153386-07-3Relevant academic research and scientific papers
Synthesis and antibacterial activity of 5-methylphenanthridium derivatives as FtsZ inhibitors
Liu, Fang,Venter, Henrietta,Bi, Fangchao,Semple, Susan J.,Liu, Jingru,Jin, Chaobin,Ma, Shutao
supporting information, p. 3399 - 3402 (2017/07/07)
5-Methylphenanthridium derivatives were designed, synthesized and evaluated for their in vitro antibacterial activity and cell division inhibitory activity against various Gram-positive and -negative bacteria. Among them, compounds 5A2, 5B1, 5B2, 5B3, 5C1 and 5C2 displayed the best on-target antibacterial activity with an MIC value of 4?μg/mL against B. subtilis ATCC9372 and S. pyogenes PS, showing over 2-fold better activity than sanguinarine. The SARs showed that the 5-methylphenanthridium derivatives with the alkyl side chains at the 2-postion, especially the straight alkyl side chains exerted better on-target antibacterial activity.
Practical Synthesis of Phenanthridinones by Palladium-Catalyzed One-Pot C-C and C-N Coupling Reaction: Extending the Substrate Scope to o-Chlorobenzamides
Liu, Hailong,Han, Weibiao,Li, Chun,Ma, Zhiyong,Li, Ruixiang,Zheng, Xueli,Fu, Haiyan,Chen, Hua
supporting information, p. 389 - 393 (2016/02/18)
A highly efficient construction of phenanthridinone derivatives from o-halobenzamides was developed by using a phosphine-free palladium catalyst in N,N-dimethylacetamide. The domino reaction proceeds through a sequential C-C and C-N bond-formation process in one pot. This protocol exhibits broad substrate scope and affords a series of phenanthridinones in up to 93 % yield. Importantly, the protocol could also be applied for the less reactive o-chlorobenzamides. The approach constitutes the first example of the synthesis of phenanthridinones from this kind of substrate. Moreover, the success of a gram-scale reaction demonstrated that this operationally simple process is scalable.
Palladium-catalyzed C-C coupling of aryl halides with isocyanides: An alternative method for the stereoselective synthesis of (3E)-(Imino)isoindolin- 1-ones and (3E)-(imino)thiaisoindoline 1,1-dioxides
Liu, Bifu,Li, Yibiao,Jiang, Huanfeng,Yin, Meizhou,Huang, Huawen
, p. 2288 - 2300 (2012/11/07)
A palladium-catalyzed, one-pot cyclization reaction to construct (3E)-(imino)isoindolin-1-ones and (3E)-(imino)thiaisoindoline 1,1-dioxides by introducing ortho-reactive functional groups on aryl halides is reported. Under optimal conditions, the cyclization reaction afforded the corresponding products in good to excellent yields (up to 93%) with high stereoselectivity. Notably, this transformation successfully extends its application for the synthesis of phenanthridines and dibenzooxazepines. This new synthetic protocol not only extends the application platform for palladium-catalyzed C-C coupling of aryl halides with isocyanides, but also opens atom-economic and step-economic synthetic routes for nitrogen-containing heterocyclic compounds with wide functional group compatibility. Copyright
Role of Hetero-halogen (F · · · X, X = Cl, Br, and I) or homo-halogen (X · · · X, X = F, Cl, Br, and I) interactions in substituted benzanilides
Nayak, Susanta K.,Kishore Reddy,Row, Tayur N. Guru,Chopra, Deepak
experimental part, p. 1578 - 1596 (2012/04/04)
A series of halogen-substituted benzanilides have been synthesized and characterized, and crystallization studies directed toward generation of polymorphs have been performed to delineate the importance of interactions involving halogens. The effect of ha
Structural development studies of anti-hepatitis C virus agents with a phenanthridinone skeleton
Nakamura, Masahiko,Aoyama, Atsushi,Salim, Mohammed T.A.,Okamoto, Mika,Baba, Masanori,Miyachi, Hiroyuki,Hashimoto, Yuichi,Aoyama, Hiroshi
scheme or table, p. 2402 - 2411 (2010/06/20)
A phenanthridinone skeleton was derived from our previous researches on thalidomide and retinoids as a multi-template for generation of anti-viral lead compounds. Structural development studies focusing on anti-hepatitis C virus activity afforded 5-butyl-2-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenanthridin-6(5H)-one (10) and 5-butylbenzo[b]phenanthridin-6(5H)-one (39), which showed EC50 values of approximately 3.7 and 3.2 μM, respectively.
Cyclizations. Part 1. Electrochemical and Photochemical Reactions of 1-(4-Fluorophenyl)-5-(2-halogenophenyl)tetrazoles
Donnelly, Shileen,Grimshaw, James,Trocha-Grimshaw, Jadwiga
, p. 1557 - 1562 (2007/10/02)
Electrochemical reduction of the title compounds, where the halogen substituent is Cl, Br or I, leads to cleavage of the carbon-halogen bond to leave a phenyl radical.Competition then follows between intramolecular radical substitution giving 7-fluorotetrazolophenanthridine and further reduction of the radical, then protonation, giving 1-(4-fluorophenyl)-5-phenyltetrazole.Substitution predominates but reduction and protonation becomes a more competing reaction when the halogen is Br or I.Photochemical reaction of the title compounds shows competition between carbon-halogen bond cleavage to give 7-fluorotetrazolophenanthridine and loss of nitrogen followed by cyclization to give 2-halogenophenyl-5-fluorobenzimidazole.Carbon-halogen bond cleavage predominates and becomes the only reaction when the halogen is I.The fluorine substituent allows the determination of product yields by 19F NMR spectroscopy.
