128550-06-1

Usage

Uses

Used in Organic Synthesis:
(N^1,N^4,N^9,N^13-tetra-tert-butoxycarbonyl)-1,16-diamino-4,9,13-triazahexadecane is used as a protecting group in organic synthesis. The reason for this application is that the tert-butoxycarbonyl groups can be selectively removed under mild conditions, revealing the amino groups and allowing for further reactions.
Used in Pharmaceutical Applications:
In the pharmaceutical industry, (N^1,N^4,N^9,N^13-tetra-tert-butoxycarbonyl)-1,16-diamino-4,9,13-triazahexadecane is used as a building block for the development of new drugs. The presence of multiple amino groups and the triazahexadecane backbone provides flexibility and rigidity, which can be exploited in the design of novel drug candidates.
Used in Peptide Bond Formation:
(N^1,N^4,N^9,N^13-tetra-tert-butoxycarbonyl)-1,16-diamino-4,9,13-triazahexadecane is also used in the formation of peptide bonds. The multiple amino groups in the compound facilitate the creation of these bonds, which are crucial for the structure and function of proteins and peptides.

Upstream product

• 128550-05-0 2-(2-cyanoethyl)-6,11-bis<(1,1-dimethylethoxy)carbonyl>-2,6,11,15-tetraazahexadecanedioic acid bis(1,1-dimethylethyl) ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 71-44-3 Spermine 
• 1208364-62-8 [3-(tert-butoxycarbonyl-{4-[tert-butoxycarbonyl-(3-tert-butoxycarbonylaminopropyl)-amino]-butyl}-amino)-propyl]-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-carbamic acid tertiary-butyl ester 
• 65564-05-8 3-[(benzyloxycarbonyl)amino]propanal 
• 114459-62-0 tri-Boc-spermine 
• 128550-03-8 2-(2-cyanoethyl)-7-<(1,1-dimethylethoxy)carbonyl>-2,7,11-triazadodecanedioic acid bis(1,1-dimethylethyl) ester 
• 128550-02-7 16-cyano-2,2-dimethyl-3-oxa-4-oxo-5,9,14-triazahexadecane 
• 83948-53-2 3-bromopropylamine tert-butylcarbamate 
• 201984-66-9 1-trifluoroacetyl-5,10,14-tris-Boc-spermine 
• 202145-88-8 N-(3-((4-((3-aminopropyl)amino)butyl)amino)propyl)-2,2,2-trifluoroacetamide 
• 201984-76-1 N¹,N⁵,N¹⁰-tri-tert-butoxycarbonyl-N¹⁸-benzyloxycarbonyl-1,5,10,14,18-pentaazaoctadecane 
• 128550-04-9 20-cyano-2,2-dimethyl-4-oxo-3-oxa-5,9,14,18-tetraazaeicosane-9,14-dicarboxylic acid bis(1,1-dimethylethyl) ester 
• 196704-28-6 (3-Benzyloxycarbonylamino-propyl)-[3-(tert-butoxycarbonyl-{4-[tert-butoxycarbonyl-(3-tert-butoxycarbonylamino-propyl)-amino]-butyl}-amino)-propyl]-carbamic acid tert-butyl ester 

Downstream Products

• 1208364-63-9 C₆₃H₉₀N₆O₁₈ 
• 128549-97-3 N-(20-amino-4-hydroxy-4,8,12,17-tetraazaeicos-1-yl)-4-hydroxy-1H-indole-3-acetamide 
• 128549-99-5 N-(20-amino-4-hydroxy-4,8,12,17-tetraazaeicos-1-yl)-2,5-dihydroxybenzamide 
• 128549-98-4 N-(20-amino-4-hydroxy-4,8,12,17-tetraazaeicos-1-yl)-4-hydroxybenzamide 
• 128550-18-5 1-<2,5-bis(methoxymethoxy)phenyl>-6-hydroxy-26,26-dimethyl-1,24-dioxo-25-oxa-2,6,10,14,19,23-hexaazaheptacosane-10,14,19-tricarboxylic acid tris(1,1-dimethylethyl) ester 
• 133416-41-8 1-<2,5-bis(methoxymethoxy)phenyl>-26,26-dimethyl-1,24-dioxo-25-oxa-2,6,10,14,19,23-hexaazaheptacosane-10,14,19-tricarboxylic acid tris(1,1-dimethylethyl) ester 
• 128550-17-4 1-<4-(methoxymethoxy)phenyl>-6-hydroxy-26,26-dimethyl-1,24-dioxo-25-oxa-2,6,10,14,19,23-hexaazaheptacosane-10,14,19-tricarboxylic acid tris(1,1-dimethylethyl) ester 
• 128550-15-2 1-<4-(methoxymethoxy)phenyl>-26,26-dimethyl-1,24-dioxo-25-oxa-2,6,10,14,19,23-hexaazaheptacosane-10,14,19-tricarboxylic acid tris(1,1-dimethylethyl) ester 
• 930265-72-8 [3-({3-[bis-(2-cyano-ethyl)-amino]-propyl}-tert-butoxycarbonyl-amino)-propyl]-{4-[tert-butoxycarbonyl-(3-tert-butoxycarbonylamino-propyl)-amino]-butyl}-carbamic acid tert-butyl ester 
• 128550-26-5 [3-(tert-Butoxycarbonyl-{4-[tert-butoxycarbonyl-(3-tert-butoxycarbonylamino-propyl)-amino]-butyl}-amino)-propyl]-[3-(2-cyano-ethylamino)-propyl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Homologation of polyamines in the synthesis of lipo-spermine conjugates and related lipoplexes

Polyamine amides are useful in gene delivery as synthetic (non-viral) vectors or mimics of polycationic histones. The application of a homologation strategy, based upon reductive alkylation, allows unsymmetrical polyamine amides to be prepared in good yie

A polyamine-modified near-infrared fluorescent probe for selective staining of live cancer cells

We report the synthesis of novel polyamine-modified near-infrared (NIR) probes, which show excellent water-solubility and good optical properties. One probe was taken up efficiently by living cancer cell lines whereas no staining of the non-cancer cells was observed.

NEW (POLY)AMINOALKYLAMINOALKYLAMIDE, ALKYL-UREA, OR ALKYL-SULFONAMIDE DERIVATIVES OF EPIPODOPHYLLOTOXIN, A PROCESS FOR PREPARING THEM, AND APPLICATION THEREOF IN THERAPY AS ANTICANCER AGENTS

The present invention relates to new derivatives of epipodophyllotoxin 4-substituted with an optionally substituted (poly)aminoalkylaminoalkylamidc, or alkyl-urea or alkyl- sulfonamide chain, a process for preparing them and their use as a medicine as an anticancer agent. Formula (1) wherein: - R represents hydrogen or C1-4alkyI, - A represents CO(CH2)n or CONH(CH2)n where n = 2, 3, 4, or 5, - R1 and R2 are as described herein.

Oligonucleotide-polyamine conjugates: Influence of length and position of 2′-attached polyamines on duplex stability and antisense effect

Tethering cationic ligands to oligonucleotides results in zwitterionic molecules with often improved target affinity and better cell membrane permeation. Due to the ideal distance between cationic groups, polyamines are perfect counter ions for oligonucleotides. Using an easy and versatile procedure for attaching ligands to the 2′-position, polyamines were conjugated to distinct terminal and internal positions of oligonucleotides. With polyamines attached to terminal nucleosides, the affinity to complementary DNA or RNA strands increased with growing number of cationic amines. Tethering polyamines to an internal nucleoside of wild type DNA oligonucleotides resulted in a considerable decrease in duplex stability, but in phosphorothioates, no significant decrease was detected. Conjugates exhibited progressively higher target downregulation ability with increasing polyamine chain length in a human melanoma cell culture assay.

Polycationic sulfonamides for the sequestration of endotoxin

Lipopolysaccharides (LPS) play a key role in the pathogenesis of septic shock, a major cause of mortality in the critically ill patient. We had previously shown that monoacylated polyamine compounds specifically bind to and neutralize the activity of LPS with high in vitro potency and afford complete protection in a murine model of endotoxic shock. Fatty acid amides of polyamines may be rapidly cleared from systemic circulation due to their susceptibility to nonspecific serum amidases and, thus, would be predicted to have a short duration of action. In a systematic effort to increase the likelihood of better bioavailability properties together with structural modifications that may result in gains in activity, we now report structure-activity relationships pertaining to endotoxin-binding and -neutralizing activities of homologated polyamine sulfonamides.

Polycationic sulfonamides and use thereof

Certain lipophilic polycationic sulfonamides are provided and are useful for treating various diseases or conditions and particularly sepsis.

Polyamines and their use as antibacterial and sensitizing agents

Polyamines with varying chain-lengths were evaluated for antimicrobial activity in order to test the hypothesis that these bis-cationic amphipathic compounds may also bind to and permeabilize intact Gram negative bacterial membranes. The compounds were found to possess significant antimicrobial activity and mediated via permeabilization of bacterial membranes. Homologated spermine, bis-acylated with C8 or C9 chains was found to profoundly sensitize E. coli to hydrophobic antibiotics such as rifampicin.

Effect of spermine conjugation on the cytotoxicity and cellular transport of acridine

Polyamines are believed to be potent vectors for the selective delivery of chemotherapeutic agents into cancer cells. In this paper, we report the effect of spermine conjugation on the cytotoxic and transport properties of acridine. Six derivatives, composed of a spermine chain attached at its N1 position to an acridine via an aliphatic chain, were synthesized. The aliphatic linker, comprised of 3-5 methylene units, was connected to the position-9 of the heterocycle through either an amide (amidoacridines 8-10) or an amine (aminoacridines 11-13) linkage. Independently of their architecture, all ligands showed a high affinity for DNA binding but a limited DNA sequence selectivity. In a whole cell assay with L1210 and Chinese hamster ovary (CHO) cells, the aminoacridines (IC50 values around 2 μM) were more potent than the amidoacridines (IC50 values between 20 and 40 μM). This was related to a less efficient transport for the latter. As determined from competitive uptake studies with [14C] spermidine, all conjugates had a high affinity for the polyamine transport system (PTS). However, on the basis of competitive studies with an excess of spermidine and on the differential effect on cell growth and accumulation in CHO and in the mutant PTS deficient CHO-MG cells, the accumulation of the conjugates through the PTS was found to be poor but still more efficient for the aminoacridines. α-Difluoromethylornithine (DFMO), an inhibitor of ornithine decarboxylase, which induces an up-regulation of the activity of the PTS, enhanced accumulation of all acridine conjugates through the PTS and had a synergistic effect on the potency of the acridine conjugates to inhibit cell growth. Despite their high affinity for the PTS, the low amount of derivatives transiting through the PTS is likely to be related to their ability to repress rapidly and efficiently the activity of the PTS and, consequently, to inhibit their own uptake via this system.

Homologation of polyamines in the rapid synthesis of lipospermine conjugates and related lipoplexes

Lipopolyamine amides are useful cationic lipids, synthetic vectors for non-viral gene delivery. Desymmetrisation of readily available symmetrical polyamines is an important first step in the synthesis of such compounds. The application of trifluoroacetyl

Synthesis and pharmacological activity of philanthotoxin-343 analogs: Antagonists of ionotropic glutamate receptors

The synthesis of two classes of Philanthotoxin-343 analogs is described. Quantitative information on the antagonism of quisqualate-sensitive ionotropic glutamate receptors of insect muscle by these compounds is presented.