- Flow-mediated synthesis of Boc, Fmoc, and Dd iv monoprotected diamines
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A series of monoprotected aliphatic diamines (21 examples) were synthesized via continuous flow methods. The carbamates and enamines were obtained in 45-91% yields using a 0.5 mm diameter PTFE tubular flow reactor. Using readily accessible protecting group precursors, the procedure serves as an attractive alternative to existing batch-mode synthetic routes by providing direct, multigram access to N-Boc-, N-Fmoc-, and N-Ddiv-protected compounds with productivity indexes of 1.2-3.6 g/h.
- Jong, Thingsoon,Bradley, Mark
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supporting information
p. 422 - 425
(2015/03/03)
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- New ianthelliformisamine derivatives as antibiotic enhancers against resistant gram-negative bacteria
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A series consisting of ianthelliformisamimes A, B, and C as well as its synthetic analogues was prepared in high chemical yield, from 27 to 91%, using peptide coupling as the key step, and the compounds were evaluated for their in vitro antibiotic enhancer properties against resistant Gram-negative bacteria and clinical isolates. The mechanism of action of one of these derivatives against Pseudomonas aeruginosa when combined with doxycycline was precisely evaluated utilizing bioluminescence to measure ATP efflux and fluorescence to evaluate membrane depolarization.
- Pieri, Cyril,Borselli, Diane,Di Giorgio, Carole,De Méo, Michel,Bolla, Jean-Michel,Vidal, Nicolas,Combes, Sébastien,Brunel, Jean Michel
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p. 4263 - 4272
(2014/06/09)
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- Design, synthesis and antimalarial/anticancer evaluation of spermidine linked artemisinin conjugates designed to exploit polyamine transporters in Plasmodium falciparum and HL-60 cancer cell lines
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A series of artemisinin-spermidine conjugates designed to utilise the upregulated polyamine transporter found in cancer cells have been prepared. These conjugates were evaluated against human promyelocytic leukaemia HL-60 cells and chloroquine-sensitive 3
- Chadwick, James,Jones, Michael,Mercer, Amy E.,Stocks, Paul A.,Ward, Stephen A.,Park, B. Kevin,O'Neill, Paul M.
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experimental part
p. 2586 - 2597
(2010/06/16)
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- Synthesis and pharmacological testing of polyaminoquinolines as blockers of the apamin-sensitive Ca2+-activated K+ channel (SKCa)
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The synthesis and pharmacological testing of a series of non-peptidic blockers of the SKCa (SK-3) channel is described. Target compounds were designed to mimic the spatial relationships of selected key residues in the energy-minimised structure of the octadecapeptide apamin, which are a highly potent blocker of this channel. Structures consist of a central unit, either a fumaric acid or an aromatic ring, to which are attached two alkylguanidine or two to four alkylaminoquinoline substituents. Potency was tested by the ability to inhibit the SKCa channel-mediated after-hyperpolarization (AHP) in cultured rat sympathetic neurones. It was found that bis-aminoquinoline derivatives are significantly more potent as channel blockers than are the corresponding guanidines. This adds to the earlier evidence that delocalisation of positive charge through the more extensive aminoquinolinium ring system is important for effective channel binding. It was also found that an increase in activity can be gained by the addition of a third aminoquinoline residue to give non-quaternized amines which have submicromolar potencies (IC50 = 0.13-0.36 μM). Extension to four aminoquinoline residues increased the potency to IC50 = 93 nM.
- Fletcher, David I.,Ganellin, C. Robin,Piergentili, Alessandro,Dunn, Philip M.,Jenkinson, Donald H.
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p. 5457 - 5479
(2008/09/18)
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- Fluorobenzamides and uses thereof
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The invention relates to fluorobenzamide derivatives of the formula wherein R1, R2, R3 R4, R5, R6 and R7 are as defined herein. =, The compounds of the invention are selective monoamine oxidase B inhibitors and therefore they are suitable for the treatment of diseases mediated by monoamine oxidase B, such as Alzheimer's disease or senile dementia.
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- Synthesis of Carbamate Protected Spermidine Homologues Through α,ω-Alkanediamines
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The total synthesis of three triamines selectively protected in the primary amino groups (1a-c) and two triamines protected in the secondary amino function and in one of the primary amino functions (2a and 2c), based on a simple and efficient procedure, is described.
- Arasujo, M. Joso S. M. P.,Ragnarsson, Ulf,Trigo, M. Joaquina S. A. Amaral,Almeida, M. Lurdes S.
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p. 2143 - 2161
(2007/10/03)
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- Search for the pharamcophore of the K+ channel blocker, apamin
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The suggestion that the arginine residues, 13Arg and 14Arg, in the octadecapeptide apamin 1 are critically important to its action in blocking Ca2+-dependent K+ channels (and hence part of the 'pharmacophore') has been investigated by examining small peptides containing Arg-Arg or Lys-Arg. Bisguanidine derivatives modelled on the Arg-Arg partial pharmacophore have also been synthesised and tested; in particular, N-(2-guanidinoethyl)-3[N1-(2-guanidinoethyl)carbamoyl]-trans-propena mide 11 and its higher homologue 12. None of the compounds showed more than weak activity (K(i) > 10-5 M) indicating that although the Arg-Arg fragment may be necessary, it is not a sufficient atom grouping for the pharmacophore.
- Demonchaux,Granellin,Dunn,Haylett,Jenkinson
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p. 915 - 920
(2007/10/02)
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- Mono-protected Diamines. N-tert-Butoxycarbonyl-α,ω-alkanediamines from α,ω-Alkanediamines
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We wish to report a convenient pathway to N-tert-butoxycarbonyl-α,ω-alanediamines 2a-e by treatment of the corresponding α,ω-alkanediamine with di-tert-butyl dicarbonate in dioxane as the solvent.Only small amounts of the bis-substituted N,N'-tert-butoxycarbonyl-α,ω-aldnediamines 3a-e were formed (2-9percent) which were easily removed by an aquous workup.The α,ω-alkane-aza-diamine 4 was also mono-protected (62percent yield of 5) by the same methodology.
- Krapcho, A. Paul,Kuell, Christopher S.
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p. 2559 - 2564
(2007/10/02)
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