19218-83-8Relevant academic research and scientific papers
FACILE OXIDATION OF ALCOHOLS BY 3-HYDROXY-N-METHYLACRIDINIUM ION (A NEW NAD+ MODEL COMPOUND)
Shinkai, Seiji,Hamada, Hisatake,Kuroda, Hideo,Manabe, Osamu
, p. 1235 - 1238 (1980)
3-Hydroxy-N-methylacridinium iodide (Ac+OH) oxidized alcohols with the aid of potassium t-butoxide, whereas N-methylacridinium iodide (Ac+) could not oxidize alcohols under the same reaction conditions.The results indicate that the 3
Design, synthesis and evaluation of acridine derivatives as multi-target Src and MEK kinase inhibitors for anti-tumor treatment
Cui, Zhishan,Li, Xi,Li, Lulu,Zhang, Bin,Gao, Chunmei,Chen, Yuzong,Tan, Chunyan,Liu, Hongxia,Xie, Weiyi,Yang, Ti,Jiang, Yuyang
supporting information, p. 261 - 269 (2015/12/31)
Clinical studies have shown enhanced anticancer effects of combined inhibition of Src and MEK kinases. Development of multi-target drugs against Src and MEK is of potential therapeutic advantage against cancers. As a follow-up of our previous studies, and by using molecular docking method, we designed and synthesized a new series of 9-anilinoacridines containing phenyl-urea moieties as potential novel dual Src and MEK inhibitors. The anti-proliferative assays against K562 and HepG-2 tumor cells showed that most of the derivatives displayed good cytotoxicity in vitro. In particular, kinase inhibition assays showed that compound 8m inhibited Src (59.67%) and MEK (43.23%) at 10 μM, and displayed moderate inhibitory activity against ERK and AKT, the downstream effectors of both Src and MEK. Moreover, compound 8m was found to induce K562 cells apoptosis. Structure-activity relationships of these derivatives were analyzed. Our study suggested that acridine scaffold, particularly compound 8m, is of potential interest for developing novel multi-target Src and MEK kinase inhibitors.
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.
, 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.
Structure-activity relationship studies of acridones as potentialantipsoriatic agents.1.Synthesis and antiproliferative activity of simple N-unsubstituted 10H-acridin-9-ones against human keratinocyte growth
Putic, Aleksandar,Stecher, Lambert,Prinz, Helge,Mueller, Klaus
scheme or table, p. 3299 - 3310 (2010/08/19)
A series of N-unsubstituted hydroxy-10H-acridin-9-ones were synthesized and evaluated for inhibitory action against HaCaT keratinocyte growth,in order to explore their potential as antipsoriatic agents. For structureeactivity relationship studies,the numb
QUINAZOLINE POTASSIUM CHANNEL INHIBITORS
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Page/Page column 28, (2008/06/13)
The present invention relates to compounds having the structure (I) useful as potassium channel inhibitors to treat cardiac arrhythmias, and the like.
Coenzyme Models. 28. Facile Oxidation of Alcohols and Amines by 3-Hydroxy-N-methylacridinium Ion, a New NAD+ Model Compound
Shinkai, Seiji,Hamada, Hisatake,Kuroda, Hideo,Manabe, Osamu
, p. 2333 - 2338 (2007/10/02)
The title compound (Ac+OH) was synthesized for the purpose of developing a new NAD+ model compound which is capable of oxidizing alcohols and amines.The absorption spectrum of Ac+OH was similar to that of N-methylacridinium ion (Ac+) in the acidic pH region and to that of 5-deazaflavin in the basic pH region.The absorption spectrum of the reduced form was analogous to that of 3-aminophenol.The reduced form which was prepared by NaBH4 reduction was promptly reoxidized by molecular oxygen.With the aid of potassium tert-butoxide, Ac+OH oxidized benzyl alcoholand cyclohexanol to the corresponding aldehyde and ketone in almost quantitative yields.In contrast, Ac+ was totally useless as an oxidant under the same reaction conditions.Benzylamine was oxidized by Ac+ to benzaldehyde in low yields (11-24percent).On the other hand, the oxidation by Ac+OH occurred in good yields (82-88percent).When the reaction was carried out under an oxygen stream, the yield calculated on the basis of Ac+OH was enhanced up to 1800-2200percent.The results indicate that Ac+OH acts as an effective turnover oxidizing agent and that the 3-hydroxyl group plays a crucial role in the redox reactions occurring on the acridinium nucleus.This is the first example of the facile oxidation of alcohols and amines which mimics the catalytic behavior of NAD+ coenzyme.
