20116-65-8Relevant academic research and scientific papers
Synthesis and reactions of rhenium enyne, and vinylalkenylidene complexes
Casey, Charles P.,Ha, Yunkyoung,Powell, Douglas R.
, p. 185 - 194 (1994)
Reaction of Cp*Re(CO)2(THF) with HCCC(CH3)=CH2 produced the conjugated enyne complex Cp*(CO)2Re2-HCCC(CH3)=CH2> (1).Attempted preparation of an η3-propargyl complex by protonation of 1 with HBF4 failed.T
Phthalate plasticizers covalently linked to PVC via copper-free or copper catalyzed azide-alkyne cycloadditions
Earla, Aruna,Li, Longbo,Costanzo, Philip,Braslau, Rebecca
, p. 1 - 12 (2017)
Plasticization of PVC was carried out by covalently linking phthalate derivatives via copper-free (thermal) or copper catalyzed azide-alkyne cycloadditions. Di(2-ethylhexyl) phthalate derivatives (DEHP-ether and DEHP-ester) were synthesized and appended to PVC at two different densities. The glass transition temperatures of the modified PVC decreased with increasing content of plasticizer. PVC-DEHP-ether gave lower glass transition temperatures than PVC-DEHP-ester, reflecting the enhanced flexibility of the ether versus ester linker.
Elaboration of a fragment library hit produces potent and selective aspartate semialdehyde dehydrogenase inhibitors
Thangavelu, Bharani,Bhansali, Pravin,Viola, Ronald E.
, p. 6622 - 6631 (2015)
Aspartate-β-semialdehyde dehydrogenase (ASADH) lies at the first branch point in the aspartate metabolic pathway which leads to the biosynthesis of several essential amino acids and some important metabolites. This pathway is crucial for many metabolic processes in plants and microbes like bacteria and fungi, but is absent in mammals. Therefore, the key microbial enzymes involved in this pathway are attractive potential targets for development of new antibiotics with novel modes of action. The ASADH enzyme family shares the same substrate binding and active site catalytic groups; however, the enzymes from representative bacterial and fungal species show different inhibition patterns when previously screened against low molecular weight inhibitors identified from fragment library screening. In the present study several approaches, including fragment based drug discovery (FBDD), inhibitor docking, kinetic, and structure-activity relationship (SAR) studies have been used to guide ASADH inhibitor development. Elaboration of a core structure identified by FBDD has led to the synthesis of low micromolar inhibitors of the target enzyme, with high selectivity introduced between the Gram-negative and Gram-positive orthologs of ASADH. This new set of structures open a novel direction for the development of inhibitors against this validated drug-target enzyme.
Ni-Catalyzed Direct Carboxylation of Aryl C?H Bonds in Benzamides with CO2
Li, Bin,Pei, Chunzhe,Wang, Baiquan,Zong, Jiarui
, (2021/12/08)
The direct carboxylation of inert aryl C?H bond catalyzed by abundant and cheap nickel is still facing challenge. Herein, we report the Ni-catalyzed direct carboxylation of aryl C?H bonds in benzamides under 1 atm of CO2 to afford various methyl carboxylates or phthalimides, dealing with different post-processing. The reaction displays excellent functional group tolerance and affords moderate to high carboxylation yields under mild conditions. Detail mechanistic studies suggest that a Ni(0)?Ni(II)?Ni(I) catalytic cycle may be involved in this reaction. (Figure presented.).
Organocatalyzed Synthesis of Highly Functionalized Phthalimides via Diels-Alder Reaction Employing Two Dienophiles
Akhtar, Muhammad Saeed,Lee, Yong Rok
, p. 15129 - 15138 (2020/12/02)
An efficient and facile protocol for the synthesis of biologically and pharmaceutically important phthalimides is developed by l-proline-catalyzed reaction between two dienophiles of α,β-unsaturated aldehydes and maleimides. The reaction involves an efficient benzannulation that proceeds via a formal [4 + 2] cycloaddition of azadiene intermediates generated in situ from enals and N-substituted maleimides. This protocol provides a variety of functionalized phthalimide derivatives, including a potent COX-2 enzyme inhibitor.
Highly-functionalized arene synthesis based on palladium on carbon-catalyzed aqueous dehydrogenation of cyclohexadienes and cyclohexenes
Yasukawa, Naoki,Yokoyama, Hiroki,Masuda, Masahiro,Monguchi, Yasunari,Sajiki, Hironao,Sawama, Yoshinari
supporting information, p. 1213 - 1217 (2018/03/28)
Transition metal-catalyzed dehydrogenation is a clean oxidation method requiring no additional oxidants. We have accomplished a heterogeneous Pd/C-catalyzed aqueous dehydrogenation of 1,4-cyclohexadienes and cyclohexenes to give the corresponding highly-functionalized arenes. Furthermore, various arenes could be efficiently constructed in a one-pot manner via a Diels-Alder reaction and the following dehydrogenation.
Design and optimization of aspartate N-acetyltransferase inhibitors for the potential treatment of Canavan disease
Thangavelu, Bharani,Mutthamsetty, Vinay,Wang, Qinzhe,Viola, Ronald E.
, p. 870 - 885 (2017/02/05)
Canavan disease is a fatal neurological disorder caused by defects in the metabolism of N-acetyl-L-aspartate (NAA). Recent work has shown that the devastating symptoms of this disorder are correlated with the elevated levels of NAA observed in these patients, caused as a consequence of the inability of mutated forms of aspartoacylase to adequately catalyze its breakdown. The membrane-associated enzyme responsible for the synthesis of NAA, aspartate N-acetyltransferase (ANAT), has recently been purified and examined (Wang et al., Prot Expr Purif. 2016;119:11). With the availability, for the first time, of a stable and soluble form of ANAT we can now report the identification of initial inhibitors against this biosynthetic enzyme, obtained from the screening of several focused compound libraries. Two core structures of these moderate binding compounds have subsequently been optimized, with the most potent inhibitors in these series possessing sub-micromolar inhibition constants (Kivalues) against ANAT. Slowing the production of NAA via the inhibition of ANAT will lower the elevated levels of this metabolite and can potentially serve as a treatment option to moderate the symptoms of Canavan disease.
POTENT PHTHALATE INHIBITORS OF ASPARTATE N-ACETYLTRANSFERASE AND SELECTIVE ASPARTATE PATHWAY INHIBITORS
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Paragraph 0033; 00139; 00140, (2017/03/21)
Phthalate derivatives that are aspartate-P-semialdehyde dehydrogenase (ASADH) inhibitor compounds, aspartate N-acetyltransferase (ANAT) inhibitor compounds, or both, are described, as well as methods of making the same, and methods of using the same.
Sequential hydroformylation/Diels-Alder processes: One-pot synthesis of polysubstituted cyclohexenes, cyclohexadienes, and phthalates from alkynes
Fang, Xianjie,Jackstell, Ralf,Beller, Matthias
supporting information, p. 7939 - 7942 (2014/07/07)
A novel, one-pot hydroformylation/Diels-Alder sequence for the synthesis of multisubstituted cyclohexenes, cyclohexadienes, and phthalates has been developed. Various alkynes were efficiently converted into the corresponding products in good yields and with excellent diastereoselectivity through palladium-catalyzed hydroformylation followed by an AAD-type reaction (AAD: Amides-Aldehydes-Dienophiles). In view of the availability of the substrates, the atom-efficiency of the overall process, and the convenient introduction of substituents in the cyclohexene ring, this method complements current methods for the preparation of polysubstituted cyclohexane derivatives. Putting it together: A one-pot procedure for the diversity-oriented synthesis of multisubstituted cyclohexenes, cyclohexadienes, and phthalates through hydroformylation of alkynes followed by a Diels-Alder reaction has been developed (see scheme; EWG=electron-withdrawing group).
The d10 route to dye-sensitized solar cells: Step-wise assembly of zinc(ii) photosensitizers on TiO2 surfaces
Bozic-Weber, Biljana,Constable, Edwin C.,Hostettler, Nik,Housecroft, Catherine E.,Schmitt, Ralf,Schoenhofer, Ewald
supporting information; experimental part, p. 5727 - 5729 (2012/07/27)
Dye-sensitized solar cells have been assembled using a sequential approach: a TiO2 surface was functionalized with an anchoring ligand, followed by metallation with Zn(OAc)2 or ZnCl2, and subsequent capping with a chromophore functionalized 2,2′:6′,2″- terpyridine; the DSCs exhibit surprisingly good efficiencies confirming the effectiveness of the new strategy for zinc-based DSC fabrication.
