite informative to evaluate the level of mimicking. The MD simulation study clearly distinguishes the 5-6-6 and 5-7-6 tricyclic scaffolds, and also shows substantial difference in the conformational stability of the tubulin-bound structures between 2 and REDOR-Taxol. The latter may account for the large difference in potency, and provides critical information for possible improvement in the future design of paclitaxel mimics.
