- Insights into the antiproliferative mechanism of (C^N)-chelated half-sandwich iridium complexes
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Transition metal-based anticancer compounds, as an alternative to platinum derivatives, are raising scientific interest as they may present distinct although poorly understood mechanisms of action. We used a structure-activity relationship-based methodology to investigate the chemical and biological features of a series of ten (C^N)-chelated half-sandwich iridiumIII complexes of the general formula [IrCp?(phox)Cl], where (phox) is a 2-phenyloxazoline ligand forming a 5-membered metallacycle. This series of compounds undergoes a fast exchange of their chlorido ligand once solubilised in DMSO. They were cytotoxic to HeLa cells with IC50 values in the micromolar range and induced a rapid activation of caspase-3, an apoptosis marker. In vitro, the oxidative power of all the complexes towards NADH was highlighted but only the complexes bearing substituents on the oxazoline ring were able to produce H2O2 at the micromolar range. However, we demonstrated using a powerful HyPer protein redox sensor-based flow cytometry assay that most complexes rapidly raised intracellular levels of H2O2. Hence, this study shows that oxidative stress can partly explain the cytotoxicity of these complexes on the HeLa cell line and gives a first entry to their mechanism of action. This journal is
- Ramos, Robin,Zimbron, Jérémy M.,Thorimbert, Serge,Chamoreau, Lise-Marie,Munier, Annie,Botuha, Candice,Karaiskou, Anthi,Salmain, Michèle,Sobczak-Thépot, Jo?lle
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p. 17635 - 17641
(2020/12/30)
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- Oxazolinyl-Assisted Ru(II)-Catalyzed C?H Functionalization Based on Carbene Migratory Insertion: A One-Pot Three-Component Cascade Cyclization
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A rare, ruthenium-catalyzed, oxazolinlyl assisted C?H functionalization and three-component cascade cyclization for the synthesis of isoquinolinones via a metal-carbene migratory insertion is reported. The transformation is unique since it involves the fo
- Kumar, Gangam Srikanth,Khot, Nandkishor Prakash,Kapur, Manmohan
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supporting information
p. 73 - 78
(2018/12/11)
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- A 2 - substituted oxazoline or 2 - substituted piperazine synthetic method (by machine translation)
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The invention discloses a method for synthesizing 2 - substituted oxazoline or 2 - substituted oxazine new method, by nitrile and amino ethanol or 3 - amino - 1 - propanol as raw material, in the absence of solvent, can be used for the recycling of the sulfur to induce synthesis of 2 - substituted oxazoline and 2 - substituted piperazine. The method of the invention has low cost, simple reaction process, mild reaction conditions, the reaction time is short, the yield and the like, is suitable for the industrial generation. (by machine translation)
- -
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Paragraph 0021; 0034
(2017/08/25)
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- A 2 - aryl - 2 - oxazoline preparation method
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The invention discloses a 2-aryl-2-oxazoline preparation method and belongs to the field of chemistry. According to the method, an aryl-amide compound and 1,2-dichloroethane are reacted for synthesis, and the synthesis reaction is conducted under the alka
- -
-
Paragraph 0010-0020
(2017/06/21)
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- Microwave-Assisted Synthesis of 2-Aryl-2-oxazolines, 5,6-Dihydro-4H-1,3-oxazines, and 4,5,6,7-Tetrahydro-1,3-oxazepines
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The first general procedure for the synthesis of 5- to 7-membered cyclic iminoethers by microwave-assisted cyclization of ω-amido alcohols promoted by polyphosphoric acid (PPA) esters is presented. 2-Aryl-2-oxazolines and 5,6-dihydro-4H-1,3-oxazines were efficiently prepared using ethyl polyphosphate/CHCl3. Trimethylsilyl polyphosphate in solvent-free conditions allowed for the synthesis of hitherto-unreported 4,5,6,7-tetrahydro-1,3-oxazepines. The method involves good to excellent yields and short reaction times.The reaction mechanism and the role of PPA esters were investigated in a chiral substrate.
- Mollo, María C.,Orelli, Liliana R.
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p. 6116 - 6119
(2016/12/09)
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- Sulfonimidation via ring-opening of 2-oxazolines with acidic sulfonimide nucleophiles
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Acidic sulfonimide nucleophiles including dibenzenesulfonimide, o-benzenesulfonimide, dimethanesulfonimide, and N-(methylsulfonyl)-benzenesulfonamide are discovered to open a variety of alkyl-, aryl- and heteroaryl-2-oxazoline rings to provide the sulfonimidation products in refluxing 1,4-dioxane. The electron-rich 2-oxazoline substrates worked well for the nucleophilic ring-opening reactions while no reaction took place for the electron-poor 2-oxazoline substrates.
- Gutierrez, David A.,Dean, Dayton R.,Laxamana, Candace M.,Migliozzi-Smith, Madyson,O'Brien, Connor J.,O'Neill, Claire L.,Li, Jie Jack
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p. 261 - 276
(2016/07/06)
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- Willgerodt–Kindler reaction-driven one pot solventless entry to 2-oxazolines
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We report an efficient and green protocol for the synthesis of 2-oxazolines by the reaction of aromatic nitriles with β-aminoalcohols using sulfur under solvent-free conditions. The reaction occurs via the Willgerodt-Kindler mechanism followed by transami
- Bansal, Shivani,Gupta, Poonam,Halve
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p. 971 - 974
(2016/07/06)
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- HEPARAN SULFATE BIOSYNTHESIS INHIBITORS FOR THE TREATMENT OF DISEASES
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Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions in need of inhibition of heparan sulfate biosynthesis.
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-
Paragraph 000381; 000883
(2016/05/02)
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- A Mild and Regioselective Route to Functionalized Quinazolines
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A Rh-catalyzed ortho-amidation cyclocondensation sequence gave a range of 4-aminoquinazolines in high yield. The method features a remarkably mild C(sp2)-H activation step and can be exploited to rapidly access compounds with established biological activity.
- Maiden, Tracy M. M.,Swanson, Stephen,Procopiou, Panayiotis A.,Harrity, Joseph P. A.
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p. 14342 - 14346
(2015/10/05)
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- Ruthenium(II) 8-quinolinolates: Synthesis, characterization, crystal structure and catalysis in the synthesis of 2-oxazolines
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Abstract New octahedral ruthenium(II) complexes (1-4) have been synthesized from the reaction of ruthenium(II) precursors [RuHCl(CO)(EPh3)3] (E = P or As) with the bidentate Schiff base ligands, 2-((2,6-dimethylphenylimino)methyl)quinolin-8-ol (L1) and 2-((2,6-diisopropylphenylimino)methyl)quinolin-8-ol (L2) in ethanol. These complexes have been characterized by elemental analyses, IR, UV-Vis, 1H, 13C and 31P NMR and ESI-Mass spectroscopy. The molecular structure of the complex [RuCl(CO)(PPh3)2(L2)] (2) was determined by single-crystal X-ray diffraction, which reveals a distorted octahedral geometry around ruthenium(II) ion. The catalytic activity of the new complexes was evaluated for the condensation of nitriles with ethanolamine under solvent free conditions. The processes were operative with aromatic and heteroaromatic nitriles and tolerated several substitutional groups. The studies on the effect of substitution over ligands, coligands, reaction time, temperature and catalyst loading were carried out in order to find the best catalyst in this series of complexes and favorable reaction conditions. A probable mechanism for the catalytic condensation of nitrile has also been proposed. The catalyst was recovered and recycled up to five times without significant loss of its activity.
- Anitha,Manikandan,Prakash,Pachiyappan,Viswanathamurthi,Malecki
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p. 266 - 273
(2015/06/22)
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- Ruthenium(II) 9,10-phenanthrenequinone thiosemicarbazone complexes: Synthesis, characterization, and catalytic activity towards the reduction as well as condensation of nitriles
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The ligands 9,10-phenanthrenequinone-N4-substituted thiosemicarbazones (HL1-3) and their ruthenium(II) complexes were synthesized and characterized by elemental and spectroscopic methods. The ligands are tridentate, monobasic chelating ligands with O, N, and S as the donor sites and are in the thiol form in all the complexes. Catalytic studies showed that all the complexes displayed good catalytic activity towards the reduction of nitriles and also the condensation of nitriles with 2-aminoalcohol under solvent-free conditions.
- Anitha, Panneerselvam,Viswanathamurthi, Periasamy,Kesavan, Devarayan,Butcher, Ray Jay
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p. 321 - 334
(2015/10/20)
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- An efficient one-pot synthesis of 2-oxazolines with molecular iodine under ultrasound irradiation
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A series of 2-oxazolines were prepared by the condensation of aldehydes with 2-aminoethanol in the presence of molecular iodine and potassium carbonate in t-BuOH at 35-40 °C under ultrasound irradiation. The easy work-up procedure and moderate to good yie
- Xiao, Nan,Wang, Sen Hao,Zhang, Ai Ying,Li, Hong Yang,Wang, Peng,Li, Wei,Chen, Bao Hua,Chen, Guo Feng,Li, Na
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p. 9731 - 9742
(2016/01/12)
-
- Polynuclear copper(ii) pyrazolate complexes: Temperature-dependent protonolysis reactions, crystal structures and high catalytic activity toward the condensation of nitriles with 2-aminoalcohol
-
Reaction of Cu(OAc)2·H2O and 1H-pyrazole-3,5-dicarboxylic acid dimethyl ester (Hdcmpz) in MeOH at room temperature afforded one tetranuclear Cu(ii)/pyrazolate complex [{Cu 2(μ-OAc)2}2(μ-dcmpz)2/
- Wang, Ling,Guo, Bin,Li, Hong-Xi,Li, Qi,Li, Hai-Yan,Lang, Jian-Ping
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p. 15570 - 15580
(2013/11/06)
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- S-Co(II) cascade catalysis: Cyclocondensation of aromatic nitriles with alkamine
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A solvent-free S/Co(NO3)2 cascade catalyzed cyclocondensation reaction of aromatic nitriles with 3-amino-1-propanol or 2-aminoethanol has been successfully developed under thermal and microwave conditions. By this two-component protocol, mono- and bis-oxazines and oxazolines were selectively synthesized both in good to excellent yields and short reaction times. This catalytic system exhibits excellent chemoselectivity, and can be reused at least seven times without significant loss of activity in subsequent reactions.
- Ge, Haixia,Liu, Ping,Li, Xiangnan,Sun, Wei,Li, Jianli,Yang, Bingqin,Shi, Zhen
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p. 6591 - 6597
(2013/07/26)
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- DDQ-induced dehydrogenation of heterocycles for c-c double bond formation: Synthesis of 2-thiazoles and 2-oxazoles
-
Strong as an Ox: 2-Thiazoles and 2-oxazoles are formed by oxidation of 2-thiazolines and 2-oxazolines without requiring substituents at the C4 and C5 positions. DDQ plays an important role as the oxidant in this transformation and metal is unnecessary. This general procedure shows good functional group tolerance and provides a wide variety of 2-thiazoles and 2-oxazoles in moderate to excellent yields.
- Li, Xiangnan,Li, Cheng,Yin, Bing,Li, Cong,Liu, Ping,Li, Jianli,Shi, Zhen
-
supporting information
p. 1408 - 1411
(2013/07/26)
-
- Synthesis and biological activities of 4-N-(anilinyl-n-[oxazolyl])-7- chloroquinolines (n = 3′ or 4′) against Plasmodium falciparum in in vitro models
-
The synthesis (Pd-mediated coupling strategy) and characterization (NMR, IR, elemental analysis, etc.) of a short series of quinoline-oxazole hybrid compounds has been carried out. These materials are found to be moderately active against Plasmodium falci
- Gordey, Erin E.,Yadav, Paras N.,Merrin, Marcus P.,Davies, Jill,Ward, Steven A.,Woodman, Grant M.J.,Sadowy, Amber L.,Smith, Todd G.,Gossage, Robert A.
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scheme or table
p. 4512 - 4515
(2011/09/15)
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- A convenient synthesis of 2-oxazolines and 2-benoxazoles with PPh3-DDQ as the dehydrating reagent
-
2-Oxazolines and 2-benoxazoles were synthesized in high yields from acylamino alcohols and acylaminophenols, respectively, with triphenylphosphine- 2,3-dichloro-5,6-dicyanobenzoquinone (PPh3-DDQ) as the dehydrating and activating reagent. The synthesis was accomplished under neutral conditions.
- Xu, Quancai,Li, Zhengning,Chen, Huiying
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experimental part
p. 925 - 932
(2012/01/03)
-
- Synthesis of 2-oxazolines via boron esters of N-(2-hydroxyethyl) amides
-
A new, convenient, one-pot process is presented for the synthesis of 2-oxazolines in high yields (75-94%) via boron esters of N-(2-hydroxyethyl) amides. The procedure involves thermolysis of the boron esters at 240-260 °C, in the presence of solid CaO as an acid scavenger and allows the preparation of oxazolines from hydroxyethyl amides of aliphatic and aromatic monocarboxylic acids.
- Ilkgul, Baris,Gunes, Deniz,Sirkecioglu, Okan,Bicak, Niyazi
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experimental part
p. 5313 - 5315
(2010/11/03)
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- Poly(N-bromo-N-ethyl-benzene-1,3-disulfonamide), N,N,N′,N′- tetrabromobenzene-1, 3-disulfonamide as new efficient reagents for conversion of alcohols to THP ethers and aldehydes to oxazoline compounds
-
This paper is concerned with an easy preparation of THP ethers from primary, secondary and tertiary alcohols and oxazoline compounds from various aldehydes using poly(N-bromo-N-ethyl-benzene-1,3-disulfonamide), N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide [TBBDA] as new and efficient reagents under ambient conditions without over-oxidation.
- Ghorbani-Vaghei,Akbari-Dadamahaleh,Amiri
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experimental part
p. 301 - 307
(2010/09/03)
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- A facile synthesis of 2-oxazolines using a PPh3-DDQ system
-
A facile and efficient synthesis of 2-oxazolines from N-(2-hydroxyethyl)amides using a triphenylphosphine-2,3-dichloro-5,6-dicyanobenzoquinone (PPh3-DQQ) system is described. The reaction proceeds under neutral and mild conditions, and excellent yields are obtained.
- Xu, Quancai,Li, Zhengning
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experimental part
p. 6838 - 6840
(2010/04/29)
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- The use of phosphonium anhydrides for the synthesis of 2-oxazolines, 2-thiazolines and 2-dihydrooxazine under mild conditions
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β-Hydroxy amides 6 and 7 were treated with triphenylphosphonium anhydride trifluoromethane sulfonate (3), or the cyclic analogue 4, to generate 2-oxazolines 5 and 8 under mild conditions. The reaction was optimised by examining the number of equivalents of reagents 3 or 4, or diisopropylethyl amine required to best effect cyclisation. The effects of altering the reaction temperature, reaction time, concentration, solvent, and addition rate also were investigated. However, it was found that use of a trityl group to block reaction at the hydroxyl or thiol group of the starting amides, and subsequent in situ detritylation, in the absence of base, led to greatly improved yields. Reagent 4 offered significant advantages in the purification of products and was used to dehydrate a range of trityl derivatives to form simple oxazolines, thiazolines, and a dihydro-1,3-oxazine, in high yield (85-99%), as well as a tetrahydro-1,3-oxazepine (31%).
- Petersson, Maria J.,Jenkins, Ian D.,Loughlin, Wendy A.
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supporting information; experimental part
p. 739 - 746
(2009/06/20)
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- An efficient oxidative conversion of aldehydes into 2-substituted 2-oxazolines using 1,3-diiodo-5,5-dimethylhydantoin
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Various aromatic and aliphatic aldehydes were converted into the corresponding 2-aryl and 2-alkyl-2-oxazolines, respectively, in good to high yields by reaction with 2-aminoethanol and 1,3-diiodo-5,5-dimethylhydantoin. Moreover, chiral bis-2-oxazolines, which can be used as chiral ligands in asymmetric synthesis, could be also prepared in moderate yields by the reaction of dialdehydes with (R)-(-)-2-phenylglycinol under the same conditions. Georg Thieme Verlag Stuttgart.
- Takahashi, Shogo,Togo, Hideo
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experimental part
p. 2329 - 2332
(2010/03/01)
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- Efficient oxidative conversion of aldehydes to 2-substituted oxazolines and oxazines using (diacetoxyiodo)benzene
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An efficient synthesis of 2-substituted oxazolines from aldehydes and 2-amino alcohol using (diacetoxyiodo)benzene as an oxidant, is reported. (Diacetoxyiodo)benzene acts as a mild dehydrogenating agent to convert the initially formed oxazolidine from ald
- Karade, Nandkishor N.,Tiwari, Girdharilal B.,Gampawar, Sumit V.
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p. 1921 - 1924
(2008/03/27)
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- Direct oxidative conversion of aldehydes and alcohols to 2-imidazolines and 2-oxazolines using molecular iodine
-
Aldehydes were converted to the corresponding 2-imidazolines and 2-oxazolines in good yields by the reaction with ethylenediamine and aminoethanol, respectively, using molecular iodine and potassium carbonate. Moreover, primary alcohols were directly converted to the corresponding 2-imidazolines and 2-oxazolines via aldehydes in one-pot manner with ethylenediamine and aminoethanol, respectively, using molecular iodine and potassium carbonate.
- Ishihara, Midori,Togo, Hideo
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p. 1474 - 1480
(2007/10/03)
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- An efficient, eco-friendly, one-pot protocol for the synthesis of 2-oxazolines promoted by ionic liquid/indium chloride
-
2-Oxazolines have been synthesized using a solventless ionic liquid melt in good yields at ambient temperatures. The efficiency of various Lewis acid catalysts for the same reaction has been compared. The effectiveness of different alkyl chains in the ionic liquids for the synthesis of oxazolines has been studied and a butylmethylimidazolinium chloride/indium chloride melt has been found to be the best media for promoting the reaction. CSIRO 2006.
- Kamakshi,Reddy, Boreddy S.R.
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p. 463 - 467
(2007/10/03)
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- HYDRAZONE DERIVATIVE
-
A compound represented by the following formula (I): wherein R1 represents hydrogen, aryl which may have a substituent, a saturated or unsaturated 5- to 7-membered heterocyclic group which may have a substituent, etc.; R2 represents hydrogen, aryl which may have a substituent, a saturated or unsaturated 5- to 7-membered heterocyclic group which may have a substituent, etc.; R3 represents hydrogen, etc.; Ar represents a divalent group derived from aromatic hydrocarbon, etc.; X represents a single bond, linear or branched alkylene having from 1 to 3 carbon atoms which may have a substituent, etc.; and G represents halogen, a saturated or unsaturated 5- or 6-membered cyclic hydrocarbon group which may have a substituent, a saturated or unsaturated 5- to 7-membered heterocyclic group which may have a substituent, etc., a salt thereof or a solvate thereof; and an agent for inhibiting aggregation and/or deposition of an amyloid protein or an amyloid-like protein, which comprises the compound, a salt thereof or a solvate thereof
- -
-
Page/Page column 36-37
(2010/11/08)
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- A convenient synthesis of oxazolines and imidazolines from aromatic aldehydes with pyridinium hydrobromide perbromide in water
-
Various 2-oxazolines were prepared from aromatic aldehydes and 2-aminoethanol with pyridinium hydrobromide perbromide in water at room temperature. 2-Imidazolines were also obtained in good yields from aromatic aldehydes and ethylenediamine under the same reaction conditions. Georg Thieme Verlag Stuttgart.
- Sayama, Shinsei
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p. 1479 - 1484
(2007/10/03)
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- Reactions of 2,3-diaryl-1-methyl-4,5-dihydroimidazolium iodides with nucleophilic reagents
-
2,3-Diaryl imidazolium salts, represented by 1 and 2, reacted with 2-ethanolamine or ethylenediamine to produce 2-aryl oxazolines or imidazolines 5-8 respectively. Their hydrolysis resulted in ring-opened ethylenediamine derivatives 9 and 10. The reduction of 1 and 2 produced partially reduced imidazolidines 11, 12 and 11 reacted further with tryptamine to provide 2,3,4,9-tetrahydro-1-phenyl 1H-pyrido[3,4-b]indole, 13. In all these reactions one-carbon units were successfully transferred to the nucleophilic acceptors, which mimic the one-carbon unit transfer function for tetrahydrofolate coenzymes.
- Xia, Chizhong,Hao, Junsheng,Tang, Yiqing,Ni, Yanping,Zhou, Peiwen
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p. 1457 - 1464
(2007/10/03)
-
- N-Nitroso Compounds. Part 1. Structure and Decomposition of N-Nitroso-2-arylimidazolines in Aqueous Acidic Media
-
Kinetic measurements for the acid-catalysed decomposition of N-nitroso-2-arylimidazolines are reported.Reactions are first-order in both +>.Two products are formed; an oxazoline, which is the product of hydrolysis of the amidine moiety, and the parent imidazoline formed by denitrosation of the substrate.These products arise from two competing pathways both of which are acid catalysed.The solvent isotope effects for the denitrosation, and amidine hydrolysis, , are 3.1 and 3.5, respectively.The denitrosation pathway, but not amidine hydrolysis, is catalysed by nucleophilic anions, and a value of 1.7 for the Swain-Scott constant, s, is obtained.In the abscence of nucleophilic anions, amidine hydrolysis is preferred over denitrosation, being twice as large as at 25 deg C.Substituents in the 2-aryl ring affect the rate of decomposition giving Hammett ρ values of 0.7 for denitrosation and 1.0 for amidine hydrolysis, which reflect the proximity of the reacting centres to the substituents.Values of the activation parameters are ΔH*NO 74 kJ/mol, ΔH*A 74 kJ/mol, ΔS*NO -48 J/K*mol and ΔS*A -43 J/K*mol.The data are interpreted in terms of a fast equilibrium protonation of the substrate, followed by competitive attack at the protonated substrate, either of water or nucleophilic anions at the nitroso nitrogen atom, or of water at the amidine carbon atom.Protonation is required to activate the substrate, the substrate being recovered from neutral or alkaline solutions unchanged.The mechanism is discussed with reference to the analogous reactions of N-nitrosoamines and N-nitrosoamides.
- Iley, Jim,Norberto, Fatima,Rosa, Eduarda
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p. 1471 - 1476
(2007/10/02)
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- A New Simple and Mild Synthesis of 2-Substituted 2-Oxazolines
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N-Acylated β-aminoalcohols were converted to 2-oxazolines under very mild conditions employing commonly used phosphorylating reagents.
- Sund, Christian,Ylikoski, Jyrki,Kwiatkowski, Marek
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p. 853 - 854
(2007/10/02)
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- A MILD PROCEDURE FOR THE PREPARATION OF 2-OXAZOLINES
-
A general procedure using triphenylphosphine and diethylazodicarboxylate to prepare 2-oxazolines is described.
- Roush, David M.,Patel, Manorama M.
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p. 675 - 680
(2007/10/02)
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