328977-86-2

Basic information

• Product Name: 2-[(4-oxo-1,4-dihydroquinazolin-2-yl)sulfanyl]propanoic acid
• Synonyms: 2-[(4-Oxo-1,4-dihydroquinazolin-2-yl)sulfanyl]propanoic acid; Propanoic acid, 2-[(1,4-dihydro-4-oxo-2-quinazolinyl)thio]-; propanoic acid, 2-[(3,4-dihydro-4-oxo-2-quinazolinyl)thio]-
• CAS NO: 328977-86-2
• Molecular Formula: C₁₁H₁₀N₂O₃S
• Molecular Weight: 250.2737
• Mol File: 328977-86-2.mol

Chemical Properties

• Boiling Point: 470.8°C at 760 mmHg
• Flash Point: 238.5°C
• Density: 1.49g/cm³
• Vapor Pressure: 1.14E-09mmHg at 25°C
• Refractive Index: 1.695
• CAS DataBase Reference: 2-[(4-oxo-1,4-dihydroquinazolin-2-yl)sulfanyl]propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(4-oxo-1,4-dihydroquinazolin-2-yl)sulfanyl]propanoic acid(328977-86-2)
• EPA Substance Registry System: 2-[(4-oxo-1,4-dihydroquinazolin-2-yl)sulfanyl]propanoic acid(328977-86-2)

Safety Data

• Hazardous Substances Data: 328977-86-2(Hazardous Substances Data)

Usage

Derivative of quinazolinone

Indicates the compound is based on a heterocyclic molecule with potential biological activities.

Sulfanyl group attached

Makes the compound a thiol, which has a wide range of applications in various fields.

Propanoic acid moiety

Indicates the presence of a carboxylic acid functional group in the compound.

Potential pharmacological activity

Suggests the compound may have potential uses in medicine, but further research is needed to confirm its properties and applications.

Upstream product

• 598-72-1 2-Bromopropionic acid 
• 13906-09-7 2-mercapto-3H-quinazolin-4-one 
• 28144-70-9 anthranilic acid amide 
• 118-92-3 anthranilic acid 
• 13906-09-7 2-thioxo-2,3-dihydro-1H-quinazolin-4-one 

Relevant articles and documents

2-Mercapto-Quinazolinones as Inhibitors of Type II NADH Dehydrogenase and Mycobacterium tuberculosis: Structure-Activity Relationships, Mechanism of Action and Absorption, Distribution, Metabolism, and Excretion Characterization

Mycobacterium tuberculosis (MTb) possesses two nonproton pumping type II NADH dehydrogenase (NDH-2) enzymes which are predicted to be jointly essential for respiratory metabolism. Furthermore, the structure of a closely related bacterial NDH-2 has been reported recently, allowing for the structure-based design of small-molecule inhibitors. Herein, we disclose MTb whole-cell structure-activity relationships (SARs) for a series of 2-mercapto-quinazolinones which target the ndh encoded NDH-2 with nanomolar potencies. The compounds were inactivated by glutathione-dependent adduct formation as well as quinazolinone oxidation in microsomes. Pharmacokinetic studies demonstrated modest bioavailability and compound exposures. Resistance to the compounds in MTb was conferred by promoter mutations in the alternative nonessential NDH-2 encoded by ndhA in MTb. Bioenergetic analyses revealed a decrease in oxygen consumption rates in response to inhibitor in cells in which membrane potential was uncoupled from ATP production, while inverted membrane vesicles showed mercapto-quinazolinone-dependent inhibition of ATP production when NADH was the electron donor to the respiratory chain. Enzyme kinetic studies further demonstrated noncompetitive inhibition, suggesting binding of this scaffold to an allosteric site. In summary, while the initial MTb SAR showed limited improvement in potency, these results, combined with structural information on the bacterial protein, will aid in the future discovery of new and improved NDH-2 inhibitors.

Synthesis of novel 2-[1-(1H-benzimidazol-2-yl)-ethylsulfanyl]-3H- quinazolin-4-ones

Condensation of 2-(4-oxo-3,4-dihydroquinazolin-2-ylsulfanyl)-propionic acid (1) with o-phenylenediamine (2) gave 2-[1-(1H-benzimidazol-2-yl)-ethylsulfanyl] -3H-quinazolin-4-one (3). The latter can also be prepared by the reaction of 2-(1-chloroethyl)-1H-benzimidazole (4) with 2-mercapto-3W-quinazolin-4-one (5) either in acetone/ triethylamine or in DMF / K2CO3 in the presence of TBAB as phase transfer catalyst. 3 can also be prepared yet by an alternative method involving reaction of 4 with potassium ethylthioxanthate yielding dithiocarbonic acid S-[1 H-benzomidazol-2-yl) ethyl) ethyl ester (6) and subsequent condensation of the latter with o-aminobenzamide (7), in the presence of TFA, under reflux in toluene.