38256-25-6Relevant academic research and scientific papers
Selective Oxidations with Activated Carbon: Applications to Substrates containing Acidic Allylic Methine and Methylene Groups
Ananda, G. D. Sriyani,Cremins, Peter J.,Stoodley, Richard J.
, p. 882 - 883 (1987)
Butenoates substituted at the γ-position with an acidifying group, e.g., COR, CO2R, SO2R, and PO(OR)2, undergo a regioselective oxidation (in which a methine group is converted into a carbinol function and a methylene group into a keto moiety) in the presence of activated carbon.
Organic Syntheses Based on 2-Oxoglutaric Acid. III. Synthesis and Reactions of Dimethyl (E)-2-oxoglutaconate
Blitzke, T.,Hartenstein, H.,Sicker, D.,Wilde, H.
, p. 683 - 686 (1993)
Dimethyl (E)-2-oxoglutaconate 1 obtained by dehydrobromination of dimethyl 3-bromo-2-oxoglutarate reacts with o-phenylendiamine to form the quinoxalin-2(1H)-one 2, and with phenylhydrazine to yield the 4,5-dihydropyrazole 3.Furthermore, a Doebner-von Miller-type reaction affords the 8-carboxy quinoline derivative 4.Finally, addition of bromine leads diastereoselectively to the racemate of dimethyl 3S,4R- and 3R,4S-dibromo-2-oxoglutarate 5.
TREATMENT OF DISORDERS ASSOCIATED WITH OXIDATIVE STRESS AND COMPOUNDS FOR SAME
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Page/Page column 49; 56, (2021/09/17)
The present invention relates to the treatment of disorders associated with oxidative stress including neuropathic pain and small synthetically derived compounds for treating such disorders.
SAR insights into TET2 catalytic domain inhibition: Synthesis of 2-Hydroxy-4-Methylene-pentanedicarboxylates
Tiwari, Anand D.,Guan, Yihong,Grabowski, Dale R.,Maciejewski, Jaroslaw P.,Jha, Babal K.,Phillips, James G.
, (2021/04/23)
The TET (Ten-Eleven Translocation) dioxygenase enzyme family comprising 3 members, TET1-3, play key roles in DNA demethylation. These processes regulate transcription programs that determine cell lineage, survival, proliferation, and differentiation. The impetus for our investigations described here is derived from the need to develop illuminating small molecule probes for TET enzymes with cellular activity and specificity. The studies were done so in the context of the importance of TET2 in the hematopoietic system and the preponderance of loss of function somatic TET2 mutations in myeloid diseases. We have identified that 2-hydroxy-4-methylene-pentanedicarboxylic acid 2a reversibly competes with the co-substrate α-KG in the TET2 catalytic domain and inhibits the dioxygenase activity with an IC50 = 11.0 ± 0.9 μM at 10 μM α-KG in a cell free system and binds in the TET2 catalytic domain with Kd = 0.3 ± 0.12 μM.
Convergent Synthesis of Diverse Nitrogen Heterocycles via Rh(III)-Catalyzed C-H Conjugate Addition/Cyclization Reactions
Weinstein, Adam B.,Ellman, Jonathan A.
supporting information, p. 3294 - 3297 (2016/07/13)
The development of Rh(III)-catalyzed C-H conjugate addition/cyclization reactions that provide access to synthetically useful fused bi- and tricyclic nitrogen heterocycles is reported. A broad scope of C-H functionalization substrates and electrophilic olefin coupling partners is effective, and depending on the nature of the directing group, cyclic imide, amide, or heteroaromatic products are obtained. An efficient synthesis of a pyrrolophenanthridine alkaloid natural product, oxoassoanine, highlights the utility of this method.
SYNTHESIS OF PYRROLOQUINOLINE QUINONE (PQQ)
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Page/Page column 8; 12-13, (2010/11/24)
The invention relates to a novel nine step process for synthesizing PQQ (methoxatin). This process is efficient and reliably provides PQQ in excellent purity and high yield.
Synthesis and in vitro pharmacology of substituted quinoline-2,4-dicarboxylic acids as inhibitors of vesicular glutamate transport
Carrigan, Christina N.,Bartlett, Richard D.,Esslinger, C. Sean,Cybulski, Kimberly A.,Tongcharoensirikul, Pakamas,Bridges, Richard J.,Thompson, Charles M.
, p. 2260 - 2276 (2007/10/03)
The vesicular glutamate transport (VGLUT) system selectively mediates the uptake of L-glutamate into synaptic vesicles. Uptake is linked to an H+-ATPase that provides coupling among ATP hydrolysis, an electrochemical proton gradient, and glutamate transport. Substituted quinoline-2,4-dicarboxylic acids (QDCs), prepared by condensation of dimethyl ketoglutaconate (DKG) with substituted anilines and subsequent hydrolysis, were investigated as potential VGLUT inhibitors in synaptic vesicles. A brief panel of substituted QDCs was previously reported (Carrigan et al. Bioorg. Med. Chem. Lett. 1999, 9, 2607-2612)1 and showed that certain substituents led to more potent competitive inhibitors of VGLUT. Using these compounds as leads, an expanded series of QDC analogues were prepared either by condensation of DKG with novel anilines or via aryl-coupling (Suzuki or Heck) to dimethyl 6-bromoquinolinedicarboxylate. From the panel of almost 50 substituted QDCs tested as inhibitors of the VGLUT system, the 6-PhCH=CH-QDC (Ki = 167 μM), 6-PhCH2CH2-QDC (Ki = 143 μM), 6-(4′-phenylstyryl)-QDC (Ki = 64 μM), and 6-biphenyl-4-yl-QDC (Ki=41 μM) were found to be the most potent blockers. A preliminary assessment of the key elements needed for binding to the VGLUT protein based on the structure-activity relationships for the panel of substituted QDCs is discussed herein. The substituted QDCs represent the first synthetically derived VGLUT inhibitors and are promising templates for the development of selective transporter inhibitors.
