87813-06-7Relevant academic research and scientific papers
Electrochemical Generation of a Nonstabilized Azomethine Ylide: Access to Substituted N-Heterocycles
Kumar, Rakesh,Banerjee, Prabal
, p. 16104 - 16113 (2021/11/18)
Azomethine ylides are fascinating 1,3-dipoles for [3 + 2] cycloaddition reactions toward the construction ofN-heterocycles. Herein, an efficient and environmentally benign electrochemical approach for the generation of a nonstabilized azomethine ylide has been established under metal-free and external oxidant-free conditions. The resulting 1,3-dipole undergoes a [3 + 2] cycloaddition reaction with olefins. This electrosynthetic methodology indulges a straightforward and facile approach for the construction of substituted pyrrolidines.
Diprovocims: A New and Exceptionally Potent Class of Toll-like Receptor Agonists
Morin,Wang, Ying,Jones, Brian T.,Mifune, Yuto,Su, Lijing,Shi, Hexin,Moresco, Eva Marie Y.,Zhang, Hong,Beutler, Bruce,Boger, Dale L.
supporting information, p. 14440 - 14454 (2018/10/24)
A screen conducted with nearly 100000 compounds and a surrogate functional assay for stimulation of an immune response that measured the release of TNF-α from treated human THP-1 myeloid cells differentiated along the macrophage line led to the discovery of the diprovocims. Unique to these efforts and of special interest, the screening leads for this new class of activators of an immune response came from a compound library designed to promote cell-surface receptor dimerization. Subsequent comprehensive structure-activity relationship studies improved the potency 800-fold over that of the screening leads, providing diprovocim-1 and diprovocim-2. The diprovocims act by inducing cell-surface toll-like receptor (TLR)-2 dimerization and activation with TLR1 (TLR1/TLR2 agonist), bear no structural similarity to any known natural or synthetic TLR agonist, and are easy to prepare and synthetically modify, and selected members are active in both human and murine systems. The most potent diprovocim (3, diprovocim-1) elicits full agonist activity at extraordinarily low concentrations (EC50= 110 pM) in human THP-1 cells, being more potent than the naturally derived TLR1/TLR2 agonist Pam3CSK4 or any other known small molecule TLR agonist.
COMPOSITIONS AND METHODS FOR THE TREATMENT OF BACTERIAL INFECTIONS
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Page/Page column 256, (2018/02/28)
Compositions and methods for the treatment of bacterial infections include compounds containing dimers of cyclic heptapeptides. In particular, compounds can be used in the treatment of bacterial infections caused by Gram-negative bacteria.
Synthesis and biological activity of Δ-5,6-norcantharimides: importance of the 5,6-bridge
Thaqi, Ali,Scott, Janet L.,Gilbert, Jayne,Sakoff, Jennette A.,McCluskey, Adam
supporting information; experimental part, p. 1717 - 1723 (2010/07/02)
Cantharidin (1) and norcantharidin (2) are potent protein phosphatase 1 and 2A inhibitors that also display high levels of anticancer activity against a broad range of tumor cells lines. Surprisingly, Δ-5,6-ethyl norcantharidin (3, cis-tetrahydrofurano[3,4-c]furan-1,3-dione) displays neither phosphatase inhibition nor anticancer activity. This suggests that the 5,6-ethyl bridge is pivotal to both anti-cancer and protein phosphatase activity. Additionally bioisosteric replacement of the ethereal oxygen has no effect on biological activity nor does modification of the anhydride moiety. Unlike the parent norcantharidin, anhydride ring opening has no effect on either protein phosphatase inhibition or anti-cancer activity. Additionally, this work highlights the discovery of the octyl substituted, cis-5-benzyl-2-hexyltetrahydro-2H,3aH-pyrrolo[3,4-c]pyrrole-1,3-dione, 9p, and the octyl substituted, cis-octyltetrahydro-5H-furo[3,4-c]pyrrole-4,6-dione, 8p, as two new cytotoxic agents which are equipotent (9p) with, and more potent (8p) than norcantharidin. Crown Copyright
Small molecule inhibitors of Myc/Max dimerization and Myc-induced cell transformation
Shi, Jin,Stover, James S.,Whitby, Landon R.,Vogt, Peter K.,Boger, Dale L.
scheme or table, p. 6038 - 6041 (2010/04/05)
The preparation and evaluation of a series of inhibitors of Myc/Max dimerization and Myc-induced cell transformation are described providing mycmycin-1 (3) and mycmycin-2 (4).
Tris(pentafluorophenyl)borane-catalyzed synthesis of N-benzyl pyrrolidines
Srihari, Pabbaraja,Yaragorla, Srinivasa Rao,Basu, Debjit,Chandrasekhar, Srivari
, p. 2646 - 2648 (2008/02/04)
1,3-Dipolar cycloaddition of in situ generated azomethine ylides to electron deficient olefins catalyzed tris(pentafluorophenyl)borane is described. Georg Thieme Verlag Stuttgart.
1,2,-Disubstituted cyclic inhibitors of matrix metalloproteases and TNF-alpha
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, (2008/06/13)
The present application describes novel 1,2-disubsituted cyclic derivatives of formula I: or pharmaceutically acceptable salt forms thereof, wherein ring B is a 3-8 membered non-aromatic ring consisting of: carbon atoms, 0-1 carbonyl groups, 0-1 double bo
Sequential two-electron oxidation of α,α′-disilylmethylamines to generate non-stabilized azomethine ylide: An ideal approach for the construction of substituted and fused pyrrolidine ring systems
Pandey, Ganesh,Lakshmaiah,Gadre, Smita R.
, p. 91 - 98 (2007/10/03)
α,α′-Di(trimethylsilylmethyl)amines undergo sequential double desilylation processes, by two-electron oxidation initiated either by photoinduced electron transfer (PET) or Ag(I)F, to produce non-stabilized azomethine ylides efficiently which upon trapping with appropriate dipolarophiles give the corresponding pyrrolidines. Application of this strategy to cyclic analogue for the rapid construction of biologically important 1-azabicyclo[m,3.0]alkane framework is discussed.
A versatile cycloaddition for the generation of pyrrolidine derivatives via C-N-C 1,3-dipoles
Torii, Sigeru,Okumoto, Hiroshi,Genba, Akiko
, p. 747 - 748 (2007/10/03)
The condensation of N-(trimethylsilylmethyl)benzylamine and aldehydes spontaneously gave azomethine ylides, which react with electron deficient olefins to yield cycloadducts under mild conditions.
