5993-69-1Relevant articles and documents
Novel 2,4-disubstituted quinazoline analogs as antibacterial agents with improved cytotoxicity profile: Optimization of the 2,4-substituents
Aboushady, Dina,Rasheed, Sari S.,Herrmann, Jennifer,Maher, Ahmed,El-Hossary, Ebaa M.,Ibrahim, Eslam S.,Abadi, Ashraf H.,Engel, Matthias,Müller, Rolf,Abdel-Halim, Mohammad,Hamed, Mostafa M.
, (2021/10/27)
The emergence of bacterial resistance has triggered a multitude of efforts to develop new antibacterial agents. There are many compounds in literature that were reported as potent antibacterial agents, however, they lacked the required safety to mammalian cells or no clear picture about their toxicity profile was presented. Inspired by discovered hit from our in-house library and by previously reported 2,4-diaminosubstituted quinazolines, we describe the design and synthesis of novel 2,4-disubstituted-thioquinazolines (3–13 and 36), 2-thio-4-amino substituted quinazolines (14–33) and 6-substituted 2,4-diamonsubstituted quinazolines (37–39). The synthesized compounds showed potent antibacterial activity against a panel of Gram-positive, efflux deficient E.coli and Mycobacterium smegmatis. The panel also involved resistant strains including methicillin-resistant Staphylococcus aureus, penicillin-resistant Streptococcus pneumoniae, vancomycin-resistant Enterococcus faecalis and vancomycin-resistant Enterococcus faecium, in addition to Mycobacterium smegmatis. The newly synthesized compounds revealed MIC values against the tested strains ranging from 1 to 64 μg/mL with a good safety profile. Most of the 2-thio-4-amino substituted-quinazolines showed significant antimycobacterial activity with the variations at position 2 and 4 offering additional antibacterial activity against the different strains. Compared to previously reported 2,4-diaminosubstituted quinazolines, the bioisosteric replacement of the 2-amino with sulfur offered a successful approach to keep the high antibacterial potency while substantially improving safety profile as indicated by the reduced activity on different cell lines and a lack of hemolytic activity.
A highly efficient way to capture CX2 (O, S) mildly in reusable ReILs at atmospheric pressure
Zheng, Hui,Cao, Xianting,Du, Kui,Xu, Jun,Zhang, Pengfei
, p. 3142 - 3148 (2014/06/10)
The highly efficient transformation of CX2 (O, S) into valuable chemicals at atmospheric pressure is an attractive topic. A novel method of preparing quinazoline derivatives by capturing CX2 (O, S) in reusable, room-temperature, reversible ionic liquids (ReILs) with high yields (up to 98%) at 40 °C and atmospheric pressure was developed in this paper. The different reaction conditions were optimized and the products were easily separated from the ReILs which could be reused at least six times without considerable loss in yield. The plausible mechanism of capturing CX2 (O, S) in the ReILs was proposed and it provides a green, efficient protocol to capture CX2 (O, S) in ReILs to synthesize quinazoline derivatives. This journal is the Partner Organisations 2014.
Kilogram-scale synthesis of a highly selective α1-adrenoceptor antagonist (DL-028A)
Chou, Shan-Yen,Yin, Wei-Kung,Chung, Yuh-Shan,Chang, Lien-Shange,Liu, Chin-Wei,Chen, Shyh-Fong,Shih, Kae-Shyang
, p. 273 - 278 (2013/09/06)
This work presents an improved eight-step process, leading to kilogram quantities of high-quality DL-028A, an antihypertensive agent. The improvements include reducing the levels of toxic reagents and the removal of dangerous processes and waste gas treatment. Moreover, specification and impurity profiles were determined.
