23434-40-4

Upstream product

• 1002-57-9 8-Aminooctanoic acid 
• 501-53-1 benzyl chloroformate 
• 1074-51-7 cyclooctanone oxime 

Downstream Products

• 23434-41-5 8-Benzyloxycarbonylamino-octansaeure-methylamid 
• 108257-18-7 8-Benzyloxycarbonylamino-octanoic acid 2,5-dioxo-pyrrolidin-1-yl ester 
• 92120-89-3 8,8'-bis(benzyloxycarbonylamino)-N,N'-octamethylenedioctanamide 
• 195302-72-8 (S)-1-[(R)-2-(8-Benzyloxycarbonylamino-octanoylamino)-4-phenyl-butyryl]-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 162877-42-1 (S)-2-(8-Benzyloxycarbonylamino-octanoylamino)-pentanedioic acid di-tert-butyl ester 
• 158726-54-6 N'-(2,2-Diphenyl-[1,3]dioxolan-4-ylmethyl)-N,N-dimethyl-octane-1,8-diamine 
• 158726-53-5 N-(2,2-diphenyl-<1,3>dioxolan-4-ylmethyl)-N,N',N'-trimethyloctane-1,8-diamine 
• 108257-24-5 (7-{[(2R,3S,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-carbamoyl}-heptyl)-carbamic acid benzyl ester 
• 129687-93-0 1,26-diamino-8,19-dibenzyldiazahexacosane 
• 129687-95-2 1,10-dibenzyl-18,29-tetraazacyclohexatriacontane 
• 129687-94-1 18,27-dibenzyl-8,17,28-trioxo-9,18,27-triazapentatriacontane lactam 
• 1228359-81-6 1-O-[8-(benzyloxycarbonylamino)octanoyl]-2,3-O,O'-isopropylidene-sn-glycerol 

Relevant academic research and scientific papers

Novel macrocyclic amidinoureas: Potent non-azole antifungals active against wild-type and resistant Candida species

Novel macrocyclic amidinourea derivatives 11, 18, and 25 were synthesized and evaluated as antifungal agents against wild-type and fluconazole resistant Candida species. Macrocyclic compounds 11 and 18 were synthesized through a convergent approach using as a key step a ring-closing metathesis macrocyclization reaction, whereas compounds 25 were obtained by our previously reported synthetic pathway. All the macrocyclic amidinoureas showed antifungal activity toward different Candida species higher or comparable to fluconazole and resulted highly active against fluconazole resistant Candida strains showing in many cases minimum inhibitory concentration values lower than voriconazole.

MACROCYCLIC COMPOUNDS USEFUL AS CHITINASE INHIBITORS

The present invention relates to macrocyclic compounds of formula (I) and their use as chitinase inhibitors as well as to pharmaceutical compositions and methods of preparation thereof. The compounds can in particular be used in the treatment, prevention and/or amelioration of asthma.

LUMINALLY-ACTING N-(PIPERIDIN-4-YL)BENZAMIDE DERIVATIVES

Disclosed are compounds of Formula 1, and pharmaceutically acceptable salts thereof, wherein m, R1, R2, R3, R4, R5, R6, X1, X2, X3 and X4 are defined in the specification. This disclosure also relates to materials and methods for preparing compounds of Formula 1, to pharmaceutical compositions which contain them, and to their use for treating diseases, disorders, and conditions associated with the 5-HT4 receptor.

A gram-scale synthesis of a macrocyclic amidinourea with strong antifungal activity through a Fukuyama tri-protected polyamine intermediate

Systemic fungal infections are, nowadays, of crucial importance and, thus, in the last decade, we explored the great potential of natural and synthetic guanylated compounds, a great amount of work that led to the development of new non-azole antifungal co

Design and synthesis of a novel inhibitor of T. Viride chitinase through an in silico target fishing protocol

In the last ten years, we identified and developed a new therapeutic class of antifungal agents, the macrocyclic amidinoureas. These compounds are active against several Candida species, including clinical isolates resistant to currently available antifungal drugs. The mode of action of these molecules is still unknown. In this work, we developed an in-silico target fishing procedure to identify a possible target for this class of compounds based on shape similarity, inverse docking procedure and consensus score rank-by-rank. Chitinase enzyme emerged as possible target. To confirm this hypothesis a novel macrocyclic derivative has been produced, specifically designed to increase the inhibition of the chitinase. Biological evaluation highlights a stronger enzymatic inhibition for the new derivative, while its antifungal activity drops probably because of pharmacokinetic issues. Collectively, our data suggest that chitinase represent at least one of the main target of macrocyclic amidinoureas.

NEW MACROCYCLIC AMIDINOUREA DERIVATIVES, METHODS OF PREPARATION AND USES THEREOF AS CHITINASE INHIBITORS

The present invention relates to macrocyclic amidinourea derivatives of formula 8, methods of preparation and uses thereof, pharmaceutical compositions in particular to be used as chitinase inhibitors in the treatment of a fungal infection.

Regioselective approach to phosphatidylinositol 3,5-bisphosphates: Syntheses of the native phospholipid and biotinylated short-chain derivative

Figure presented A selective bis-silylation of 1D-O-TBDPS-myo-inositol leads to a 1,3,5-trisubstituted inositol, which can be advanced to the headgroup of phosphatidylinositol-3,5-bisphosphate [PI(3,5)P2]. A mild, regioselective method for construction of the diacylglycerol moiety containing differing fatty acid chains, including the naturally occurring lipids, was developed. Their union in the synthesis of the cell-signaling molecule PI(3,5)P2 containing the sn-1-stearoyl and sn-2-arachidonoyl groups is described. The methodology was also used to generate dioctanoyl-PI(3,5)P 2 and a previously unreported biotin-PI(3,5)P2 conjugate, which was coupled to neutravidin beads and used to pull down PI(3,5)P 2-binding proteins from the cytosolic extract of adrenal neurosecretory cells. We report the specific pull-down of the PI(3,5)P 2-binding protein svp1p, a known PI(3,5)P2 effector involved in membrane trafficking.

Benzyl and tert-butyl carbamate derivatives of 1,ω-amino acids as simple yet efficient gelators

We report the synthesis and a study of the gelation properties of a series of N-protected long-chain amino acids. Especially, benzyl and tert-butyl carbamate derivatives of 11-aminoundecanoic acid in their deprotonated form can gelate polar organic solvents and water at very low concentration (less than 5 mM). This is explained by the contribution of multiple forces-H-bond, van der Waals and ionic interactions-in the gel aggregate formation and stabilization, which is confirmed by the experimental data. Among the series of compounds investigated, only a dimer of 11-aminoundecanoic acid is capable of gelating toluene, which stems from the increased number of hydrogen bonding sites in the main aliphatic chain.

Preparation of Large Macrocyclic Tetra-amines Consisting of a Methylene Backbone and a Cyclophane Type Skeleton

Efficient synthetic routes to 1,10,19,28-tetraazacyclohexatriacontane, a 36-membered ring compound with a methylene backbone, and bis(N,N'-octamethylene-4,4'-diaminodiphenylmethane), a 38-membered tetraamine with a cyclophane skeleton, have been developed

NOVEL 5-AMINO-4-HYDROXYVALERYL DERIVATIVES

Compounds of the formula STR1 in which R 1 represents hydrogen or acyl, A represents an optionally N-alkylated α-amino acid residue which is bonded N-terminally to R 1 and C-terminally to the group--NR 2--, R 2 represents hydrogen or lower alkyl, R 3 represents hydrogen, lower alkyl, optionally etherified or esterified hydroxy-lower alkyl, cycloalkyl, cycloalkyl-lower alkyl, bicycloalkyl-lower alkyl, tricycloalkyl-lower alkyl, aryl or aryl-lower alkyl, R 4 represents hydroxy or etherified or esterified hydroxy, R 5 represents lower alkyl having 2 or more carbon atoms, optionally etherified or esterified hydroxy-lower alkyl, cycloalkyl, cycloalkyl-lower alkyl, bicycloalkyl, bicycloalkyl-lower alkyl, tricycloalkyl, tricycloalkyl-lower alkyl, aryl, aryl-lower alkyl, optionally substituted carbamoyl, optionally substituted amino, optionally substituted hydroxy or optionally substituted mercapto and R 6 represents substituted amino, and salts of such compounds having salt-forming groups inhibit the blood pressure-increasing action of the enzyme renin and can be used as antihypertensives.