33105-94-1

Usage

Synonyms

1,3-diboc-2,2,4,4-tetramethyl-1,3-diazecane

Usage

Commonly used in organic synthesis and chemical research

Classification

A derivative of BOC-protected diamines

Application

Often used as a building block in the synthesis of various molecules and pharmaceuticals

Physical state

White to off-white solid at room temperature

Solubility

Soluble in organic solvents such as dichloromethane and methanol

Safety precautions

Important to handle with caution due to potential health and safety risks if not used properly

Upstream product

• 41840-28-2 S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine 
• 109-76-2 Trimethylenediamine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 

Relevant academic research and scientific papers

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

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

Efficient and expeditious chemoselective BOC protection of amines in catalyst and solvent-free media

A green and eco-friendly route for the almost quantitative BOC protection of a large variety of aliphatic and aromatic amines, amino acids, and amino alcohols is reported in catalyst and solvent-free media under mild reaction conditions. The products were confirmed by 1H, 13C NMR, IR spectroscopy, and in some cases, elemental analysis. This protocol does not require any water quenches, solvent separations, and purification steps, such as recrystallization and column chromatography.

Flow-mediated synthesis of Boc, Fmoc, and Dd iv monoprotected diamines

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.

New ianthelliformisamine derivatives as antibiotic enhancers against resistant gram-negative bacteria

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.

Synthesis and pharmacological testing of polyaminoquinolines as blockers of the apamin-sensitive Ca2+-activated K+ channel (SKCa)

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.

A folded conformation around the methylene group in simple Boc-NH-(CH2)3-NH-Boc: An X-ray diffraction study

Structural studies on model compounds Boc-NH-(CH2)2-NH-Boc (1) and Boc-NH-(CH2)3-NH-Boc (2) have shown the inherent tendency of the propylene group to adopt a folded conformation, which may help in peptide and peptide nucleic acid (PNA) design.

Inhibitors of retroviral proteases

The present invention relates to compounds of the formula I STR1 wherein A, Y, R2, R3, R4, R5, R6, l, m and the corresponding radicals labeled with * are defined as stated in the description, a process for their preparation and their use for the inhibition of retroviral proteases.

Search for the pharamcophore of the K+ channel blocker, apamin

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.

Mono-protected Diamines. N-tert-Butoxycarbonyl-α,ω-alkanediamines from α,ω-Alkanediamines

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.

A New Method for the Synthesis of Amides from Amines: Ruthenium Tetroxide Oxidation of N-Protected Alkylamines

A simple synthetic method for the preparation of amides from the corresponding primary alkylamines was elaborated using ruthenium tetroxide (RuO4) oxidation as a key step.