- Continuous flow synthesis of lipophilic cations derived from benzoic acid as new cytotoxic chemical entities in human head and neck carcinoma cell lines
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Continuous flow chemistry was used for the synthesis of a series of delocalized lipophilic triphenylphosphonium cations (DLCs) linked by means of an ester functional group to several hydroxylated benzoic acid derivatives and evaluated in terms of both reaction time and selectivity. The synthesized compounds showed cytotoxic activity and selectivity in head and neck tumor cell lines. The mechanism of action of the molecules involved a mitochondrial uncoupling effect and a decrease in both intracellular ATP production and apoptosis induction. This journal is
- Aguilera, Jocelyn,Castro-Castillo, Vicente,Ferreira, Jorge,Gajardo-De La Fuente, Javier,Olmedo, Ivonne,Palominos, Charlotte,Ramires-Fernandez, Ricardo,Valencia, Marcelo,Catalán, Mabel,Domínguez, Marta,Jara, José A.,Molina-Berríos, Alfredo,Souto, José A.
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- Mitoapocynin, a mitochondria targeted derivative of apocynin induces mitochondrial ROS generation and apoptosis in multiple cell types including cardiac myoblasts: a potential constraint to its therapeutic use
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Mitoapocynin is a triphenylphosphonium conjugated derivative of apocynin that specifically locates to the mitochondria. It has been developed as a mitochondrially targeted therapeutic antioxidant. We attempted to attenuate the mitochondrial ROS induced in
- Mahmood, Amena,Bisoyi, Padmini,Banerjee, Rajkumar,Yousuf, Md,Goswami, Shyamal K.
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p. 2047 - 2059
(2021/02/01)
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- METABOLICALLY STABLE PRODRUGS
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Provided are prodrugs of various therapeutic agents that provide enhanced bioavilabilty of the therapeutic agent, and methods of treatment conditions in a subject by administration of the one or prodrugs. As provided herein a prodrug includes a therapeutic agent covalently attached to a cap, the cap having a structure according to formula (I) where: R1 is a branched or linear substituted or unsubstituted C2-C6 alkyl, alkenyl, or alkynl; X is -S(0)2-; R2 is a branched or linear substituted or unsubstituted C4-C20 alkyl, alkenyl, or alkynyl; and R3 is -H, C3-C5 cycloalkyl, C3-C5 cycloheteroalkyl, -C(CH3)3, -CF3, -C(CF3)3, or a substituted or unsubstituted phenyl.
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Paragraph 00103; 00104
(2020/01/24)
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- Method for synthesizing grassland spodoptera litura sex pheromone active ingredients
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The invention belongs to the technical field of green pesticide synthesis, and discloses a novel method for synthesizing grassland spodoptera litura sex pheromone active ingredients (Z)-9-dodecene-1-alcohol acetate, (Z)-9-tetradecene-1-alcohol acetate and (Z)-11-hexadecene-1-alcohol acetate. The method comprises the steps: using bromo-alcohol as a starting raw material; and firstly generating hydroxyl phosphonium salt with triphenylphosphine, then respectively carrying out Wittig coupling reaction with propionaldehyde and valeraldehyde to generate Z-type enol, and finally carrying out acetylation reaction with acetic anhydride to prepare (Z)-9-dodecene-1-alcohol acetate, (Z)-9-tetradecene-1-alcohol acetate and (Z)-11-hexadecene-1-alcohol acetate. According to the method, hydroxyl phosphonium salt is used for Wittig reaction, two steps of hydroxyl protection and deprotection are omitted, the synthetic route is simplified, and the method has the advantages of being environmentally friendly and the like.
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Paragraph 0032-0034
(2020/07/02)
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- Antiproliferative and uncoupling effects of delocalized, lipophilic, cationic gallic acid derivatives on cancer cell lines. Validation in vivo in singenic mice
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Tumor cells principally exhibit increased mitochondrial transmembrane potential (Δψm) and altered metabolic pathways. The therapeutic targeting and delivery of anticancer drugs to the mitochondria might improve treatment efficacy. Gallic acid e
- Jara, José A.,Castro-Castillo, Vicente,Saavedra-Olavarría, Jorge,Peredo, Liliana,Pavanni, Mario,Ja?a, Fabián,Letelier, María Eugenia,Parra, Eduardo,Becker, María Inés,Morello, Antonio,Kemmerling, Ulrike,Maya, Juan Diego,Ferreira, Jorge
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p. 2440 - 2454
(2014/04/17)
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- Synthesis of (Z/E)-11-tetradecen-1-ol, a component of Ostrinia nubilalis sex pheromone
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11-Tetradecen-1-ol acetate is a mixture of geometric isomers with the Z/E-conformations in a 94:6 ratio that is used as an attractant to trap corn pests. It has a powerful attractive action similar to that of an isomeric mixture of 11-tetradecenyl acetate with the Z/E-conformation in a 95:5 ratio that was extracted from the peritoneal cavity of male Ostrinia nubilalis Hubner in Xinjing (PRC).
- Li,Yong,Aisa
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p. 224 - 226
(2008/12/22)
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- Cuticular hydrocarbons and novel alkenediol diacetates from wheat stem sawfly (Cephus cinctus): Natural oxidation to pheromone components
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The cuticular lipids of the wheat stem sawfly Cephus cinctus (Hymenoptera: Cephidae) were investigated as part of a chemical ecology project with this species. The major cuticular lipids were n-alkenes and n-alkanes. Alkenes were the most abundant and exhibited dramatic sexual dimorphism. (Z)-9-Tricosene accounted for about half of the total hydrocarbon in males but was nearly absent from females. The dominant alkenes in females were (Z)-9-pentacosene and (Z)-9-heptacosene. The alkane profiles were similar in both sexes, with n-tricosane being the most abundant, followed by n-pentacosane and n-heptacosane. In both sexes, there were minor amounts of alkanes and alkenes with other chain lengths and n-alkadienes of 29 and 31 carbons. In males, about one tenth of the surface lipids consisted of (Z)-9-alkene-1, ω-diol diacetates with 22-, 24-, and 26-carbon chains. The same compounds were also detected from females but in much smaller amounts. The structures of these novel diacetates were proven by synthesis. By analogy to methyl oleate, a well-studied food lipid, the alkenes and diacetates were expected to undergo slow oxidation in air to release specific aldehydes and other volatile products, and these were generally detected in volatiles collected from living sawflies. Atmospheric oxidation of the diacetates was also demonstrated in the absence of sawflies. One product from the diacetates, 9-acetyloxynonanal, was shown in other research to be particularly active electrophysiologically and was also attractive in the field. Aldehydes from the alkenes also showed strong electrophysiological activity. The concept of volatile pheromones originating from heavy, unsaturated cuticular lipids is discussed.
- Bartelt, Robert J.,Cosse, Allard A.,Petroski, Richard J.,Weaver, David K.
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p. 385 - 405
(2007/10/03)
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- The synthesis of β-keto lactones via cyclization of β-keto ester dianions or the cyclization of Meldrum's acid derivatives
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Two new methods to synthesize macrocyclic β-keto lactones have been developed.The first involves the synthesis of ω-halo-β-keto esters and an intramolecular alkylation of the dianions to these compounds.The reaction is complicated by elimination in the small and medium ring systems and by difficulties in purifying the final products.However, it is possible to obtain modest yields of the desired β-keto lactones.This procedure was used to synthesize the 25- and 27-membered ring β-hydroxy lactones that are the constituents of termite defense compounds.The second method involves the thermolysis of acylated Meldrum's acid derivatives, which leads directly to β-keto lactones.This process gives modest yields of macrocyclic systems and good yield of the unsubstituted 3-oxopentan-5-olide (25) .The 14-membered macrocyclic β-keto lactone 9j has a complex 1H NMR spectrum, which has been interpreted in terms of multiple conformations.The temperature dependence of the NMR spectrum of 9j is consistent with entropic, rather than enthalpic, control of the equilibrium.Quasiharmonic entropy calculations are consistent with this model.
- Lermer, Leonard,Neeland, Edward G.,Ounsworth, James P.,Sims, Russell J.,Tischler, Samuel A.,Weiler, Larry
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p. 1427 - 1445
(2007/10/02)
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- A CONVENIENT SYNTHESIS OF (11E,13E)-11,13-HEXADECADIENAL AND (11Z,13E)-HEXADECADIENAL
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A simple method for synthesizing (11E,13E)-11,13-hexadecadienal 7, a component of the female sex pheromone of cabbage webworm, and its geometrical isomer (11Z,13E)-11,13-hexadecadienal 8 is described.
- Lo, Veng Meng,Shiao, Min-Jen
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p. 1647 - 1656
(2007/10/02)
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