574-25-4Relevant articles and documents
Huang et al.
, p. 1363,1364,1366 (1975)
Chemoselective Perfluoromethylation of Thio- And Selenoamides
Xu, Tao,Xu, Xianhong,Zhang, Jianyu
supporting information, (2020/11/13)
A chemo- and regioselective perfluoromethylation using thioamides/selenoamides (prepared one step from corresponding lactams) as starting materials has been discovered. The reaction demonstrated complementary chemoselectivity to the C-H trifluoromethylation of (hetero)arenes as well as remarkable functional group compatibility especially toward radical sensitive olefin-, alkyne-, and arylhalide-bearing substrates. The examples of perfluorothio-/selenolated drug molecules indicated application potential of this strategy in drug modification and drug-analogue preparation.
Thio- or seleno-amide compound and preparation method thereof
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Paragraph 0058-0061, (2020/07/24)
The invention discloses a thio- or seleno-amide compound and a preparation method thereof. The preparation method comprises the following steps of dissolving a chlorinated aromatic heterocyclic compound 1 in an EtOH solution, adding 1.0-2.0 times of equivalent thiourea or selenourea, stirring at 50-120 DEG C for 1-8 hours, and reacting to obtain a compound 2, namely the required thio- or seleno-amide compound. Each step of the synthetic route can be amplified, the yield can reach 85 percent, the synthesized compound provides a medical intermediate for synthesizing purine derivatives containingSCF3 or SeCF3, the synthetic route provided by the invention brings a simpler and more effective way for synthesizing compounds with biological activity, the yield is high, large-scale preparation can be realized, and the application prospect is very wide.
α,β-Methylene-ADP (AOPCP) Derivatives and Analogues: Development of Potent and Selective ecto-5′-Nucleotidase (CD73) Inhibitors
Bhattarai, Sanjay,Freundlieb, Marianne,Pippel, Jan,Meyer, Anne,Abdelrahman, Aliaa,Fiene, Amelie,Lee, Sang-Yong,Zimmermann, Herbert,Yegutkin, Gennady G.,Str?ter, Norbert,El-Tayeb, Ali,Müller, Christa E.
, p. 6248 - 6263 (2015/08/24)
ecto-5′-Nucleotidase (eN, CD73) catalyzes the hydrolysis of extracellular AMP to adenosine. eN inhibitors have potential for use as cancer therapeutics. The eN inhibitor α,β-methylene-ADP (AOPCP, adenosine-5′-O-[(phosphonomethyl)phosphonic acid]) was used as a lead structure, and derivatives modified in various positions were prepared. Products were tested at rat recombinant eN. 6-(Ar)alkylamino substitution led to the largest improvement in potency. N6-Monosubstitution was superior to symmetrical N6,N6-disubstitution. The most potent inhibitors were N6-(4-chlorobenzyl)- (10l, PSB-12441, Ki 7.23 nM), N6-phenylethyl- (10h, PSB-12425, Ki 8.04 nM), and N6-benzyl-adenosine-5′-O-[(phosphonomethyl)phosphonic acid] (10g, PSB-12379, Ki 9.03 nM). Replacement of the 6-NH group in 10g by O (10q, PSB-12431) or S (10r, PSB-12553) yielded equally potent inhibitors (10q, 9.20 nM; 10r, 9.50 nM). Selected compounds investigated at the human enzyme did not show species differences; they displayed high selectivity versus other ecto-nucleotidases and ADP-activated P2Y receptors. Moreover, high metabolic stability was observed. These compounds represent the most potent eN inhibitors described to date.
