68076-36-8

Usage

Uses

Used in Pharmaceutical Industry:
t-Butyl N-(4-aminobutyl)carbamate is used as an intermediate for the preparation of pharmacologically active compounds for various medical applications. Its ability to introduce a C4-spacer makes it a valuable component in the development of new drugs.
Used in Synthesis of Spermidine Analogues:
In the field of organic chemistry, t-Butyl N-(4-aminobutyl)carbamate is used as a key intermediate in the synthesis of spermidine analogues. These analogues have potential applications in various biological and pharmaceutical research areas.
Used in Suzuki Reaction:
t-Butyl N-(4-aminobutyl)carbamate also plays a role in the Suzuki reaction, a widely used cross-coupling reaction in organic chemistry. This reaction is essential for the formation of carbon-carbon bonds, which are crucial in the synthesis of complex organic molecules, including those with potential pharmaceutical applications.

InChI:InChI=1/C9H20N2O2/c1-9(2,3)13-8(12)11-7-5-4-6-10/h4-7,10H2,1-3H3,(H,11,12)/p+1

Upstream product

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 333-93-7 putrescine dihydrochloride 
• 26364-65-8 2-(N-cyanoimino)thiazolidine 
• 62146-59-2 Z-NH-(CH₂)4-NH-Boc 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 110-60-1 1,4-diaminobutane 
• 73371-96-7 2-<<(tert-butoxycarbonyl)oxy>imino>-2-phenylacetonitrile 
• 34619-03-9 tert-butyldicarbonate 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 33545-97-0 1,4-bis(tert-butoxycarbonylamino)butane 
• 24424-99-5 di-tert-butyl dicarbonate 
• 116861-31-5 tert-butyl N-(3-chloropropyl)carbamate 
• 181780-35-8 C₂₀H₂₇Cl₃N₂O₆ 
• 75178-87-9 (4-hydroxybutyl)carbamic acid tert-butyl ester 

Downstream Products

• 118734-04-6 N⁴-Boc-N¹-(Z-βAla)-tetramethylenediamine 
• 117498-76-7 <4-<<3-<(tert-butoxycarbonyl)amino>butyl>amino>-3-nitrophenyl>(2-thienyl)methanone 
• 117861-36-6 (10R,13S,16S,19S,22R)-19-Benzyl-13-carbamoylmethyl-22-(4-ethoxy-benzyl)-16-isopropyl-12,15,18,21,24-pentaoxo-7,8-dithia-11,14,17,20,23-pentaaza-spiro[5.19]pentacosane-10-carboxylic acid (4-amino-butyl)-amide 
• 99733-17-2 (S)-1-[(10R,13S,16S,19S,22R)-19-Benzyl-13-carbamoylmethyl-22-(4-ethoxy-benzyl)-16-isopropyl-12,15,18,21,24-pentaoxo-7,8-dithia-11,14,17,20,23-pentaaza-spiro[5.19]pentacosane-10-carbonyl]-pyrrolidine-2-carboxylic acid (4-amino-butyl)-amide 
• 33545-98-1 N-(4-aminobutyl)carbaminsaeure-(tert-butyl)ester-hydrochlorid 
• 158331-42-1 N-<4-butyl>-2-anthraquinonesulfonamide 
• 62146-59-2 Z-NH-(CH₂)4-NH-Boc 
• 186179-24-8 1,1-dimethylethyl {4-{[(4-methylphenyl)sulfonyl]amino}butyl}carbamate 
• 194040-98-7 {4-[4-(3-Oxo-3-phenyl-propionyl)-benzoylamino]-butyl}-carbamic acid tert-butyl ester 
• 221525-73-1 (S)-2-(4-tert-Butoxycarbonylamino-butylamino)-3-phenyl-propionic acid 
• 223449-74-9 [3-(4-tert-butoxycarbonylamino-butylcarbamoyl)-5-(dimethoxy-phosphorylmethyl)-benzyl]-phosphonic acid dimethyl ester 
• 879484-86-3 1,1-dimethylethyl {4-[(4-fluorophenyl)amino]butyl}carbamate 
• 378785-51-4 [4-(benzylideneamino)butyl]carbamic acid tert-butyl ester 
• 294625-16-4 N-[4-(tert-butoxycarbonyl)aminobutyl]-2(R)-(carbobenzoxy)amino-4-methylpentanamide 

Relevant academic research and scientific papers

Designing the polyamine pharmacophore: Influence of N-substituents on the transport behavior of polyamine conjugates

N-Ethylated N-arylmethyl polyamine conjugates were synthesized and evaluated for their ability to target the polyamine transporter (PAT). To understand the effect of N-ethylation upon PAT selectivity, ethyl groups were appended onto a PAT-selective N1-anthracenenylmethyl homospermidine derivative. 1b. Bioevaluation in L1210 murine leukemia cells and in two Chinese hamster ovary cell lines (PAT-active CHO and PAT-deficient CHO-MG) revealed a dramatic decrease in PAT targeting ability upon N1 or N5 ethylation of the pharmacophore 1b. Experiments using the amine oxidase inhibitor, aminoguanidine (AG, 2 mM), revealed that the N9-ethyl and N9-methyl analogues were able to retain their PAT selectivity and cytotoxicity properties in the presence or absence of AG. In contrast, the lead compound 1b (containing a terminal NH2 group) revealed a dramatic reduction in both its PAT-targeting ability and cytotoxicity in the absence of AG. An improved balance between these three properties of PAT-targeting, cytotoxicity and metabolic stability can be attained via N-methylation at the N9-position.

Synthesis and biological properties of Quilamines II, new iron chelators with antiproliferative activities

To selectively target tumor cells expressing an overactive Polyamine Transport System (PTS), we designed, synthesized, and evaluated the biological activity of a new generation of iron chelators, derived from the lead compound HQ1-44, which we named Quilamines II. The structures of four new antiproliferative agents were developed. They differ in the size of the linker (HQ0-44 and HQ2-44) or in the nature of the linker (HQCO-44 and HQCS-44) between a hydroxyquinoline moiety (HQ) and a homospermidine (44) chain, the best polyamine vector. The Quilamines II were obtained after 6 to 9 steps by Michael addition, peptide linkage, and reductive amination or by using the Willgerodt-Kindler reaction. The biological evaluation of these second-generation Quilamines showed that modifying the size of the linker increased the selectivity of these compounds for the PTS. In addition, measurement of the toxicity of Quilamines HQ0-44 and HQ2-44 highlighted their marked antiproliferative nature on several cancerous cell lines as well as a differential activity on nontransformed cells (fibroblasts). In contrast, Quilamines HQCO-44 and HQCS-44 presented low selectivity for the PTS, probably due to a loss of electrostatic interaction. We also demonstrated that the HCT116 cell line, originating from a human colon adenocarcinoma, was the most responsive to the various Quilamines. As deduced from the calcein and HVA assays, the higher iron chelating capacity of HQ1-44 could explain its higher antiproliferative efficiency.

Synthesis and structure-property relationship of polyester-urethanes and their evaluation for the regeneration of contractile tissues

The structure-property relationship of degradable polyurethanes from non toxic building blocks was studied by synthesising four different biodegradable poly(ester urethanes) from poly(s-caprolactone) (PCL) diol, 1,4- diisocyanatobutane and different chain extenders. For instance, the chain extenders were an amino acid derivative diamine, an amino acid derivative diol, a cyclic diol and a custom made diamine, containing an enzymatically degradable peptide (Ala-Ala sequence). Physicochemical and morphological characterisation (SEC, DSC, DMA, AFM) was performed, showing the influence of the chain extender on the polyurethane properties. A correlation between surface domain morphologies and thermal properties was highlighted and a relationship between the biological response and surface morphologies was observed. Collecting mechanical characterisation and myoblast cell culture results together, the polyurethane synthesised with the amino acid derivative diamine resulted the most promising candidate for fabricating scaffolds supporting the regeneration of muscle tissues.

Selective alkylation of T-T mismatched DNA using vinyldiaminotriazine-acridine conjugate

The alkylation of the specific higher-order nucleic acid structures is of great significance in order to control its function and gene expression. In this report, we have described the T-T mismatch selective alkylation with a vinyldiaminotriazine (VDAT)-acridine conjugate. The alkylation selectively proceeded at the N3 position of thymidine on the T-T mismatch. Interestingly, the alkylated thymidine induced base flipping of the complementary base in the duplex. In a model experiment for the alkylation of the CTG repeats DNA which causes myotonic dystrophy type 1(DM1), the observed reaction rate for one alkylation increased in proportion to the number of T-T mismatches. In addition, we showed that primer extension reactions with DNA polymerase and transcription with RNA polymerase were stopped by the alkylation. The alkylation of the repeat DNA will efficiently work for the inhibition of replication and transcription reactions. These functions of the VDAT-acridine conjugate would be useful as a new biochemical tool for the study of CTG repeats and may provide a new strategy for the molecular therapy of DM1.

Ion pairing between the chain ends induces folding of a flexible zwitterion in methanol

A well defined folded loop structure can be induced in a flexible zwitterion 10 in the polar and protic solvent methanol by charge interactions between the two termini of the zwitterion. In 10 a (guanidiniocarbonyl)pyrrole moiety, a highly efficient oxoan

Prospective study directed to the synthesis of unsymmetrical linked bis-5-arylidene rhodanine derivatives via "one-pot two steps" reactions under microwave irradiation with their antitumor activity

We here report on the synthesis of new unsymmetrical linked bis-5-arylidene rhodanine derivatives with stereocontrolled Z-configuration. The 6 steps synthesis was achieved and the key steps are the construction of the two 5-arylidene rhodanine moieties using an "one-pot two-steps" method under microwave dielectric heating in a closed reactor. The intermediates 6, 7 and desired unsymmetrical compounds 9 have been also evaluated for their in vitro inhibition of cell proliferation (Huh7 D12, Caco2, MDA-MB 231, HCT116, and NCI-H727 tumoral cell lines). Two of all compounds have shown potent activity against Huh7 D12, Caco2, and MDA-MB 231. Graphical Abstract: [Figure not available: see fulltext.].

Potentiation of BCNU cytotoxicity by molecules targeting abasic lesions in DNA

We describe the synthesis, DNA binding measurements and pharmacological properties of a series of new heterodimeric molecules, in which a 2,6-diaminopurine is linked to a 9-aminoacridine chrimophore. The linking chain contains a central N,N′-disubstituted guanidine, connected to the two chromophores by polymethylenic units of variable length. Copyright

Peptoid Library Agar Diffusion (PLAD) Assay for the High-Throughput Identification of Antimicrobial Peptoids

Rapid emergence of antimicrobial resistant organisms necessitates equally rapid methods for the development of new antimicrobial compounds. Of recent interest have been mimics of antimicrobial peptides known as antimicrobial peptoids, which exhibit simila

Synthesis and characterization of segmented copoly(ether urea)s with uniform hard segments

Employing protective group strategy and novel isocyanate chemistry, segmented copoly-(ether urea)s with uniform hard segments were prepared. Amine-terminated poly(tetrahydrofuran) served as the soft segment of these polymers. The size of the hard segments and the number of urea groups it contains were varied systematically, and their influence on the properties was investigated. The strength of hydrogen bonding between the urea groups in monodisperse hard segments containing exactly 1 to exactly 4 urea groups was studied by infrared spectroscopy and compared with materials containing polydisperse hard segments. The strength of hydrogen bonding in polymers possessing exactly two urea groups per hard segment resulted in an optimal balance between excellent mechanical properties and good processability and solubility.

An attempt to chemically state the cross-talk between monomers of COX homodimers by double/hybrid inhibitors mofezolac-spacer-mofezolac and mofezolac-spacer-arachidonic acid

Cardiovascular diseases (CVDs) account for over 17 million death globally each year, including arterial thrombosis. Platelets are key components in the pathogenesis of this disease and modulating their activity is an effective strategy to treat such throm