28322-40-9Relevant articles and documents
Method for removing triphenylphosphine oxide
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Paragraph 0107-0108; 0110-0111, (2021/02/13)
The invention discloses a method for removing triphenylphosphine oxide. The method comprises: adding water into a reaction mixture of the compound shown in the formula I and isopentyltriphenylphosphine bromide for quenching reaction, adding an extracting agent into the reaction mixture, stirring, standing for layering, and washing an obtained organic phase with water; concentrating under reduced pressure, replacing with methanol to be thick, cooling to crystallize, filtering, and drying a filter cake to obtain a compound shown as a formula II which basically does not contain triphenylphosphine; or carrying out water precipitation to obtain the compound shown in the formula II which basically does not contain triphenylphosphine oxide.
Screening of a virtual mirror-image library of natural products
Noguchi, Taro,Oishi, Shinya,Honda, Kaori,Kondoh, Yasumitsu,Saito, Tamio,Ohno, Hiroaki,Osada, Hiroyuki,Fujii, Nobutaka
supporting information, p. 7653 - 7656 (2016/07/06)
We established a facile access to an unexplored mirror-image library of chiral natural product derivatives using d-protein technology. In this process, two chemical syntheses of mirror-image substances including a target protein and hit compound(s) allow the lead discovery from a virtual mirror-image library without the synthesis of numerous mirror-image compounds.
Conjugated dienes as prohaptens in contact allergy: In vivo and in vitro studies of structure-activity relationships, sensitizing capacity, and metabolic activation
Bergstroem, Moa Andresen,Luthman, Kristina,Nilsson, J. Lars G.,Karlberg, Ann-Therese
, p. 760 - 769 (2007/10/03)
There is a great interest in developing in vitro/in silico methods for the prediction of contact allergenic activity. However, many proposed methods do not take the activation of prohaptens to sensitizers by skin metabolism into account. As a consequence, consumer products containing potent sensitizers could be marketed. To identify prohaptens, studies regarding their structure-activity relationships and the mechanisms of their activation must be conducted. In the present investigation, we have studied the structure-activity relationships for alkene prohaptens. A series of seven alkenes (1-7), all of the same basic structure but with variation in the number and position(s) of the double bond(s), were designed and screened for sensitizing capacity using the murine local lymph node assay. Compounds 1-7 were also incubated with liver microsomes in the presence of glutathione to trap and identify reactive metabolites. The metabolic conversion of three alkenes (9-11) to epoxides (12-15) was also studied along with comparison of their sensitizing capacity. Our results show that conjugated dienes in or in conjunction with a six-membered ring are prohaptens that can be metabolically activated to epoxides and conjugated with GSH. Related alkenes containing isolated double bonds and an acyclic conjugated diene were shown to be weak or nonsensitizers. For the first time, the naturally occurring monoterpenes α-phellandrene, β-phellandrene, and α-terpinene were demonstrated to be prohaptens able to induce contact allergy. The difference in sensitizing capacity of conjugated dienes as compared to alkenes with isolated double bonds was found to be due to the high reactivity and sensitizing capacity of the allylic epoxides metabolically formed from conjugated dienes. We recommend that these structure-activity relationship rules are incorporated into in silico predictive databases and propose that the prediction of contact allergenic activity of suspected prohaptens is based on assessment of susceptibility to metabolic activation and chemical reactivity of potential metabolites.