14316-16-6

Basic information

• Product Name: N-(2-aminoethyl)-4-methyl-benzenesulfonamide
• Synonyms: N-(2-aminoethyl)-4-methyl-benzenesulfonamide;N-Tosylethylenediamine;2-[[(4-Methylphenyl)sulfonyl]aMino]ethylaMine;N-(2-AMinoethyl)-4-toluene- sulfonaMide;N-(2-AMinoethyl)-p-toluenesulfonaMide;N-(4-Toluenesulfonyl)ethylene- 1,2-diaMine;N-p-TolylsulfonylethylenediaMine;NSC 177937
• CAS NO: 14316-16-6
• Molecular Formula: C₉H₁₄N₂O₂S
• Molecular Weight: 214.28
• Product Categories: Nitrogen Compounds;Organic Building Blocks;Polyamines;Amines;Aromatics;Sulfur & Selenium Compounds
• Mol File: 14316-16-6.mol
• Article Data: 47

Chemical Properties

• Melting Point: 122-126 °C
• Boiling Point: 363.1°Cat760mmHg
• Flash Point: 173.4°C
• Appearance: /
• Density: 1.214g/cm³
• Vapor Pressure: 1.85E-05mmHg at 25°C
• Refractive Index: 1.555
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 11.24±0.10(Predicted)
• CAS DataBase Reference: N-(2-aminoethyl)-4-methyl-benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-aminoethyl)-4-methyl-benzenesulfonamide(14316-16-6)
• EPA Substance Registry System: N-(2-aminoethyl)-4-methyl-benzenesulfonamide(14316-16-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 14316-16-6(Hazardous Substances Data)

Usage

Description

N-(2-aminoethyl)-4-methyl-benzenesulfonamide is an organic compound with the molecular formula C9H14N2O2S. It is a white crystalline solid and is a key intermediate in the synthesis of various chemical compounds, particularly in the field of supramolecular chemistry.

Uses

Used in Chemical Synthesis:
N-(2-aminoethyl)-4-methyl-benzenesulfonamide is used as a synthetic intermediate for the preparation of N-(2-tosylamidoethyl)monoazacrown ethers. These crown ethers are a class of macrocyclic compounds that have the ability to selectively bind and transport metal ions, making them useful in various applications such as sensors, catalysts, and drug delivery systems.
In the Synthesis of N-(2-tosylamidoethyl)monoazacrown Ethers:
N-(2-aminoethyl)-4-methyl-benzenesulfonamide is used as a key building block for the synthesis of N-(2-tosylamidoethyl)monoazacrown ethers. These crown ethers exhibit high selectivity and affinity for specific metal ions, which can be exploited in various applications, such as the development of ion-selective electrodes, ionophores, and ion carriers. The synthesis of these crown ethers involves the reaction of N-(2-aminoethyl)-4-methyl-benzenesulfonamide with appropriate starting materials, followed by a series of chemical transformations to form the final macrocyclic product.

InChI:InChI=1/C9H14N2O2S/c1-8-2-4-9(5-3-8)14(12,13)11-7-6-10/h2-5,11H,6-7,10H2,1H3

Upstream product

• 4556-90-5 N-(2-bromo-ethyl)-4-methyl-benzenesulfonamide 
• 6331-00-6 N-(2-chloroethyl)-4-methylbenzenesulfonamide 
• 107-15-3 ethylenediamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 208525-21-7 [2-(Toluene-4-sulfonylamino)-ethyl]-carbamic acid benzyl ester 
• 57260-73-8 N-BOC-1,2-diaminoethane 
• 14316-14-4 N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide 
• 261912-63-4 N-(2-azidoethyl)-4-methylbenzenesulfonamide 
• 1153-45-3 4-nitrophenyl 4-methylbenzenesulfonate 
• 3634-89-7 N-(p-toluenesulfonyl)aziridine 

Downstream Products

• 14316-17-7 Benzyloxycarbonyl--N-(β-tosylamino)-ethylamid 
• 92431-24-8 1-<2-p-Toluolsulfonylamino-ethyl>-3-butyl-harnstoff 
• 77429-97-1 N¹,N⁵-ditosyl-3-azapentane-1,5-diamine 
• 208525-21-7 [2-(Toluene-4-sulfonylamino)-ethyl]-carbamic acid benzyl ester 
• 303172-50-1 4-Methyl-N-{2-[2-methyl-prop-(E)-ylideneamino]-ethyl}-benzenesulfonamide 
• 888710-12-1 N-[N-(2-ethylhexyl)-2-aminoethyl]-4-methylbenzenesulfonamide 
• 351491-57-1 N-{2-[(4-methoxy-benzylidene)-amino]-ethyl}-4-methyl-benzenesulfonamide 
• 87484-85-3 Methyl 2-[2-Hydroxy-3-[N-[2-[N-(4-methylphenylsulfonyl)amino]ethyl]amino]propoxy]benzoate Oxalate 
• 75483-20-4 1-(4-methylphenylsulfonyl)imidazolidine-2-thione 
• 75120-93-3 N-(2-(4-methylphenylsulfonamido)ethyl)benzamide 
• 1429060-12-7 phenyl-(4-tosyl-3,4-dihydropyrazin-1(2H)-yl)methanone 
• 134360-52-4 N-(t-butyloxycarbonyl)-N'-(p-toluenesulfonyl)ethylenediamine 
• 1429060-05-8 tert-butyl 2-(N-ethynyl-4-methylphenylsulfonamido)ethylcarbamate 
• 1429060-08-1 tert-butyl 4-tosyl-3,4-dihydropyrazine-1(2H)-carboxylate 

Relevant articles and documents

Design, synthesis, in vitro antiproliferative evaluation, and kinase inhibitory effects of a new series of imidazo[2,1- b ]thiazole derivatives

Design and synthesis of a new series of 5,6-diarylimidazo[2,1-b]thiazole derivatives possessing terminal aryl sulfonamide moiety are described. Their in vitro antiproliferative activities against a panel of 57 human cancer cell lines of nine different cancer types were tested at the NCI. Compounds 8a, 8b, 8n, 8q, 8t, and 8u showed the highest mean % inhibition values over the 57 cell line panel at 10 1/4M, and they were further tested in 5-dose testing mode to determine their IC50 values. Among the six compounds, compound 8u possessing terminal para-hydroxybenzenesulfonamido moiety and ethylene linker showed the highest potency. It demonstrated superior potency than Sorafenib against eight different cell lines, and was equipotent to Sorafenib against COLO 205 colon cancer cell line. Its IC50 values over NCI-H460 non-small cell lung cancer cell line and MCF7 breast cancer cell line were 0.845 1/4M and 0.476 1/4M, respectively. Compounds 8a, 8b, 8q, 8t, and 8u showed high selectivity indices towards cancer cells over L132 normal lung cell line. Compound 8u showed potential inhibitory effects over the components of ERK pathway. Its IC50 value over V600E-B-RAF and C-RAF kinases were 39.9 nM and 19.0 nM, respectively.

Structural optimization of imidazothiazole derivatives affords a new promising series as B-Raf V600E inhibitors; synthesis, in vitro assay and in silico screening

BRAF mutation is commonly known in a number of human cancer types. It is counted as a potential component in treating cancer. In this study, based on structural optimization of previously reported inhibitors (3-fluro substituted derivatives of imidazo[2,1-b]thiazole-based scaffold), we designed and synthesized sixteen new imidazo[2,1-b]thiazole derivatives with m-nitrophenyl group at position 6. The electron withdrawing properties was reserved while the polarity was modified compared to previously synthesized compounds (-F). Furthermore, the new substituted group (–NO2) provided an additional H-bond acceptor(s) which may bind with the target enzyme through additional interaction(s). In vitro cytotoxicity evaluation was performed against human cancer cell line (A375). In addition, in vitro enzyme assay was performed against mutated B-Raf (B-Raf V600E). Compounds 13a, 13g and 13f showed highest activity on mutated B-Raf with IC50 0.021, 0.035 and 0.020 μM. All target compounds were tested for in vitro cytotoxicity against NCI 60 cell lines. Compounds 13a and 13g were selected for 5 doses test mode. Moreover, in silico molecular simulation was explored in order to explore the possible interactions between the designed compounds and the B-Raf V600E active site.

An epidermal growth factor receptor-targeted and endoplasmic reticulum-localized organic photosensitizer toward photodynamic anticancer therapy

The endoplasmic reticulum (ER), as the largest organelle in eukaryotic cells, plays complex but pivotal roles in multiple intracellular metabolic functions, including biosynthesis, sensing, and signal transduction, especially in proteins folding and post-translation modification. The ER is regarded as a promising target for anticancer therapy. Based on previous tumor-targeted photodynamic therapy (PDT), we chemically modified the phthalocyanine-based photosensitizer molecule with the small molecular anticancer-targeting drug erlotinib and the ER-targetable moiety methyl sulfonamide to develop an advanced photosensitizer EB-ER-Pc that can specifically target the subcellular organelle ER of EGFR-overexpressing cancer cells. The in vitro experiments show that the dual-target photosensitizer EB-ER-Pc can generate ROS in situ in the ER of the tumor target region to induce ER stress, upregulate Ca2+ ion level, and decrease mitochondrial membrane potential (MMP) to mediate cancer cells death and ablation. The results suggest that EB-ER-Pc is a promising candidate for effective photodynamic cancer therapy.

An endoplasmic reticulum targetable turn-on fluorescence probe for imaging application of carbon monoxide in living cells

Carbon monoxide (CO) is a significant mediator in regulating endoplasmic reticulum (ER) stress, and its level may play a potential role in the treatment of vascular diseases combined with ER stress. In-situ visualization of CO in the ER helps to elucidate

Design, synthesis and anticancer profile of new 4-(1H-benzo[d]imidazol-1-yl)pyrimidin-2-amine-linked sulfonamide derivatives with V600EBRAF inhibitory effect

A new series of 4-(1H-benzo[d]imidazol-1-yl)pyrimidin-2-amine linked sulfonamide derivatives 12a–n was designed and synthesized according to the structure of well-established V600EBRAF inhibitors. The terminal sulfonamide moiety was linked to the pyrimidine ring via either ethylamine or propylamine bridge. The designed series was tested at fixed concentration (1 μM) against V600EBRAF, finding that 12e, 12i and 12l exhibited the strongest inhibitory activity among all target compounds and 12l had the lowest IC50 of 0.49 μM. They were further screened on NCI 60 cancer cell lines to reveal that 12e showed the most significant growth inhibition against multiple cancer cell lines. Therefore, cell cycle analysis of 12e was conducted to investigate the effect on cell cycle progression. Finally, virtual docking studies was performed to gain insights for the plausible binding modes of vemurafenib, 12i, 12e and 12l.

Discovery of New Imidazo[2,1- b]thiazole Derivatives as Potent Pan-RAF Inhibitors with Promising in Vitro and in Vivo Anti-melanoma Activity

BRAF is an important component of MAPK cascade. Mutation of BRAF, in particular V600E, leads to hyperactivation of the MAPK pathway and uncontrolled cellular growth. Resistance to selective inhibitors of mutated BRAF is a major obstacle against treatment of many cancer types. In this work, a series of new (imidazo[2,1-b]thiazol-5-yl)pyrimidine derivatives possessing a terminal sulfonamide moiety were synthesized. Pan-RAF inhibitory effect of the new series was investigated, and structure-activity relationship is discussed. Antiproliferative activity of the target compounds was tested against the NCI-60 cell line panel. The most active compounds were further tested to obtain their IC50 values against cancer cells. Compound 27c with terminal open chain sulfonamide and 38a with a cyclic sulfamide moiety showed the highest activity in enzymatic and cellular assay, and both compounds were able to inhibit phosphorylation of MEK and ERK. Compound 38a was selected for testing its in vivo activity against melanoma. Cellular and animal activities are reported.