211512-13-9

Usage

Uses

Used in Pharmaceutical Industry:
1-AMINO-4-(2-NITROBENZENESULFONAMIDO)BUTANE is used as a potential pharmaceutical agent for its enzyme-inhibiting properties, which may be harnessed to develop treatments targeting specific biological pathways or conditions. 1-AMINO-4-(2-NITROBENZENESULFONAMIDO)BUTANE's structure allows for the possibility of being modified or used as a building block in the synthesis of drugs with therapeutic applications.
Used in Chemical Synthesis:
1-AMINO-4-(2-NITROBENZENESULFONAMIDO)BUTANE is used as a chemical intermediate for the synthesis of more complex molecules, taking advantage of its reactive amino and nitro groups. This application is based on the compound's ability to participate in various chemical reactions, facilitating the creation of new compounds with potential uses in different industries.
Used in Research and Development:
1-AMINO-4-(2-NITROBENZENESULFONAMIDO)BUTANE serves as a subject of study in research and development, where its properties and potential uses are further investigated. This application is driven by the need to understand the compound's behavior in biological systems and its potential as a precursor for new molecular entities with practical applications.

InChI:InChI=1/C10H15N3O4S/c11-7-3-4-8-12-18(16,17)10-6-2-1-5-9(10)13(14)15/h1-2,5-6,12H,3-4,7-8,11H2

Upstream product

• 6032-29-7 (+/-)-2-pentanol 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 110-60-1 1,4-diaminobutane 

Downstream Products

• 211512-15-1 1-(2-nitrobenzenesulfonyl)amino-4-(tert-butoxycarbonyl)aminobutane 
• 425644-02-6 N-(2-nitrobenzenesulfonyl)-N'-(benzyloxycarbonyl)-1,4-diaminobutane 
• 211512-27-5 3,8,14,22-tetrakis(2-nitrobenzenesulfonyl)-3,8,14,22,28,29-hexaazatricyclo[20.3.1^1,24.1^16,20]nonacosa-1⁽²⁸⁾,16⁽²⁹⁾,17,19,24,26-hexaene 
• 211512-21-9 N¹,N⁵,N¹⁰-tris(2-nitrobenzenesulfonyl)-1,10-diamino-5-azadecane 
• 211512-17-3 N¹,N¹⁰-bis(tert-butoxycarbonyl)-N⁵-(2-nitrobenzenesulfonyl)-1,10-diamino-5-azadecane 
• 240423-15-8 N-[16-tert-butoxycarbonylamino-5,9,13-tris(2-nitrobenzenesulfonyl)-5,9,13-triazahexadecan-1-yl]-1H-indole-3-acetamide 
• 240423-16-9 N-[16-amino-5,9,13-tris(2-nitrobenzenesulfonyl)-5,9,13-triazahexadecan-1-yl]-1H-indole-3-acetamide 
• 437718-24-6 {4-[(3-Benzyloxycarbonylamino-propyl)-(2-nitro-benzenesulfonyl)-amino]-butyl}-[2-(5-{(S)-2-[2-(2,4-bis-benzyloxy-phenyl)-acetylamino]-3-carbamoyl-propionylamino}-pentylcarbamoyl)-ethyl]-carbamic acid benzyl ester 
• 437718-29-1 {3-[{3-[{4-[3-carbamoyl-2-(2-1H-indol-3-yl-acetylamino)-propionylamino]-butyl}-(2-nitro-benzenesulfonyl)-amino]-propyl}-(2-nitro-benzenesulfonyl)-amino]-propyl}-carbamic acid benzyl ester 
• 437718-32-6 N-[N^α-(1H-indol-3-ylacetyl)-L-asparaginyl]-N'-[7-((benzyloxycarbonyl)amino)-3-(2-nitrobenzenesulfonyl)-3-azaheptanoyl]-1,5-diaminopentane 

Relevant academic research and scientific papers

Syntheses and biological activities of fluorescent-labeled analogs of acylpolyamine toxin NPTX-594 isolated from the venom of Madagascar Joro spider

Acylpolyamine-type spider toxins are known to be potent and specific blockers against glutamate receptors (GluRs). The present study describes the syntheses and biological activities of several fluorescent-labeled analogs related to a Madagascar Joro spider toxin NPTX-594 to analyze visually the unknown interaction between spider toxins and GluRs.

Design, synthesis, and biological evaluation of tricyclic heterocycle-tetraamine conjugates as potent NMDA channel blockers

We have developed a new class of N-methyl-d-aspartate (NMDA) channel blockers having a conjugate structure that consists of a nitrogenous heterocyclic head and a tetraamine tail. Among them, dihydrodibenzazepine-homospermine conjugate (8) exhibited potent

Fukuyama-Mitsunobu alkylation in amine synthesis on solid phase revisited: N-alkylation with secondary alcohols and synthesis of curtatoxins

The Fukuyama-Mitsunobu amination strategy has emerged as an efficient means of N-alkylation of peptides and sulfonamides, as well as a method for synthesis of polyamines on solid phase. Here, an array of reagent combinations for solid-phase alkylation wit

Synthesis of 3-substituted bicyclic imidazo[1,2-d][1,2,4]thiadiazoles and tricyclic benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazoles

A versatile synthetic route to potentially useful fused-ring [1,2,4]thiadiazole scaffolds (e.g., 7a and 10b) via exchange reactions of the precursor [1,2,4]thiadiazol-3-(2H)one derivatives (e.g., 6 and 9) with appropriately substituted nitriles (e.g., cyanogen bromide or p-toluenesulfonyl cyanide) under mild conditions is described. For example, the tricyclic 3-bromo [1,2,4]THD derivative (7a) underwent SNAr substitution with a variety of nucleophiles, which included amines, malonate esters and alcohols. Likewise, the bicyclic 3-p-tosyl [1,2,4]THD (10b) was employed as a template in reaction with diamines, and the resulting substituted diamines (e.g., 12a or 12e) were further selectively derivatized at the N1 and/or N2 positions in a linear fashion. The X-ray crystal structure of the 3-methyl bicyclic [1,2,4]THD (21) was obtained, and selective methylation at the N1 position via a protection-alkylation-deprotection protocol, as illustrated in Scheme 6, was confirmed. Alternatively, a short convergent synthesis of N1-functionalized derivatives from the reaction of 10b with appropriately substituted secondary amines was also developed. Hence, these synthetic strategies were advantageously exploited to provide access to a variety of diversely derivatized 3-substituted fused-ring [1,2,4]thiadiazole derivatives.

The choice of phosphane reagent in Fukuyama-Mitsunobu alkylation: Intramolecular selectivity between primary and secondary alcohols in the preparation of asymmetric tetraamine building blocks for synthesis of philanthotoxins

Philanthotoxin-433 (PhTX-433) is a polyamine wasp toxin that antagonizes certain ionotropic receptors noncompetitively. Four analogues of PhTX-433, C-methylated in the polyamine chain, were synthesized from (RS)-1,3-butanediol, two diamine building blocks, and an activated/protected tyrosine derivative. Use of a phosphane reagent more bulky than trimethylphosphane gave a high intramolecular selectivity between primary and secondary hydroxy groups in the Fukuyama-Mitsunobu reaction. Thus, trimethylphosphane proved to be the only phosphane reagent that enabled alkylation of 2-nitrobenzenesulfonamides with a wide range of secondary alcohols, whereas tributylphosphane was selective for primary alcohol groups. This selectivity was utilized to obtain orthogonally protected, asymmetric, branched tetraamines, employed for solution-phase synthesis of philanthotoxin analogues. The branched philanthotoxin analogues thus obtained were tested in an electrophysiological assay using rat brain ionotropic glutamate receptors expressed in Xenopus laevis oocytes. Their potencies proved to be similar to the corresponding nonbranched analogues. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Substituted cyclic compounds and mixtures comprising same

Novel chemical compounds and mixtures of same are provided having antibacterial and other utilities. The mixtures preferably are formed by reacting a cyclic scaffold moiety with a set of chemical substituients. Libraries formed in accordance with the inve

2-nitro- and 2,4-dinitrobenzenesulfonamides as protecting groups for primary amines

Procedures for the deprotection of the 2-nitro- and 2,4-dinitrobenzenesulfonamides to give the corresponding primary amines were developed. The 2-Nitrobenzenesulfonyl group was effectively removed by HSCH2CH2OH/DBU or PhSH/Cs2/

Total synthesis of polyamine toxin HO-416b and Agel-489 using a 2-nitrobenzenesulfonamide strategy

Total synthesis of spider toxins HO-416b (1) and Agel-489 (2) was accomplished using the 2-nitrobenzenesulfonamide (Ns) group as both a protecting and activating group. In this strategy, the C-N bonds were constructed by alkylation of sulfonamides with alkyl halides or Mitsunobu reaction with the corresponding alcohol. Beginning with monoprotection of the symmetrical diamine, the construction of the backbone from diamine 3 was efficiently accomplished in 7 steps for 14 and 9 steps for 29. Removal of the Ns group while the substrate was attached to a novel solid support enabled the efficient isolation of this highly polar compound.

Total synthesis of polyamine toxin HO-416b utilizing the 2- nitrobenzenesulfonamide protecting group

The total synthesis of HO-416b (1) was accomplished using the 2- nitrobenzenesulfonamide (Ns) group as both a protecting and activating group. Starting with monosulfonylated diamines 2 and 3, three C-N bonds were constructed via alkylation of sulfonamides with alkyl halides. Removal of the Ns groups while the substrate was attached to a novel solid support enabled the efficient isolation of pure 1.

Synthesis of novel polyazadipyridinocyclophane scaffolds and their application for the generation of libraries

Six novel, asymmetric, 19- to 26-membered polyazadipyridinocyclophane scaffolds 1-6 have been synthesized in high yields by an efficient cyclization of ditosylate 39 with the appropriate six fully protected triamines 40-45, followed by removing the 2-nitr