4443-23-6

Basic information

• Product Name: 2-phthalimidoethanesulfonamide
• Synonyms: 2-phthalimidoethanesulfonamide;2-(1,3-dioxoisoindolin-2-yl)ethanesulfonamide;2-(1,3-diketoisoindolin-2-yl)ethanesulfonamide;2-(1,3-dioxo-2-isoindolinyl)ethanesulfonamide;2-(1,3-dioxoisoindol-2-yl)ethanesulfonamide;2H-Isoindole-2-ethanesulfonamide, 1,3-dihydro-1,3-dioxo-;2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid amide
• CAS NO: 4443-23-6
• Molecular Formula: C₁₀H₁₀N₂O₄S
• Molecular Weight: 254.27
• Mol File: 4443-23-6.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 476.7°C at 760 mmHg
• Flash Point: 242.1°C
• Appearance: /
• Density: 1.542g/cm³
• Vapor Pressure: 2.98E-09mmHg at 25°C
• Refractive Index: 1.645
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-phthalimidoethanesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phthalimidoethanesulfonamide(4443-23-6)
• EPA Substance Registry System: 2-phthalimidoethanesulfonamide(4443-23-6)

Safety Data

• Hazardous Substances Data: 4443-23-6(Hazardous Substances Data)

Usage

General Description

2-Phthalimidoethanesulfonamide also known as N-(2-Sulfamoyl-ethyl)-phthalimide, is a chemical compound consisting of sulfur, nitrogen, hydrogen, oxygen, and carbon atoms. It's an organic compound related to the sulfonamide group, often used in the field of organic synthesis. Its molecular formula is C10H11N2O4S. Although the specific uses of this compound aren't widely documented, compounds in the sulfonamide family are typically known for their antibacterial properties and are commonly used in medicinal chemistry. Phthalimide derivatives like 2-phthalimidoethanesulfonamide are important synthons that are often used in the synthesis of a variety of biologically active compounds.

InChI:InChI=1/C10H10N2O4S/c11-17(15,16)6-5-12-9(13)7-3-1-2-4-8(7)10(12)14/h1-4H,5-6H2,(H2,11,15,16)

Upstream product

• 85-44-9 phthalic anhydride 
• 110475-43-9 sodium 2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)ethane-1-sulfonate 
• 4443-24-7 NCS 731 
• 4403-36-5 2-phthalimido-ethanesulfonyl chloride 

Downstream Products

• 1585225-80-4 3-(3-(4-chloro-3,5-dimethylphenoxy)propyl)-N-((2-(1,3-dioxoisoindolin-2-yl)ethyl)sulfonyl)-1H-indole-2-carboxamide 
• 1585226-43-2 6-chloro-3-(3-(4-chloro-3,5-dimethylphenoxy)propyl)-N-((2-(1,3-dioxoisoindolin-2-yl)ethyl)sulfonyl)-1H-indole-2-carboxamide 
• 4378-70-5 2-aminoethanesulfonamide 
• 89756-60-5 taurinamide hydrochloride 

Relevant articles and documents

Design, synthesis, cytotoxic activity, and apoptosis inducing effects of 4- And N-substituted benzoyltaurinamide derivatives

In this study, a group of 4-substituted benzoyltaurinamide derivatives were designed, synthesized, and investigated for their anticancer activity against three cancer cell lines and one nontumorigenic cell line by MTT assay. Among the final compounds, methoxyphenyl derivatives 14, 15, 16 were found to be effective against all the tested cancerous cell lines with promising selectivity. The most active compounds were further evaluated to determine the molecular mechanism of their anticancer activity by using western blot assay and the Annexin V-FITC/PI test. Compound 14 (in SH-SY5Y and MDA-MB-231 cell lines) and 15 (in SH-SY5Y cell line) were found to induce intrinsic apoptotic pathway by upregulating BAX, caspase-3, and caspase-9, while downregulating Bcl-2 and Bcl-xL expression levels. According to mechanistic studies, compounds displayed their anticancer activity via three different mechanisms: a. caspase-dependent, b. caspase-independent, and c. caspase-dependent pathway that excluded caspase-9 activation. As a result, this study provides interesting data which can be used to design new taurine-based anticancer derivatives.

An Unusual Natural Product Primary Sulfonamide: Synthesis, Carbonic Anhydrase Inhibition, and Protein X-ray Structures of Psammaplin C

Psammaplin C is one of only two described natural product primary sulfonamides. Here we report the synthesis of psammaplin C and evaluate the inhibition profile against therapeutically relevant carbonic anhydrase (CA) zinc metalloenzymes. The compound exhibited unprecedented inhibition of an important cancer-associated isozyme, hCA XII, with a Ki of 0.79 nM. The compound also displayed good isoform selectivity for hCA XII over other CAs. We present the first reported protein X-ray crystal structures of psammaplin C in complex with human CAs. We engineered the easily crystallized hCA II enzyme to mimic both the hCA IX and hCA XII binding sites and then utilized protein X-ray crystallography to determine the binding pose of psammaplin C within the hCA II, hCA IX, and hCA XII mimic active sites, all to high resolution. This is the first time a natural product primary sulfonamide inhibitor has been assessed for inhibition and binding to CAs.

Quinazolines and related heterocyclic compounds and their therapeutic use

A compound of the formula wherein X is CR1 or N; Y is CR3 or N; R1, R3, R4, R5 and R6 are independently H, F, Cl, Br, I, or a hydrocarbon group which optionally contains one or more heteroatoms; R7 is a heterocyclic group including one or more N atoms; R' is Rx or NRyRz wherein Rx, Ry and Rz are each H or the same or different groups, including cyclic groups formed by Ry and Rz with the N atom, of up to 20 C atoms and optionally including up to 3 further heteroatoms selected from N, O and S; or a pharmaceutically acceptable salt, ester or solvate thereof, has therapeutic utility.