- A comparative experimental and theoretical investigation of hydrogen-bond, halogen-bond and π-π interactions in the solid-state supramolecular assembly of 2- and 4-formylphenyl arylsulfonates
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To explore the operational role of noncovalent interactions in supramolecular architectures with designed topologies, a series of solid-state structures of 2- and 4-formylphenyl 4-substituted benzenesulfonates was investigated. The compounds are 2-formylp
- Andleeb, Hina,Khan, Imtiaz,Bauzá, Antonio,Tahir, Muhammad Nawaz,Simpson, Jim,Hameed, Shahid,Frontera, Antonio
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Read Online
- Synthesis of (1,3,4-thiadiazol-2-yl)-acrylamide derivatives as potential antitumor agents against acute leukemia cells
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A lead compound with the (1,3,4-thiadiazol-2-yl)-acrylamide scaffold was discovered to have significant cytotoxicity on several tumor cell lines in an in-house cell-based screening. A total of 60 derivative compounds were then synthesized and tested in a CCK-8 cell viability assay. Some of them exhibited improved cytotoxic activities. The most potent compounds had IC50 values of 1–5 μM on two acute leukemia tumor cell lines, i.e. RS4;11 and HL-60. Flow cytometry analysis of several active compounds and detection of caspase activation indicated that they induced caspase-dependent apoptosis. It was also encouraging to observe that these compounds did not have obvious cytotoxicity on normal cells, i.e. IC50 > 50 μM on HEK-293T cells. Although the molecular targets of this class of compound are yet to be revealed, our current results suggest that this class of compound represents a new possibility for developing drug candidates against acute leukemia.
- An, Ran,Guo, Chun,Li, Qing,Li, Yan,Wang, Renxiao,Xu, Yaochun,Zhou, Mi
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supporting information
(2020/03/25)
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- Thiazole amide compound and preparation method, pharmaceutical composition and application thereof
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The invention discloses a thiazole amide compound and a preparation method thereof, a pharmaceutical composition and application thereof. The thiazole amide compound as shown in a formula I and a pharmaceutically acceptable salt thereof are provided, and
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Paragraph 0207; 0229; 0230; 0231
(2019/01/08)
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- Concise approach to mono- And disubstituted luotonin A analogs and their cytotoxicity test
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A concise approach for the preparation of luotonin A analogs has been developed. The new synthetic route contains an anion-assisted intramolecular double hetero Diels Alder reaction and a direct oxidative cross coupling reaction. Some synthetic luotonin A analogs show cytotoxic activities against Daudi and Jurkat human cancer cells as potent as camptothecin.
- Kagawa, Natsuko,Nishimura, Kimiko,Abe, Shinya,Masuko, Takashi,Toyota, Masahiro
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p. 514 - 522
(2019/07/31)
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- One-Pot Multicomponent Synthesis of Novel 2-Tosyloxyphenylpyrans under Green and Conventional Condition with Anti-inflammatory Activity
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A mild, efficient, and environmentally green protocol for the synthesis of 2-tosyloxyphenylpyran derivatives 3, 4, 5, 6, 7, 8, 9, 10, 11 via reaction of 2-tosyloxybenzaldehyde (1) with malononitrile and some ketonic reagents in one-pot, three component re
- Khodairy, Ahmed,Ali, Ali M.,Aboelez, Moustafa O.,El-Wassimy
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p. 1442 - 1449
(2017/03/27)
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- Asymmetric addition of phenylacetylene to aldehydes catalyzed by complex of O-sulfonyl camphor derivatives and titanium
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Several novel ligands that are based on the camphor skeleton or contain the O-sulfonyl group were synthesized and used in the asymmetric addition of phenylacetylene to aldehydes. This enantioselective reaction afforded chiral propargylic alcohols in high
- Lee, Dong-Sheng,Gau, Chang-Weu,Chen, Yu-Yang,Lu, Ta-Jung
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p. 242 - 246
(2016/04/05)
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- Access to phthalazinones via palladium-catalyzed three-component cycloamino-carbonylation of 2-formylaryl tosylates, hydrazines and CO
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The palladium-catalyzed three-component cycloaminocarbonylation of 2-formylaryl tosylates with hydrazines and carbon monoxide has been established, which provides an efficient method for synthesis of substituted phthalazinones. In addition, by applying this protocol as the key step, Hydralazine can easily be synthesized in 65% yield.
- Liu, Bin,Zhang, Chunlei,Zhou, Xigeng
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supporting information
p. 8282 - 8286
(2016/12/02)
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- Coordinating effect in ring-opening polymerization of ε-caprolactone using aluminum complexes bearing bisphenolate as catalysts
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A series of Al complexes bearing diphenolate ligands was synthesized and their application for the ring-opening polymerization of ε-caprolactone was studied. Positional variation of the substituent on the aryl ring of the RCH(4,6-di-t-butylphenol)2 ligand was shown to have a considerable influence on the catalysis result. Complexes with a ortho-substituent showed greater catalytic activity than those with a para-substituent. Substitutions of an aryl moiety by H or methyl groups resulted in the catalytic activity falling between that of the ortho-substitution Al complexes and that of the para ones. Our results demonstrate that the coordinated functional group in the ortho-position of the phenyl ring could increase the catalytic activity. Moreover, X-rays of the structure and DFT analysis revealed that the coordinated functional group in the ortho-position could bridge two Al centers resulting in the transformation of a dinuclear Al complex with bridging benzyl alkoxide into a complex with terminal benzyl alkoxide, further promoting the efficacy of the initiator.
- Chen, Hsing-Yin,Lee, Ying-Hsien,Chiang, Michael Y.,Lu, Wei-Yi,Tseng, Hsi-Ching,Tsai, Hsin-Yi,Chen, Yu-Hsieh,Lai, Yi-Chun,Chen, Hsuan-Ying
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p. 82018 - 82026
(2015/10/12)
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- Synthesis and antiproliferative evaluation of 2'-arenesulfonyloxy-5- benzylidene-thiazolidine-2,4-diones
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A series of 2'-arenesulfonyloxy-5-benzylidene-thiazolidine-2,4-diones (TZDs) were synthesized and examined for their antiproliferative effects on a panel of carcinoma cell lines. Our results indicated that initial synthesis of 5-[2'-hydroxybenzylidene]-2,
- Chen, Emily M.,Lu, Pei-Jung,Shaw, Arthur Y.
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p. 792 - 798
(2012/10/29)
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- Synthesis, characterization and structures of 2-(3,5-dimethylpyrazol-1-yl) ethylseleno derivatives and their probable glutathione peroxidase (GPx) like activity
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A series of 2-(3,5-dimethylpyrazol-1-yl)ethylseleno derivatives has been synthesized. The glutathione peroxidase like catalytic activity of these compounds has been studied in a model system, in which reduction of hydrogen peroxide with dithiothreitol (DTTred), in the presence of an organoselenium compound was investigated by 1H NMR spectroscopy. All these compounds exhibit GPx like catalytic activities and the catalytic reaction proceeds through a selenoxide intermediate, identified by 77Se{ 1H} NMR spectroscopy.
- Hodage, Ananda S.,Phadnis, Prasad P.,Wadawale, Amey,Priyadarsini,Jain, Vimal K.
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supporting information; experimental part
p. 2992 - 2998
(2011/06/16)
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- Natural products-based insecticidal agents 11. Synthesis and insecticidal activity of novel 4α-arylsulfonyloxybenzyloxy-2β- chloropodophyllotoxin derivatives against Mythimna separata Walker in vivo
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In continuation of our program aimed at the discovery and development of natural products-based insecticidal agents, 14 novel 4α- arylsulfonyloxybenzyloxy-2β-chloropodophyllotoxin derivatives were stereoselectively semisynthesized from podophyllotoxin, an
- Xu, Hui,Zhang, Jun-Liang
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scheme or table
p. 5177 - 5180
(2011/10/02)
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- Synthesis and structural studies of heterobimetallic alkoxide complexes supported by bis(phenolate) ligands: Efficient catalysts for ring-opening polymerization of l-lactide
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A series of heteroblmetallic titanium(IV) complexes [LTi(O′Pr)(μ- O′Pr)2Li(THF)2], [LTi(O′Pr)(μ-O′Pr) 2Na(THF)2], [LTi(μ-O′Pr)2Zn(O′ Pr)2], and [LTi(μ-O′Pr)2Mg(O′Pr) 2] (where L = bidentate bisphenol ligands) have been synthesized and characterized including a structural determination of [L1Ti(μ 2-O′Pr)2(O′Pr)Li(THF)2] (1a). These complexes were investigated for their utility in the ring-opening polymerization (ROP) of L-lactide (LA). Polymerization activities have been shown to correlate with the electronic properties of the substituent within the bisphenol ligand. In contrast to monometallic titanium Initiator 1e, all the heterobimetallic titanium initiators (Ti-Li, Ti-Na, Ti-Zn, and Ti-Mg) show enhanced catalytic activity toward ring-opening polymerization (ROP) of L-LA. In addition, the use of electron-donating methoxy or methylphenylsulfonyl functional ligands reveals the highest activity. The bisphenol bimetallic complexes give rise to controlled ring-opening polymerization, as shown by the linear relationship between the percentage conversion and the number-average molecular weight. The polymerization kinetics using 2c as an initiator were also studied, and the experimental results indicate that the reaction rate is first-order with respect to both monomer and catalyst concentration with a polymerization rate constant, k = 81.64 M-1 min-1.
- Chen, Hsuan-Ying,Liu, Mei-Yu,Sutar, Alekha Kumar,Lin, Chu-Chieh
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experimental part
p. 665 - 674
(2010/03/25)
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- The first general palladium catalyst for the Suzuki-Miyaura and carbonyl enolate coupling of aryl arenesulfonates
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The first general method for the palladium-catalyzed Suzuki-Miyaura and carbonyl enolate coupling of unactivated aryl arenesulfonates was developed utilizing XPhos, 1, and Pd(OAc)2. This is of significant interest because aryl tosylates and aryl benzenesulfonates are more easily handled and considerably less expensive than aryl triflates. This catalyst system effects the coupling of a variety of aryl, heteroaryl, and extremely hindered arylboronic acids with different aryl tosylates, under mild conditions. The same catalyst was employed in the first carbonyl enolate coupling of aryl arensulfonates. Copyright
- Nguyen, Hanh Nho,Huang, Xiaohua,Buchwald, Stephen L.
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p. 11818 - 11819
(2007/10/03)
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- Revisiting the Ullmann-ether reaction: A concise and amenable synthesis of novel dibenzoxepino[4,5-d]pyrazoles by intramolecular etheration of 4,5-(o,o′-halohydroxy)arylpyrazoles
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A concise synthesis of a series of novel dibenzoxepino[4,5-d]pyrazoles was accomplished by implementation of an intramolecular Ullmann-ether reaction on o,o'-halohydroxy-4,5-diarylpyrazoles mediated by CuBr·DMS. An alternative useful approach based on the palladium-catalyzed biarylether linkage formation (Buchwald-Hartwig reaction) was also successfully applied, offering limitations with regard to the steric demand of the substituents. The synthesis of the key o,o′-halohydroxy-4,5-diarylpyrazole intermediates proceeds through the construction of the heterocyclic ring by a tandem amine-exchange/heterocyclization sequence of 3-N,N-(dimethylamino)-1,2-diarylpropenones with phenylhydrazine followed by basic hydrolysis for deprotection. The enamino ketone precursors were conveniently prepared from the corresponding O-sulfonyloxy and O-benzoyloxy ortho-substituted 1,2-diarylethanones, starting from inexpensive salicylaldehyde or phenylacetic derivatives. Preliminary binding affinity experiments against peripheral and central nervous system receptors have been done with negative results.
- Olivera, Roberto,SanMartin, Raul,Churruca, Fatima,Dominguez, Esther
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p. 7215 - 7225
(2007/10/03)
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- Bis(isoquinoline N-oxide) pincers as a new type of metal cation dual channel fluorosensor.
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[structure: see text] A new type of donor-spacer-acceptor podand system has been synthesized and proved as an efficient dual channel fluorosensor for Li+, Mg2+, and Ca2+. The known ability for the N-oxide function to bind Lewis acids is the key step in th
- Collado, Daniel,Perez-Inestrosa, Ezequiel,Suau, Rafael,Desvergne, Jean-Pierre,Bouas-Laurent, Henri
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p. 855 - 858
(2007/10/03)
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- A concise approach to the preparation of 2-hydroxydiarylketones by an intramolecular acyl radical ipso substitution
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Substituted 2-hydroxydiarylketones have been simply prepared using an intramolecular acyl radical [1,6] ipso substitution reaction. (C) 2000 Elsevier Science Ltd.
- Motherwell,Vazquez
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p. 9667 - 9671
(2007/10/03)
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- The effects of the reaction conditions on the metalation of phenyl p- Toluenesulfonate (Phenyl Tosylate)
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Directed ortho metalation of phenyl p-toluenesulfonate (phenyl tosylate) was carried out and the reaction was found to be controlled by the conditions (base, solvent, temperature, with or without ligand) to some extent.
- Kimachi, Tetsutaro
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p. 139 - 141
(2007/10/03)
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- Studies on the Conformation of 5,15-Diarylporphyrins with (Arylsulfonyl)oxy Substituents
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Dimeso-substituted octaalkylporphyrins, carrying an (arylsulfonyl)oxy group at the ortho position of the two (meso) phenyl groups, were synthesized from dipyrrolylmethanes and aldehydes.On account of a 1H NMR upfield shift in CDCl3 solution of 2-5 ppm for the aryl protons, a folded conformation is assumed in which the substituted aryl groups lie right above and below the porphyrin plane.In CDCl3/CF3COOH solution the upfield shifts are absent.The results of low-temperature 1H NMR measurements and ring-current calculations agreed with our assumptions.The sulfonyloxy group promotes folding of the molecule more than the ester, sulfonyl, sulfinyl, thio, or methylene group.In zinc porphyrins carrying anthraquinone substituents, intramolecular coordination was observed. ΔG, ΔH, and ΔS values for the various conformational equilibria were calculated from the NMR data.We suggest van der Waals interactions with a contribution of charge transfer as the driving force for the folding of the molecule.
- Sanders, Georgine M.,Dijk, Marinus van,Veldhuizen, Albertus van,Plas, Henk C. van der,Hofstra, Ulbert,Schaafsma, Tjeerd J.
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p. 5272 - 5281
(2007/10/02)
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