17874-79-2Relevant academic research and scientific papers
A New Family of Insulin-Mimetic Vanadium Complexes Derived from 5-Carboalkoxypicolinates
Gaetjens, Jessica,Meier, Beate,Kiss, Tamas,Nagy, Eszter M.,Buglyo, Peter,Sakurai, Hiromu,Kawabe, Kenji,Rehder, Dieter
, p. 4924 - 4935 (2003)
The reaction of 5-carboalkoxypicolinic acid (5ROpicH, R= Me, Et, iPr, sBu; 1a-d) with vanadyl sulfate yielded the complexes [VO(H 2O)(5ROpic)2], 2a-d, with H2O and one of the picolinato ligands in the equatorial positions, and the second picolinate occupying equatorial (N) and axial (O) positions. Reaction of 1a with [NH 4][VO3] yielded [NH4][VO 2(5MeOpic)2], [NH4]-3, in which the N functions of the picolinates are trans to the doubly bonded, cis-positioned oxo groups. Complexes 1a · H2O, 1b, 1c, 2a · 3.5H 2O and [NH4]-3 · 4H2O have been structurally characterised. A detailed pH-potentiometric solution speciation analysis of the system VO2+-1a revealed a dominance of VO(5OMepic)2 between pH 2 and 6, with the same coordination pattern, evidenced by EPR spectroscopy, as in the crystalline solid state. In ternary systems containing physiological concentrations of the low molecular mass biogenic binders (B) lactate, oxalate, citrate or phosphate, ternary species of general composition VO(5MeOpic)B dominate at physiological pH, with citrate being the most effective competitor for picolinate. All of the complexes trigger glucose uptake and degradation by simian virus modified mice fibroblasts at non-toxic concentrations (a, [VO 2(pic)2]- and [VO2(dipic)] - being at least as effective as insulin. Vanadium uptake by the cells is most effective in the case of 2a. 2a also effectively inhibits free fatty acid release by rat adipocytes treated with epinephrine, thus mimicking the inhibition of lipolysis by insulin.
Carboxyl Methyltransferase Catalysed Formation of Mono- and Dimethyl Esters under Aqueous Conditions: Application in Cascade Biocatalysis
Ashbrook, Chloe,Carnell, Andrew J.,Goulding, Ellie,Hatton, Harry,Johnson, James R.,Kershaw, Neil M.,McCue, Hannah V.,Rigden, Daniel J.,Ward, Lucy C.
supporting information, (2022/02/21)
Carboxyl methyltransferase (CMT) enzymes catalyse the biomethylation of carboxylic acids under aqueous conditions and have potential for use in synthetic enzyme cascades. Herein we report that the enzyme FtpM from Aspergillus fumigatus can methylate a broad range of aromatic mono- and dicarboxylic acids in good to excellent conversions. The enzyme shows high regioselectivity on its natural substrate fumaryl-l-tyrosine, trans, trans-muconic acid and a number of the dicarboxylic acids tested. Dicarboxylic acids are generally better substrates than monocarboxylic acids, although some substituents are able to compensate for the absence of a second acid group. For dicarboxylic acids, the second methylation shows strong pH dependency with an optimum at pH 5.5–6. Potential for application in industrial biotechnology was demonstrated in a cascade for the production of a bioplastics precursor (FDME) from bioderived 5-hydroxymethylfurfural (HMF).
INHIBITORS OF COLLAGEN PROLYL 4-HYDROXYLASE
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, (2016/10/17)
Biheteroaryl dicarboxylates and esters, and salts thereof which are useful as modulators of CP4H activity and more particularly as inhibitors of CP4H. Compounds of formula: and salts thereof where: X is S, O, NH, or NR, where R is an alkyl group having 1-3 carbon atoms; R1 and R2 independently are —OR7, or —NHSO2R8, where R7 is selected from: hydrogen, alkyl, alkenyl, alkoxyalkyl, —R′—CO—R″, —R′—CO—O—R″, —CO—R″, —R′—O—CO—R″, —R′—CO—NR″, —CO—NR″, or —R′—O—CO—NR″, and R8 is selected from hydrogen, alkyl, aryl, arylalkyl; R3, R4 and R6 independently are hydrogen, alkyl, alkoxy, alkenyl, alkenoxy, halo alkyl, haloalkenyl, halogen, hydroxyl, hydroxyalkyl, hydroxyalkenyl, aryl, aryloxy, arylalkyl or arylalkyloxy; R5 is hydrogen, halogen, alkyl having 1-3 carbon atoms, or alkoxy having 1-3 carbon atoms; —R′— is a divalent straight chain or branched alkylene, and —R″ is an alkyl, alkenyl, arylalkyl, or aryl group. Methods for inhibition of CP4H in vivo and in vitro.
THERAPEUTIC COMPOUNDS
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Page/Page column 20; 21, (2013/03/28)
The invention provides compounds of formulae (I), (II), (III), and (IV): and salts thereof, as well as pharmaceutical compositions comprising such compounds. The compounds are useful for treating cancers and Alzheimer's disease.
Modeling, synthesis, and biological evaluation of potential retinoid X receptor (RXR) selective agonists: Novel analogues of 4-[1-(3,5,5,8,8- Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic Acid (Bexarotene) and (E)-3-(3-(1,2,3,4-tetrahydro-1,1,
Jurutka, Peter W.,Kaneko, Ichiro,Yang, Joanna,Bhogal, Jaskaran S.,Swierski, Johnathon C.,Tabacaru, Christa R.,Montano, Luis A.,Huynh, Chanh C.,Jama, Rabia A.,Mahelona, Ryan D.,Sarnowski, Joseph T.,Marcus, Lisa M.,Quezada, Alexis,Lemming, Brittney,Tedesco, Maria A.,Fischer, Audra J.,Mohamed, Said A.,Ziller, Joseph W.,Ma, Ning,Gray, Geoffrey M.,Van Der Vaart, Arjan,Marshall, Pamela A.,Wagner, Carl E.
, p. 8432 - 8454 (2013/12/04)
Three unreported analogues of 4-[1-(3,5,5,8,8-pentamethyl-5-6-7-8- tetrahydro-2-naphthyl)ethynyl]benzoic acid (1), otherwise known as bexarotene, as well as four novel analogues of (E)-3-(3-(1,2,3,4-tetrahydro-1,1,4,4,6- pentamethylnaphthalen-7-yl)-4-hydr
Enantioselective Fujiwara-Moritani indole and pyrrole annulations catalyzed by chiral palladium(II)-NicOx complexes
Schiffner, Julia A.,Woeste, Thorsten H.,Oestreich, Martin
supporting information; experimental part, p. 174 - 182 (2010/04/02)
The catalytic asymmetric Fujiwara-Moritani ring closures of several indole-and pyrrole-based cyclization precursors are reported. These unprecedented oxidative palladium(II)-catalyzed annulations allow for the formation of a stereogenic quaternary carbon atom, and decent levels of enantiocontrol are seen in 5-exo-trig cyclizations (54% ee for an indole and 76% ee for a pyrrole) while 6-exo-trig ring closures afford essentially racemic material. Novel oxazoline ligands with a nicotine platform (NicOx) are pivotal for good catalytic turnover as conventional PyOx ligands failed to produce acceptable chemical yields. The preparation of these NicOx ligands as well as the syntheses of the cyclization precursors are described in detail.
CONJUGATES OF ARTEMISININ-RELATED ENDOPEROXIDES AND HYDRAZONE DERIVATIVES FOR THE TREATMENT OF CANCER
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, (2008/06/13)
Compounds having an artemisinin-related endoperoxide moiety covalently coupled to a hydrazone moiety through a linker. Compositions and methods for treating cancer using the compounds.
COVALENT CONJUGATES BETWEEN ENDOPEROXIDES AND TRANSFERRIN AND LACTOFERRIN RECEPTOR-BINDING AGENTS
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Page/Page column 14, (2008/06/13)
The invention relates to covalent conjugates between endoperoxides and small peptides and organic compounds that bind to molecular cavities on the transferrin or lactoferrin receptor, and the use of compositions comprising these conjugates to treat cancer, hyperproliferative disorders, inflammatory diseases, and infections.
Characterizing the "shell phase" formed from amphiphilic picolinates
Menger, Fredric M.,Galloway, Ashley L.,Lundberg, Dan
, p. 11914 - 11915 (2007/10/03)
The shell phase forms when certain picolinates are subjected to energy input (via sonication or vortexing) while exposed to a water/toluene mixture. A shell, about 600 A thick and containing the picolinate and (very likely) toluene, surround the water droplets that are always produced during the mixing process. Solubility in either phase appears to be deleterious to shell formation. The shells, stable for months, are not easily distorted but can be punctured, even skewered, with a syringe needle without destroying the sphere, yet there is enough mobility among the molecules to repair the physical damage after the needle is removed. This, plus the absence of evidence for crystallinity, suggests a solid or semisolid film forms when picolinates, with the aid of an aromatic solvent, are provided the energy to rearrange themselves on water droplet surfaces. Structure-activity comparisons among the 10 compounds studied indicate that chain-chain association and intermolecular hydrogen bonding are dominant forces in a side-by-side self-assembly of the molecules within the shells. Copyright
Ligand creation via linking - A rapid and convenient method for construction of novel supported PyOX-ligands
Oila, Markku J.,Tois, Jan E.,Koskinen, Ari M.P.
, p. 10748 - 10756 (2007/10/03)
A novel supported amino alcohol linker was synthesized and utilized for attachment of picolinic acid derivatives onto different supports. When the resin bound molecule was further activated, the PyOX-moiety could be constructed reliably in enantiopure form. Furthermore, an efficient Pd-catalyzed modification of a picolinic acid derivative is presented.
