18741-38-3

Upstream product

• 103-72-0 phenyl isothiocyanate 
• 5326-47-6 2-amino-5-iodobenzoic acid 

Downstream Products

• 116862-08-9 C₂₈H₁₆I₂N₄O₂S 
• 116862-01-2 C₂₈H₁₆I₂N₄O₂S₂ 
• 77747-22-9 2-Hydrazino-6-iod-3-phenylchinazol-4-on 
• 77747-32-1 1-Hydroxy-7-iodo-4-phenyl-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one 
• 77747-33-2 1-Ethoxycarbonyl-4-phenyl-7-iod-s-triazolo<4,3-a>chinazol-5-on 
• 77747-34-3 (7-Iodo-5-oxo-4-phenyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinazolin-1-yl)-acetic acid ethyl ester 
• 77066-27-4 7-Iodo-4-phenyl-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one 
• 77747-35-4 7-Iodo-4-phenyl-4H-tetrazolo[1,5-a]quinazolin-5-one 
• 77066-29-6 7-Iodo-1-methyl-4-phenyl-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one 
• 77066-34-3 7-Iodo-1-mercapto-4-phenyl-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one 
• 77066-30-9 7-Iodo-1,4-diphenyl-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one 
• 77066-20-7 C₂₁H₁₆IN₅OS 
• 180995-69-1 (6-iodo-4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-ylsulfanyl)-acetic acid ethyl ester 
• 1402932-18-6 C₁₉H₁₇IN₂OS 

Relevant academic research and scientific papers

Synthesis, Structure-Activity Relationship, and Mechanistic Studies of Aminoquinazolinones Displaying Antimycobacterial Activity

Phenotypic whole-cell screening against Mycobacterium tuberculosis (Mtb) in glycerol-alanine-salts supplemented with Tween 80 and iron (GASTE-Fe) media led to the identification of a 2-aminoquinazolinone hit compound, sulfone 1 which was optimized for solubility by replacing the sulfone moiety with a sulfoxide 2. The synthesis and structure-activity relationship (SAR) studies identified several compounds with potent antimycobacterial activity, which were metabolically stable and noncytotoxic. Compound 2 displayed favorable in vitro properties and was therefore selected for in vivo pharmacokinetic (PK) studies where it was found to be extensively metabolized to the sulfone 1. Both derivatives exhibited promising PK parameters; however, when 2 was evaluated for in vivo efficacy in an acute TB infection mouse model, it was found to be inactive. In order to understand the in vitro and in vivo discrepancy, compound 2 was subsequently retested in vitro using different Mtb strains cultured in different media. This revealed that activity was only observed in media containing glycerol and led to the hypothesis that glycerol was not used as a primary carbon source by Mtb in the mouse lungs, as has previously been observed. Support for this hypothesis was provided by spontaneous-resistant mutant generation and whole genome sequencing studies, which revealed mutations mapping to glycerol metabolizing genes indicating that the 2-aminoquinazolinones kill Mtb in vitro via a glycerol-dependent mechanism of action.

Eco-friendly rapid synthesis of 3-substituted-2-thioxo-2,3-dihydroquinazolin-4(1H)-ones in choline chloride based deep eutectic solvent

A series of 3-substituted-2-thioxo-2,3-dihydroquinazolin-4(1H)-ones and 6-iodo-3-substituted-2-thioxo-2,3-dihydroquinazolin-4(1H)-ones were synthesized in choline chloride/urea deep eutectic solvent. Substituted 2-mercapto-4(3H)-quinazolinones were synthesized from anthranilic acid or 5-iodoanthranilic acid and appropriate isothiocyanates in good to excellent yields. Isolation of final product was easy and required no further purification. Synthesis of these compounds was rapid, selective, and catalyst free, while preparation of deep eutectic solvent was easy, components are readily available, cheap, and environmentally friendly.

Discovery of selective small molecule type III phosphatidylinositol 4-kinase alpha (PI4KIIIα) inhibitors as anti hepatitis C (HCV) agents

Hepatitis C virus (HCV) assembles many host cellular proteins into unique membranous replication structures as a prerequisite for viral replication, and PI4KIIIα is an essential component of these replication organelles. RNA interference of PI4KIIIα results in a breakdown of this replication complex and cessation of HCV replication in Huh-7 cells. PI4KIIIα is a lipid kinase that interacts with the HCV nonstructural 5A protein (NS5A) and enriches the HCV replication complex with its product, phosphoinositol 4-phosphate (PI4P). Elevated levels of PI4P at the endoplasmic reticulum have been linked to HCV infection in the liver of HCV infected patients.1 We investigated if small molecule inhibitors of PI4KIIIα could inhibit HCV replication in vitro. The synthesis and structure-activity relationships associated with the biological inhibition of PI4KIIIα and HCV replication are described. These efforts led directly to identification of quinazolinone 28 that displays high selectivity for PI4KIIIα and potently inhibits HCV replication in vitro.

Design, synthesis and biological activity evaluation of 2-mercapto-4(3H)-quinazolinone derivatives as novel inhibitors of protein tyrosine phosphatase 1B

A series of novel 2-mercapto-4(3H)-quinazolinone derivatives have been synthesized and their inhibitory effects on PTP1B and TCPTP are evaluated for the first time. Most of these derivatives showed good inhibitory activity on PTP1B and reasonable selectivity for PTP1B over TCPTP, among them 32 was the most potent PTP1B inhibitor (IC50 = 1.50 μ ;g/mL), and 27 possessed the best selectivity of 3.0-fold.