- Design, synthesis and biological evaluation of anilide (dicarboxylic acid) shikonin esters as antitumor agents through targeting PI3K/Akt/mTOR signaling pathway
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Triple-negative breast cancer (TNBC) has an unfavorable prognosis attribute to its low differentiation, rapid proliferation and high distant metastasis rate. PI3K/Akt/mTOR as an intracellular signaling pathway plays a key role in the cell proliferation, m
- Ma, Yingying,Yang, Xiaorong,Han, Hongwei,Wen, Zhongling,Yang, Minkai,Zhang, Yahan,Fu, Jiangyan,Wang, Xuan,Yin, Tongming,Lu, Guihua,Qi, Jinliang,Lin, Hongyan,Wang, Xiaoming,Yang, Yonghua
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- Unlocking Amides through Selective C–N Bond Cleavage: Allyl Bromide-Mediated Divergent Synthesis of Nitrogen-Containing Functional Groups
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We report a new set of reactions based on the unlocking of amides through simple treatment with allyl bromide, creating a common platform for accessing a diverse range of nitrogen-containing functional groups such as primary amides, sulfonamides, primary amines, N-acyl compounds (esters, thioesters, amides), and N-sulfonyl esters. The method has potential industrial applicability, as demonstrated through gram-scale syntheses in batch and in a continuous flow system.
- Govindan, Karthick,Chen, Nian-Qi,Chuang, Yu-Wei,Lin, Wei-Yu
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supporting information
p. 9419 - 9424
(2021/11/30)
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- Metal-Free Synthesis of N-Aryl Amides using Organocatalytic Ring-Opening Aminolysis of Lactones
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Catalytic ring-opening of bio-sourced non-strained lactones with aromatic amines can offer a straightforward, 100 % atom-economical, and sustainable pathway towards relevant N-aryl amide scaffolds. Herein, the first general, metal-free, and highly efficient N-aryl amide formation is reported from poorly reactive aromatic amines and non-strained lactones under mild operating conditions using an organic bicyclic guanidine catalyst. This protocol has high application potential as exemplified by the formal syntheses of drug-relevant molecules.
- Guo, Wusheng,Gómez, José Enrique,Martínez-Rodríguez, Luis,Bandeira, Nuno A. G.,Bo, Carles,Kleij, Arjan W.
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p. 1969 - 1975
(2017/05/16)
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- Chemoselective hydrogenation of imides catalyzed by Cp*Ru(PN) complexes and its application to the asymmetric synthesis of paroxetine
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This work represents the first catalytic hydrogenation of imides into amides and primary alcohols, in which the unique chemoselectivity is originated from the bifunctional nature of ruthenium-NH moiety in the catalyst. Copyright
- Ito, Masato,Sakaguchi, Ayaka,Kobayashi, Chika,Ikariya, Takao
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p. 290 - 291
(2008/04/18)
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- Efficient synthesis of trisimidazole and glutaric acid bearing porphyrins: Ligands for active-site models of bacterial nitric oxide reductase
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Ligands (1) for active-site models of bacterial nitric oxide reductase (NOR) have been efficiently synthesized. These compounds (1) feature three imidazolyl moieties and one carboxylic acid residue at the FeB site, which represent the closest available synthetic model ligands of NOR active center. The stereo conformations of these ligands are established on the basis of steric effects and 1H NMR chemical shifts under the ring current effect of the porphyrin.
- Collman, James P.,Yan, Yi-Long,Lei, Jianping,Dinolfo, Peter H.
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p. 923 - 926
(2007/10/03)
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- Mercaptoamide-based non-hydroxamic acid type histone deacetylase inhibitors
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Inhibitors of histone deacetylases (HDAC) are emerging as a promising class of anti-cancer agents. A mercaptoamide functionality was designed as a bidentate zinc chelator and incorporated into the hydroxamic acid based SAHA (1) scaffold in order to identify non-hydroxamate compounds as potential inhibitors of histone deacetylases. Two sets of mercaptoamides 2 and 3 with varying spacer length were synthesized and their HDAC inhibitory activity was evaluated. Low micromolar inhibition was observed for mercaptoamides 2e, 3b, and 3d.
- Anandan, Sampath-Kumar,Ward, John S.,Brokx, Richard D.,Bray, Mark R.,Patel, Dinesh V.,Xiao, Xiao-Xi
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p. 1969 - 1972
(2007/10/03)
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- Structural biasing elements for in-cell histone deacetylase paralog selectivity
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We use the structural dissection of two 1,3-dioxanes with in-cell histone deacetylase (HDAC) paralog selectivity to identify key elements for selective HDAC inhibitors. We demonstrate that o-aminoanilides are inactive toward HDAC6 while apparently inhibit
- Wong, Jason C.,Hong, Roger,Schreiber, Stuart L.
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p. 5586 - 5587
(2007/10/03)
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- Rational Design of an Indolebutanoic Acid Derivative as a Novel Aldose Reductase Inhibitor Based on Docking and 3D QSAR Studies of Phenethylamine Derivatives
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A series of 45 phenethylamine derivatives were synthesized and evaluated for their inhibitory activity against pig kidney aldose reductase (ALR2, EC 1.1.1.21). Their IC50 values ranged from 400 μM to 24 μM. The binding modes of compounds at the active site of ALR2 were examined using flexible docking. The results indicated that phenethylamine derivatives nicely fit into the active pocket of ALR2 by forming various hydrogen bonding and hydrophobic interactions. 3D-QSAR analysis was also conducted using FlexX-docked alignment of the compounds. The best prediction was obtained by CoMSIA combined with hydrophobic and hydrogen bond donor/acceptor field (q 2 = 0.557, r2 = 0.934). A new derivative, 4-oxo-4-(4-hydroxyindole)butanoic acid, was designed, taking into account the CoMSIA field and the binding mode derived by FlexX docking. This rationally designed compound exhibits an ALR2 inhibition with an IC50 value of 7.4 μM, which compares favorably to that of a well-known ALR2 inhibitor, tolrestat (IC50 = 16 μM) and represents a potency approximately 240-fold higher than that of an original phenethylamine lead compound, YUA001.
- Sun, Won Suck,Park, Yoon Sun,Yoo, Jakyung,Park, Ki Duk,Kim, Sung Han,Kim, Jung-Han,Park, Hyun-Ju
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p. 5619 - 5627
(2007/10/03)
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- Antinociceptive properties of N-aryl-glutaramic acids and N-aryl-glutarimides
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This study describes the antinociceptive activity of some N-aryl-glutaramic acids and N-aryl-glutarimides in writhing and formalin tests, two classical models of pain in mice. These compounds show high activity, being more active than acetyl salycilic aci
- Stiz,Souza,Golin,Neto,Correa,Nunes,Yunes,Cechinel-Filho
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p. 942 - 944
(2007/10/03)
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- A convenient acylation procedure of alcohols and amines
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The reaction of carboxylic acids with primary and secondary alcohols in the presence of aromatic sulfochlorides (mesitylenesulfonyl chloride and 2,4,6-triisopropylbenzenesulfonyl chloride) or aromatic sulfotetrazoles (mesytilenesulfonyl tetrazolide and 2,4,6-triisopropylbenzenesulfonyltetrazole) and usual acylation catalysts was shown to be a convenient procedure for the synthesis of esters. Reaction of carboxylic acids with primary aliphatic or aromatic amines in the presence of the same tetrazolides and catalysts is a useful procedure for the synthesis of amides. Syntheses of twenty compounds are presented as examples.
- Misharin,Chernov
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p. 616 - 620
(2007/10/03)
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- Inhibition of the HER2 tyrosine kinase and characterization of a hydrophobic site near the nucleotide binding domain
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A series of compounds was prepared to investigate the hydrophobic character of the HER2 receptor tyrosine kinase active site, These bisubstrate analogs contained hydrophobic moieties in place of the polar triphosphate and nucleoside fragments of the natural ATP ligand. Despite these modifications, good affinity was observed as measured by inhibition of receptor autophosphorylation.
- Maddry, Joseph A.,Kussner, Conrad,Truss, Jackie W.,Niwas, Shri,White, E. Lucile,Kwong, Cecil D.
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p. 2109 - 2114
(2007/10/03)
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- 1-phenyl-piperdine-2,6-diones with herbicidal activity
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The invention relates to new 1-phenyl-piperidine-2,6-diones of the formula I STR1 wherein R is C3 -C7 -cycloalkyl, R1 is hydrogen or halogen; R2 is hydrogen, cyano, nitro or halogen; and A is hydrogen, cyano, nitro or is an ether or carboxylic acid radical as defined in the description. The salts, complexes as well as the stereoisomeric forms of these compounds, their preparations, use and agrochemical compositions which contains them form also part of this invention.
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