53197-57-2Relevant articles and documents
An effective synthesis method for tilorone dihydrochloride with obvious IFN-α inducing activity
Zhang, Junren,Yao, Qizheng,Liu, Zuliang,De Sousa, Maria Emília
, p. 21458 - 21463 (2016/01/25)
Tilorone dihydrochloride (1) has great potential for inducing interferon against pathogenic infection. In this paper, we describe a convenient preparation method for 2,7-dihydroxyfluoren-9-one (2), which is a usual pharmaceutical intermediate for preparing tilorone dihydrochloride (1). In the novel method, methyl esterification of 4,4′-dihydroxy-[1,1′-biphenyl]-2-carboxylic acid (4) was carried out under milder conditions with higher yield and played an important role in the preparation of compound 2. The structures of the relative intermediates and target compound were characterized by melting point, IR, MS, and 1H-NMR. Furthermore, the synthesized tilorone dihydrochloride exhibited an obvious effect on induction of interferon-α (IFN-α) in mice within 12 h, and the peak level was observed until 24 h. This fruitful work has resulted in tilorone dihydrochloride becoming available in large-scale and wide application in clinics, which has a good pharmaceutical development prospects.
Chronobiotic activity of N-[2-(2,7-dimethoxyfluoren-9-yl)ethyl]- propanamide. Synthesis and melatonergic pharmacology of fluoren-9-ylethyl amides
Epperson, James R.,Bruce, Marc A.,Catt, John D.,Deskus, Jeffrey A.,Hodges, Donald B.,Karageorge, George N.,Keavy, Daniel J.,Mahle, Cathy D.,Mattson, Ronald J.,Ortiz, Astrid A.,Parker, Michael F.,Takaki, Katherine S.,Watson, Brett T.,Yevich, Joseph P.
, p. 4601 - 4611 (2007/10/03)
Compound 2b demonstrated full agonism at both human MT1 and MT2 receptors and demonstrated chronobiotic activity in both acute and chronic rat models, producing an acute phase advance of 32 min at 1 mg/kg and chronically entraining free-running rats with a mean effective dose of 0.23 mg/kg. This compound was significantly less efficacious than melatonin in constricting human coronary artery. A series of fluoren-9-yl ethyl amides (2) were synthesized and evaluated for human melatonin MT1 and MT 2 receptor binding. N-[2-(2,7-dimethoxyfluoren-9-yl)ethyl]propanamide (2b) was selected and evaluated in functional assays measuring intrinsic activity at the human MT1 and MT2 receptors and demonstrated full agonism at both receptors. The chronobiotic properties of 2b were demonstrated in both acute and chronic rat models where 2b produced an acute phase advance of 32 min at 1 mg/kg and chronically entrained free-running rats with a mean effective dose of 0.23 mg/kg. Compound 2b is significantly less efficacious than melatonin in constricting human coronary artery.
