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1,4,8-Tri-Boc-1,4,8,11-tetraazacyclotetradecane is a cyclic tetra-amine compound characterized by its molecular formula C20H38N4O6. It features a ring structure with four nitrogen atoms and four carbon atoms, and is distinguished by the presence of tert-butoxycarbonyl (Boc) groups that serve as protecting agents for amine groups in organic synthesis. 1,4,8-Tri-Boc-1,4,8,11-tetraazacyclotetradecane is a versatile building block in the synthesis of complex molecules, particularly in the field of peptide chemistry, where it plays a crucial role in shielding amine groups from unwanted reactions.

170161-27-0

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  • 1,4,8,11-Tetraazacyclotetradecane-1,4,8-tricarboxylic acid, tris(1,1-dimethylethyl) ester

    Cas No: 170161-27-0

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170161-27-0 Usage

Uses

Used in Organic Synthesis:
1,4,8-Tri-Boc-1,4,8,11-tetraazacyclotetradecane is used as a protecting group in organic synthesis for amine groups to prevent them from participating in unwanted side reactions during the synthesis process. The Boc groups can be selectively removed when needed, allowing for the controlled formation of desired products.
Used in Peptide Chemistry:
In the field of peptide chemistry, 1,4,8-Tri-Boc-1,4,8,11-tetraazacyclotetradecane is utilized as a protecting agent for amine groups in the synthesis of peptides. This ensures that the amine groups remain unreacted until the appropriate stage of the synthesis, facilitating the formation of the desired peptide sequence.
Used in the Synthesis of Complex Molecules:
1,4,8-Tri-Boc-1,4,8,11-tetraazacyclotetradecane serves as a versatile building block in the synthesis of complex molecules. Its ability to protect amine groups and its cyclic structure make it a valuable component in the creation of intricate molecular architectures.
Used in Pharmaceutical Industry:
1,4,8-Tri-Boc-1,4,8,11-tetraazacyclotetradecane is used in the pharmaceutical industry as a key intermediate in the synthesis of various drug molecules. Its protective properties and structural features enable the development of new therapeutic agents with specific biological activities.
Used in Chemical Research:
In chemical research, 1,4,8-Tri-Boc-1,4,8,11-tetraazacyclotetradecane is employed as a model compound to study the reactivity and selectivity of amine groups in various chemical reactions. This helps in understanding the fundamental principles of organic chemistry and contributes to the development of new synthetic strategies and methodologies.

Check Digit Verification of cas no

The CAS Registry Mumber 170161-27-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,0,1,6 and 1 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 170161-27:
(8*1)+(7*7)+(6*0)+(5*1)+(4*6)+(3*1)+(2*2)+(1*7)=100
100 % 10 = 0
So 170161-27-0 is a valid CAS Registry Number.
InChI:InChI=1/C25H48N4O6/c1-23(2,3)20(30)35-29-16-10-12-26-13-17-27(21(31)33-24(4,5)6)14-11-15-28(18-19-29)22(32)34-25(7,8)9/h26H,10-19H2,1-9H3

170161-27-0 Well-known Company Product Price

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  • Alfa Aesar

  • (H26741)  1,4,8-Tri-Boc-1,4,8,11-tetraazacyclotetradecane   

  • 170161-27-0

  • 250mg

  • 3372.0CNY

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170161-27-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,4,8-Tri-Boc-1,4,8,11-tetraazacyclotetradecane

1.2 Other means of identification

Product number -
Other names tritert-butyl 1,4,8,11-tetrazacyclotetradecane-1,4,8-tricarboxylate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:170161-27-0 SDS

170161-27-0Downstream Products

170161-27-0Relevant articles and documents

Structural Differences and Redox Properties of Unsymmetric Diiron PDIxCy Complexes

Hess, Corinna R.,Hofmann, Andreas J.,Jandl, Christian

, p. 499 - 505 (2020)

We present two bimetallic iron complexes, [Fe2(PDIeCy)(OTf)4] (1) and [Fe2(PDIpCy)(THF)(OTf)4] (2) coordinated by an unsymmetric ligand. The new ligand, PDIeCy (PDI = pyridyldiimine; e = ethyl; Cy = cyclam), is

Copper(ii) complexes ofN-propargyl cyclam ligands reveal a range of coordination modes and colours, and unexpected reactivity

Counsell, Andrew J.,Yu, Mingfeng,Shi, Mengying,Jones, Angus T.,Batten, James M.,Turner, Peter,Todd, Matthew H.,Rutledge, Peter J.

, p. 3931 - 3942 (2021)

The coordination chemistry ofN-functionalised cyclam ligands has a rich history, yet cyclam derivatives with pendant alkynes are largely unexplored. This is despite the significant potential and burgeoning application ofN-propargyl cyclams and related com

Dual-Function Polymeric HPMA Prodrugs for the Delivery of miRNA

Peng, Zheng-Hong,Xie, Ying,Wang, Yan,Li, Jing,Oupicky, David

, p. 1395 - 1404 (2017)

An HPMA-based polymeric prodrug of a CXCR4 antagonist, AMD3465 (P-SS-AMD), was developed as a dual-function carrier of therapeutic miRNA. P-SS-AMD was synthesized by a copolymerization of HPMA with a methacrylamide monomer in which the AMD3465 was attached via a self-immolative disulfide linker. P-SS-AMD showed effective release of the parent AMD3465 drug following treatment with intracellular levels of glutathione (GSH). The AMD3465 was released in the cells and exhibited functional CXCR4 antagonism, demonstrated by inhibition of the CXCR4-mediated cancer cell invasion. Due to its cationic character, P-SS-AMD could form polyplexes with miRNA and mediate efficient transfection of miR-200c mimics to downregulate expression of a downstream target ZEB-1 in cancer cells. The combined P-SS-AMD/miR-200c polyplexes showed improved ability to inhibit cancer cell migration when compared with individual treatments. The reported findings validate P-SS-AMD as a dual-function delivery vector that can simultaneously deliver a therapeutic miRNA and function as a polymeric prodrug of CXCR4 antagonist.

Biotin-tagged fluorescent sensor to visualize 'mobile' Zn2+ in cancer cells

Fang, Le,Trigiante, Giuseppe,Kousseff, Christina J.,Crespo-Otero, Rachel,Philpott, Michael P.,Watkinson, Michael

, p. 9619 - 9622 (2018)

A cancer cell-targeting fluorescent sensor has been developed to image mobile Zn2+ by introducing a biotin group. It shows a highly selective response to Zn2+in vitro, no toxicity in cellulo and images 'mobile' Zn2+ specifically in cancer cells. We believe this probe has the potential to help improve our understanding of the role of Zn2+ in the processes of cancer initiation and development.

Tri-N-Boc-tetraazamacrocycle-nucleoside conjugates: Synthesis and anti- HIV activities

Dessolin,Vlieghe,Bouygues,Medou,Quelever,Camplo,Chermann,Kraus

, p. 957 - 968 (1998)

As far as linear N-Boc-polyamines conjugates elicited remarkable anti- HIV activity, the synthesis and anti-HIV properties of cyclic N-Boc- polyamines conjugates such as tetraazamacro-cycle-nucleoside were studied. These new conjugates include an ester linkage between the two moieties. They were synthesized using Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate coupling reagent, in the case of N-alkyl polyazamacrocycle derivatives, or through direct condensation of the acyl chloride derivative with nucleoside in the case of Nacyl polyazamacrocycle compounds. None of the new conjugates presented anti-HIV activity greater than that of the corresponding parent nucleosides.

Covalent attachment of [Ni(alkynyl-cyclam)]2+ catalysts to glassy carbon electrodes

Zhanaidarova, Almagul,Moore, Curtis E.,Gembicky, Milan,Kubiak, Clifford P.

, p. 4116 - 4119 (2018)

Surface modification of glassy carbon electrodes (GCEs) with molecular electrocatalysts is an important step towards developing more efficient heterogeneous CO2 reduction materials. Here, we report direct anodic electrografting of [Ni(alkynyl-cyclam)]2+ catalysts to the surface of GCEs in one simple step using inexpensive earth-abundant chemicals. When modified, these electrodes show reversible electrochemistry in organic solvents with zero peak-to-peak separations (ΔE = 0) and non-diffusive I (V) profiles that are typical for heterogeneous redox materials. CPE of these electrodes showed enhanced formation of H2 gas relative to CO compared to homogeneous catalysts.

Synthesis and evaluation of [99mTc]TcAMD3465 as a SPECT tracer for CXCR4 receptor imaging

Wu, Yitian,Zhu, Hong,Zhang, Xiaojun,Yu, Peng,Gui, Yuan,Xu, Zhihong,Zhang, Jinming,Tian, Jiahe

, p. 627 - 633 (2021)

CXCR4 plays an important role in a number of immunological-based diseases and cancers. The development of radiotracers targeting CXCR4 can provide a valuable tool for the diagnosis and monitoring of conditions involving deregulation of the receptor. The i

A functional model for the cysteinate-ligated non-heme iron enzyme superoxide reductase (SOR)

Kitagawa, Terutaka,Dey, Abhishek,Lugo-Mas, Priscilla,Benedict, Jason B.,Kaminsky, Werner,Solomon, Edward,Kovacs, Julie A.

, p. 14448 - 14449 (2006)

Superoxide reductases (SORs) are cysteine-ligated, non-heme iron enzymes that reduce toxic superoxide radicals (O2-). The functional role of the trans cysteinate, as well as the mechanism by which SOR reduces O2-, is unknown. Herein is described a rare example of a functional metalloenzyme analogue, which catalytically reduces superoxide in a proton-dependent mechanism, via a trans thiolate-ligated iron-peroxo intermediate, the first example of its type. Acetic-acid-promoted H2O2 release, followed by Cp2Co reduction, regenerates the active Fe(II) catalyst. The thiolate ligand and its trans positioning relative to the substrate are shown to contribute significantly to the catalyst's function, by lowering the redox potential, changing the spin state, and dramatically lowering the νFe-O stretching frequency well-below that of any other reported iron-peroxo, while leaving νO-O high, so as to favor superoxide reduction and Fe-O, as opposed to O-O, bond cleavage. Thus we provide critical insight into the relationship between the SOR structure and its function, as well as important benchmark parameters for characterizing highly unstable thiolate-ligated iron-peroxo intermediates. Copyright

Synthesis of cyclam-capped β-cyclodextrin-bonded silica particles for use as chiral stationary phases in capillary electrochromatography

Gong, Yinhan,Xue, Guoping,Xiang, Yanqiao,Bradshaw, Jerald S,Lee, Milton L,Lee, Hian Kee

, p. 2463 - 2466 (2002)

β-Cyclodextrin (β-CD) was anchored onto silica particles at its C(2) position, derivatized primarily at the C(6) position by treatment with bromoacetyl bromide, and finally reacted with two types of cyclams to form cyclam-capped β-CD-bonded silica particles. When used as chiral stationary phases in capillary electrochromatography, these novel bonded silica particles exhibited excellent enantioselectivities for chiral separations.

Cyclam-Modified PEI for Combined VEGF siRNA Silencing and CXCR4 Inhibition to Treat Metastatic Breast Cancer

Zhou, Yiwen,Yu, Fei,Zhang, Feiran,Chen, Gang,Wang, Kaikai,Sun, Minjie,Li, Jing,Oupicky, David

, p. 392 - 401 (2018)

Chemokine receptor CXCR4 plays an important role in cancer cell invasion and metastasis. Recent findings suggest that anti-VEGF therapies upregulate CXCR4 expression, which contributes to resistance to antiangiogenic therapies. Here, we report the develop

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