3575-05-1

Basic information

• Product Name: 4-(5-nitro-1H-benzo[d]iMidazol-2-yl)thiazole
• Synonyms: 4-(5-nitro-1H-benzo[d]iMidazol-2-yl)thiazole;6-Nitro-2-(4-thiazolyl)-1H-benziMidazole
• CAS NO: 3575-05-1
• Molecular Formula: C10H6N4O2S
• Molecular Weight: 246.24524
• Mol File: 3575-05-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 247-249 °C
• Boiling Point: 537.8±48.0 °C(Predicted)
• Appearance: /
• Density: 1.589±0.06 g/cm3(Predicted)
• PKA: 8.76±0.10(Predicted)
• CAS DataBase Reference: 4-(5-nitro-1H-benzo[d]iMidazol-2-yl)thiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(5-nitro-1H-benzo[d]iMidazol-2-yl)thiazole(3575-05-1)
• EPA Substance Registry System: 4-(5-nitro-1H-benzo[d]iMidazol-2-yl)thiazole(3575-05-1)

Safety Data

• Hazardous Substances Data: 3575-05-1(Hazardous Substances Data)

Usage

Description

4-(5-nitro-1H-benzo[d]iMidazol-2-yl)thiazole is a chemical compound that consists of a benzimidazole ring fused with a thiazole ring. The presence of a nitro group at the 5-position of the benzimidazole ring and a thiazolyl group at the 4-position gives this compound unique chemical and biological properties.

Uses

Used in Pharmaceutical Industry:
4-(5-nitro-1H-benzo[d]iMidazol-2-yl)thiazole is used as a key intermediate in the synthesis of methionine aminopeptidase inhibitors. These inhibitors play a crucial role in the development of novel therapeutic agents for the treatment of various diseases, including cancer and neurodegenerative disorders, by targeting specific enzymes involved in their pathogenesis.

Upstream product

• 3364-80-5 1,3-thiazole-4-carbaldehyde 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 148-79-8 thiabendazole 

Downstream Products

• 25893-06-5 5-aminothiabendazole 

Relevant articles and documents

Synthesis and biological evaluation of novel benzimidazole derivatives and analogs targeting the NLRP3 inflammasome

A series of benzo[d]imidazole analogues of thiabenzole were synthesized and their anti-inflammatory activities toward NLRP3 (nucleotide-binding domain leucine-rich repeat containing protein family, pyrin domain-containing 3, also known as cryopyrin or NALP3) inflammasome were evaluated in vitro. Two lead compounds, TBZ-09 and TBZ-21, were identified by anti-production of IL-1β. In the second round of biological evaluation, based on the lead, 34 more compounds were synthesized and their in vitro anti-inflammatory activities were investigated. Several compounds were identified as anti-inflammatory agents that can reduce IL-1β expression in a dose-dependent manner. A preliminary structure-activity relationship is also summarized here.

Metal-mediated inhibition of escherichia coli methionine aminopeptidase: Structure-activity relationships and development of a novel scoring function for metal-ligand interactions

We report the discovery of thiabendazole as a potent inhibitor (K 1 = 0.4 μM) of Escherichia coli methionine aminopeptidase (ecMetAP) and the synthesis and pharmacological evaluation of thiabendazole congeners with activity in the upper nanomolar range, Elucidation of the X-ray structure of ecMetAP in complex with thiabendazole and an unrelated inhibitor that was independently described by another group showed that that both compounds bind to an additional CoII ion at the entrance of the active site. This unexpected finding explains the inactivity of the compounds under in vivo conditions. It also allows us to discuss the structure-activity relationships of this series of compounds in a meaningful way, based upon docking runs with an auxiliary metal ion, We describe a new scoring function for the evaluation of metal-mediated inhibitor binding that, unlike the previously used scoring function implemented in the docking program, allows us to distinguish between active and inactive compounds, Finally, conclusions for the structure-based design of in vivo-active inhibitors of ecMetAP are drawn.