- Synthesis, biological evaluation and molecular modeling studies of Schiff bases derived from 4-methylsalicylic acid as potential immunosuppressive agents
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A series of Schiff bases derived from 4-methylsalicylic acid (4a-4s) were synthesized, 14 of which (4a-4h, 4j-4l, 4n, 4q, and 4s) were reported for the first time. All the synthesized compounds were evaluated for their immunosuppressive activities for the
- Yan, Ru,Liu, Peng-Gang,Zhang, Zhi-Ming,Fang, Xian-Ying,Zhang, Xue-Wei,Deng, Jia-Li,Zhu, Hai-Liang
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- Overcoming the Deallylation Problem: Palladium(II)-Catalyzed Chemo-, Regio-, and Stereoselective Allylic Oxidation of Aryl Allyl Ether, Amine, and Amino Acids
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We report herein a Pd(II)/bis-sulfoxide-catalyzed intramolecular allylic C-H acetoxylation of aryl allyl ether, amine, and amino acids with the retention of a labile allyl moiety. Mechanistically, the reaction proceeds through a distinct double-bond isomerization from the allylic to the vinylic position followed by intramolecular carboxypalladation and the β-hydride elimination pathway. For the first time, C-H oxidation of N-allyl-protected amino acids to furnish five-membered heterocycles through 1,3-syn-addition is established with excellent diastereoselectivity.
- Begam, Hasina Mamataj,Jana, Ranjan,Manna, Kartic,Samanta, Krishanu
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supporting information
p. 7443 - 7449
(2020/10/09)
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- Containing 2 - mercapto acetophenone 1, 3, 4 - oxadiazole derivative and its preparation and anti-tumor activity
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The invention relates to a 2-mercaptoacetophenone-containing 1, 3, 4-oxadiazole derivative, which is characterized by having a general formula as the following. In the formula, R1 represents the following, and R2 represents -H -Br. The 2-mercaptoacetophen
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Paragraph 0028; 0029; 0030; 0043; 0044; 0045
(2017/08/25)
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- Pd-catalyzed sp2 C-H hydroxylation with TFA/TFAA via weak coordinations
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An efficient sp2 C-H hydroxylation has been developed for the synthesis of a wide range of functionalized phenols with aryl ketones, benzoates, benzamides, acetanilides and sulfonamides through palladium(II) catalysis. A trifluoroacetic acid (TFA)/trifluoroacetic anhydride (TFAA) co-solvent system serves as the oxygen source and is the critical factor for weak coordination promoted C-H activation. Georg Thieme Verlag Stuttgart New York.
- Rao, Yu
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p. 2472 - 2476
(2013/12/04)
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- SUBSTITUTED TRICYCLIC COMPOUNDS WITH ACTIVITY TOWARDS EP1 RECEPTORS
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The present invention belongs to the field of EP1 receptor ligands. More specifically it refers to compounds of general formula (I) having great affinity and selectivity for the EP1 receptor. The invention also refers to the process for their preparation, to their use as medicament for the treatment and/or prophylaxis of diseases or disorders mediated by the EP1 receptor as well as to pharmaceutical compositions comprising them.
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Page/Page column 146
(2013/10/22)
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- Novel 1,3,4-oxadiazole thioether derivatives targeting thymidylate synthase as dual anticancer/antimicrobial agents
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A series of novel 1,3,4-oxadiazole thioether derivatives (compounds 9-44) were designed and synthesized as potential inhibitors of thymidylate synthase (TS) and as anticancer agents. The in vitro anticancer activities of these compounds were evaluated against three cancer cell lines by the MTT method. Among all the designed compounds, compound 18 bearing a nitro substituent exhibited more potent in vitro anticancer activities with IC50 values of 0.7 ± 0.2, 30.0 ± 1.2, 18.3 ± 1.4 μM, respectively, which was superior to the positive control. In the further study, it was identified as the most potent inhibitor against two kinds of TS protein (for human TS and Escherichia coli TS, IC50 values: 0.62 and 0.47 μM, respectively) in the TS inhibition assay in vitro and the most potent antibacterial agents with MIC (minimum inhibitory concentrations) of 1.56-3.13 μg/mL against the tested four bacterial strains. Molecular docking and 3D-QSAR study supported that compound 18 can be selected as dual antitumor/antibacterial candidate in the future study.
- Du, Qian-Ru,Li, Dong-Dong,Pi, Ya-Zhou,Li, Jing-Ran,Sun, Jian,Fang, Fei,Zhong, Wei-Qing,Gong, Hai-Bin,Zhu, Hai-Liang
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p. 2286 - 2297
(2013/05/09)
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- Ruthenium(II)-catalyzed synthesis of hydroxylated arenes with ester as an effective directing group
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An unprecedented Ru(II) catalyzed ortho-hydroxylation has been developed for the facile synthesis of a variety of multifunctionalized arenes from easily accessible ethyl benzoates with ester as an efficient directing group. Both the TFA/TFAA cosolvent system and oxidants serve as the critical success factors in this transformation. The reaction demonstrates excellent reactivity, good functional group tolerance, and high yields.
- Yang, Yiqing,Lin, Yun,Rao, Yu
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supporting information; experimental part
p. 2874 - 2877
(2012/07/28)
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- Pd-catalyzed C-H oxygenation with TFA/TFAA: Expedient access to oxygen-containing heterocycles and late-stage drug modification
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Functionalized phenols are valuable industrial chemicals related to pharmaceuticals, agrochemicals, and polymers. Therefore, the direct catalytic hydroxylation of arenes to produce phenols has attracted much attention. Although tremendous progress has been made in this field, there are still difficult substrates which remain unmet challenges for direct hydroxylation in terms of regio- and chemoselectivity, as well as the practicality of current methods (Scheme 1). For example, 2-hydroxy aromatic ketones are useful synthetic intermediates for the preparation of various oxygen-containing heterocycles such as benzofuranone, chromanone, benzoxazole, and dibenzooxazepine; they also serve as key building blocks for drugs such as celiprolol, acebutolol, and propafenone. Traditional strategies for accessing 2-hydroxy aromatic ketones have mainly involved the oxidation of benzylic alcohols, the hydrolysis of aromatic halides, Fries rearrangement of esters or the demethylation of methyl phenyl ether. These methods generally suffer from one limitation or another, such as tedious reaction procedures, harsh reaction conditions, low yields, or the formation of side products. Hence, direct transformation of readily available aromatic ketones into valuable 2-hydroxylated products by transition metal-catalyzed C-H functionalization is arguably a highly efficient and atom-economic method to access these compounds. Moreover, developing a more general strategy for the regio- and chemoselective C-H oxygenation of a variety of challenging arenes would be especially desirable for phenol synthesis (Scheme 1).
- Shan, Gang,Yang, Xinglin,Ma, Linlin,Rao, Yu
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supporting information
p. 13070 - 13074
(2013/02/26)
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- Synthesis, biological evaluation and molecular docking studies of 1,3,4-oxadiazole derivatives as potential immunosuppressive agents
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A series of 1,3,4-oxadiazole derivatives derived from 4-methoxysalicylic acid or 4-methylsalicylic acid (6a-6z) have been first synthesized for their potential immunosuppressive activity. Among them, compound 6z displayed the most potent biological activity against lymph node cells (inhibition = 38.76% for lymph node cells and IC50 = 0.31 μM for PI3Kγ). The preliminary mechanism of compound 6z inhibition effects was also detected by flow cytometry (FCM) and the compound exerted immunosuppressive activity via inducing the apoptosis of activated lymph node cells in a dose dependent manner. Docking simulation was performed to position compound 6z into the PI3Kγ structure active site to determine the probable binding model.
- Zhang, Zhi-Ming,Zhang, Xue-Wei,Zhao, Zong-Zheng,Yan, Ru,Xu, Rui,Gong, Hai-Bin,Zhu, Hai-Liang
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scheme or table
p. 3359 - 3367
(2012/07/14)
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- Design, synthesis, structure, and dehydrogenation reactivity of a water soluble o-iodoxybenzoic acid derivative bearing a trimethylammonium group
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5-Trimethylammonio-1, 3-dioxo-1, 3-dihydro-1λ5-benzo[d][1, 2]iodoxol-1-ol anion (AIBX 1a), an o-iodoxybenzoic acid (IBX) derivative having the trimethylammonium moiety on its phenyl ring, possesses very good solubility in water and distinct oxidative properties from IBX, which is demonstrated in the oxidation of various β-keto esters to the corresponding dehydrogenated products using water as cosolvent. The regeneration of AIBX 1a can be easily realized from the reaction mixture due to its good water solubility.2011 American Chemical Society.
- Cui, Li-Qian,Dong, Zhi-Lei,Liu, Kai,Zhang, Chi
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supporting information; scheme or table
p. 6488 - 6491
(2012/02/02)
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- Synthesis, antibacterial activity, and quantitative structure-activity relationships of new (Z)-2-(nitroimidazolylmethylene)-3(2 H)-benzofuranone derivatives
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A new series of (Z)-2-(1-methyl-5-nitroimidazole-2-ylmethylene)-3(2 H)-benzofuranones (11a-p) and (Z)-2-(1-methyl-4-nitroimidazole-5-ylmethylene)-3(2 H)-benzofuranones (12a-m) were synthesized and assayed for their antibacterial activity against Gram-positive and Gram-negative bacteria. Most of the 5-nitroimidazole analogues (11a-p) showed a remarkable inhibition of a wide spectrum of Gram-positive bacteria (Staphylococcus aureus, Streptococcus epidermidis, MRSA, and Bacillus subtilis) and Gram-negative Klebsiella pneumoniae, whereas 4-nitroimidazole analogues (12a-m) were not effective against selected bacteria. The quantitative structure-activity relationship investigations were applied to find out the correlation between the experimentally evaluated activities with various parameters of the compounds studied. The QSAR models built in this work had reasonable predictive power and could be explained by the observed trends in activities.
- Hadj-esfandiari, Narges,Navidpour, Latifeh,Shadnia, Hooman,Amini, Mohsen,Samadi, Nasrin,Faramarzi, Mohammad Ali,Shafiee, Abbas
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p. 6354 - 6363
(2008/09/21)
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- Method for preparing scenting compositions and scented products, and resulting products
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The present invention relates to a process for the production of perfuming compositions, to perfumed products, and to products obtained therefrom. More specifically, the present invention concerns a process for the production of perfuming compositions, perfumed products and substances for perfumery characterized in that they comprise, as an active ingredient with an influence on the scent, an effective quantity of an alkylsalicylic acid ester.
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- Boronic compound complexing reagents and complexes
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Boron compound complexing reagents, boron compound complexes, and methods of synthesizing these reagents and complexes are disclosed. These reagents and complexes include those shown in General Formula III, General Formula IV, and General Formula VI. In one embodiment, the reagents of General Formula III may be used to produce, after condensation with a bioactive species (BAS), the reagent of General Formula IV. The reagent of General Formula IV may be used to form a complex with a boron compound, such as a complex shown in General Formula VI. STR1
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- Boronic compound complexing reagents and highly stable complexes
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Boron compound complexing reagents, boron compound complexes, and methods of synthesizing these reagents and complexes are disclosed. These reagents and complexes include those shown in General Formula CIII, General Formula CIV, and General Formula CVI. In one embodiment, the reagents of General Formula CIII may be used to produce, after condensation with a bioactive species (BAS), the reagent of General Formula CIV. The reagent of General Formula CIV may be used to form a complex with a boron compound, such as a complex shown in General Formula CVI. STR1
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- Reformatsky Reaction on α-Oxo Ketene Dithioacetals: Synthesis of Substituted and Fused Ethyl 2-Hydroxy-6-(methylthio)benzoates, 6-(Methylthio)pyran-2-ones, and 6-(Methylthio)-2(1H)-pyridone Derivatives
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A novel cycloaromatization reaction leading to substituted and annelated ethyl 2-hydroxy-6-(methylthio)benzoates 4 by condensation of α-oxo-ketene dithioacetals with an excess of Reformatsky reagent from ethyl bromoacetates through intermediate dienes 3 has been described.The reaction has also been extended for the synthesis of substituted ethyl 3-hydroxy-5-(methylthio)stilbenecarboxylates 9 by using cinnamoyl ketene dithioacetals 8.A few of the benzoates 4 were desulfurized to the corresponding salicylate derivatives 5.Reaction of acyclic oxo ketene dithioacetals with ethyl(bromozincio)acetate in the presence of cuprous iodide afforded 4- (or 4,5-)substituted 6-(methylthio)pyran-2-ones 15 in moderate to good yields.A probable mechanism for the formation of 15 is suggested.Cyclization of the acyclic dienes 3 or the carbinols 10 with ammonium acetate in refluxing acetic acid afforded the corresponding 4- (or 4,5-)substituted 6-(methylthio)-2(1H)-pyridones 22.
- Datta, Apurba,Ila, Hiriyakkanavar,Junjappa, Hiriyakkanavar
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p. 5589 - 5594
(2007/10/02)
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- NOVEL CYCLOAROMATIZATION IN REFORMATSKY REACTION ON α-OXOKETENE DITHIOACETALS: A REGIOSELECTIVE SYNTHESIS OF SUBSTITUTED ETHYL 2-HYDROXY-6-METHYLTHIOBENZOATES
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A novel cycloaromatization reaction leading to substituted ethyl 2-hydroxy-3-methyl-thiobenzoates 6 by condensation of α-oxoketene dithioacetals 1 with excess of Reformatsky reagent 2 from ethyl bromoacetate through intermediate dienes 3 has been reported.
- Datta, Apurba,Ila, Hiriyakkanavar,Junjappa, Hiriyakkanavar
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p. 497 - 500
(2007/10/02)
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