153214-82-5Relevant articles and documents
Poly(carbonate-ester)s of dihydroxyacetone and lactic acid as potential biomaterials
Weiser, Jennifer R.,Zawaneh, Peter N.,Putnam, David
, p. 977 - 986 (2011)
The synthesis of new polymeric biomaterials using biocompatible building blocks is important for the advancement of the biomedical field. We report the synthesis of statistically random poly(carbonate-ester)s derived from lactic acid and dihydroxyacetone by ring-opening polymerization. The monomer mole feed ratio and initiator concentration were adjusted to create various copolymer ratios and molecular weights. A dimethoxy acetal protecting group was used to stabilize the dihydroxyacetone and was removed using elemental iodine and acetone at reflux to produce the final poly(lactide-co-dihydroxyacetone) copolymers. The characteristics of the copolymers in their protected and deprotected forms were characterized by 1H NMR, 13C NMR, GPC, TGA, and DSC. Hydrolytic degradation of the deprotected copolymers was tracked over an 8-week time frame. The results show that faster degradation occurred with increased carbonate content in the copolymer backbone. The degradation pattern of the copolymers was visualized using SEM and revealed a trend toward surface erosion as the primary mode of degradation.
In-chain functionalization through the combination of ring opening copolymerization and oxime “Click” reaction towards X-ray opaque polylactide copolymers
Wang, Wenhuan,Sang, Lin,Kong, Weizong,Zhao, Yiping,Wei, Zhiyong,Li, Yang
, p. 551 - 553 (2020)
X-ray imaging functionalization of biodegradable polyesters is a great demand and challenge in biomedical applications. In this work, a strategy of in-chain functionalization through the combination of ring opening copolymerization and oxime “Click” postfunctionalization was developed towards X-ray opaque polylactide copolymers. A functionalized cyclic carbonate was first synthesized and used as comonomer of polylactide copolymers, which were subjected to postfunctionalization of oxime “Click” reaction towards iodinated polylactide copolymers. The chemical structure and physical properties of the target products were traced and confirmed. In vitro cytotoxicity evaluation with 3T3-Swiss albino by Alamar blue demonstrated a low cytotoxicity. The X-ray radiopacity was analyzed by Micro-CT and quantified by Hounsfield Units value, which could be tailorable by the feedstock. It is a promising X-ray visible implantable biomaterial in biomedical applications.
Preparation method 3 - oxocyclobutane-based carboxylic acid
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Paragraph 0024-0026, (2021/10/27)
The invention discloses a preparation method of 3 -oxocyclobutane-based carboxylic acid, and belongs to the technical field of synthesis of medical intermediates. The ketone is protected from 1, 3 -dihydroxyacetone by condensation with trimethyl orthoformate to give 2, 2 -dimethoxy -1, 3 -propanediol, followed by reaction with malonate to give 3, 3 -dimethylcyclobutyl -1, 1 -dicarboxylic acid diester, followed by hydrolysis under acidic conditions. Decarboxylation and deprotection to yield 3 -oxocyclobutane-based carboxylic acids. The method has the advantages of high yield, common and easily available raw materials, simple flow and industrial amplification prospect.
Dihydroxyacetone phosphate, DHAP, in the crystalline state: monomeric and dimeric forms
?lepokura, Katarzyna,Lis, Tadeusz
scheme or table, p. 512 - 529 (2010/04/27)
It was shown that dihydroxyacetone phosphate may exist in both monomeric DHAP (C3H7O6P) and dimeric DHAP-dimer (C6H14O12P2) form. Monomeric DHAP was obtained in the form of four crystalline salts: CaCl(DHAP)·2.9H2O (7a), Ca2Cl3(DHAP)·5H2O (7b), CaCl(DHAP)·2H2O (7c), and CaBr(DHAP)·5H2O (7d) by crystallization from aqueous solutions containing DHAP acid and CaCl2 or CaBr2, or by direct crystallization from a solution containing DHAP precursor and CaCl2. At least one of the salts is stable and may be stored in the crystalline state at room temperature for several months. The dimeric form was obtained by slow saturation of free DHAP syrup with ammonia at -18 °C and isolated in the form of its hydrated diammonium salt (NH4)2(DHAP-dimer)·4H2O (8). The synthesis of the compounds, their crystallization, and crystal structures determined by X-ray crystallography are described. In all 7a-d monomeric DHAP exists in the monoanionic form in an extended (in-plane) cisoid conformation, with both hydroxyl and ester oxygen atoms being synperiplanar to the carbonyl O atom. The crucial structural feature is the coordination manner, in which the terminal phosphate oxygen atoms act as chelating as well as bridging atoms for the calcium cations. Additionally, the DHAP monoanions chelate another Ca2+ by the α-hydroxycarbonyl moiety, in a manner observed previously in dihydroxyacetone (DHA) calcium chloride complexes. In dimeric 8 the anion is a trans isomer with the dioxane ring in a chair conformation with the hydroxyl groups in axial positions and the phosphomethyl group in an equatorial position.
CATIONIC LIPIDS AND USES THEREOF
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Page/Page column 78, (2009/12/02)
Cationic lipids, cationic lipid based drug delivery systems, ways to make them and methods of treating diseases using them are disclosed.
Oxetanes as promising modules in drug discovery
Wuitschik, Georg,Rogers-Evans, Mark,Mueller, Klaus,Fischer, Holger,Wagner, Bjoern,Schuler, Franz,Polonchuk, Liudmila,Carreira, Erick M.
, p. 7736 - 7739 (2007/10/03)
(Chemical Equation Presented) Ring the changes: Introduction of an oxetane ring results in remarkably improved physico- and biochemical properties of the underlying scaffold. The oxetane ring confers enhanced solubility, reduces the metabolic degredation, lipophilicity, and amphiphilicity, and modulates the basicity of a nearby amine group.
Aromatic or chiral heterocycle - Balance between 1,3-oxazoline-2-thione and 1,3-oxazolidine-2-thione
Leconte, Nicolas,Silva, Sandrina,Tatibou?t, Arnaud,Rauter, Amelia P.,Rollin, Patrick
, p. 301 - 305 (2007/10/03)
1,3-Oxazoline-2-thiones (OXT) and bis-1,3-oxazol-idine-2-thiones (bis-OZT) were selectively prepared depending on the conditions and starting materials used, and then underwent some N- and S-selective reactions. Georg Thieme Verlag Stuttgart.
Prodrug-oriented molecular design of neonicotinoids: Preparation of imidacloprid-related 5,5-dimethoxy-1,3-diazacyclohexane derivatives and their insecticidal activity
Kagabu, Shinzo,Hibi, Manabu,Nishimura, Keiichiro
, p. 705 - 713 (2008/02/03)
Prodrug-oriented molecular design was attempted for the potent acyclic neonicotinoid insecticide, clothianidin (1-(2-chloro-5-thiazolylmethyl)-3- methyl-2-nitroguanidine). Molecules bearing a CH2COCH2 bridge linking the 1,3-NH ends o
Improved straightforward chemical synthesis of dihydroxyacetone phosphate through enzymatic desymmetrization of 2,2-dimethoxypropane-1,3-diol
Charmantray, Franck,El Blidi, Lahssen,Gefflaut, Thierry,Hecquet, Laurence,Bolte, Jean,Lemaire, Marielle
, p. 9310 - 9312 (2007/10/03)
Dihydroxyacetone phosphate (DHAP) was synthesized in high purity and yield in four steps starting from dihydroxyacetone dimer (DHA) (47% overall yield). DHA was converted into 2,2-dimethoxypropane-1,3-diol, which was desymmetrized by acetylation with lipase AK. The alcohol function was phosphorylated to give dibenzyl phosphate ester 4. From 4, two routes were investigated for large-scale synthesis of DHAP. First, acetate hydrolysis was performed prior to hydrogenolysis of the phosphate protective groups. The acetal hydrolysis was finally catalyzed by the phosphate group itself. Second, acetate and acetal hydrolysis were performed in one single step after hydrogenolysis.
Crystal structures of dihydroxyacetone and its derivatives
Slepokura, Katarzyna,Lis, Tadeusz
, p. 1994 - 2007 (2007/10/03)
The crystal and molecular structures of three crystalline forms of the dihydroxyacetone dimer, C6H12O6, DHA-dimer: α (1a), β (1b), and γ (1c), the hydrated calcium chloride complex of dihydroxyacetone monomer, CaCl(C3H6O3)*H2O, CaCl2(DHA)2*H2O (2a), the tetrahydrated calcium chloride complex of dihydroxyacetone monomer, CaCl2(C3H6O3)*4H2O, CaCl2(DHA)*4H2O (2b), thr dihydroxyacetone monomer, C3H6O3, DHA (2c), and dihydroxyacetone dimethyl acetal, C5H12O4, (MeO)2DHA (3) are described. Compounds 1a and 2b crystallize in the triclinic system, and 1b,c, 2a,c, and 3 are monoclinic. Molecules of all forms of dihydroxyacetone dimer 1a,b, and 1c are the trans isomers, with the 1,4-dioxane ring in the chair conformation and the hydroxyl and hydroxymethyl groups in axial and equatorial dispositions, respectively. The Ca2+ ions in 2a and 2b are bridged by the carbonyl O atoms from two symmetry-related DHA molecules to form centrosymmetric dimers with Ca...Ca distance of 4.307(2) Angstroem in 2a and 4.330(2) and 4.305(2) Angstroem in two crystallographically independent dimers in 2b. DHA molecules coordinate to the Ca2+ ions by hydroxyl and carbonyl oxygen atoms. The eight-coordinate polyhedra of Ca2+ are completed by water molecule and Cl- ion in 2a and by four water molecules in 2b. The dihydroxyacetone molecules in 2a,b, and 2c are in an extended conformation, with both hydroxyl groups being synperiplanar (sp) to the carbonyl O atom. All hydroxyl groups in 2c (along with water molecules in 2a and 2b) are involved as donors in medium strong and weak intermolecular O-H...O hydrogen bonding. Some of them, as well as carbonyl O atoms or Cl- ions in 2a and 2b, act as acceptors in C-H...O (and C-H...Cl) hydrogen interactions.
