4403-36-5

Basic information

• Product Name: 2-PHTHALIMIDOETHANESULFONYL CHLORIDE
• Synonyms: AKOS BBS-00004578;AKOS MSC-0752;2-PHTHALIMIDOETHANESULFONYL CHLORIDE;2-(1,3-DIOXO-1,3-DIHYDRO-ISOINDOL-2-YL)-ETHANESULFONYL CHLORIDE;2-(1,3-Dioxo-2,3-dihydro-1H-isoindol-2-yl)ethane-1-sulfonyl chloride;2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-ethanesulfonyl chloride;2H-Isoindole-2-ethanesulfonyl chloride, 1,3-dihydro-1,3-dioxo-;2-Phthalimidoethanesulfonyl chlorid
• CAS NO: 4403-36-5
• Molecular Formula: C₁₀H₈ClNO₄S
• Molecular Weight: 273.69
• Product Categories: Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds
• Mol File: 4403-36-5.mol

Chemical Properties

• Melting Point: 158-163℃
• Boiling Point: 416.5 °C at 760 mmHg
• Flash Point: 205.7 °C
• Appearance: Yellow to orange to brown/Slurry
• Density: 1.585 g/cm³
• Vapor Pressure: 3.81E-07mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: 2-8°C
• PKA: -2.47±0.20(Predicted)
• Water Solubility: Reacts with water.
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: 2-PHTHALIMIDOETHANESULFONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHTHALIMIDOETHANESULFONYL CHLORIDE(4403-36-5)
• EPA Substance Registry System: 2-PHTHALIMIDOETHANESULFONYL CHLORIDE(4403-36-5)

Safety Data

• Hazard Codes: Xi,C
• Statements: 34
• Safety Statements: 26-36/37/39-45-60
• RIDADR: 3261
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 4403-36-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-PHTHALIMIDOETHANESULFONYL CHLORIDE is used as a key intermediate for the synthesis of various pharmaceutical compounds. Its unique chemical properties allow it to be incorporated into the development of new drugs and medications, contributing to advancements in healthcare and medicine.
Used in Agro-based Industry:
In the agro-based industry, 2-PHTHALIMIDOETHANESULFONYL CHLORIDE is utilized as a vital component in the production of agrochemicals. Its role in this sector is essential for the development of effective and innovative products that can enhance agricultural practices and improve crop yields.
Used in Dye Stuff Industry:
2-PHTHALIMIDOETHANESULFONYL CHLORIDE is employed as a significant raw material in the dye stuff industry. Its presence in the synthesis of dyes and pigments contributes to the creation of a diverse range of colorants used in various applications, such as textiles, plastics, and printing inks.

InChI:InChI=1/C10H8ClNO4S/c11-17(15,16)6-5-12-9(13)7-3-1-2-4-8(7)10(12)14/h1-4H,5-6H2

Upstream product

• 85-44-9 phthalic anhydride 
• 107-35-7 Tau 

Downstream Products

• 21581-17-9 2-phthalimido-ethanesulfonic acid-(4-chloro-anilide) 
• 919854-54-9 2-phthalimido-ethanesulfonic acid-(N-ethyl-anilide) 
• 63178-67-6 N-(4-nitrophenyl)-2-phthalimidoethanesulfonamide 
• 81428-07-1 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)ethanesulfonic acid dimethylamide 
• 25840-58-8 2-(1,3-dioxoisoindolin-2-yl)-N-phenylethanesulfonamide 
• 4443-23-6 2-phthalimidoethane sulfonamide 
• 81428-01-5 2-(1,3-dioxoisoindolin-2-yl)-N-methylethanesulfonamide 
• 81428-04-8 taltrimide 
• 811794-13-5 2-(1,3-dioxoisoindolin-2-yl)-N,N-bis(4-methoxybenzyl)ethanesulfonamide 
• 1004290-12-3 C₁₈H₁₈N₂O₄S 
• 1004290-06-5 C₁₇H₁₆N₂O₅S 
• 1004290-05-4 C₁₇H₁₆N₂O₅S 
• 1004290-10-1 N-(3-chlorophenyl)-2-phthalimidoethanesulfonamide 
• 1004290-09-8 N-(2-Chlorophenyl)-2-phthalimidoethanesulfonamide 

Relevant articles and documents

Unconventional amino acids in medicinal chemistry: First report on taurine merged within carbonic anhydrase inhibitors

This study reports the design, synthesis of a series of taurine containing benzenesulfonamide derivatives which were all screened in vitro against the physiological relevant human (h) expressed Carbonic Anhydrase (CA; EC 4.2.1.1) I, II, IX, XII isozymes. Compound 2, 5, 11–16 displayed superior inhibitory activities against the tumor associated hCA IX over the reference drug Acetazolamide (AAZ). Both hCA IX and XII isoforms were selectively inhibited only by compound 3, whereas the chloro-containing compound 12 was showed as the most selective and effective inhibitor profile for the CA IX isoforms. To the best of our knowledge the data reported herein are the first of this kind and introduce in the literature new compounds worth for future development within the Medicinal Chemistry field.

Synthesis and antiviral, insecticidal, and fungicidal activities of gossypol derivatives containing alkylimine, oxime or hydrazine moiety

Gossypol is a part of the cotton plant's defense system against pathogens and herbivorous insects. To discover gossypol analogs with broad spectrum and high activity, a series of gossypol alkylamine Schiff base, oxime and hydrazone derivatives were synthesised and bioassayed. The biological results indicated that most of these derivatives exhibited higher anti-TMV activity than gossypol. Interestingly, the activities of compounds 10, 15, 18, 20, 23 and 26 were much higher than that of ribavirin. Furthermore, compound 26, which was low toxicity to rat, showed better activity than control plant virus inhibitors in the field. Additionally, allyl amine Schiff base (9) displayed remarkable insecticidal activities against Mythimna separata, Helicoverpa armigera and Ostrinia nubilalis, whereas (pyridin-3-yl)methanamine Schiff base (13) showed excellent activity against Culex pipiens pallens. The fungicidal results revealed that all of compounds exhibited good activity against Physalospora piricola.

Taurultams incorporating arylsulfonamide: First in vitro inhibition studies of α-, β- and γ-class Carbonic Anhydrases from Vibrio cholerae and Burkholderia pseudomallei

A new series of taurultambenzenesulfonamides 1–17 were prepared and considered for their inhibitory activity in vitro against the Carbonic Anhydrases from Vibrio cholerae (VchCA-α, VchCA-β and VchCA-γ) and Burkholderia pseudomallei (BpsCA-β and BpsCA-γ). Among the compounds tested, derivatives 4, 5, 7, 10, 12, and 16 resulted in highly effective VchCAα inhibitors (KI values spanning within the 6.1–9.6 nM range) and endowed with excellent Selectivity Indexes (SIs; KI VchCA-α/KI hCA II) all comprised between 0.04 and 0.09. Potent in vitro inhibitors for the BpsCA-γ were also identified (KIs of 18.9–19.5 nM). The results here reported may represent the blueprint for the future development of a new generation of CA-based antibiotics integrated with free of resistance mechanisms of action adopted from known drugs.

Sultam based Carbonic Anhydrase VII inhibitors for the management of neuropathic pain

We report a series of compounds 1–17 derived from the antiepileptic drug Sulthiame (SLT) from which both the benzenesulfonamide and the sultam moiety were retained. All compounds were tested in vitro for their inhibition activity against the human (h) Carbonic Anhydrase (CA; EC 4.2.1.1) I, II, VII, IX and XII isoforms. Among the series, derivatives 1 and 11 showed great enhancement of both inhibition potency and selectivity towards the hCA VII isoform, when compared to the reference SLT drug. The binding mode of 11 within the hCA VII active site was deciphered by means of X-ray crystallography and revealed the sultam moiety being exposed to the rim of the active site. In vivo experiments on a model of neuropathic pain induced by oxaliplatin clearly showed 11 being an effective pain relieving agent and therefore worth of further exploitation towards the validation of the hCA VII as new target for the management of neuropathies.

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.

Synthesis method of 2-(phthalimido)ethanesulfonyl chloride

The invention discloses a synthesis method of 2-(phthalimido)ethanesulfonyl chloride. The specific reaction steps are as follows: (1) taking phthalic anhydride and ethanolamine as raw materials, and preparing to obtain N-(2-hydroxyethyl)phthalimide at appropriate temperature and in an appropriate solvent; (2) reacting the N-(2-hydroxyethyl)phthalimide synthesized in the step (1) with thiourea under appropriate temperature and solvent conditions, to obtain an isothiourea compound; (3) reacting the isothiourea compound synthesized in the step (2) under appropriate chlorination reagent, temperature and solvent conditions to obtain 2-(phthalimido)ethanesulfonyl chloride. A novel synthetic route is adopted to prepare 2-(phthalimido)ethanesulfonyl chloride, and the target product obtained by theprocess has high purity, reaction conditions are mild, the yield is high, the operation is simple and convenient, the production cost is low, and the suitability for amplifying production is achieved.

Amides of N-Deacetyllappaconitine and Amino Acids

Amides were prepared from N-deacetyllappaconitine and the amino acids glycine, taurine, and γ-aminobutyric acid.

First homology model of Plasmodium falciparum glucose-6-phosphate dehydrogenase: Discovery of selective substrate analog-based inhibitors as novel antimalarial agents

In Plasmodium falciparum the bifunctional enzyme glucose-6-phosphate dehydrogenase?6-phosphogluconolactonase (PfG6PD?6PGL) is involved in the catalysis of the first reaction of the pentose phosphate pathway. Since this enzyme has a key role in parasite development, its unique structure represents a potential target for the discovery of antimalarial drugs. Here we describe the first 3D structural model of the G6PD domain of PfG6PD?6PGL. Compared to the human enzyme (hG6PD), the 3D model has enabled the identification of a key difference in the substrate-binding site, which involves the replacement of Arg365 in hG6PD by Asp750 in PfG6PD. In a prospective validation of the model, this critical change has been exploited to rationally design a novel family of substrate analog-based inhibitors that can display the necessary selectivity towards PfG6PD. A series of glucose derivatives featuring an α-methoxy group at the anomeric position and different side chains at position 6 bearing distinct basic functionalities has been synthesized, and their PfG6PD and hG6PD inhibitory activities and their toxicity against parasite and mammalian cells have been assessed. Several compounds displayed micromolar affinity (Ki up to 23 μM), favorable selectivity (up to > 26-fold), and low cytotoxicity. Phenotypic assays with P. falciparum cultures revealed high micromolar IC50 values, likely as a result of poor internalization of the compounds in the parasite cell. Overall, these results endorse confidence to the 3D model of PfG6PD, paving the way for the use of target-based drug design approaches in antimalarial drug discovery studies around this promising target.

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.