25636-49-1Relevant articles and documents
Methyl homologues of methyl jasmonate and methyl dihydrojasmonate (Hedione) from sorbyl alcohol
Giersch, Wolfgang,Farris, Iris
, p. 1601 - 1606 (2004)
Treatment of cycloalkanone dimethyl acetals 3-6 with sorbyl alcohol (=(2E,4E)-hexa-2,4-dien-1-ol; 1) in the presence of acids afforded the novel cycloalkenones 8, 9, 11, and 13 via a domino reaction (Claisen rearrangement with intramolecular ene reaction and retro-ene reaction). Cyclopentenone 8 was readily transformed into 14 and 15, methyl homologues of racemic methyl jasmonate (16) and methyl dihydrojasmonate (= Hedione; 17), respectively. The organoleptic properties of 14 and 15 are also discussed.
Ecofriendly fast batch synthesis of dioxolanes, dithiolanes, and oxathiolanes without solvent under microwave irradiation
Perio, Bertrand,Dozias, Marie-Joelle,Hamelin, Jack
, p. 428 - 430 (1998)
2,2-Dimethoxypropane and 3,3-dimethoxypentane react with 1,2-ethanediol, thio, and oxathio analogues to give the corresponding protected carbonyls in high yield under mild solvent-free conditions. These environmentally benign conditions under microwave irradiation are applied to a large-scale synthesis.
Design of chemically stable, potent, and efficacious MDM2 inhibitors that exploit the retro-mannich ring-opening-cyclization reaction mechanism in spiro-oxindoles
Aguilar, Angelo,Sun, Wei,Liu, Liu,Lu, Jianfeng,McEachern, Donna,Bernard, Denzil,Deschamps, Jeffrey R.,Wang, Shaomeng
, p. 10486 - 10496 (2015/02/19)
Inhibition of the MDM2-p53 protein-protein interaction is being actively pursued as a new anticancer therapeutic strategy, and spiro-oxindoles have been designed as a class of potent and efficacious small-molecule inhibitors of this interaction (MDM2 inhibitors). Our previous study showed that some of our first-generation spiro-oxindoles undergo a reversible ring-opening-cyclization reaction that, from a single compound in protic solution, results in an equilibrium mixture of four diastereoisomers. By exploiting the ring-opening-cyclization reaction mechanism, we have designed and synthesized a series of second-generation spiro-oxindoles with symmetrical pyrrolidine C2 substitution. These compounds undergo a rapid and irreversible conversion to a single, stable diastereoisomer. Our study has yielded compound 31 (MI-1061), which binds to MDM2 with Ki = 0.16 nM, shows excellent chemical stability, and achieves tumor regression in the SJSA-1 xenograft tumor model in mice.
4-chloro-3,5-dimethyl-2-sulfonyl pyridines
-
Referential example 2, (2010/11/29)
2-Sulfonylpyridine derivatives can be industrially produced efficiently by reacting a sulfonyl cyanide derivative with an α,β-unsaturated carbonyl compound and a 2-{[(2-pyridyl)methyl]thio}-1H-benzimidazole skeleton can be formed in one step in a good yield by reacting this type of the 2-sulfonylpyridine derivative with a 2-methylthio-1H-benzimidazole derivative in the presence of an organolithium compound.