- Diversified AIE and mechanochromic luminescence based on carbazole derivative decorated dicyanovinyl groups: Effects of substitution sites and molecular packing
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Aggregation-induced emission (AIE) properties have been widely investigated not only because they thoroughly circumvent the notorious aggregation-caused quenching effect encountered in conventional fluorophores but also due to their promising applications in organic light-emitting diodes, fluorescent sensors and bioimaging. In this work, we reported a study of the molecular packing and luminescence properties of AIE active positional isomers (m-BPCDM and p-BPCDM) with carbazole and dicyanovinyl groups. The compound m-BPCDM based on meta-substitution showed more evident AIE processes than the compound p-BPCDM based on para-substitution, which can be attributed to the strong π-π stacking effect brought by the spatial structure of p-BPCDM. Moreover, the two positional isomers also exhibited distinct mechanochromic luminescence properties.
- Guo, Zhiyong,Han, Mingxi,Qian, Li,Wang, Kai,Wu, Xianfeng,Xiao, Hui,Zhan, Hongbing
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- Synthesis and biochemical evaluation of benzoylbenzophenone thiosemicarbazone analogues as potent and selective inhibitors of cathepsin L
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Upregulation of cathepsin L in a variety of tumors and its ability to promote cancer cell invasion and migration through degradation of the extracellular matrix suggest that cathepsin L is a promising biological target for the development of anti-metastatic agents. Based on encouraging results from studies on benzophenone thiosemicarbazone cathepsin inhibitors, a series of fourteen benzoylbenzophenone thiosemicarbazone analogues were designed, synthesized, and evaluated for their inhibitory activity against cathepsins L and B. Thiosemicarbazone inhibitors 3-benzoylbenzophenone thiosemicarbazone 1, 1,3-bis(4-fluorobenzoyl)benzene thiosemicarbazone 8, and 1,3-bis(2-fluorobenzoyl)-5-bromobenzene thiosemicarbazone 32 displayed the greatest potency against cathepsin L with low IC50 values of 9.9 nM, 14.4 nM, and 8.1 nM, respectively. The benzoylbenzophenone thiosemicarbazone analogues evaluated were selective in their inhibition of cathepsin L compared to cathepsin B. Thiosemicarbazone analogue 32 inhibited invasion through Matrigel of MDA-MB-231 breast cancer cells by 70% at 10 μM. Thiosemicarbazone analogue 8 significantly inhibited the invasive potential of PC-3ML prostate cancer cells by 92% at 5 μM. The most active cathepsin L inhibitors from this benzoylbenzophenone thiosemicarbazone series (1, 8, and 32) displayed low cytotoxicity toward normal primary cells [in this case human umbilical vein endothelial cells (HUVECs)]. In an initial in vivo study, 3-benzoylbenzophenone thiosemicarbazone (1) was well-tolerated in a CDF1 mouse model bearing an implanted C3H mammary carcinoma, and showed efficacy in tumor growth delay. Low cytotoxicity, inhibition of cell invasion, and in vivo tolerability are desirable characteristics for anti-metastatic agents functioning through an inhibition of cathepsin L. Active members of this structurally diverse group of benzoylbenzophenone thiosemicarbazone cathepsin L inhibitors show promise as potential anti-metastatic, pre-clinical drug candidates.
- Parker, Erica N.,Song, Jiangli,Kishore Kumar,Odutola, Samuel O.,Chavarria, Gustavo E.,Charlton-Sevcik, Amanda K.,Strecker, Tracy E.,Barnes, Ashleigh L.,Sudhan, Dhivya R.,Wittenborn, Thomas R.,Siemann, Dietmar W.,Horsman, Michael R.,Chaplin, David J.,Trawick, Mary Lynn,Pinney, Kevin G.
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p. 6974 - 6992
(2015/11/11)
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- COMPOSITIONS AND METHODS FOR INHIBITION OF CATHEPSINS
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This invention is directed to compound of Formula I and methods of using these compounds in the treatment of conditions in which modulation of a cathepsin, particularly cathepsin K or cathepsin L, will be therapeutically useful.
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Paragraph 0133
(2013/10/08)
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- A phosphane-free, atom-efficient cross-coupling reaction of triarylbismuths with acyl chlorides catalyzed by MCM-41-immobilized palladium complex
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The first phosphane-free, heterogeneous, atom-efficient cross-coupling reaction of triarylbismuths and acyl chlorides was achieved in N-methylpyrrolidone (NMP) with Bu3N as the base at 80 °C in the presence of 1.5 mol-% MCM-41-immobilized bidentate nitrogen palladium complex [MCM-41-2N-Pd(OAc)2, MCM = mobile crystalline material] to yield a variety of unsymmetrical biaryl ketones in good to excellent yields. This heterogeneous palladium catalyst exhibited a high activity, which was similar to that of Pd(PPh3)4. The catalyst can be recovered by a simple filtration of the reaction solution and recycled in at least 10 consecutive trials without any decrease in activity. Our system not only avoids the use of phosphane ligands, but also solves the basic problem of palladium catalyst recovery and reuse. The first phosphane-free, heterogeneous, atom-efficient cross-coupling reaction of triarylbismuth compounds and acyl chlorides was achieved in N-methylpyrrolidone with Bu3N as the base at 80 °C in the presence of 1.5 mol-% MCM-41-immobilized bidentate nitrogen palladium complex [MCM-41-2N-Pd(OAc)2] to yield a variety of unsymmetrical biaryl ketones in good to excellent yields. Copyright
- Zhao, Hong,Yin, Lin,Cai, Mingzhong
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p. 1337 - 1345
(2013/04/10)
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- Atom-efficient cross-coupling reactions of triarylbismuths with acyl chlorides under Pd(0) catalysis
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The atom-efficient cross-coupling reaction of triarylbismuths with a variety of aliphatic, aromatic, and hetero-aromatic acyl chlorides was demonstrated to afford high yields of cross-coupled ketones under palladium catalysis. The corresponding cross-coupling reaction with diacid chlorides also furnished bis-coupled ketones in good yields.
- Rao, Maddali L.N.,Venkatesh, Varadhachari,Banerjee, Debasis
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p. 12917 - 12926
(2008/03/28)
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- Synthesis and photochromism of novel phenylene-linked photochromic bispyrans
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(Chemical Equation Presented) Phenylene-linked bisnaphthopyrans were synthesized in good yields via the one-pot reaction of bis-propargyl alcohols with naphthols. Temperature-dependent photochromism in 1,4-phenylene-linked bispyrans leads to up to 60 nm bathochromic shift between the colored species formed at room temperature and at -20°C. Better fatigue resistance and higher colorability was observed in 1,4-phenylene-linked bis-[2H]-naphtho[1,2-b] pyrans by comparison to the 1,3-phenylene linked bis-[2H]-naphtho[1,2-b]pyrans.
- Zhao, Weili,Carreira, Erick M.
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