129368-70-3Relevant articles and documents
Effective synthesis of ferrulactone II based on the use of 2-carboxyethyltriphenylphosphonium bromide
Cheskis, B. A.,Shpiro, N. A.,Moiseenkov, A. M.
, p. 760 - 763 (1993)
A simple synthesis of S,3Z-dodecen-11-olide, a component of the aggregation pheromone of the rusty grain beetle Cryptolestes ferrugineus (Stephen), was developed.The key stage was Wittig olefination of C9-aldehyde, prepared from S-propylene oxide, with C3
Synthesis and antitumor activity of novel pyridinium fullerene derivatives
Yasuno, Takumi,Ohe, Tomoyuki,Ikeda, Hitomi,Takahashi, Kyoko,Nakamura, Shigeo,Mashino, Tadahiko
, p. 6325 - 6337 (2019)
Purpose: We have previously reported that some cationic fullerene derivatives exhibited anticancer activity, and they are expected to be a potential lead compound for an anti-drug resistant cancer agent. However, they are bis-adducts and a mixture of multiple regioisomers, which cannot be readily separated due to the variability of substituent positions on the fullerene cage. To overcome this issue, we evaluated the antiproliferative activities of a set of mono-adduct derivatives and examined their structure-activity relationship. In addition, the in vivo antitumor activity of selected derivatives was also examined. Methods: Nineteen pyridinium fullerene derivatives were newly designed and synthesized in this study. Their antiproliferative activities were evaluated using several cancer cell lines including drug-resistant cells. Furthermore, in vivo antitumor activity of several derivatives was investigated in mouse xenograft model of human lung cancer. Results: The derivatives inhibited the proliferation of cancer cell lines, including cisplatin-resistant cells and doxorubicin-resistant cells. It was also shown that compound 10 (10 μM), 13 (10 μM) and cis-14 (10 μM) induced the intracellular oxidative stress. In addition, compound 13 (20 mg/kg) and cis-14 (15 mg/kg) significantly exhibited antitumor activity in mouse xenograft model of human lung cancer. Conclusion: We synthesized a novel set of mono-adduct fullerene derivatives functionalized with pyridinium groups and found that most of them show potent antiproliferative activities against cancer cell lines and some of them show significant antitumor activities in vivo. We propose that these fullerene derivatives serve as the lead compounds for a novel type of antitumor agents.
Weinreb Amide, Ketone and Amine as Potential and Competitive Secondary Molecular Stations for Dibenzo-[24]Crown-8 in [2]Rotaxane Molecular Shuttles
Coutrot, Frédéric,Gauthier, Maxime
supporting information, p. 17576 - 17580 (2021/12/09)
This paper reports the synthesis and study of new pH-sensitive DB24C8-based [2]rotaxane molecular shuttles that contain within their axle four potential sites of interaction for the DB24C8: ammonium, amine, Weinreb amide, and ketone. In the protonated state, the DB24C8 lay around the best ammonium site. After either deprotonation or deprotonation-then-carbamoylation of the ammonium, different localizations of the DB24C8 were seen, depending on both the number and nature of the secondary stations and steric restriction. Unexpectedly, the results indicated that the Weinreb amide was not a proper secondary molecular station for the DB24C8. Nevertheless, through its methoxy side chain, it slowed down the shuttling of the macrocycle along the threaded axle, thereby partitioning the [2]rotaxane into two translational isomers on the NMR timescale. The ketone was successfully used as a secondary molecular station, and its weak affinity for the DB24C8 was similar to that of a secondary amine.
LIPID NANOPARTICLE
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Paragraph 0082-0085, (2019/12/03)
PROBLEM TO BE SOLVED: To provide lipid nanoparticles useful as a carrier for drug active ingredients such as siRNA and having excellent delivery efficiency even if the particle diameter has become small. SOLUTION: Provided is a lipid nanoparticle containing a cationic lipid represented by the following general formula (I) [a is an integer from 3 to 5; b is 0 or 1; R1 and R2 are each independently a group having 20 or more carbon atoms represented by the following general formula (A) (q represents an integer from 1 to 9, r represents 0 or 1, s represents an integer from 1 to 3, t represents 0 or 1, u represents an integer from 1 to 8, c represents 0 or 1, v represents an integer from 4 to 12); X represents a group represented by the following general formula (B) (d is an integer of 0 to 3, R3 and R4 are each independently a C1-4 alkyl group or a C2-4 alkenyl group) or a 5- to 7-membered non-aromatic heterocyclic group]; and a neutral lipid with a hydrophilic group having 2 or more carbon atoms and a linear hydrophobic group. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT