125217-91-6Relevant academic research and scientific papers
NIS-mediated intramolecular oxidative α-functionalization of tertiary amines: Transition metal-free synthesis of 1,2-dihydro-(4H)-3,1-benzoxazin-4-one derivatives
Liu, Le,Du, Liang,Zhang-Negrerie,Du, Yunfei
, p. 29774 - 29781 (2015/05/20)
A novel method for direct α-functionalization of tertiary amines via NIS-mediated oxidative C-O bond formation, where NIS serves as both an oxidant and an iodination reagent, has been developed. The method provides easy access to either iodinated or non-iodinated 1,2-dihydro-(4H)-3,1-benzoxazin-4-ones, depending on the nature of the reactant, via a regioselective transition metal-free approach. This journal is
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.
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
Natural Products Chemistry. Part 124. Revised Structure and Synthesis of a New Acridone Alkaloid, Hallacridone from Ruta graveolens Tissue Cultures
Reisch, Johannes,Gunaherath, G. M. Kamal B.
, p. 1047 - 1051 (2007/10/02)
The synthesis of 6-hydroxy-2,12-dimethyl-3H-pyranoacridine-3,7(12H)-dione (1) by two different routes revealed the previously proposed structure of hallacridone, , to be incorrect.Careful examination of the spectral characteristics, of an authentic
