- Glycidyl Tosylate: Polymerization of a “Non-Polymerizable” Monomer permits Universal Post-Functionalization of Polyethers
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Glycidyl tosylate appears to be a non-polymerizable epoxide when nucleophilic initiators are used because of the excellent leaving group properties of the tosylate. However, using the monomer-activated mechanism, this unusual monomer can be copolymerized
- Jung, Philipp,Ziegler, Arthur D.,Blankenburg, Jan,Frey, Holger
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- Synthesis and noncovalent DNA-binding properties of thiazole derivatives related to leinamycin
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A series of compounds related to the macrocyclic portion of the DNA-damaging antitumor agent leinamycin were prepared as tools to characterize noncovalent DNA binding by this natural product. Acyclic (Z,E)-dienes were assembled via a Sonogashira coupling followed by partial hydrogenation. A Stille coupling was used in the cyclization step leading to a macrocyclic thiazole-diene analogue. Results obtained using the synthetic analogues reported here indicate that the extended π-system on the 'left-hand side' of leinamycin is required for noncovalent association of the natural product with duplex DNA.
- Breydo, Leonid,Zang, Hong,Gates, Kent S.
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- Synthesis and characterization of new 3-(4-arylpiperazin-1-yl)-2-hydroxypropyl 4-propoxybenzoates and their hydrochloride salts
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Five new 3-(4-arylpiperazin-1-yl)-2-hydroxypropyl 4-propoxybenzoates were designed and synthesized as potential dual antihypertensive agents. The compounds were prepared as free bases and subsequently transformed to hydrochloride salts. The position of pr
- Marvanova, Pavlina,Padrtova, Tereza,Pekarek, Tomas,Brus, Jiri,Czernek, Jiri,Mokry, Petr,Humpa, Otakar,Oravec, Michal,Jampilek, Josef
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- A safe two-step process for manufacturing glycidyl nitrate from glycidol involving solid-liquid phase-transfer catalysis
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A new and safer two-step process for manufacturing glycidyl nitrate from glycidol is reported. In the first step glycidyl tosylate is obtained by reacting glycidol with p-tosyl chloride in the presence of triethylamine according to any one of the well-known procedures for obtaining tosyl esters described in the literature. In the second step, glycidyl tosylate is reacted with NaNO3 in refluxing acetonitrile under solid-liquid phase-transfer catalysis conditions using tetrabutylammonium nitrate as catalyst. Acetonitrile and the phase-transfer catalyst were recycled 12 times without deactivation, yielding 99% pure glycidyl nitrate in a cumulative isolated yield of 81.5% with a catalyst turnover number of 85.7 mol substrate per mol phase-transfer catalyst. This procedure avoids the use of the dangerous reactants used in the current manufacturing processes of glycidyl nitrate and could be useful as a safe and general method for obtaining nitrate esters.
- Ochoa-Gomez, Jose R.,Blanco-Gomez, Juan J.
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- Dihydroquinozinone carboxylic acid compound and application thereof (by machine translation)
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The invention belongs to the field of, pharmaceutical chemistry, and relates to (HBV) a dihydroquinozinone carboxylic acid compound with the activity of, and resisting hepatitis B virus (hepatitis B virus) .and a preparation method of the dihydroquinozino
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Paragraph 0078-0081
(2020/02/14)
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- An integrative study to identify novel scaffolds for sphingosine kinase 1 inhibitors
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Sphingosine kinase 1 (SphK1), the enzyme that produces the bioactive sphingolipid metabolite, sphingosine-1-phosphate, is a promising new molecular target for therapeutic intervention in cancer and inflammatory diseases. In view of its importance, the main objective of this work was to find new and more potent inhibitors for this enzyme possessing different structural scaffolds than those of the known inhibitors. Our theoretical and experimental study has allowed us to identify two new structural scaffolds (three new compounds), which could be used as starting structures for the design and then the development of new inhibitors of SphK1. Our study was carried out in different steps: virtual screening, synthesis, bioassays and molecular modelling. From our results, we propose a new dihydrobenzo[b]pyrimido[5,4-f]azepine and two alkyl{3-/4-[1-hydroxy-2-(4-arylpiperazin-1-yl)ethyl]phenyl}carbamates as initial structures for the development of new inhibitors. In addition, our molecular modelling study using QTAIM calculations, allowed us to describe in detail the molecular interactions that stabilize the different Ligand-Receptor complexes. Such analyses indicate that the cationic head of the different compounds must be refined in order to obtain an increase in the binding affinity of these ligands.
- Vettorazzi, Marcela,Angelina, Emilio,Lima, Santiago,Gonec, Tomas,Otevrel, Jan,Marvanova, Pavlina,Padrtova, Tereza,Mokry, Petr,Bobal, Pavel,Acosta, Lina M.,Palma, Alirio,Cobo, Justo,Bobalova, Janette,Csollei, Jozef,Malik, Ivan,Alvarez, Sergio,Spiegel, Sarah,Jampilek, Josef,Enriz, Ricardo D.
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p. 461 - 481
(2017/08/21)
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- Synthesis and determination of physicochemical properties of new 3-(4-arylpiperazin-1-yl)-2-hydroxypropyl 4-alkoxyethoxybenzoates
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Nine new dihydrochloride salts of 3-(4-arylpiperazin-1-yl)-2-hydroxypropyl 4-alkoxyethoxybenzoates were designed and synthesized. The physicochemical properties such as lipophilicity index (log kw) and dissociation constant (pKa) wer
- Marvanova, Pavlina,Padrtova, Tereza,Odehnalova, Klara,Hosik, Ondrej,Oravec, Michal,Mokry, Petr
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- Synthesis of chiral ND-322, ND-364 and ND-364 derivatives as selective inhibitors of human gelatinase
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Compounds 10 (ND-322) and 15 (ND-364) are potent selective inhibitors for gelatinases, matrix metalloproteinase 2 (MMP2) and matrix metalloproteinase 9 (MMP9). However, both of them are racemates. Herein we report facile synthesis of optically active (R)-
- Yan, Yugang,Chen, Xueying,Yang, Xinying,Zhang, Jian,Xu, Wenfang,Zhang, Yingjie
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p. 6632 - 6640
(2015/10/19)
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- Hf(IV)-catalyzed enantioselective epoxidation of N-alkenyl sulfonamides and N-tosyl imines
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Asymmetric epoxidation of allylic and homoallylic amine derivatives catalyzed by Hf(IV)-bishydroxamic acid complexes is described. Under similar conditions, aldimine and ketimine produced oxaziridines. The sulfonyl group is demonstrated to be an effective directing group for these transformations.
- Olivares-Romero, Jose Luis,Li, Zhi,Yamamoto, Hisashi
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supporting information; experimental part
p. 5440 - 5443
(2012/05/20)
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- Poly(per)fluoroalkanesulfonyl fluoride promoted olefin epoxidation with 30% aqueous hydrogen peroxide
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Epoxidation of various electron rich olefins with a novel oxidation system of poly(per)fluoroalkanesulfonyl fluoride/hydrogen peroxide/base is reported.
- Yan, Zhaohua,Tian, Weisheng
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p. 2211 - 2213
(2007/10/03)
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- Synthesis and antibacterial evaluation of oxazolidin-2-ones structurally related to linezolid
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Compounds structurally related to the known antimicrobial drug linezolid were selected in order to evaluate the influence of electron-withdrawing properties and altered geometric features as a result of the N-substituent modification. After a preliminary
- Ammazzalorso, Alessandra,Amoroso, Rosa,Bettoni, Giancarlo,Fantacuzzi, Marialuigia,De Filippis, Barbara,Giampietro, Letizia,Maccallini, Cristina,Paludi, Domenico,Tricca, Maria L.
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p. 685 - 690
(2007/10/03)
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- Process for preparation of glycidyl sulfonate derivative
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A process for preparation of a glycidyl sulfonate derivative with high purity and in high yield, which is characterized in reacting glycidol which is prepared from treating 3-chloro-1,2-propanediol in an aqueous solvent in the basic condition, without iso
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