111186-67-5Relevant academic research and scientific papers
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 (1996)
The condensation of N-(trimethylsilylmethyl)benzylamine and aldehydes spontaneously gave azomethine ylides, which react with electron deficient olefins to yield cycloadducts under mild conditions.
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.
DIPROVOCIMS: A NEW AND POTENT CLASS OF TLR AGONISTS
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Page/Page column 150; 151, (2018/02/28)
A diprovocim compound that corresponds in structure to structural Formula V is disclosed, wherein A, W, Z, R1, R2, R3 and R4 (when present) are defined within. A diprovocim compound has immune-adjuvant properties on human and mouse cells in culture and on in vivo immunization of mice. A composition containing a diprovocim and a method of using a compound are also disclosed. The immunostimulatory activity of a diprovocim compound is similar to that of LPS, to which there is no apparent structural similarity. A contemplated compound bears no structural similarity to either the TLR1/TLR2 lipoprotein agonists nor to any other synthetic TLR agonist, and is remarkably easy to prepare and synthetically modify.
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.
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).
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.
Parent and N-substitued azomethine ylides from α-amino acids and formaldehyde. An easy access to 2,5-unsubstituted pyrrolidines. Evidence for oxazolidin-5-ones as direct precursor of these reactive intermediates
Joucla, Marc,Mortier, Jacques
, p. 579 - 583 (2007/10/02)
Formaldehyde reacts with α-amino acids and electron deficient alkenes to produce pyrrolidines.Azomethine ylides involved as intermediates in these reactions have been generated from isolated oxazolidin-5-ones which can be considered as the direct precursors of these ylides.
Simple Generation of Nonstabilized Azomethine Ylides through Decarboxylative Condensation of α-Amino Acids with Carbonyl Compounds via 5-Oxazolidinone Intermediates
Tsuge, Otohiko,Kanemasa, Shuji,Ohe, Masayuki,Takenaka, Shigeori
, p. 4079 - 4090 (2007/10/02)
Heating α-amino acids with a variety of carbonyl compounds generates N-unsubstituted or N-substituted azomethine ylides of nonstabilized types through the elimination of water and carbon dioxide.The ylides are captured by olefinic, acetylenic, and carbonyl dipolarophiles producing pyrrolidines, pyrrolines, and oxazolidines.The reaction involves intermediary 5-oxazolidinones which can be sometimes isolated.Some synthetic equivalents of parent azomethine ylide, methaniminium methylide, are accessible by this route.
