27693-73-8Relevant academic research and scientific papers
4-methylaminoacridine-N-phenylbenzamide compound and preparation method and application thereof
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Paragraph 0021; 0033, (2019/11/14)
The invention discloses a 4-aminomethylacridine-N-phenylbenzamide compound and a preparation method and application thereof. The compound is characterized in that the compound is a compound with a structural formula shown in the formula I or a pharmaceutically acceptable salt, ester or solvate of the compound with the structural formula shown in the formula I, wherein R1 is H, OCH3, OCH2CH3, Cl, Br, CF3, NO2 or a linear alkyl group with 1 to 5 carbon atoms, R2 is H, OCH3, OCH2CH3, Cl, Br, CF3, NO2 or a linear alkyl group with 1 to 5 carbon atoms, R3 is H, OCH3, OCH2CH3, Cl, Br, CF3, NO2 or a linear alkyl group with 1 to 5 carbon atoms, and n = 1, 2, 3 or 4, the advantages are that the compound can effectively inhibit the activity of DNA topoisomerases, inhibits the proliferation of eukaryotic tumor cells, and prevents and / or treats tumors.
Design, synthesis and biological research of novel N-phenylbenzamide-4-methylamine acridine derivatives as potential topoisomerase I/II and apoptosis-inducing agents
Zhang, Bin,Dou, Zhende,Xiong, Zheng,Wang, Ning,He, Shan,Yan, Xiaojun,Jin, Haixiao
supporting information, (2019/10/28)
A series of novel N-phenylbenzamide-4-methylamine acridine derivatives were designed and synthesized based initially on the structure of amsacrine (m-AMSA). Molecular docking suggested that the representative compound 9a had affinity for binding DNA topoisomerase (Topo) II, which was comparable with that of m-AMSA, and furthermore that 9a could have preferential interactions with Topo I. After synthesis of 9a and analogues 9b-9f, these were all tested in vitro and the synthesized compounds displayed potent antiproliferative activity against three different cancer cell lines (K562, CCRF-CEM and U937). Among them, compounds 9b, 9c and 9d exhibiting the highest activity with IC50 value ranging from 0.82 to 0.91 μM against CCRF-CEM cells. In addition, 9b and 9d also showed high antiproliferative activity against U937 cells, with IC50 values of 0.33 and 0.23 μM, respectively. The pharmacological mechanistic studies of these compounds were evaluated by Topo I/II inhibition, western blot assay and cell apoptosis detection. In summary, 9b effectively inhibited the activity of Topo I/II and induced DNA damage in CCRF-CEM cells and, moreover, significantly induced cell apoptosis in a concentration-dependent manner. These observations provide new information and guidance for the structural optimization of more novel acridine derivatives.
N-substituted-3(10H)-acridones as visible-light photosensitizers for organic photoredox catalysis
Chen, Kun,Cheng, Yong,Chang, Yongzhi,Li, Enqin,Xu, Qing-Long,Zhang, Can,Wen, Xiaoan,Sun, Hongbin
, p. 483 - 489 (2017/12/26)
N-Substituted-3(10H)-acridones have been established as visible-light organic photocatalyst. These photosensitizers are efficient for oxidative coupling reaction of N-aryl tetrahydroisoquinolines with various nucleophiles. Notably, N-methyl-3(10H)-acridon
10-substituted acridine-3(10)-ketone compound, and preparation method and application thereof
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Paragraph 0068; 0069; 0070; 0071; 0072, (2017/05/27)
The invention relates to a photosensitizer in photodynamic therapy, in particular to a 10-substituted acridine-3(10)-ketone compound shown in the formula I, a preparation method of the compound and application of the compound serving as the photosensitize
Synthesis and biological evaluation of benzimidazole acridine derivatives as potential DNA-binding and apoptosis-inducing agents
Gao, Chunmei,Li, Bin,Zhang, Bin,Sun, Qinsheng,Li, Lulu,Li, Xi,Chen, Changjun,Tan, Chunyan,Liu, Hongxia,Jiang, Yuyang
supporting information, p. 1800 - 1807 (2015/03/30)
The discovery of new effective DNA-targeted antitumor agent is needed because of their clinical significance. As acridines can intercalate into DNA and benzimidazoles have the ability to bind in the DNA minor groove, a series of novel benzimidazole acridine derivatives were designed and synthesized to be new DNA-targeted compounds. MTT assay indicated that most of the synthesized compounds displayed good antiproliferative activity, among which compound 8l demonstrated the highest activity against both K562 and HepG-2 cells. Further experiments showed that 8l displayed good DNA-binding capability and inhibited topoisomerase I activity. Moreover, compound 8l could induce apoptosis in K562 cell lines through mitochondrial pathway. These data suggested that compound 8l might be potential as new DNA-binding and apoptosis-inducing antitumor agents.
Synthesis and characterization of 1-carboxyphenothiazine derivatives bearing nitrogen mustard as promising class of antitubercular agents
Kataria,Solanki,Trivedi,Shah
, p. 951 - 956 (2013/12/04)
A series of 1-carboxyphenothiazines bearing nitrogen mustard was synthesized, characterized, and evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv. The results showed that compounds 5h, 5i and 5j found most active with percentage inhibition of 96, 91, and 92, respectively, at minimum inhibitory concentration (MIC) of 6.25 μg/mL. The structures of synthesized compounds were elucidated by various spectroscopic tools like IR, 1H NMR, 13C NMR, mass and elemental analysis. 2013 Bentham Science Publishers.
Development of potent and selective inhibitors of aldo-keto reductase 1C3 (type 5 17β-hydroxysteroid dehydrogenase) based on N -phenyl-aminobenzoates and their structure-activity relationships
Adeniji, Adegoke O.,Twenter, Barry M.,Byrns, Michael C.,Jin, Yi,Chen, Mo,Winkler, Jeffrey D.,Penning, Trevor M.
supporting information; experimental part, p. 2311 - 2323 (2012/05/04)
Aldo-keto reductase 1C3 (AKR1C3; type 5 17β-hydroxysteroid dehydrogenase) is overexpressed in castration resistant prostate cancer (CRPC) and is implicated in the intratumoral biosynthesis of testosterone and 5α-dihydrotestosterone. Selective AKR1C3 inhibitors are required because compounds should not inhibit the highly related AKR1C1 and AKR1C2 isoforms which are involved in the inactivation of 5α-dihydrotestosterone. NSAIDs, N-phenylanthranilates in particular, are potent but nonselective AKR1C3 inhibitors. Using flufenamic acid, 2-{[3-(trifluoromethyl)phenyl]amino}benzoic acid, as lead compound, five classes of structural analogues were synthesized and evaluated for AKR1C3 inhibitory potency and selectivity. Structure-activity relationship (SAR) studies revealed that a meta-carboxylic acid group relative to the amine conferred pronounced AKR1C3 selectivity without loss of potency, while electron withdrawing groups on the phenylamino B-ring were optimal for AKR1C3 inhibition. Lead compounds did not inhibit COX-1 or COX-2 but blocked the AKR1C3 mediated production of testosterone in LNCaP-AKR1C3 cells. These compounds offer promising leads toward new therapeutics for CRPC.
Acridone-benzimidazole ring-fused ligands: A new class of sensitizers of lanthanide luminescence via low-energy excitation
Deiters, Emmanuel,Gumy, Frederic,Buenzli, Jean-Claude G.
scheme or table, p. 2723 - 2734 (2010/08/21)
Two monotopic tridentate ligands, namely HLAB1 and HL AB2 have been synthesized which feature an acridone chromophore fused on a benzimidazolepyridine framework. They differ from each other by their connection points between a N-meth
Structure-activity relationships in the acronycine and benzo[b]acronycine series: Role of the pyran ring
Do, Quyen,Thi Mai, Huong Doan,Gaslonde, Thomas,Pfeiffer, Bruno,Leonce, Stephane,Pierre, Alain,Michel, Sylvie,Tillequin, Francois,Dufat, Hanh
scheme or table, p. 2677 - 2687 (2009/04/11)
In order to explore the structure-activity relationships in the acronycine series, simplified analogues of cis-1,2-diacetoxy-1,2-dihydroacronycine and cis-1,2-diacetoxy-1,2-dihydrobenzo[b]acronycine (S23906-1, under clinical trials) lacking the fused pyran ring, but possessing an acetoxymethyl leaving group at position 4 were prepared. These new analogues only displayed marginal antiproliferative activity compared to the parent compounds. The presence of the angularly fused dimethylpyran ring appears as an indispensable structural requirement to observe significant cytotoxic activity in this series.
Acridone derivatives: Design, synthesis, and inhibition of breast cancer resistance protein ABCG2
Boumendjel, Ahcene,Macalou, Sira,Ahmed-Belkacem, Abdelhakim,Blanc, Madeleine,Di Pietro, Attilio
, p. 2892 - 2897 (2007/10/03)
The breast cancer resistance protein (BCRP, ABCG2) is among the latest discovered ABC proteins to be involved in MDR phenotype and for which only few inhibitors are known. In continuing our program aimed at discovering efficient multidrug resistance modul
