ChemInform Abstract: REACTION OF ALKYLTRIFLUOROMETHYLDIACETYLENES WITH MERCAPTOPURINES

Turbanova, E. S.; Орлова, Н. А.; Ratsino, E. V.; Sokolov, L.B.

doi:10.1002/chin.198135269

Cited by 2 publications

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“…PTA synthesis was carried out using the method of Turbanova et al [ 36 ]. 6-mercaptopurine (816 mg, 4.8 mmoL) was dispersed in 32 mL methanol, and then sodium methoxide (952 mg, 17.6 mmoL) was added under constant stirring conditions.…”

Section: Methodsmentioning

confidence: 99%

Folate Receptor-Targeted and GSH-Responsive Carboxymethyl Chitosan Nanoparticles Containing Covalently Entrapped 6-Mercaptopurine for Enhanced Intracellular Drug Delivery in Leukemia

et al. 2018

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For enhanced intracellular accumulation of 6-mercaptopurine (6-MP) in leukemia, a folate receptor-targeted and glutathione (GSH)-responsive polymeric prodrug nanoparticle was made. The nanoparticles were prepared by conjugating 6-MP to carboxymethyl chitosan via a GSH-sensitive carbonyl vinyl sulfide linkage, ultrasonic self-assembly and surface decoration with folate. The TEM graphs shows that the as-synthesized nanoparticles are spherical with a particle size of 170~220 nm. In vitro drug release of nanoparticles demonstrated acceptable stability in PBS containing 20 μM GSH at pH 7.4. However, the cumulative drug release rate of the samples containing 20 mM and 10 mM GSH medium reached 78.9% and 64.8%, respectively, in pH 5.0 at 20 h. This indicated that this nano-sized system is highly sensitive to GSH. The inhibition ratio of folate-modified nanoparticles compared to unmodified nanoparticles was higher in cancer cells (human promyelocytic leukemia cells, HL-60) while their cytotoxicity was lower in normal cells (mouse fibroblast cell lines, L929). Furthermore, in vitro cancer cell incubation studies confirmed that folate-modified nanoparticles therapeutics were significantly more effective than unmodified nanoparticles therapeutics. Our results suggest that folate receptor-targeting and GSH-stimulation can significantly elevate tumour intracellular drug release. Therefore, folate-modified nanoparticles containing chemoradiotherapy is a potential treatment for leukemia therapy.

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Section: Methodsmentioning

confidence: 99%

Folate Receptor-Targeted and GSH-Responsive Carboxymethyl Chitosan Nanoparticles Containing Covalently Entrapped 6-Mercaptopurine for Enhanced Intracellular Drug Delivery in Leukemia

et al. 2018

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“…Our initial studies began with the preparation of trifluoromethylated diyne derivatives [15–22]. Thus, treatment of 2,3,3,3-tetrafluoro-1-iodo-1-propene ( 1 ), which could be easily prepared from 2,2,3,3,3-pentafluoropropanol in three steps [23], with 1.2 equiv of terminal alkynes 2 and 1.5 equiv of Et 3 N in the presence of 5 mol % of Pd(OAc) 2 and 10 mol % each of PPh 3 and CuI in DMF at room temperature for 24 h, gave the corresponding Sonogashira cross-coupling products 3a – e in good to high yields [24–26] (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Highly stereocontrolled synthesis of trans-enediynes via carbocupration of fluoroalkylated diynes

Konno¹,

Kishi²,

Ishihara³

2012

Beilstein J. Org. Chem.

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SummaryTreatment of readily prepared (Z)-6-benzyloxy-1,1,1,2-tetrafluoro-6-methyl-2-hepten-4-yne with 1.5 equiv of LHMDS in −78 °C for 1 h gave the corresponding trifluoromethylated diyne in an excellent yield. This diyne was found to be a good substrate for the carbocupration with various higher-ordered cyanocuprates to give the corresponding vinylcuprates in a highly regio- and stereoselective manner. The in situ generated vinylcuprates could react very smoothly with an excess amount of iodine, the vinyl iodides being obtained in high yields. Thus-obtained iodides underwent a very smooth Sonogashira cross-coupling reaction to afford various trans-enediynes in high yields.

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ChemInform Abstract: REACTION OF ALKYLTRIFLUOROMETHYLDIACETYLENES WITH MERCAPTOPURINES

Abstract: Additionen von 6‐Mercaptopurin (III) oder 8‐Mercaptohypoxanthin (VII) in Gegenwart eines Namethoxid‐Überschusses an Trifluormethylacetylen bzw. Propiolsäure liefern regio‐ und stereospezifisch die cis‐Ethenylthio‐Derivate (I) und (VI).

Cited by 2 publications

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Folate Receptor-Targeted and GSH-Responsive Carboxymethyl Chitosan Nanoparticles Containing Covalently Entrapped 6-Mercaptopurine for Enhanced Intracellular Drug Delivery in Leukemia

Folate Receptor-Targeted and GSH-Responsive Carboxymethyl Chitosan Nanoparticles Containing Covalently Entrapped 6-Mercaptopurine for Enhanced Intracellular Drug Delivery in Leukemia

Highly stereocontrolled synthesis of trans-enediynes via carbocupration of fluoroalkylated diynes

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