2424-05-7Relevant academic research and scientific papers
Synthesis and characterization of macrocyclic polyether N,N′-Diallyl-7,16-diaza-1,4,10,13-tetraoxa-dibenzo-18-crown-6
Toeri, Julius,Laborie, Marie-Pierre,McPhee, Derek J.
, (2016)
In this study an efficient and direct production procedure for a macrocyclic polyether N,N′-diallyl-7,16-diaza-1,4,10,13-tetraoxa-dibenzo-18-crown-6 from the reaction of catechol and N, N-bis(2-chloroethyl)prop-2-en-1-amine in n-butanol in the presence of a strong base is reported. The synthesis involves a two-step addition of sodium hydroxide to enhance the cyclization process, and at the end of the reaction, the reaction mixture is neutralized and the solvent replaced with water in-situ through distillation to afford a relatively pure precipitate that is easily recrystallized from acetone. The yield of the macrocycle was 36%-45% and could be scaled-up to one-mole quantities. The structure and purity of this compound was verified on the basis of elemental analysis, IR, UV-Vis,1 H-, 13C-NMR, 2D-NMR, mass spectroscopy, and thermal analysis. The white crystalline compound has a sharp melting point of 124 °C and a crystallization temperature of 81.4 °C determined by differential scanning calorimetry. Our motivation behind the synthesis of the bibracchial lariat azacrown polyether ligand was to examine its possible applications in ion-selective polymer-supported materials.
Unique spirocyclopiperazinium salt III: Further investigation of monospirocyclopiperazinium (MSPZ) salts as potential analgesics
Sun, Qi,Yue, Cai-Qin,Ye, Jia,Li, Chang-Ling,Cheng, Tie-Ming,Li, Run-Tao
, p. 6245 - 6249 (2008/04/07)
Two novel classes of monospirocyclopiperazinium salts were designed, synthesized, and evaluated for their in vivo analgesic activities. Some interesting structure-activity relationships are revealed: (1) Spirocyclopiperazinium moiety is favorable to improve the analgesic activity; (2) The size and conformation of spirocyclopiperazinium moiety significantly affects the analgesic activity; (3) Phenylethyl group of 3d is a crucial pharmacophore. Among the compounds synthesized, 3d exhibited the most potent activity with low toxicity. Further antinociceptive mechanism studies of 3d showed that these compounds will be a new kind of analgesics.
Synthesis of azacrown ethers modified with side-chains containing germanium
Suzuki, Ryoko,Matsumoto, Takashi,Tanaka, Katsumi,Takeuchi, Yoshito,Taketomi, Tamotsu
, p. 108 - 123 (2007/10/03)
The reaction between ethanolamine (4) and tri- or tetraethylene tosylate (5) and (13) gave 9- and 12-membered monoazacrowns with a -CH2CH2OH residue on nitrogen, A-OH and B-OH, together with 18- and 24-membered diazacrown ethers with the same substituent on nitrogen, E-OH and F-OH. If 2-(2-aminoethoxy)ethanol (12) was used in the reaction described above, instead of 4, the final products, G-OH and H-OH, and K-OH and L-OH, have a longer side chain, -CH2CH2OCH2CH2OH, on nitrogen (Route 1). A series of reactions involving bromoethanol (6) and diethanolamine (9) formed, with 5 or 13, 18- and 24-membered monoazacrowns with the shorter substituent as described above, a 15-membered monoazacrown ether C-OH and an 18-membered D-OH. If 2-(2-chloroethoxy)ethanol (14) is used instead of 6, I-OH and J-OH are obtained (Route 2′). All these hydroxy azacrown ethers were made to react with 3-trimethylgermylpropionic acid (18) to give the corresponding germanium-containing A-L. A preliminary investigation was carried out on the cation transport capability of these germanium-containing azacrown ethers to observe whether germanium might enhance their cation transporting capability.
POLYAZACYCLIC COMPOUNDS. PART I. SYNTHESIS OF ARYLSULFONYL DERIVATIVES OF 1,4,7,10-TETRAAZACYCLODODECANE AND 1-OXA-4,7,10-TRIAZACYCLODODECANE SUBSTITUTED AT REQUIRED NITROGEN ATOMS
Sienkiewicz, Juliusz,Goss, Ewa,Stanczak, Andrzej
, p. 77 - 86 (2007/10/02)
A method of preparation of new polyazamacrocyclic compounds substituted at required nitrogen atoms is given based on the example of synthesis of the title derivatives.The method consists in the cyclocondensation of substrates, of which at least one has a tertiary amino group present in the macrocyclic compound.
Nitrogen-containing polyether macrocycles with a sidearm containing neutral electron donor groups
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, (2008/06/13)
This invention relates to novel crown ether compositions which have been given the cognomen "lariat ethers". They have been designed with one or more arms bearing neutral donor groups capable of interacting with a complexed metal ion and thereby affording enhanced cation binding compared to simple crown ethers. Evidence of enhanced cation binding has been obtained and the compounds have also shown utility as phase transfer catalysts.
LARIAT ETHERS. 3. MACROCYCLIC POLYETHERS BEARING DONOR GROUPS ON FLEXIBLE ARMS ATTACHED AT A NITROGEN PIVOT POINT
Schultz, Rose Ann,Dishong, Dennis M.,Gokel, George W.
, p. 2623 - 2626 (2007/10/02)
The binding of lariat ethers utilizing a nitrogen pivot atom for the donor sidearm is enhanced considerably relative to the carbon-based systems and this may be explicable in terms of diminished "sidedness."
