1191-69-1

Usage

Uses

Used in Pharmaceutical Industry:
Decyl isocyanate is used as a key intermediate compound for the synthesis of proteasome inhibitors, which play a crucial role in the development of novel therapeutic agents. These inhibitors target the proteasome, a cellular protein complex responsible for the degradation of unneeded or damaged proteins, and have shown potential in treating various diseases, including cancer and neurodegenerative disorders.
1. DECYL ISOCYANATE 98 is used as a precursor for the synthesis of proteasome inhibitors for targeting the proteasome in the treatment of diseases like cancer and neurodegenerative disorders.
2. DECYL ISOCYANATE 98 is used as a building block for the development of potential proteasome inhibitors such as decyl-urea-Val-NHNHBoc, decyl-urea-Val-Leu2-VS, and decyl-urea-Val-Leu2-EK, which are designed to modulate cellular processes and target specific diseases.
Used in Biotechnology Industry:
Decyl isocyanate is utilized in the development of innovative biotechnological applications, where proteasome inhibitors can be employed to study the role of the proteasome in cellular processes and to develop new strategies for disease management.
1. DECYL ISOCYANATE 98 is used as a starting material for the creation of proteasome inhibitors in biotechnological research to understand the proteasome's role in cellular functions and develop new therapeutic approaches.
2. DECYL ISOCYANATE 98 is used as a component in the design and synthesis of proteasome inhibitors for biotechnological applications, aiming to improve the understanding of disease mechanisms and the development of targeted therapies.

InChI:InChI=1/C11H21NO/c1-2-3-4-5-6-7-8-9-10-12-11-13/h2-10H2,1H3

Upstream product

• 112-37-8 undecylenic acid 
• 2016-57-1 1-aminodecane 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 17746-05-3 undecanoyl chloride 
• 1025502-64-0 tert-butyl decylcarbamate 
• 503-38-8 trichloromethyl chloroformate 
• 75-44-5 phosgene 

Downstream Products

• 1219818-85-5 4-chloro-2-(4-chlorophenylcarbamoyl)phenyl decylcarbamate 
• 1219818-76-4 4-chloro-2-(3,4-dichlorophenylcarbamoyl)phenyl decylcarbamate 
• 1219818-67-3 4-chloro-2-(3-chlorophenylcarbamoyl)phenyl decylcarbamate 
• 1013930-83-0 C₃₂H₄₆N₂O₄ 
• 904695-95-0 1-decyl-3-(4-fluorophenyl)urea 
• 904695-92-7 1-decyl-3-(2-fluorophenyl)urea 
• 384810-34-8 3-decyl-1-methyl-1-phenylurea 
• 1161362-92-0 (S)-1-decyl-3-(1-phenylethyl)urea 
• 122149-01-3 N-benzyloxy-N'-decylurea 
• 1337527-58-8 (R)-tert-butyl 2-(benzyloxycarbonylamino)-3-((R)-2,3-bis(decylcarbamoyloxy)propylthio)propanoate 

Relevant academic research and scientific papers

New lipophilic isoniazid derivatives and their 1,3,4-oxadiazole analogues: Synthesis, antimycobacterial activity and investigation of their mechanism of action

The development of novel drugs is essential for the treatment of tuberculosis and other mycobacterial infections in future. A series of N-alkyl-2-isonicotinoylhydrazine-1-carboxamides was synthesized from isoniazid (INH) and then cyclized to N-alkyl-5-(pyridin-4-yl)-1,3,4-oxadiazole-2-amines. All derivatives were characterised spectroscopically. The compounds were screened for their in vitro antimycobacterial activity against susceptible and multidrug-resistant Mycobacterium tuberculosis (Mtb.) and nontuberculous mycobacteria (NTM; M. avium, M. kansasii). The most active carboxamides were substituted by a short n-alkyl, their activity was comparable to INH with minimum inhibitory concentrations (MICs) against Mtb. of 0.5–2 μM. Moreover, they are non-toxic for HepG2, and some of them are highly active against INH-resistant NTM (MICs ≥4 μM). Their cyclization to 1,3,4-oxadiazoles did not increase the activity. The experimentally proved mechanism of action of 2-isonicotinoylhydrazine-1-carboxamides consists of the inhibition of enoyl-ACP reductase (InhA) in a way similar to INH, which is blocking the biosynthesis of mycolic acids. N-Dodecyl-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine as the most efficacious oxadiazole inhibits growth of both susceptible and drug-resistant Mtb. strains with uniform MIC values of 4–8 μM with no cross-resistance to antitubercular drugs including INH. The mechanism of action is not elucidated but it is different from INH. Obtained results qualify these promising derivatives for further investigation.

N-Guanidino Derivatives of 1,5-Dideoxy-1,5-imino-d-xylitol are Potent, Selective, and Stable Inhibitors of β-Glucocerebrosidase

A series of lipidated guanidino and urea derivatives of 1,5-dideoxy-1,5-imino-d-xylitol were prepared from d-xylose using a concise synthetic protocol. Inhibition assays with a panel of glycosidases revealed that the guanidino analogues display potent inhibition against human recombinant β-glucocerebrosidase with IC50 values in the low nanomolar range. Related urea analogues of 1,5-dideoxy-1,5-imino-d-xylitol were also synthesized and evaluated in the same fashion and found to be selective for β-galactosidase from bovine liver. No inhibition of human recombinant β-glucocerebrosidase was observed for the urea analogues. Computational studies provided insight into the potent activity of analogues bearing the substituted guanidine moiety in the inhibition of lysosomal glucocerebrosidase (GBA).

Triaminoformate long-carbon-chain organosilane quaternary ammonium salt compound as well as preparation and application thereof

The invention relates to a triaminoformate long carbon chain organosilane quaternary ammonium salt compound as well as preparation and an application thereof. The structure of the compound is shown ina general formula (I). The preparation method comprises the following steps: firstly, using long-chain aliphatic amine as a raw material to prepare long-carbon-chain isocyanate in an organic solvent;reacting the long-carbon-chain isocyanate with triethanolamine in an organic solvent, and carrying out recrystallization to obtain a triaminoformate fatty chain intermediate; and reacting the obtained intermediate with haloalkyl trimethoxysilane to obtain an organosilane quaternary ammonium salt compound. The organosilane quaternary ammonium salt compound can be applied to preparation of a hierarchical pore ZSM-5 zeolite molecular sieve. The obtained hierarchical pore channel ZSM-5 zeolite molecular sieve is beneficial to diffusion of macromolecular reactants and products, and has a potentialapplication prospect in macromolecular reaction catalysis.

Article novel sulfamethoxazole ureas & oxalamide as potential antimycobacterial agents

Infections caused by Mycobacterium tuberculosis (Mtb.) and nontuberculous mycobacteria (NTM) are considered to be a global health problem; current therapeutic options are limited. Sulfonamides have exhibited a wide range of biological activities including those against mycobacteria. Based on the activity of 4-(3-heptylureido)-N-(5-methylisoxazol-3-yl)benzenesulfonamide against NTM, we designed a series of homologous sulfamethoxazole-based n-Alkyl ureas (C1-C12), as well as several related ureas and an oxalamide. Fifteen ureas and one oxalamide were synthesized by five synthetic procedures and characterized. They were screened for their activity against Mtb. and three NTM strains (M. avium, M. kansasii). All of them share antimycobacterial properties with minimum inhibitory concentration (MIC) values starting from 2 μM. The highest activity showed 4,40-[carbonylbis(azanediyl)]bis[N-(5-methylisoxazol-3-yl)benzenesulfonamide] with MIC of 2-62.5 μM(i.e., 1.07-33.28 μg/mL). Among n-Alkyl ureas, methyl group is optimal for the inhibition of both Mtb. and NTM. Generally, longer alkyls led to increased MIC values, heptyl being an exception for NTM. Some of the novel derivatives are superior to parent sulfamethoxazole. Several urea and oxalamide derivatives are promising antimycobacterial agents with low micromolar MIC values.

Discovery of a potent and highly β1 specific proteasome inhibitor from a focused library of urea-containing peptide vinyl sulfones and peptide epoxyketones

Syringolins, a class of natural products, potently and selectively inhibit the proteasome and show promising antitumour activity. To gain insight in the mode of action of syringolins, the ureido structural element present in syringolins is incorporated in

Synthesis and transdermal permeation-enhancing activity of carbonate and carbamate analogs of Transkarbam 12

Transkarbam 12 (5-(dodecyloxycarbonyl)pentylammonium-5-(dodecyloxycarbonyl)pentylcarbamate, T12) is a highly effective skin permeation enhancer. In this study, ester groups in the molecule of T12 were replaced by carbonate and carbamate ones, respectively. The in vitro permeation-enhancing activities were evaluated using porcine skin and compared with those of T12 and previously prepared series of amide, ketone, and alkyl analogs. According to the activities and behavior of the compounds in donor samples, ester group is essential for the activity of T12; its replacement not only decreases the enhancing potency, but is likely to change the mechanism of action.

Semicarbazides as gel forming agents for common solvents and liquid crystals

This paper describes the synthesis of 14 new gelling agents with semicarbazide groups as H-bonding motifs and alkyl- and/or azobenzene side groups. They gel solvents like decaline, 1,2-dichlorobenzene and toluene and liquid crystalline mixtures. X-Ray structure analysis shows that the semicarbazides are connected by H-bonds, each molecule to four neighbours. As a result a ribbon is formed with a core of H-bonded semicarbazide groups and alkyl chains sticking to the side. IR measurements show an unchanged H-bonding motif in large crystals and in the gel fibres, even in LC-mixture. During heating the gel melts (rheology), while the H-bonding motif of the crystal disappears (IR and DSC measurements). First experiments show that these gel-forming agents can be used to gel LC-phases and to stabilise the director pattern present during gel formation. The Royal Society of Chemistry 2006.

Piperidine-containing histamine H3 receptor antagonists of the carbamate series: The alkyl derivatives

A series of N-alkyl urethanes, potential histamine H3 receptor antagonists, was prepared. Carbamate derivatives were synthesized from appropriate isocyanates and N-piperidinoalkan-1-ols. The novel compounds were evaluated for histamine H3 receptor activity in vitro on the guinea pig ileum. Some selected compounds were tested in vivo after p.o. application to mice and in vitro for selectivity towards other histamine receptors (H 1, H2) in functional assays in the guinea pig. The most potent H3 receptor antagonist in vitro was compound 14 (pA 2 = 7.2). Compound 14 was equipotent at M3 receptors and lacked H3 receptor activity in vivo. Predictions of octanol-water partition coefficient (Pallas) and metabolic fate (MetabolExpert, METEOR) were used to explore potential reasons for this absence of in vivo activity.

Process for the preparation of organic mono- and polyisocyanates

A process for the preparation of organic mono- and polyisocyanates is described, in which a hydrogen chloride adduct of a trisubstituted urea is thermally decomposed to form the isocyanate. The hydrogen chloride adduct at minimum contains the stoichiometric amount of HCl, and at maximum a 10 mole-% excess. The process is carried out in a closed system at a temperature between about 80° and 180° C.; the reaction is effected either in a melt or in the presence of an inert organic solvent.