55602-36-3Relevant academic research and scientific papers
Synthesis and antiproliferative activity of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing the 2-oxo-4-chloro-1,2-dihydroquinoline-3-carboxamide moiety
Tang, Qidong,Zhai, Xin,Tu, Yayi,Wang, Ping,Wang, Linxiao,Wu, Chunjiang,Wang, Wenhui,Xie, Hongbo,Gong, Ping,Zheng, Pengwu
, p. 1794 - 1798 (2016/12/22)
A series of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing the 2-oxo-4-chloro-1,2-dihydroquinoline-3-carboxamide moiety were synthesized, and evaluated for their antiproliferative activity against 5 cancer cell lines (H460, HT-29, MKN-45, A549, and U87MG). Most compounds showed moderate to excellent potency, and compared to foretinib, the most promising analog 42 (c-Met/Flt-3 IC50= 1.21/2.15 nM) showed a 6.1-fold increase in activity against H460 cell line in vitro. The enzymatic assays (c-Met, VEGFR-2, Flt-3, PDGFR-β, c-Kit, and EGFR) of compound 42 were evaluated in vitro. Docking analysis showed that compound 42 could form three hydrogen bonds with c-Met. Structure–activity relationship studies indicated that a more water-soluble cyclic tertiary amine and electron-withdrawing groups at 4-position of the phenyl ring contribute to the antitumour activity.
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.
Hydrogen-bonded dimer stacking induced emission of aminobenzoic acid compounds
Zhou, Tianlei,Li, Feng,Fan, Yan,Song, Weifeng,Mu, Xiaoyue,Zhang, Hongyu,Wang, Yue
supporting information; experimental part, p. 3199 - 3201 (2009/12/01)
A series of aminobenzoic acid crystals with stacking-induced emission properties has been achieved and the packing structures of the hydrogen-bonded acid dimers provided an explanation for the emission characteristics of the crystals.
Structure-activity relationships in a series of anti-inflammatory N-arylanthranilic acids
Kaltenbronn,Scherrer,Short,Jones,Beatty,Saka,Winder,Wax,Williamson
, p. 621 - 627 (2007/10/02)
A large series of N-arylanthranilic acids has been prepared. Many of these compounds show high anti-inflammatory activity as measured by the anti-UV-erythema test. From this series have come the clinically useful nonsteroidal anti-inflammatory agents, flufenamic acid (Arlef), mefenamic acid (Ponstel), and the latest and most potent agent, N-(2,6-dichloro-m-tolyl)anthranilic acid (meclofenamic acid, Meclomen = the sodium salt). The structure-activity relationships of this series is discussed and a graphical representation is presented which allows the prediction of activity of new agents.
