115398-62-4Relevant articles and documents
Syntheses of 2-nitroimidazole derivatives conjugated with 1,4,7-triazacyclononane- N, N ′-diacetic acid labeled with F-18 using an aluminum complex method for hypoxia imaging
Hoigebazar, Lathika,Jeong, Jae Min,Lee, Ji-Youn,Shetty, Dinesh,Yang, Bo Yeun,Lee, Yun-Sang,Lee, Dong Soo,Chung, June-Key,Lee, Myung Chul
, p. 3155 - 3162 (2012)
Hypoxia imaging is important for diagnosis of ischemic diseases, and thus various 18F-labeled radiopharmaceuticals have been developed. However, 18F-labeling requires multistep procedures including azeotropic distillation, which is complicated and difficult to automate. Recently, 18F-labeling method using Al-F complex in aqueous solution was devised that offered a straightforward 18F-labeling procedure. We synthesized nitroimidazole derivatives conjugated with 1,4,7-triazacyclononane- 1,4-diacetic acid (NODA) that can be labeled with 18F using Al-F complex and examined their radiochemistries, in vitro and in vivo biological properties, and animal PET imaging characteristics. We found that the synthesized derivatives have excellent 18F-labeling efficiencies, high stabilities, specific uptakes in cultured hypoxic tumor cells, and high tumor to nontumor ratios in xenografted mice. Furthermore, the derivatives were labeled with 18F in a straightforward manner within 15 min at high labeling efficiencies and radiochemical purities. In conclusion, 18F-labeled NODA-nitroimidazole conjugates were developed and proved to be promising hypoxia PET agents.
Design, synthesis and biological evaluation of 6-(nitroimidazole-1 H -alkyloxyl)-4-anilinoquinazolines as efficient EGFR inhibitors exerting cytotoxic effects both under normoxia and hypoxia
Cheng, Weiyan,Zhu, Shijun,Ma, Xiaodong,Qiu, Ni,Peng, Peng,Sheng, Rong,Hu, Yongzhou
, p. 826 - 834 (2015/01/08)
A series of novel 6-(nitroimidazole-1H-alkyloxyl)-4-anilinoquinazoline derivatives (15a-15r) were designed, synthesized and evaluated as efficient EGFR inhibitors through introduction of hypoxia activated nitroimidazole moiety into the quinazoline scaffold of EGFR inhibitors. The majority of these newly synthesized compounds exhibited comparable EGFR inhibitory activities to gefitinib and moderate to excellent anti-proliferative activities against HT-29 cells under normoxia and hypoxia. The most promising compound 15c displayed the IC50 value of 0.47 nM against EGFR kinase and excellent cytotoxic effect against HT-29 cells under normoxia and hypoxia with the IC50 values of 2.21 μM and 1.62 μM, respectively. The mimic reductive activation study revealed that compound 15c exerted reductive activation properties under hypoxia, which were consistent with the in vitro metabolic study, wherein 15c was easily reductive activated under hypoxia and much more stable under normoxia. All these results suggested that 15c was a potential cancer therapeutic agent both under normoxia and hypoxia and was worth of further development.
Synthesis of nitroimidazole derived oxazolidinones as antibacterial agents
Varshney, Vandana,Mishra, Nripendra N.,Shukla, Praveen K.,Sahu, Devi P.
scheme or table, p. 661 - 666 (2010/04/04)
A series of N-alkylated derivatives of nitroimidazolyl oxazolidinones 6a-i with various substituent at N-1 position of the nitroimidazole were synthesized and their in-vitro antibacterial activities were evaluated against several Gram-positive and Gram-ne
An efficient procedure for the 1-alkylation of 2-nitroimidazoles and the synthesis of a probe for hypoxia in solid tumours
Long,Parrick,Hodgkiss
, p. 709 - 713 (2007/10/02)
The N-alkylation of 2-nitroimidazole through its 'naked' anion, formed from its alkali metal salts in the presence of crown ethers and in homogeneous solution, is shown to be a useful preparative procedure. The reactions of α,ω-dihaloalkanes can be controlled to afford either the mono- or diheteroarylalkane. The procedure has been used to alkylate theophylline and to prepare a compound of use as a probe to identify, locate and quantify hypoxia in sections from solid tumours.
