98351-83-8Relevant academic research and scientific papers
Cascade approach to substituted 6-aryl-phenanthridines from aromatic aldehydes, anilines, and benzenediazonium-2-carboxylate
Shou, Wang-Ge,Yang, Yun-Yun,Wang, Yan-Guang
, p. 9241 - 9243 (2006)
(Chemical Equation Presented) Aromatic aldehydes reacted with anilines and benzenediazonium-2-carboxylate to afford 6-aryl-phenanthridines. The reaction furnishes a rapid and direct construction of substituted phenanthridine rings from readily available starting materials via a one-pot cascade process.
Synthesis of phenanthridines by I2-mediated sp3C-H amination
Chang, Junbiao,Fang, Benyao,Hou, Jiao,Tian, Jinyue,Yu, Wenquan
, p. 3312 - 3323 (2020/05/14)
An I2-mediated synthesis of phenanthridinesviaintramolecular sp3C-H amination of readily accessible aniline precursors is reported. The present synthetic process is straightforward and applicable to a broad variety of unprotected ani
Optimization of Drug Candidates That Inhibit the D-Loop Activity of RAD51
Budke, Brian,Tueckmantel, Werner,Miles, Kelsey,Kozikowski, Alan P.,Connell, Philip P.
supporting information, p. 1031 - 1040 (2019/04/30)
RAD51 is the central protein in homologous recombination (HR) repair, where it first binds ssDNA and then catalyzes strand invasion via a D-loop intermediate. Additionally, RAD51 plays a role in faithful DNA replication by protecting stalled replication forks; this requires RAD51 to bind DNA but may not require the strand invasion activity of RAD51. We previously described a small-molecule inhibitor of RAD51 named RI(dl)-2 (RAD51 inhibitor of D-loop formation #2, hereafter called 2 h), which inhibits D-loop activity while sparing ssDNA binding. However, 2 h is limited in its ability to inhibit HR in vivo, preventing only about 50 % of total HR events in cells. We sought to improve upon this by performing a structure–activity relationship (SAR) campaign for more potent analogues of 2 h. Most compounds were prepared from 1-(2-aminophenyl)pyrroles by forming the quinoxaline moiety either by condensation with aldehydes, then dehydrogenation of the resulting 4,5-dihydro intermediates, or by condensation with N,N′-carbonyldiimidazole, chlorination, and installation of the 4-substituent through Suzuki–Miyaura coupling. Many analogues exhibited enhanced activity against human RAD51, but in several of these compounds the increased inhibition was due to the introduction of dsDNA intercalation activity. We developed a sensitive assay to measure dsDNA intercalation, and identified two analogues of 2 h that promote complete HR inhibition in cells while exerting minimal intercalation activity.
Pd/Fe3O4 supported on nitrogen-doped reduced graphene oxide for room-temperature isocyanide insertion reactions
Singh, Karandeep,Singh, Ajay K.,Singh, Devendra,Singh, Rakhi,Sharma, Siddharth
, p. 3723 - 3726 (2016/06/14)
A versatile Pd/Fe3O4 supported on N-doped reduced graphene oxide (N-rGO) catalyst was developed to carry out the synthesis of quinazolinones and phenanthridines under extremely mild conditions through isocyanide insertion cascades. T
Metal-free nitrogenation of 2-acetylbiphenyls: Expeditious synthesis of phenanthridines
Tang, Conghui,Yuan, Yizhi,Jiao, Ning
, p. 2206 - 2209 (2015/05/13)
An intermolecular nitrogenation reaction toward the synthesis of phenanthridines has been developed. This metal-free protocol provides a novel nitrogen-incorporation transformation using azides as the nitrogen source. Phenanthridines, which are of great interest in pharmaceutical and medicinal chemistry, are synthesized efficiently in one step. Moreover, the byproducts derived from the Schmidt reaction are inhibited, which further demonstrated the high chemoselectivity of this transformation.
Synthesis of phenanthridine derivatives via cascade annulation of diaryliodonium salts and nitriles
Li, Jian,Wang, Hongni,Sun, Jiangtao,Yang, Yang,Liu, Li
, p. 7904 - 7908 (2014/12/12)
A cascade coupling reaction toward a variety of phenanthridine derivatives has been developed. This cascade transformation proceeds via the copper-catalyzed coupling reaction of diaryliodonium salts and nitriles, and undergoes cyclization into the phenanthridine core.
Bronsted acid-mediated reactions of aldehydes with 2-vinylaniline and biphenyl-2-amine
Zhang, Xu,Xu, Xuefeng,Yu, Lintao,Zhao, Qiang
supporting information, p. 2280 - 2282 (2014/04/17)
Herein we report simple Bronsted acid-mediated reactions of aldehydes with 2-vinylaniline and biphenyl-2-amine. Ultimately, the useful nitrogen-containing heterocycle derivatives are obtained. The electronic properties of the substituents on the aldehydes and 2-vinylaniline were investigated. It was found that molecules with both electron-donating and -withdrawing substituents were perfectly suitable substrates for this transformation, and the expected products were obtained in moderate to excellent yields.
Palladium and radical routes to phenanthridines
Bowman, W. Russell,Lyon, Jessica E.,Pritchard, Gareth J.
, p. 210 - 227 (2013/01/16)
Two routes to phenanthridines are reported; a palladium-mediated route using imidoyl-selanides as precursors and a modified radical route using aryl imines as starting materials. ARKAT-USA, Inc.
Trifluoroacetic acid-mediated facile construction of 6-substituted phenanthridines
Youn, So Won,Bihn, Joon Hyung
supporting information; experimental part, p. 4598 - 4601 (2009/10/11)
The trifluoroacetic acid-mediated reaction of 2-arylanilines with arylaldehydes has been developed to give a variety of 6-substituted phenanthridines. This is a very simple and convenient one-pot process for library construction.
Medium and Substituent Effects on the Photochemistry of Phenanthridine N-Oxides. Is an Intermediate of Diradical Character involved in the Photorearrangement of Heterocyclic N-Oxides?
Albini, Angelo,Fasani, Elisa,Frattini, Valeria
, p. 235 - 240 (2007/10/02)
The photochemistry of several 6-substituted phenanthridine N-oxides has been investigated, or reinvestigated, in benzene and ethanol.The main processes observed are: (a) 1,2-oxygen and substituent shift to yield N-substituted phenanthridones (2) and (b) ring enlargements to dibenzo-1,3-oxazepines (7).With 6-diphenylmethylphenanthridine N-oxide (1b) rearrangement (a) predominates and occurs with 45percent substituent loss in benzene (but only 2percent in ethanol).With the 6-phenylderivative (1c) process (a) predominates in ethanol and process (b) in benzene and with the 6-p-nitrophenyl derivative (1d) the latter process predominates in both solvents.With 6-cyanophenanthridine N-oxide (1e) rearrangement (b) predominates in benzene; in the presence of 2,3-dimethylbutene (but not of cyclohexene) addition products are obtained; with dienes deoxygenation is the main process.Medium and substituents may change the nature of the lowest excited singlet state, but more importantly affect the stability of an intermediate of diradical character occurring along the reaction pathway, thus driving it towards rearrangement (a) or (b).Intermediate diradicals are unambiguously indicated only in particular cases but their role is probably more general.
