51644-96-3

Basic information

• Product Name: N-Boc-cadaverine
• Synonyms: TERT-BUTYL N-(5-AMINOAMYL)CARBAMATE;TERT-BUTYL N-(5-AMINOPENTYL)CARBAMATE;N-TERT-BUTYLOXYCARBONYL-1,5-DIAMINOPENTANE HYDROCHLORIDE;N-(TERT-BUTOXYCARBONYL)-1,5-DIAMINOPENTANE;N-(TERT-BUTOXYCARBONYL)-1,5-PENTANEDIAMINE;N-T-BUTYLOXYCARBONYL-1,5-DIAMINOPENTANE HYDROCHLORIDE;N-Boc-cadaverine;N-BOC-1,5-DIAMINOPENTANE
• CAS NO: 51644-96-3
• Molecular Formula: C₁₀H₂₂N₂O₂
• Molecular Weight: 202.29
• Product Categories: pharmacetical;Monoprotected Diaminoalkanes;N-Boc-diaminoalkanes;amino acids
• Mol File: 51644-96-3.mol
• Article Data: 55

Chemical Properties

• Boiling Point: 309.2 °C at 760 mmHg
• Flash Point: 109 °C
• Appearance: /
• Density: 0.972 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.000647mmHg at 25°C
• Refractive Index: n20/D 1.460
• Storage Temp.: 2-8°C
• PKA: 12.91±0.46(Predicted)
• BRN: 3603658
• CAS DataBase Reference: N-Boc-cadaverine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-cadaverine(51644-96-3)
• EPA Substance Registry System: N-Boc-cadaverine(51644-96-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2735 8/PG 3
• WGK Germany: 3
• F: 10-34
• HazardClass: 8
• PackingGroup: Ⅲ
• Hazardous Substances Data: 51644-96-3(Hazardous Substances Data)

Usage

Description

tert-Butyl (5-aminopentyl)carbamate can be used as a PROTAC linker in the synthesis of PROTACs. tert-Butyl (5-aminopentyl)carbamate is an alkane chain with terminal amine and Boc-protected amino groups. Amine group is reactive with carboxylic acids, activated NHS esters, carbonyls (ketone, aldehyde) etc. The Boc group can be deprotected under mild acidic conditions to form the free amine.

Uses

Different sources of media describe the Uses of 51644-96-3 differently. You can refer to the following data:
1. Some of the reported applications of N-Boc-cadaverine include:Synthesis of of a supermacrocycle that self-assemble to form organic nanotubes.Preparation of water-soluble unsymmetrical sulforhodamine fluorophores from monobrominated sulfoxanthene dye.Synthesis of functionalized porphyrins as biocompatible carrier system for photodynamic therapy (PDT).
2. N-Boc-cadaverine is an intermediate in the synthesis of derivative of the folic acid antagonist Methotrexate (M260675) used in the study of membrane-associated folate transporters from L1210 cells.

InChI:InChI=1/C10H22N2O2/c1-10(2,3)14-9(13)12-8-6-4-5-7-11/h4-8,11H2,1-3H3,(H,12,13)

Upstream product

• 462-94-2 1,5-diaminopentane 
• 6627-89-0 tert-butyl phenyl carbonate 
• 660-88-8 5-aminopentanoic acid 
• 126992-69-6 tert-butyl N-[5-(1,3-dioxoisoindol-2-yl)pentyl]carbamate 
• 2508-29-4 5-hydroxypentylamine 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 1476-39-7 1,5-diaminopentane dihydrochloride 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 91419-47-5 tert-butyl N-(5-amino-5-oxopentyl)carbamate 
• 27219-07-4 5-(N-tert-butyloxycarbonyl)aminopentanoic acid 
• 181780-36-9 C₂₁H₂₉Cl₃N₂O₆ 
• 75178-90-4 N-(tert-butyloxycarbonyl)-5-aminopentanol 
• 129392-86-5 (5-azido-pentyl)carbamic acid tert-butyl ester 

Downstream Products

• 181780-41-6 (5-tert-Butoxycarbonylamino-pentyl)-carbamic acid 2,2,2-trichloro-ethyl ester 
• 192212-24-1 tert-butyl 5-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)pentylcarbamate 
• 207725-70-0 {(4S,7S)-5-[(5-tert-Butoxycarbonylamino-pentylcarbamoyl)-methyl]-3,6-dioxo-2,5-diaza-tricyclo[6.2.2.0^2,7]dodec-4-yl}-acetic acid methyl ester 
• 328273-17-2 (3aS,4S,6aR)-N-[5-[(1,1-dimethylethoxy)carbonyl]aminopentyl]hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanamide 
• 694464-87-4 [5-({3'-bromo-5'-[3-(3,5-dibromo-4-hydroxy-phenyl)-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[c][1,2]oxathiol-3-yl]-2'-hydroxy-biphenyl-4-carbonyl}-amino)-pentyl]-carbamic acid tert-butyl ester 
• 667911-32-2 tert-butyl 5-(pyridin-2-ylmethylamino)pentylcarbamate 
• 872853-98-0 [5-(12-aminododecanoyl)amino-pentyl]-carbamic acid tert-butyl ester 
• 872854-14-3 4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl-methyl)-cyclohexanecarboxylic acid [5-(6-chloro-2-methoxy-acridin-9-ylamino)-pentyl]-amide 
• 872854-03-0 12-(6-chloro-2-methoxy-acridin-9-ylamino)-dodecanoic acid (5-amino-pentyl)-amide 

Relevant articles and documents

Synthesis and biological evaluation of novel farnesylthiosalicylic acid/salicylic acid hybrids as potential anti-tumor agents

A series of FTS/salicylic acid hybrids was designed and synthesized and their in vitro antitumor activities were evaluated. It was found that the anti-proliferation activities of hybrids were better than that of FTS. Compound 10a displayed the strongest antitumor activities with IC50 values of 5.72-9.76 μmol/L and selectively inhibited tumor cell proliferation. In addition, 10a induced tumor cell apoptosis in a dose-dependent manner by up-regulating the expression of Bax and caspase-3 and down-regulating Bcl-2. Our findings suggest that these novel hybrids may hold a great promise as therapeutic agents for the intervention of human cancers.

Synthesis, electrochemistry, DNA binding and in vitro cytotoxic activity of tripodal ferrocenyl bis-naphthalimide derivatives

A series of tripodal ferrocenyl bis-naphthalimide derivatives were synthesized and characterized. All of the bis-naphthalimide derivatives exhibited good DNA binding ability which was confirmed by ethidium bromide (EB) displacement experiment and ultraviolet (UV)-visible absorption titration. And the binding mode of these compounds was proved to be a hybrid binding mode by experiments. The cytotoxicity of synthesized compounds against 4 different human cancer cell lines (EC109, BGC823, SGC7901 and HEPG2) was evaluated by thiazolyl blue tetrazolium bromide (MTT) assay. All of the bis-naphthalimide derivatives exhibited good anticancer activity than the positive control drug (amonafide), which was due to the promotion of reactive oxygen species (ROS) level in test cancer cells by the reversible one-electron redox process of ferrocenyl bis-naphthalimide derivatives. Although there was no obvious relationship between the binding constants and the chain length, the structure cytotoxicity relationship revealed that the linker of n = 3, m = 1 was the best choice for the tested tripodol bis-naphthalimide derivatives. Synopsis: A series of tripodal ferrocenyl bis-naphthalimide derivatives were synthesized to study the DNA binding ability and the cytotoxicity induced by reactive oxygen species. All of the compounds exhibited good DNA binding ability. And the structure cytotoxicity relationship revealed that the structure of 5h was the best choice.

Design, synthesis and biological evaluation of tyrosinase-targeting PROTACs

The human tyrosinase is the most prominent therapeutic target for pigmentary skin disorders. However, the overwhelming majority efforts have been devoted to search mushroom tyrosinase inhibitors, which show poor inhibitory activity on human tyrosinase and certain side effects that cause skin damage in practical application. Herein, a series of degraders that directly targeted human tyrosinase was firstly designed and synthesized based on newly developed PROTAC technology. The best PROTAC TD9 induced human tyrosinase degradation obviously in dose and time-dependent manner, and its mechanism of inducing tyrosinase degradation has also been clearly demonstrated. Besides, encouraging results that low-toxicity PROTAC TD9 was applied to reduce zebrafish melanin synthesis have been obtained, highlighting the potential to treatment of tyrosinase-related disorders. Moreover, this work has innovatively expanded the application scope of PROTAC technology and laid a solid foundation for further development of novel drugs treating pigmentary skin disorders.