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Upstream product

• 26059-85-8 2-(2-thienyl)quinazolin-4(3H)-one 
• 26059-85-8 2-(thiophen-2-yl)quinazolin-4-ol 
• 5271-67-0 2-Thiophenecarbonyl chloride 
• 88-65-3 2-bromobenzoic-acid 
• 98-03-3 thiophene-2-carbaldehyde 
• 527-72-0 2-thiophenylcarboxylic acid 
• 28144-70-9 anthranilic acid amide 
• 33405-06-0 N-(2-carboxyphenyl)thiophene-2-carboxamide 
• 118-92-3 anthranilic acid 
• 26060-06-0 2-Thiophen-2-yl-4H-3,1-benzoxazin-4-one 
• 59490-98-1 N-(2-aminocarbonylphenyl)thiophene-2-carboxamide 

Downstream Products

• 1264533-94-9 2-(thiophen-2-yl)-4-(1-tosylpiperidin-4-yl)quinazoline 

Relevant academic research and scientific papers

Cyclometallated PTII complexes of 2-(2-thienyl)-4-(cycloalkylimino)-substituted quinazolines

The title complexes were prepared based on 2-(thiophen-2-yl)-4-(morpholin-4-yl)- and 2-(thiophen-2-yl)-4-(piperidin-1-yl)-substituted quinazolines and found to exhibit luminescent properties.

Copper mediated one-pot synthesis of quinazolinones and exploration of piperazine linked quinazoline derivatives as anti-mycobacterial agents

A facile method was developed for the synthesis of quinazolinone derivatives in a one-pot condensation reaction via in situ amine generation using ammonia as the amine source and with the formation of four new C-N bonds in good to excellent yields. With the optimised method, we synthesized a library of piperazine linked quinazoline derivatives and the synthesized compounds were evaluated for their inhibitory activity against Mycobacterium tuberculosis. The compounds 8b, 8e, 8f, 8m, 8n and 8v showed potent anti-mycobacterial activity with MIC values of 2-16 μg mL-1. All the synthesized compounds follow Lipinski's rules for drug likeness. This journal is

Synthesis and biological evaluation of quinazoline derivatives – A SAR study of novel inhibitors of ABCG2

Multidrug resistance (MDR) is a major obstacle for effective chemotherapeutic treatment of cancer frequently leading to failure of the therapy. MDR is often associated with the overexpression of ABC transport proteins like ABCB1 or ABCG2 which efflux harmful substances out of cells at the cost of ATP hydrolysis. One way to overcome MDR is to apply potent inhibitors of ABC transporters to restore the sensitivity of the cells toward cytostatic agents. This study focusses on the synthesis and evaluation of novel 2,4-disubstituted quinazoline derivatives regarding the structure-activity-relationship (SAR), their ability to reverse MDR and their mode of interaction with ABCG2. Hence, the inhibitory potency and selectivity toward ABCG2 was determined. Moreover, the intrinsic cytotoxicity and the reversal of MDR were investigated. Interaction type studies with the substrate Hoechst 33342 and conformational analyses of ABCG2 with 5D3 monoclonal antibody were performed for a better understanding of the underlying mechanisms. In our study we could further enhance the inhibitory effect against ABCG2 (compound 31, IC50: 55 nM) and identify the structural features that are crucial for inhibitory potency, the impact on transport activity and binding to the protein.

Novel phosphorescent iridium(III) complexes containing 2-thienyl quinazoline ligands: Synthesis, photophysical properties and theoretical calculations

The easy tailoring of organic ligands of iridium(iii) complexes provides a facile way to tune their opto-electronic properties for applications in high efficiency phosphorescent light emitting diodes. Herein, a series of yellow and red emitting phosphorescent iridium complexes based on 2-thienyl quinazoline derivatives are successfully synthesized and systematically characterized with various opto-electronic properties. The X-ray crystal structures demonstrate that the iridium centers in the complexes with bulky substituents on the 4-position of quinazolyl rings prefer to chelate with the N atoms in the 1-position of quinazolyl rings. Both experiment and theoretical studies indicate that the steric hindrance along with the electron-donating effect of substituents on the C^N ligands enhances the emission quantum yields, accompanied by significant emission shifts. Two yellow phosphorescent iridium complexes (Ir2 and Ir3) are successfully designed and exhibit moderate emission efficiencies, through the incorporation of bulky ligands with strong electron-donating abilities (piperidine for Ir2 and 2,6-dimethyl-phenoxy for Ir3, respectively). The synergistic effect of electron structure and hindrance of ligand is believed to be a promising strategy for tuning the opto-electronic properties of iridium complexes.

Evaluation of quinazoline analogues as glucocerebrosidase inhibitors with chaperone activity

Gaucher disease is a lysosomal storage disorder (LSD) caused by deficiency in the enzyme glucocerebrosidase (GC). Small molecule chaperones of protein folding and translocation have been proposed as a promising therapeutic approach to this LSD. Most small molecule chaperones described in the literature contain an iminosugar scaffold. Here we present the discovery and evaluation of a new series of GC inhibitors with a quinazoline core. We demonstrate that this series can improve the translocation of GC to the lysosome in patient-derived cells. To optimize this chemical series, systematic synthetic modifications were performed and the SAR was evaluated and compared using three different readouts of compound activity: enzymatic inhibition, enzyme thermostabilization, and lysosomal translocation of GC.

The design and synthesis of novel orally active inhibitors of AP-1 and NF-κB mediated transcriptional activation. SAR of in vitro and in vivo studies

We have developed novel orally active quinazoline analogues as inhibitors of AP-1 and NF-κB mediated transcriptional activation. Among the derivatives prepared, 1-[2-(2-thienyl)quinazolin-4-ylamino]-3-methyl-3- pyrroline-2,5-dione (10) showed significant activity in an adjuvant-induced arthritis rat model by reducing the swelling by 65% in the non-injected foot. The synthesis, structure-activity relationship, and in vivo activity are described.

Method for inhibiting neoplastic cells and related conditions by exposure to 4-aminoquinazoline derivatives

A method for inhibiting neoplastic cells and related conditions by exposing them to 4-aminoquinazoline derivatives.

Quinazoline analogs and related compounds and methods for treating inflammatory conditions

Compounds having utility as anti-inflammatory agents in general and, more specifically, for the prevention and/or treatment of immunoinflammatory and autoimmune diseases are disclosed. The compounds are quinazoline-containing compounds. Methods are also d

Discovery of potent cyclic GMP phosphodiesterase inhibitors. 2-Pyridyl- and 2-imidazolylquinazolines possessing cyclic GMP phosphodiesterase and thromboxane synthesis inhibitory activities

Moderate cyclic GMP phosphodiesterase (cGMP-PDE, PDE V) inhibitor 2- phenyl-4-anilino-quinazoline (1) was identified utilizing MultiCASE assisted drug design (MCADD) technology. Modification of compound 1 was conducted at the 2-, 4-, and 6-positions of the quinazoline ring for enhancement of cGMP- PDE inhibitory activity. The 6-substituted 2-(imidazol-1-yl)-quinazolines are 1000 times more potent in in vitro PDE V enzyme assay than the well-known inhibitor zaprinast. The 6-substituted derivatives of 2-(3- pyridyl)quinazoline 84 and 2-(imidazol-1-yl)quinazoline 86 exhibited more than 1000-fold selectivity for PDE V over the other four PDE isozymes. In addition, cGMP-PDE inhibitors 64, 65, and 73 were found to have an additional property of thromboxane synthesis inhibitory activity.

4-aminoquinazoline derivatives

The compounds of the formula: STR1 wherein R1, Y, A, R4, n, Z, CyB, R3, and m are defined in the specification.