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

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

Uses

Used in Pharmaceutical Industry:
4-[[5-(AMINOSULFONYL)-1,3,4-THIADIAZOL-2-YL]AMINO]-4-OXO-BUTANOIC ACID is used as a potential active ingredient for the development of new drugs for various diseases and health conditions. Its antimicrobial, anti-inflammatory, or antitumor properties may contribute to its effectiveness in treating a range of medical conditions.
Used in Antimicrobial Applications:
4-[[5-(AMINOSULFONYL)-1,3,4-THIADIAZOL-2-YL]AMINO]-4-OXO-BUTANOIC ACID is used as an antimicrobial agent, potentially effective against various types of bacteria and other microorganisms. Its sulfonamide group may play a role in its antimicrobial activity.
Used in Anti-inflammatory Applications:
4-[[5-(AMINOSULFONYL)-1,3,4-THIADIAZOL-2-YL]AMINO]-4-OXO-BUTANOIC ACID is used as an anti-inflammatory agent, potentially helping to reduce inflammation and alleviate symptoms associated with inflammatory conditions.
Used in Antitumor Applications:
4-[[5-(AMINOSULFONYL)-1,3,4-THIADIAZOL-2-YL]AMINO]-4-OXO-BUTANOIC ACID is used as an antitumor agent, potentially effective against various types of cancer. Its potential antitumor properties may be due to its ability to target and inhibit specific cellular processes involved in tumor growth and progression.
Note: Further research is needed to fully understand the potential uses and effectiveness of 4-[[5-(AMINOSULFONYL)-1,3,4-THIADIAZOL-2-YL]AMINO]-4-OXO-BUTANOIC ACID in these applications.

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

• 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 
• 108-30-5 succinic acid anhydride 
• 14949-00-9 5-amino-1, 3, 4-thiadiazole-2-sulfonamide 
• 108-31-6 maleic anhydride 

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.

With deficiency oxygen target tropism of polyvalent ligand drug conjugates (by machine translation)

The invention discloses a deficiency oxygen target tropism of polyvalent ligand drug conjugates, through containing mercapto homeotropic deficiency oxygen target drug derivative molecule ligand and with the maleimide derivatized dextran of connected, can realize the corresponding drug molecules on tumor tissues to [...], has good anti-tumor activity. . (by machine translation)

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.

CARBONIC ANHYDRASE IX INHIBITOR CONJUGATES AND USES THEREOF

The present disclosure relates to compositions and methods of carbonic anhydrase IX inhibitors. The present disclosure also relates to targeting conjugates of carbonic anhydrase IX inhibitors as therapeutics and imaging agents. The present disclosure also relates to the use of targeting conjugates of carbonic anhydrase IX inhibitors in imaging methods and cancer therapy.

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.

In vivo targeting of tumor-associated carbonic anhydrases using acetazolamide derivatives

We describe the synthesis and characterization of two acetazolamide derivatives containing either a charged fluorophore or an albumin-binding moiety, which restrict binding to carbonic anhydrase IX and XII present on tumor cells. In vivo studies showed th

Compounds for diagnosis, treatment and prevention of bone injury and metabolic disorders

The present invention relates to compounds of the formula or pharmaceutically acceptable salts thereof useful for the prophylaxis and treatment of degenerative bone disorders and for the acceleration of bone healing.

Acetazolamide-like carbonic anhydrase inhibitors with topical ocular hypotensive activity

New carbonic anhydrase (EC 4.2.1.1) inhibitors were synthesized as potential drugs for the topical treatment of glaucoma. They were obtained by substituting the acetyl group of acetazolamide and methazolamide with bicarboxylic acids of different chain len