6784-46-9

Usage

InChI:InChI=1/C15H27N/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11H,5-6,8,10,12,16H2,1-4H3/b14-9+,15-11+

Upstream product

• 4602-84-0 farnesol 
• 148162-66-7 N-farnesyltrifluoroacetamide 
• 123022-37-7 N-farnesylphtalimide 
• 176650-39-8 4-Methyl-N-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyl)-benzenesulfonamide 
• 106-28-5 Farnesol 
• 24163-93-7 farnesyl bromide 
• 148162-64-5 (2E,6E)-1-azido-3,7,11-trimethyldodeca-2,6,10-triene 

Downstream Products

• 147315-58-0 N-homogeranyl-N-methyl-N'-farnesylformamidine 
• 181703-94-6 (S)-2-Benzyloxycarbonylamino-3-[benzyloxycarbonyl-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyl)-amino]-propionic acid 

Relevant academic research and scientific papers

ANTIBIOTIC COMPOUNDS

Provided herein are lipidated glycopeptide compounds of formula (I); or a pharmaceutically acceptable salt, stereoisomer, solvate, or prodrug thereof. R1 is a lipid, R2 is -H or a lipid, and R3 and R4 are as defined herein. These compounds have antibiotic activity. Also provided are formulations comprising such compounds; as well as such compounds or formulations for use as a medicament. The compounds and formulations may also be used in the treatment of bacterial infection.

Potentiation of the activity of β-lactam antibiotics by farnesol and its derivatives

Farnesol, a sesquiterpene alcohol, potentiates the activity of β-lactam antibiotics against antibiotic-resistant bacteria. We document that farnesol and two synthetic derivatives (compounds 2 and 6) have poor antibacterial activities of their own, but they potentiate the activities of ampicillin and oxacillin against Staphylococcus aureus strains (including methicillin-resistant S. aureus). These compounds attenuate the rate of growth of bacteria, which has to be taken into account in assessment of the potentiation effect.

NISIN-BASED COMPOUNDS AND USE THEREOF IN THE TREATMENT OF BACTERIAL INFECTIONS

The invention relates to new antimicrobial compounds derived from nisin. In particular, the compounds are based on the unsubstituted nisin [1-12] structure, wherein said compounds have an antimicrobial activity exceeding the activity of the unsubstituted nisin [1-12] structure.

Semisynthetic Lipopeptides Derived from Nisin Display Antibacterial Activity and Lipid II Binding on Par with That of the Parent Compound

The lipid II-binding N-terminus of nisin, comprising the so-called A/B ring system, was synthetically modified to provide antibacterially active and proteolytically stable derivatives. A variety of lipids were coupled to the C-terminus of the nisin A/B ri

Synthesis of cyclopentenimines from N-allyl ynamides via a tandem aza-Claisen rearrangement-carbocyclization sequence

We describe here details of our investigations into Pd-catalyzed and thermal aza-Claisen-carbocyclizations of N-allyl ynamides to prepare a variety of α,β-unsaturated cyclopentenimines. The nature of the ynamide electron-withdrawing group and β-substituent plays critical roles in the success of this tandem cascade. With N-sulfonyl ynamides, the use of palladium catalysis is required, as facile 1,3-sulfonyl shifts dominate under thermal conditions. However, since no analogous 1,3-phosphoryl shift is operational, N-phosphoryl ynamides could be used to prepare similar cyclopentenimines under thermal conditions through zwitter ionic intermediates that undergo N-promoted H-shifts. Alternatively, by employing ynamides bearing tethered carbon nucleophiles, the zwitter ionic intermediates could be intercepted, giving rise rapidly to more complex fused bi- and tricyclic scaffolds.

Direct amination of bio-alcohols using ammonia

A slightly adapted catalyst system has been successfully applied in the direct amination of primary and secondary alcohols. Moreover, the applicability to diols has been shown, giving high selectivity towards the primary diamines. It was found that the Ru/P ratio as well as the amount of ammonia used are highly important in this system, especially for higher substrate loadings. The catalyst was employed on a larger batch scale for the conversion of isomannide to the corresponding diamine. Additionally, it was shown that the catalyst is stable for at least six consecutive runs. No significant loss of activity and selectivity was observed.

COMPOSITIONS AND METHODS FOR TREATMENT OF NEUROLOGICAL SYMPTOMS ASSOCIATED WITH ALCOHOL-WITHDRAWAL AND FOR CONVULSIVE SEIZURE

Particular aspects of the present invention provide pharmaceutical compositions comprising isoprenoid-based compounds (e.g., farnesol and/or farnesol analogues or derivatives) or dehydroisoprenoid-based compounds, and novel methods for using same in treat

Hydrogen bonding control in the oxidative cyclisation of 1,5-dienes

The regioselective dihydroxylation of a series of functionalised polyenes is described. Under acidic conditions, the osmate ester derivatives obtained from oxidation with OsO4/TMEDA undergo an intramolecular cyclisation reaction forming functionalised tetrahydrofurans with high stereoselectivity and in good yield. The generality of this method is illustrated with an application to the synthesis of a bis-tetrahydrofuran ring system.

Zwitterionic sulfobetaine inhibitors of squalene synthase

A substantial number of sulfobetaines (e.g., 10) have been synthesized and evaluated as inhibitors of squalene synthase (SS) on the basis of the idea that their zwitterionic structure would have properties conducive both to binding in the active site and to passage through cell membranes. When the simple sulfobetaine moiety is incorporated into compounds containing hydrophobic portions like those in farnesyl diphosphate (1) or presqualene diphosphate (2), inhibition of SS in a rat liver microsomal assay was indeed observed. For example, farnesylated sulfobetaine 10 has IC50 = 10 μM and aromatic derivative 35 has IC50 = 2 μM for SS inhibition. A wide variety of structural modifications, exemplified by compounds 43, 52, 76, 85, 91, 99, 111, and 115, was investigated. Unfortunately, no inhibitors in the submicromolar range were discovered, and exploration of a different type of zwitterion seems necessary if this appealing approach to inhibition of SS is going to provide a potential antihypercholesterolemic agent.

Mitsunobu-type alkylation of p-toluenesulfonamide. A convenient new route to primary and secondary amines

p-Toluenesulfonamide, which is known to form phosphine imides under Mitsunobu conditions, was shown to be alkylated in the presence of cyanomethylenetributylphosphorane to give N-substituted sulfonamides in excellent yields. The reaction can be applied to the synthesis of symmetrical and unsymmetrical N,N-disubstituted amides. When coupled with the desulfurization reactions, the reaction provides a new versatile synthetic route to primary and secondary amines from ammonia.