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
A novel method for direct conversion of tetrahydropyranyl ethers into t-butyldimethylsilyl ethers with t-butyldimethylsilyl triflate and dimethyl sulfide
Kim,Kee
, p. 2899 - 2900 (1990)
Direct conversion of THP ethers into TBS ethers has been achieved with TBSOTf and dimethyl sulfide in dichloromethane.
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.
Studies directed towards the total synthesis of (±)-himbacine
De Baecke, Govert,De Clercq, Pierre J.
, p. 7515 - 7518 (1995)
The synthesis of aldehyde 11a is reported based upon the intramolecular Diels-Alder reaction of triene 10, the butenolide-diene part of which was obtained in one step via the condensation of the enolate derived from the (Z)-enoate ester 5 with 2-acetoxypropanal. Aldehyde 11a possesses the correct stereochemistry of the tricyclic part of himbacine, an important muscarine receptor antagonist.
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.
Preparation method of alkyl nitrile compound
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Paragraph 0101-0103, (2020/05/14)
The invention discloses a preparation method of an alkyl nitrile compound shown as formula I. The preparation method comprises the following step: in a solvent, in the presence of an additive, carrying out substitution reaction as shown in the specification on a cyanation reagent and an alkyl halide shown as formula II to obtain the alkyl nitrile compound shown as formula I, wherein the cyanationreagent is Zn (CN) 2 and/or Cu (CN) 2; the additive is one or more of an inorganic base, an organic base and a quaternary ammonium salt.
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
BRIDGED COMPOUNDS FOR THE TREATMENT OF BACTERIAL INFECTIONS
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Paragraph 00153; 00157, (2016/08/23)
Novel bridged compounds are disclosed herein, along with their pharmaceutically acceptable salts, hydrates and prodrugs. Also disclosed are compositions comprising such compounds, methods of preparing such compounds and methods of using such compounds as antibacterial agents. The disclosed compounds, their pharmaceutically acceptable salts, hydrates and prodrugs, as well as compositions comprising such compounds, salts, hydrates and prodrugs, are useful for treating bacterial infections and associated diseases and conditions.
Antibacterial activities of fluorescent nano assembled triphenylamine phosphonium ionic liquids
Brunel, Frédéric,Lautard, Christelle,Garzino, Frédéric,Giorgio, Suzanne,Raimundo, Jean M.,Bolla, Jean M.,Camplo, Michel
supporting information, p. 3770 - 3773 (2016/07/21)
Staphylococcus aureus, a Gram positive coccal bacterium is a major cause of nosocomial infection. We report the synthesis of new triphenylamine phosphonium ionic liquids which are able to self-assemble into multiwall nanoassemblies and to reveal a strong
Synthesis of Macrocyclic Lactones via Ring Transformation of 4-(ω-Hydroxyalkyl)-1,3-oxazol-5(4H)-ones
Fritschi, Stephan P.,Linden, Anthony,Heimgartner, Heinz
, p. 523 - 538 (2016/07/22)
The synthesis of α-benzamido-α-benzyl lactones 23 of various ring size was achieved either via ‘direct amide cyclization’ by treatment of 2-benzamido-2-benzyl-ω-hydroxy-N,N-dimethylalkanamides 21 in toluene at 90 – 110° with HCl gas or by ‘ring transformation’ of 4-benzyl-4-(ω-hydroxyalkyl)-2-phenyl-1,3-oxazol-5(4H)-ones under the same conditions. The precursors were obtained by C-alkylations of 4-benzyl-2-phenyl-1,3-oxazol-5(4H)-one (15) with THP- or TBDMS-protected ω-hydroxyalkyl iodides. Ring opening of the THP-protected oxazolones by treatment with Me2NH followed by deprotection of the OH group gave the diamides 21, whereas deprotection of the TBDMS series of oxazolones 25 with TBAF followed by treatment with HCl gas led to the corresponding lactones 23 in a one-pot reaction.