188614-00-8

Basic information

• Product Name: Methyl 4-[(2-ethoxy-2-oxoethyl)-thio]-3-nitrobenzoate
• Synonyms: Methyl 4-[(2-ethoxy-2-oxoethyl)-thio]-3-nitrobenzoate;4-[(2-ethoxy-2-keto-ethyl)thio]-3-nitro-benzoic acid methyl ester;4-[(2-ethoxy-2-oxoethyl)thio]-3-nitrobenzoic acid methyl ester;EU-0029952;methyl 4-(2-ethoxy-2-oxo-ethyl)sulfanyl-3-nitro-benzoate;methyl 4-(2-ethoxy-2-oxoethyl)sulfanyl-3-nitrobenzoate
• CAS NO: 188614-00-8
• Molecular Formula: C₁₂H₁₃NO₆S
• Molecular Weight: 299.29972
• Mol File: 188614-00-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl 4-[(2-ethoxy-2-oxoethyl)-thio]-3-nitrobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4-[(2-ethoxy-2-oxoethyl)-thio]-3-nitrobenzoate(188614-00-8)
• EPA Substance Registry System: Methyl 4-[(2-ethoxy-2-oxoethyl)-thio]-3-nitrobenzoate(188614-00-8)

Safety Data

• Hazardous Substances Data: 188614-00-8(Hazardous Substances Data)

Upstream product

• 453-71-4 3-nitro-4-fluorobenzoic acid 
• 329-59-9 4-fluoro-3-nitro-benzoic acid methyl ester 
• 623-51-8 ethyl 2-sulfanylacetate 

Downstream Products

• 188614-01-9 methyl 3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazine-6-carboxylate 
• 1392139-26-2 (Z)-2-benzylidene-3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazine-6-carboxylic acid 
• 1392139-44-4 C₂₃H₂₅N₃O₂S 
• 226259-30-9 methyl 3,4-dihydro-2H-benzo[b][1,4]thiazine-6-carboxylate 

Relevant articles and documents

The discovery of potent small molecule activators of human STING

The adaptor protein STING plays a major role in innate immune sensing of cytosolic nucleic acids, by triggering a robust interferon response. Despite the importance of this protein as a potential therapeutic target for serious unmet medical conditions inc

Discovery of a Plasmodium falciparum Glucose-6-phosphate Dehydrogenase 6-phosphogluconolactonase Inhibitor (R,Z)-N-((1-Ethylpyrrolidin-2-yl)methyl)-2- (2-fluorobenzylidene)-3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazine-6-carboxamide (ML276) that reduces parasite growth in vitro

A high-throughput screen of the NIH's MLSMR collection of ～340000 compounds was undertaken to identify compounds that inhibit Plasmodium falciparum glucose-6-phosphate dehydrogenase (Pf G6PD). PfG6PD is important for proliferating and propagating P. falciparum and differs structurally and mechanistically from the human orthologue. The reaction catalyzed by glucose-6-phosphate dehydrogenase (G6PD) is the first, rate-limiting step in the pentose phosphate pathway (PPP), a key metabolic pathway sustaining anabolic needs in reductive equivalents and synthetic materials in fast-growing cells. In P. falciparum, the bifunctional enzyme glucose-6-phosphate dehydrogenase-6- phosphogluconolactonase (Pf GluPho) catalyzes the first two steps of the PPP. Because P. falciparum and infected host red blood cells rely on accelerated glucose flux, they depend on the G6PD activity of PfGluPho. The lead compound identified from this effort, (R,Z)-N-((1-ethylpyrrolidin-2-yl)methyl)-2-(2- fluorobenzylidene)-3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazine-6-carbox-amide, 11 (ML276), is a submicromolar inhibitor of PfG6PD (IC50 = 889 nM). It is completely selective for the enzyme's human isoform, displays micromolar potency (IC50 = 2.6 μM) against P. falciparum in culture, and has good drug-like properties, including high solubility and moderate microsomal stability. Studies testing the potential advantage of inhibiting Pf G6PD in vivo are in progress.