122248-82-2

Basic information

• Product Name: 1,5-bis-Boc-1,5,9-triazanonane
• Synonyms: 1,5-bis-Boc-1,5,9-triazanonane;N1,N4-bis-Boc-norsperMidine;N-(3-aminopropyl)-N-[3-[[(1,1-dimethylethoxy)carbonyl]amino]propyl]Carbamic acid 1,1-dimethylethyl ester
• CAS NO: 122248-82-2
• Molecular Formula: C₁₆H₃₃N₃O₄
• Molecular Weight: 331
• Mol File: 122248-82-2.mol
• Article Data: 19

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,5-bis-Boc-1,5,9-triazanonane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-bis-Boc-1,5,9-triazanonane(122248-82-2)
• EPA Substance Registry System: 1,5-bis-Boc-1,5,9-triazanonane(122248-82-2)

Safety Data

• Hazardous Substances Data: 122248-82-2(Hazardous Substances Data)

Usage

Description

1,5-bis-Boc-1,5,9-triazanonane is a versatile linker molecule that contains two Boc-protected amino groups and a terminal amine. This molecule is characterized by its ability to form covalent bonds with a variety of functional groups, such as carboxylic acids, activated NHS esters, and carbonyls (ketone, aldehyde). The Boc groups can be deprotected under mild acidic conditions, yielding the free amines. As a yellow oily liquid, 1,5-bis-Boc-1,5,9-triazanonane is a valuable component in the synthesis of various chemical compounds and has potential applications in different industries.

Uses

Used in Chemical Synthesis:
1,5-bis-Boc-1,5,9-triazanonane is used as a linker in chemical synthesis for its ability to connect different functional groups and facilitate the formation of complex molecules. The Boc-protected amino groups provide stability during the synthesis process, while the terminal amine allows for further functionalization and modification of the resulting compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,5-bis-Boc-1,5,9-triazanonane is used as a building block for the development of novel drug candidates. The molecule's reactivity with various functional groups enables the creation of diverse chemical structures with potential therapeutic properties. Additionally, the Boc protection strategy allows for the controlled deprotection of the amino groups, which can be crucial for the biological activity of the final drug molecule.
Used in Materials Science:
1,5-bis-Boc-1,5,9-triazanonane can be employed in the development of new materials with specific properties, such as polymers with tailored chemical and physical characteristics. The molecule's ability to form covalent bonds with a wide range of functional groups allows for the design of materials with unique properties, such as enhanced stability, improved mechanical strength, or specific interactions with other molecules.
Used in Research and Development:
As a versatile linker molecule, 1,5-bis-Boc-1,5,9-triazanonane is valuable in research and development efforts across various scientific disciplines. It can be used to explore new chemical reactions, develop innovative synthetic strategies, and create novel compounds with potential applications in areas such as drug discovery, materials science, and chemical engineering.

Upstream product

• 122248-81-1 {3-[(3-Benzyloxycarbonylamino-propyl)-tert-butoxycarbonyl-amino]-propyl}-carbamic acid tert-butyl ester 
• 144923-51-3 N¹,N³-bis(2-cyanoethyl)-N¹,N³-bis(1,1-dimethylethoxycarbonyl)propane-1,3-diamine 
• 647033-95-2 (3-tert-BOCamino-propyl)-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-carbamic acid tert-butyl ester 
• 147875-12-5 (3-tert-butoxycarbonylaminobutyl)-(2-cyanoethyl)carbamic acid tert-butyl ester 
• 58885-58-8 N-tert-butoxycarbonyl-3-aminopropanol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 112663-43-1 3-(tert-butoxycarbonylamino)propyl methanesulfonate 
• 845821-10-5 [3-(3-hydroxypropylamino)propyl]carbamic acid tert-butyl ester 
• 647033-91-8 (3-tert-butoxycarbonylaminopropyl)-(3-hydroxypropyl)carbamic acid tert-butyl ester 
• 34619-03-9 tert-butyldicarbonate 
• 122248-80-0 benzyl N-[3-[(3-aminopropyl)amino]propyl]carbamate 
• 181780-44-9 N¹-tert-butoxycarbonyl-N³-(2-cyanoethyl)-1,3-propanediamine 
• 75178-96-0 N-Boc-1,3-diaminopropane 
• 56-18-8 bis(3-aminopropyl)amine 

Downstream Products

• 122248-83-3 [3-(3-Benzyloxy-4-methyl-2-nitro-benzoylamino)-propyl]-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester 
• 857941-12-9 N¹,N⁴-bis(tert-butoxycarbonyl)-N⁷-(mesitylenesulfonyl)norspermidine 
• 847829-18-9 N¹,N⁴,N⁷-tris(tert-butoxycarbonyl)-N¹-[4-(tosyloxy)butyl]norspermidine 
• 847829-17-8 N¹-(4-benzyloxybutyl)-N⁴,N⁷-bis(tert-butoxycarbonyl)-N¹-(mesitylenesulfonyl)norspermidine 
• 847829-20-3 (S)-4,5-dihydro-2-[2-hydroxy-4-[12-(tert-butoxycarbonylamino)-5,9-bis(tert-butoxycarbonyl)-5,9-diazadodecyloxy]phenyl]-4-methyl-4-thiazolecarboxylic acid 
• 847829-19-0 ethyl (S)-4,5-dihydro-2-[2-hydroxy-4-[12-(tert-butoxycarbonylamino)-5,9-bis(tert-butoxycarbonyl)-5,9-diazadodecyloxy]phenyl]-4-methyl-4-thiazolecarboxylate 
• 1457958-44-9 C₂₂H₃₆N₄O₈S 
• 1130608-93-3 (R)-2-(2-fluoro-biphenyl-4-yl)-N-(3-{3-[4-(3-{3-[2-(2-fluoro-biphenyl-4-yl)-(R)-propionylamino]-propylamino}-propylamino)-3,6-dioxo-cyclohexa-1,4-dienylamino]-propylamino}-propyl)-propionamide 
• 1643593-07-0 C₂₆H₃₈Br₃N₃O₆ 

Relevant articles and documents

Potent P-glycoprotein inhibition of emodin derivative: Synthesis and biological evaluation

A new series of emodin derivatives was prepared and evaluated for their in vitro antiproliferative activity. Preliminary results revealed that these derivatives exhibited weak or negligible cytotoxicity at 10 μM against various cancer cell lines (i.e., K562, HepG2, and HCT116 cell lines) as well as normal hepatic cells (QSG7701). Interestingly, the evaluation for P-glycoprotein (P-gp) modulation indicated that they possessed potent P-gp inhibitory activity. Among them, the effect of compound 6 on P-gp inhibition was even greater than that of Verapamil, the known P-gp modulator. Therefore, the natural emodin scaffold could be employed as safe and effective modulator of P-gp mediated drug resistance in cancer chemotherapy. Springer Science+Business Media 2013.

Thiazole orange – Spermine conjugate: A potent human telomerase inhibitor comparable to BRACO-19

In this report, we synthesized a series of TO conjugates containing different amino side chains and investigated their binding to telomeric G-quadruplex DNA (G4) using several biophysical methods including fluorometric titration and thermal denaturation monitored by fluorescence and circular dichroism. The composition of side chains strongly affects the binding of these molecules to G-quadruplex DNA. Incorporation of amino side chains increases the binding affinity of TO toward G4 but has a minimal effect on its selectivity for G4 over duplex DNA. The plausible binding modes are a synergistic effect of end-stacking and groove interactions as indicated by docking studies. Inhibition of human telomerase activity by TO derivatives was determined in vitro by the TRAP assay. Several derivatives can selectively inhibit the activity of telomerase over DNA polymerase at low concentrations. More significantly, TO-spermine conjugate (16) exhibits a remarkable effect on telomerase inhibition in the submicromolar range, which is comparable to the inhibition effect of a well-known G4 ligand, BRACO-19. Our results here provide guidance of utilizing TO derivatives as a viable scaffold to design novel G4 ligands, G4 probes, and potent telomerase inhibitors.

Benzo[c, d]indolyl-2(H)-one-polyamine conjugate and preparation method and application thereof

The invention relates to a benzo[c, d]indolyl-2(H)-one-polyamine conjugate or pharmaceutical salt thereof. The benzo[c, d]indolyl-2(H)-one-polyamine conjugate or the pharmaceutical salt thereof adopts the structure shown as a FORMULA I, wherein m is 1 or 2, n is 1, 2 or 3, R is FORMULA, and X is 1, 2 or 3. The invention provides a preparation method of the benzo[c, d]indolyl-2(H)-one-polyamine conjugate or the pharmaceutical salt thereof. In addition, tests find that the benzo[c, d]indolyl-2(H)-one-polyamine conjugate or the pharmaceutical salt thereof has high anti-tumor and tumor metastasis-inhibiting activity, and has a higher therapeutic index and has a prospect in preparing medicines for preventing and treating tumor metastasis when being compared with a positive control medicine amonafide,; and moreover, the benzo[c, d]indolyl-2(H)-one-polyamine conjugate or the pharmaceutical salt thereof can be located in cellular lysosome and can be used as a cellular lysosome-targeted fluorescent probe.