34237-69-9

Upstream product

• 462-94-2 1,5-diaminopentane 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 955011-81-1 KYS₀₅₀₈₉ 
• 18807-70-0 N,N'-pentane-1,5-diyl-bis-carbamic acid dibenzyl ester 

Relevant academic research and scientific papers

Compounds that activate the mouse melanocortin-1 receptor identified by screening a small molecule library based upon the β-turn

A library of 951 compounds based upon the β-turn motif were examined for their ability to stimulate the melanocortin-1 receptor. From this screening process, we have identified two compounds possessing low micromolar agonist activity at the mMC1R. The compound EL1 with racemic Nal(2') in the i + 1 position, DPro in the i + 2 position, and Trp in the i + 3 position possesses an EC50 of 42.5 ± 6.9 μM. Compound EL2 with Trp in the i + 1 position, DLys in the i + 2 position, and Phe in the i + 3 position possesses an EC50 value of 63.4 ± 26.9 μM. The results of the library screening process are consistent with a hypothesis dating back to the 1980s proposing that a β-turn conformation involving the melanocortin 'Phe-Arg-Trp' core amino acids provides the key recognition element. Additionally, these compounds represent the first nonpeptidic heterocyclic molecules reported to date that are able to activate the MC1R, a melanocyte receptor involved in skin pigmentation and animal coat coloration.

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.

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.

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.