78851-85-1

Basic information

• Product Name: 4-[[5-(AMINOSULFONYL)-1,3,4-THIADIAZOL-2-YL]AMINO]-4-OXO-BUTANOIC ACID
• Synonyms: 4-[[5-(AMINOSULFONYL)-1,3,4-THIADIAZOL-2-YL]AMINO]-4-OXO-BUTANOIC ACID;2-succinylamido-1,3,4-thiadiazole-5-sulfonamide;4-Oxo-4-((5-sulfamoyl-1,3,4-thiadiazol-2-yl)amino)butanoic acid;4-Oxo-4-((5-sulfamoyl-1,3,4-thiadiazol-2-yl)
• CAS NO: 78851-85-1
• Molecular Formula: C₆H₈N₄O₅S₂
• Molecular Weight: 280.28
• Mol File: 78851-85-1.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Density: 1.807g/cm³
• Refractive Index: 1.654
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.17±0.10(Predicted)
• CAS DataBase Reference: 4-[[5-(AMINOSULFONYL)-1,3,4-THIADIAZOL-2-YL]AMINO]-4-OXO-BUTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[[5-(AMINOSULFONYL)-1,3,4-THIADIAZOL-2-YL]AMINO]-4-OXO-BUTANOIC ACID(78851-85-1)
• EPA Substance Registry System: 4-[[5-(AMINOSULFONYL)-1,3,4-THIADIAZOL-2-YL]AMINO]-4-OXO-BUTANOIC ACID(78851-85-1)

Safety Data

• Hazardous Substances Data: 78851-85-1(Hazardous Substances Data)

Usage

General Description

4-[[5-(aminosulfonyl)-1,3,4-thiadiazol-2-yl]amino]-4-oxo-butanoic acid is a chemical compound with potential medical and pharmaceutical applications. It contains a thiadiazole ring, a sulfonamide group, and a butanoic acid moiety. The compound may have antimicrobial, anti-inflammatory, or antitumor properties, though further research is needed to fully understand its potential uses. It also has potential as an active ingredient in the development of new drugs for various diseases and health conditions. Its structure and properties make it an interesting and potentially valuable compound for further study and potential application in the pharmaceutical industry.

InChI:InChI=1/C6H8N4O5S2/c7-17(14,15)6-10-9-5(16-6)8-3(11)1-2-4(12)13/h1-2H2,(H,12,13)(H2,7,14,15)(H,8,9,11)

Upstream product

• 108-31-6 maleic anhydride 
• 14949-00-9 5-amino-1, 3, 4-thiadiazole-2-sulfonamide 
• 108-30-5 succinic acid anhydride 
• 129504-06-9 N-(5-Sulfamoyl-[1,3,4]thiadiazol-2-yl)-succinamic acid methyl ester 
• 129504-19-4 5-((methoxysuccinyl)amino)-1,3,4-thiadiazole-2-sulfonyl chloride 

Relevant articles and documents

DUAL-TARGETED CARBONIC ANHYDRASE IX COMPLEX AND CONTRAST AGENT THEREOF

Disclosed herein are a dual-targeted carbonic anhydrase IX complex, a contrast agent comprising the same, and a synthesizing method thereof. The dual-targeted carbonic anhydrase IX complex includes a carbonic anhydrase IX (CA9) binding peptide, a sulfonamide derivative, and a metal chelating agent. The dual-targeted carbonic anhydrase IX complex has potential for use as a molecular nuclear drug.

Acetazolamide-based [18F]-PET tracer: In vivo validation of carbonic anhydrase IX as a sole target for imaging of CA-IX expressing hypoxic solid tumors

Carbonic anhydrase IX is overexpressed in many solid tumors including hypoxic tumors and is a potential target for cancer therapy and diagnosis. Reported imaging agents targeting CA-IX are successful mostly in clear cell renal carcinoma as SKRC-52 and no candidate was approved yet in clinical trials for imaging of CA-IX. To validate CA-IX as a valid target for imaging of hypoxic tumor, we designed and synthesized novel [18F]-PET tracer (1) based on acetazolamide which is one of the well-known CA-IX inhibitors and performed imaging study in CA-IX expressing hypoxic tumor model as 4T1 and HT-29 in vivo models other than SKRC-52. [18F]-acetazolamide (1) was found to be insufficient for the specific accumulation in CA-IX expressing tumor. This study might be useful to understand in vivo behavior of acetazolamide PET tracer and can contribute to the development of successful PET imaging agents targeting CA-IX in future. Additional study is needed to understand the mechanism of poor targeting of CA-IX, as if CA-IX is not reliable as a sole target for imaging of CA-IX expressing hypoxic solid tumors.

PEGylated Bis-Sulfonamide Carbonic Anhydrase Inhibitors Can Efficiently Control the Growth of Several Carbonic Anhydrase IX-Expressing Carcinomas

A series of aromatic/heterocyclic bis-sulfonamides were synthesized from three established aminosulfonamide carbonic anhydrase (CA, EC 4.2.1.1) inhibitor pharmacophores, coupled with either ethylene glycol oligomeric or polymeric diamines to yield bis-sulfonamides with short or long (polymeric) linkers. Testing of novel inhibitors and their precursors against a panel of membrane-bound CA isoforms, including tumor-overexpressed CA IX and XII and cytosolic isozymes, identified nanomolar-potent inhibitors against both classes and several compounds with medium isoform selectivity in a detailed structure-activity relationship study. The ability of CA inhibitors to kill tumor cells overexpressing CA IX and XII was tested under normoxic and hypoxic conditions, using 2D and 3D in vitro cellular models. The study identified a nanomolar potent PEGylated bis-sulfonamide CA inhibitor (25) able to significantly reduce the viability of colon HT-29, breast MDA-MB231, and ovarian SKOV-3 cancer cell lines, thus revealing the potential of polymer conjugates in CA inhibition and cancer treatment.