- Interplay between the crystal stability and the energy of the molecular conformation
-
A specially designed new compound, 5,5′-bis(4-hydroxyphenyl)-2,2′-dihydroxy-1,1′-biphenyl, can crystallize in different crystallographic systems. The molecule adopts theC-conformation for the torsion angle of around 60° and theT-conformation for the angle of around 130°, which differ in energy by ～0.8 kJ mol?1. Theoretical studies for the gaseous phase show that theC-conformer has a lower energy. However, crystallization experiments show that the most stable crystal structure consists of only the energetically less stableT-conformer. On the other hand, fast crystal growth at low temperature and crystal growth after milling both lead to the formation of metastable crystals in which the studied molecule adopts theC-conformation. Our study shows that the total crystal net energy is the main factor in determining the molecular conformations even if the molecular conformation has a higher energy in the gaseous phase.
- Dyk, Konrad,Baran, ?ukasz,R?ysko, Wojciech,Stankevi?, Marek,Kamiński, Daniel M.
-
p. 2683 - 2694
(2021/04/19)
-
- Self-assembling behaviour of chiral calamitic monoacrylates targeted for polymer stabilisation of polar smectic phases in chiral liquid crystals
-
The stabilisation and control of synclinic and anticlinic chiral liquid crystalline phases remain an actual and highlighted task. This work presents the design and mesomorphic properties of new chiral calamitic reactive mesogens, monoacrylates, based on biphenyl benzoate and phenyl biphenyl-4-carboxylate cores with reactive terminal groups placed far from the chiral chain. The compound's structures, compatible with the components of modern ferroelectric and antiferroelectric liquid crystalline mixtures, are confirmed by mass spectrometry (electron ionization) analysis and proton/carbon nuclear magnetic resonance. All the reactive mesogens possess the self-assembling, i.e. liquid crystalline behaviour with high tendency to create smectic phases in a broad temperature range, which was confirmed by a polarizing optical microscopy, differential scanning calorimetry and broad-band dielectric spectroscopy. Doping of advanced multicomponent mixtures possessing the chiral smectic phases by the designed monoacrylates with further cross-linking procedure, can be an effective and functional tool for stabilising ferroelectric and antiferroelectric phases in various states and hence, can allow the symmetrisation of the switching times in the modes employed surface stabilised geometry; this is a very highlighted task for optoelectronics. Moreover, an evident considerable tendency for thermal polymerisation of specific reactive mesogens can reduce the drawbacks of polymer stabilisation.
- Dmochowska, Ewelina,Herman, Jakub,Czerwiński, Micha?,Stulov, Sergei,Bubnov, Alexej,Kula, Przemys?aw
-
-
- Transition-Metal-Free and Base-Promoted Carbon-Heteroatom Bond Formation via C-N Cleavage of Benzyl Ammonium Salts
-
A facile and general method for constructing carbon-heteroatom (C-P, C-O, C-S, and C-N) bonds via C-N cleavage of benzyl ammonium salts under transition-metal-free conditions was reported. The combination of t-BuOK and 18-crown-6 enabled a wide range of substituted benzyl ammonium salts to couple readily with different kinds of heteroatom nucleophiles, i.e. hydrogen phosphoryl compounds, alcohols, thiols, and amines. Good functional group tolerance was demonstrated. The scale-up reaction and one-pot synthesis were also successfully performed.
- Liu, Long,Tang, Yuanyuan,Wang, Kunyu,Huang, Tianzeng,Chen, Tieqiao
-
p. 4159 - 4170
(2021/03/09)
-
- A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions
-
A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.
- Huang, Binbin,Guo, Lin,Xia, Wujiong
-
supporting information
p. 2095 - 2103
(2021/03/26)
-
- Cooperativity within the catalyst: alkoxyamide as a catalyst for bromocyclization and bromination of (hetero)aromatics
-
Alkoxyamide has been reported as a catalyst for the activation ofN-bromosuccinimide to perform bromocyclization and bromination of a wide range of substrates in a lipophilic solvent, where adequate suppression of the background reactions was observed. The key feature of the active site is the alkoxy group attached to the sulfonamide moiety, which facilitates the acceptance as well as the delivery of bromonium species from the bromine source to the substrates.
- Mondal, Haripriyo,Sk, Md Raja,Maji, Modhu Sudan
-
supporting information
p. 11501 - 11504
(2020/10/12)
-
- N2-substituted alkoxy aromatic cyclo-2-aminopyrimidine derivative and application thereof
-
The invention provides an N2-substituted alkoxy aromatic cyclo-2-aminopyrimidine derivative and application thereof. The N2-substituted alkoxy aromatic cyclo-2-aminopyrimidine derivative comprises anoptical isomer and pharmaceutically acceptable salt thereof. Preliminary pharmacodynamic indication shows that the compound disclosed by the invention has FLT3 inhibitory activity, wherein the proliferation inhibition activity is realized on various leukemia cell strains; moreover, the derivative is effective for multiple mutations of AML, such as internal tandem repeat mutation of a near-membranestructural domain and D835 point mutation of an activated ring in a kinase structural domain and almost has no inhibition effect on c-KIT. The derivative can overcome drug resistance brought by clinical point mutation, can reduce toxic and side effects of bone marrow inhibition, and can be applied to preparation of antitumor drugs. The general structural formula of the derivative is shown in thespecification.
- -
-
Paragraph 0107-0108
(2020/09/20)
-
- The Cyclopropane Ring as a Reporter of Radical Leaving-Group Reactivity for Ni-Catalyzed C(sp3)-O Arylation
-
The ability to understand and predict reactivity is essential for the development of new reactions. In the context of Ni-catalyzed C(sp3)-O functionalization, we have developed a unique strategy employing activated cyclopropanols to aid the design and optimization of a redox-active leaving group for C(sp3)-O arylation. In this chemistry, the cyclopropane ring acts as a reporter of leaving-group reactivity, since the ring-opened product is obtained under polar (2e) conditions, and the ring-closed product is obtained under radical (1e) conditions. Mechanistic studies demonstrate that the optimal leaving group is redox-active and are consistent with a Ni(I)/Ni(III) catalytic cycle. The optimized reaction conditions are also used to synthesize a number of arylcyclopropanes, which are valuable pharmaceutical motifs.
- Mills, L. Reginald,Monteith, John J.,Dos Passos Gomes, Gabriel,Aspuru-Guzik, Alán,Rousseaux, Sophie A. L.
-
supporting information
p. 13246 - 13254
(2020/09/01)
-
- Convergent Total Synthesis of Lamellarins and Their Congeners
-
A convergent total synthesis of lamellarins S and Z is described. The synthesis features a halogen dance of an easily accessible α,β-dibromopyrrole promoted by an ester moiety. The resultant β,β′-dibromopyrrole undergoes a ligand-controlled Suzuki-Miyaura coupling to provide a range of diarylated pyrrole derivatives. The established synthetic method was also applicable to the synthesis of ningalin B and lukianols A and B.
- Morikawa, Daiki,Morii, Kazuki,Yasuda, Yuto,Mori, Atsunori,Okano, Kentaro
-
p. 8603 - 8617
(2020/07/16)
-
- Preparation and application of aminourea-sensitive amine oxidase inhibitor
-
The invention provides preparation and application of an aminourea-sensitive amine oxidase inhibitor. Specifically, the invention discloses a compound as shown in a formula I which is described in thespecification or a stereoisomer or racemate or a pharmaceutically acceptable salt thereof. The invention also discloses the capability of the compound in inhibition of aminourea-sensitive amine oxidase.
- -
-
Paragraph 0171-0175
(2020/04/17)
-
- Preparation method of hydroxyphenylboronic acid
-
The invention discloses a preparation method of hydroxyphenylboronic acid, which belongs to the technical field of boric acid synthesis in medical intermediates. The method comprises the following steps: starting from bromophenol, carrying out BOC, trimethylsilyl or benzyl protection, forming a Grignard reagent, reacting with borate, or carrying out one-pot reaction with borate and n-butyllithium,and hydrolyzing to obtain hydroxyphenylboronic acid. According to the invention, cheap and easily available protecting groups are adopted, so that the protecting groups are easy to remove during boronation reaction hydrolysis, industrial amplification is easy to realize, batch production is carried out on the scale of dozens of kilograms, and the process stability is good.
- -
-
Paragraph 0022-0024
(2020/05/08)
-
- Regioselective bromination of arenes mediated by triphosgene-oxidized bromide
-
This article first time describes triphosgene (BTC) as an oxidant while the non-toxic and easy-to-handle potassium bromide (KBr) as the source of bromine to the bromination reaction of aromatic substrates. The novel brominating protocol gives excellent para-regioselectivity of the alkoxyl/hydroxyl arenes and high yield, offering good potential of commercial scale applications. The mechanism of “Triphosgene oxidize bromide” was proposed.
- Xu, Yingzhou,Hu, Dufen,Zheng, Hui,Mei, David,Gao, Zhaobo
-
supporting information
(2019/08/30)
-
- GLUCOPYRANOSYL DERIVATIVE AND USE THEREOF
-
Provided are a glucopyranosyl derivative as a sodium-dependent glucose transporters inhibitor, especially as a SGLT1 inhibitor, a pharmaceutically acceptable salt or a stereoisomer thereof, a pharmaceutical composition thereof, and the uses of the compound and pharmaceutical composition thereof in the preparation of drugs for the treatment of diabetes and diabetes-related diseases.
- -
-
Paragraph 00227; 00351
(2019/08/12)
-
- Dehydroxymethyl Bromination of Alkoxybenzyl Alcohols by Using a Hypervalent Iodine Reagent and Lithium Bromide
-
We describe the dehydroxymethylbromination of alkoxybenzyl alcohol by using a hypervalent iodine reagent and lithium bromide in F 3 CCH 2 OH at room temperature. Selective monobromination or dibromination was possible by adjusting the molar ratios of hypervalent iodine reagent and lithium bromide.
- Shibata, Ayako,Kitamoto, Sara,Fujimura, Kazuma,Hirose, Yuuka,Hamamoto, Hiromi,Nakamura, Akira,Miki, Yasuyoshi,Maegawa, Tomohiro
-
supporting information
p. 2275 - 2278
(2018/10/20)
-
- Environmentally benign indole-catalyzed position-selective halogenation of thioarenes and other aromatics
-
Halogenated aromatic compounds are the cores of many pharmaceutical, agricultural and chemical products but they are commonly prepared using electrophilic halogenation reactions in non-green chlorinated solvents under harsh conditions. A separate problem happens in the aromatic halogenation of thioarenes because they readily undergo oxidative side-reactions. Herein we report an environmentally benign electrophilic bromination of aromatics using an indole-catalytic protocol, which is suitable for a wide range of substrates including thioarenes.
- Shi, Yao,Ke, Zhihai,Yeung, Ying-Yeung
-
supporting information
p. 4448 - 4452
(2018/10/17)
-
- CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE
-
Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.
- -
-
Paragraph 00285; 00288; 001046; 001047
(2018/07/29)
-
- NOVEL MODULATORS OF THE SIGMA-2 RECEPTOR AND THEIR METHOD OF USE
-
Pharmaceutical compositions of the invention comprise functionalized lactone derivatives having a disease-modifying action in the treatment of diseases associated with dysregulation of sigma- 2 receptor activity.
- -
-
Paragraph 0569; 0571
(2018/10/19)
-
- 5-HYDROXYTRYPTAMINE RECEPTOR 7 MODULATORS AND THEIR USE AS THERAPEUTIC AGENTS
-
Pharmaceutical compositions of the invention comprise functionalized lactone derivatives having a disease-modifying action in the treatment of diseases associated with dysregulation of 5-hydroxytryptamine receptor 7 activity.
- -
-
Paragraph 0515; 0517
(2018/10/19)
-
- NOVEL HYDRAZIDE CONTAINING COMPOUNDS AS BTK INHIBITORS
-
The present invention relates to novel hydrazide containing compounds as Bruton tyrosine kinase inhibitors, process of preparation thereof, and to the use of the compounds in the preparation of pharmaceutical compositions for the therapeutic treatment of disorders involving mediation of Bruton tyrosine kinase in humans.
- -
-
Page/Page column 49
(2018/02/03)
-
- COMPOUNDS USEFUL FOR TREATING GASTROINTESTINAL TRACT DISORDERS
-
The present disclosure is directed to compounds and methods for the treatment of disorders associated with fluid retention or salt overload, such as heart failure (in particular, congestive heart failure), chronic kidney disease, end-stage renal disease, liver disease, and peroxisome proliferator-activated receptor (PPAR) gamma agonist- induced fluid retention. The present disclosure is also directed to compounds and methods for the treatment of hypertension. The present disclosure is also directed to compounds and methods for the treatment of gastrointestinal tract disorders, including the treatment or reduction of pain associated with gastrointestinal tract disorders.
- -
-
Paragraph 0190; 0192
(2018/07/31)
-
- MODULATORS OF ESTROGEN RECEPTOR PROTEOLYSIS AND ASSOCIATED METHODS OF USE
-
The present disclosure relates to bifunctional compounds, which find utility as modulators of estrogen receptor (target protein). In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a cereblon, Von Hippel-Lindau ligase-binding moiety, Inhibitors of Apotosis Proteins, or mouse double-minute homolog 2 ligand, which binds to the respective E3 ubiquitin ligase, and on the other end a moiety which binds the target protein, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein are treated or prevented with compounds and compositions of the present disclosure.
- -
-
Paragraph 00470
(2018/08/20)
-
- Zwitterionic-Salt-Catalyzed Site-Selective Monobromination of Arenes
-
A zwitterionic-salt-catalyzed electrophilic monobromination of arenes with high regioselectivity has been developed. Under mild reaction conditions, a wide range of monobrominated aromatic compounds can be obtained in excellent yields. The reaction can be operated using an extremely low catalyst loading (0.05 mol %) with the inexpensive brominating agent N-bromosuccinimide. The versatility of this catalytic protocol has been demonstrated by the scale-up reaction with a 0.01 mol % catalyst loading to provide the selectively halogenated compound in quantitative yield.
- Xiong, Xiaodong,Tan, Fei,Yeung, Ying-Yeung
-
supporting information
p. 4243 - 4246
(2017/08/23)
-
- Oxidation-Reduction Condensation of Diazaphosphites for Carbon-Heteroatom Bond Formation Based on Mitsunobu Mechanism
-
An efficient oxidation-reduction condensation reaction of diazaphosphites with various nonacidic pronucleophiles in the presence of DIAD as a weak oxidant has been developed for carbon-heteroatom bond formation. This mild process affords structurally diverse tertiary amines, secondary amines, esters, ethers, and thioethers in moderate to excellent yields. The selective synthesis of secondary amines from primary amines has been achieved. Importantly, a practical application to the synthesis of antiparkinsonian agent piribedil has been demonstrated.
- Huang, Hai,Kang, Jun Yong
-
supporting information
p. 544 - 547
(2017/02/10)
-
- Discovery of (R)-1-(3-(4-Amino-3-(3-chloro-4-(pyridin-2-ylmethoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one (CHMFL-EGFR-202) as a Novel Irreversible EGFR Mutant Kinase Inhibitor with a Distinct Binding Mode
-
On the basis of Ibrutinib’s core pharmacophore, which was moderately active to EGFR T790M mutant, we discovered novel epidermal growth factor receptor (EGFR) inhibitor compound 19 (CHMFL-EGFR-202), which potently inhibited EGFR primary mutants (L858R, del
- Wang, Aoli,Li, Xixiang,Wu, Hong,Zou, Fengming,Yan, Xiao-E,Chen, Cheng,Hu, Chen,Yu, Kailin,Wang, Wenchao,Zhao, Peng,Wu, Jiaxin,Qi, Ziping,Wang, Wei,Wang, Beilei,Wang, Li,Ren, Tao,Zhang, Shanchun,Yun, Cai-Hong,Liu, Jing,Liu, Qingsong
-
p. 2944 - 2962
(2017/04/21)
-
- Heme Protein Catalysts for Carbon-Silicon Bond Formation In Vitro and In Vivo
-
The present invention provides compositions and methods for catalyzing the formation of carbon-silicon bonds using heme proteins. In certain aspects, the present invention provides heme proteins, including variants and fragments thereof, that are capable of carrying out in vitro and in vivo carbene insertion reactions for the formation of carbon-silicon bonds. In other aspects, the present invention provides methods for producing an organosilicon product, the method comprising providing a silicon-containing reagent, a carbene precursor, and a heme protein; and combining the components under conditions sufficient to produce an organosilicon product. Host cells expressing the heme proteins are also provided by the present invention.
- -
-
Paragraph 0260
(2017/08/26)
-
- Structurally Divergent Lithium Catalyzed Friedel–Crafts Reactions on Oxetan-3-ols: Synthesis of 3,3-Diaryloxetanes and 2,3-Dihydrobenzofurans
-
The first examples of 3,3-diaryloxetanes are prepared in a lithium-catalyzed and substrate dependent divergent Friedel–Crafts reaction. para-Selective Friedel–Crafts reactions of phenols using oxetan-3-ols afford 3,3-diaryloxetanes by displacement of the hydroxy group. These constitute new isosteres for benzophenones and diarylmethanes. Conversely, ortho-selective Friedel–Crafts reactions of phenols afford 3-aryl-3-hydroxymethyl-dihydrobenzofurans by tandem alkylation–ring-opening reactions; the outcome of the reaction diverging to structurally distinct products dependent on the substrate regioselectivity. Further reactivity of the oxetane products is demonstrated, suitable for incorporation into drug discovery efforts.
- Croft, Rosemary A.,Mousseau, James J.,Choi, Chulho,Bull, James A.
-
supporting information
p. 16271 - 16276
(2016/10/30)
-
- Quinolinone compound and application thereof in drugs
-
The invention relates to a quinolinone compound and application thereof in drugs, particularly relates to a novel quinolinone compound, a pharmaceutical composition thereof and use of the compound or the pharmaceutical composition in preparing drugs. The drug is used for protecting, disposing, treating or alleviating HIF-related and/or EPO-related diseases of patients, wherein the HIF-related and/or EPO-related diseases comprise anemia, vascular diseases, regional myocardial ischaemia, metabolic disturbance, wound healing and the like.
- -
-
Paragraph 0322; 0323; 0324; 0325; 0326
(2016/10/07)
-
- TETRASUBSTITUTED ALKENE COMPOUNDS AND THEIR USE
-
Disclosed herein are compounds, or pharmaceutically acceptable salts thereof, and methods of using the compounds for treating breast cancer by administration to a subject in need thereof a therapeutically effective amount of the compounds or pharmaceutically acceptable salts thereof. The breast cancer may be an ER-positive breast cancer and/or the subject in need of treatment may express a mutant ER-α protein.
- -
-
Page/Page column 129; 130
(2016/12/22)
-
- Design, synthesis and evaluation of potent G-protein coupled receptor 40 agonists
-
GPR40 has emerged as an attractive drug target for the treatment of type 2 diabetes due to its role in the enhancement of insulin secretion with glucose dependency. With the aim to improve the metabolic and safety profiles, a series of novel phenylpropionic acid derivatives were synthesized. Extensive structural optimization led to identification of compounds 22g and 23e as potent GPR40 agonists with moderate liver microsomal stability. All the discovery supported further exploration surrounding this scaffold.
- Huang, Jing,Guo, Bin,Chu, Wen-Jing,Xie, Xin,Yang, Yu-She,Zhou, Xian-Li
-
supporting information
p. 159 - 162
(2016/01/26)
-
- Towards New Oligomesogenic Phosphonic Acids as Stabilizers of Nanoparticles Colloids in Nematic Liquid Crystals
-
Several synthetic strategies for the construction of linear and branched oligomesogenic phosphonic acids are examined, which differ in the method of building the key bimesogen unit. An efficient synthetic approach to the most promising compounds employs regioselective Kumada cross-coupling between [11-(4′-pentylbiphenyl-4-yl)undecyl]magnesium bromide and 4-(11-bromoundecyl)-4′-iodobiphenyl as the key step. Preliminary studies on the ability of the new ligands to stabilize nanoparticles colloids in nematic liquid crystals are undertaken for the example of quantum dots.
- Prodanov, Maksym F.,Diakov, Maksym Y.,Vlasenko, Ganna S.,Vashchenko, Valerii V.
-
supporting information
p. 1905 - 1910
(2015/08/06)
-
- Selective Halogenation Using an Aniline Catalyst
-
Electrophilic halogenation is used to produce a wide variety of halogenated compounds. Previously reported methods have been developed mainly using a reagent-based approach. Unfortunately, a suitable "catalytic" process for halogen transfer reactions has yet to be achieved. In this study, arylamines have been found to generate an N-halo arylamine intermediate, which acts as a highly reactive but selective catalytic electrophilic halogen source. A wide variety of heteroaromatic and aromatic compounds are halogenated using commercially available N-halosuccinimides, for example, NCS, NBS, and NIS, with good to excellent yields and with very high selectivity. In the case of unactivated double bonds, allylic chlorides are obtained under chlorination conditions, whereas bromocyclization occurs for polyolefin. The reactivity of the catalyst can be tuned by varying the electronic properties of the arene moiety of catalyst.
- Samanta, Ramesh C.,Yamamoto, Hisashi
-
supporting information
p. 11976 - 11979
(2015/08/18)
-
- Aerobic oxidative bromination of arenes using an ionic liquid as both the catalyst and the solvent
-
A method for the bromination of alkoxy-substituted benzenes and naphthalenes was developed by using the residual oxygen in the reaction tube as the oxidant, and [Bmim]NO3 (1-butyl-3-methylimidazolium nitrate) ionic liquid as both the catalyst and the solvent. No other reagent apart from the ionic liquid and molecular bromine was used in the reactions, and basically all the bromine atoms in the bromine source were transferred to the bromination products, showing that the presented protocol is highly atom economic and practical.
- Ren, Yun-Lai,Wang, Binyu,Tian, Xin-Zhe,Zhao, Shuang,Wang, Jianji
-
supporting information
p. 6452 - 6455
(2015/11/16)
-
- Targeting dopamine D3 and serotonin 5-HT1A and 5-HT2A receptors for developing effective antipsychotics: Synthesis, biological characterization, and behavioral studies
-
Combination of dopamine D3 antagonism, serotonin 5-HT1A partial agonism, and antagonism at 5-HT2A leads to a novel approach to potent atypical antipsychotics. Exploitation of the original structure-activity relationships resulted in the identification of safe and effective antipsychotics devoid of extrapyramidal symptoms liability, sedation, and catalepsy. The potential atypical antipsychotic 5bb was selected for further pharmacological investigation. The distribution of c-fos positive cells in the ventral striatum confirmed the atypical antipsychotic profile of 5bb in agreement with behavioral rodent studies. 5bb administered orally demonstrated a biphasic effect on the MK801-induced hyperactivity at dose levels not able to induce sedation, catalepsy, or learning impairment in passive avoidance. In microdialysis studies, 5bb increased the dopamine efflux in the medial prefrontal cortex. Thus, 5bb represents a valuable lead for the development of atypical antipsychotics endowed with a unique pharmacological profile for addressing negative symptoms and cognitive deficits in schizophrenia.
- Brindisi, Margherita,Butini, Stefania,Franceschini, Silvia,Brogi, Simone,Trotta, Francesco,Ros, Sindu,Cagnotto, Alfredo,Salmona, Mario,Casagni, Alice,Andreassi, Marco,Saponara, Simona,Gorelli, Beatrice,Weikop, Pia,Mikkelsen, Jens D.,Scheel-Kruger, Jorgen,Sandager-Nielsen, Karin,Novellino, Ettore,Campiani, Giuseppe,Gemma, Sandra
-
p. 9578 - 9597
(2015/01/09)
-
- Modulated SmAb phases formed by anchor shaped liquid crystalline molecules
-
Bent-core molecules with a linear alkyl chain in the bay position (anchor shaped molecules) form new liquid crystalline phases combining periodicities with different coherence lengths in distinct directions; in these LC phases the molecules are organized on average orthogonal in modulated layers (ribbons or patches) with restricted rotation around the long axis, thus representing modulated SmAb phases.
- Geese, Karina,Prehm, Marko,Tschierske, Carsten
-
supporting information
p. 9903 - 9906
(2014/08/18)
-
- Tetrabutyl ammonium bromide-mediated benzylation of phenols in water under mild condition
-
Benzylation of phenol was successfully achieved in water under room temperature mediated by tetrabutylammonium bromide (TBAB) for only 2 h affording the corresponding benzyl phenyl ether with good to excellent yields. This protocol is very efficient, simple, avoiding catalysts, easy to work-up after reaction, and especially 'green'.
- Wang, Hailei,Ma, Yuping,Tian, Heng,Yu, Ajuan,Chang, Junbiao,Wu, Yangjie
-
p. 2669 - 2673
(2014/04/03)
-
- Choline chloride based deep eutectic solvent as an efficient solvent for the benzylation of phenols
-
Deep eutectic solvents (such as the combination of urea and choline chloride) are found to be promising solvent and phase-transfer-media for benzylation of phenol. These methods avoided the complexity of multiple alkylations giving selectively O-alkylated aromatic products. Good to excellent yields of the corresponding benzyl phenyl ether were obtained. The non-toxic, biodegradable, inexpensive, and recyclable nature of DES make this protocol green and cost-effective.
- Singh, Abhilash S.,Shendage, Suresh S.,Nagarkar, Jayashree M.
-
p. 7243 - 7246
(2015/02/02)
-
- Copper-catalyzed N- and O-alkylation of amines and phenols using alkylborane reagents
-
By the reaction of amines with alkylborane reagents in the presence of a catalytic amount of copper(II) acetate Cu(OAc)2 and di-tert-butyl peroxide, a cross-coupling reaction proceeded and alkylated amines were obtained in good to excellent yields. Phenols are also applicable for this reaction, and the corresponding alkyl aryl ethers were produced.
- Sueki, Shunsuke,Kuninobu, Yoichiro
-
supporting information
p. 1544 - 1547
(2013/06/26)
-
- Reactions of triflate esters and triflamides with an organic neutral super-electron-donor
-
The bis-pyridinylidene 13 converts aliphatic and aryl triflate esters to the corresponding alcohols and phenols respectively, using DMF as solvent, generally in excellent yields. While the deprotection of aryl triflates has been seen with other reagents and by more than one mechanism, the deprotection of alkyl triflates is a new reaction. Studies with 18O labelled DMF indicate that the C-O bond stays intact and hence it is the S-O bond that cleaves, underlining that the cleavage results from the extraordinary electron donor capability of 13. Trifluoromethanesulfonamides are converted to the parent amines in like manner, representing the first cleavage of such substrates by a ground-state organic reducing reagent.
- Jolly, Phillip I.,Fleary-Roberts, Nadia,O'Sullivan, Steven,Doni, Eswararao,Zhou, Shengze,Murphy, John A.
-
supporting information; experimental part
p. 5807 - 5810
(2012/08/28)
-
- Halodeboronation of organotrifluoroborates using tetrabutylammonium tribromide or cesium triiodide
-
Halodeboronation of organotrifluoroborates using commercially available tetrabutylammonium tribromide (TBATB) or cesium triiodide in aqueous medium is reported. The mild, transition metal-free method has proven to be tolerant of a wide range of functional groups. High regio- and chemoselectivity are observed. Two synthetic routes to (Z)-dibromoalkenes from alkynes, through stereodefined (Z)-2-bromoalkenyltrifluoroborates and (Z)-1,2-bis(boryl) alkenyltrifluoroborates, have been developed using the TBATB mediated bromodeboronation as the key step.
- Yao, Min-Liang,Kabalka, George W.,Blevins, David W.,Reddy, Marepally Srinivasa,Yong, Li
-
experimental part
p. 3738 - 3743
(2012/06/30)
-
- Synthesis, structure and conformation of terphenylene-derived oxacalixaromatics
-
Oxacalix[4]aromatics comprised of terphenylene units have been synthesized by cyclooligomerization of 5′-tert-butyl-1,1′:3′,1″- terphenyl-4,4″-diol (1) and electron-deficient meta-dihalogenated benzene and heterocycles. Single-crystal X-ray analysis revealed that oxacalix[2]terphenylene[2]pyrazine 13 adopts a chair conformation, forming a molecular cavity to trap an ethyl acetate guest molecule in the solid state. 1,3-Alternate conformations are adopted by other oxacalix[2]terphenylene[2] aromatics (11, 12 and 15), which form a narrow tweezer-like molecular cavity that is incapable of encapsulating any guest molecules. Oxacalix[4]aromatics comprised of terphenylene units have been synthesized, andtheir structures and conformations have been elucidated. Copyright
- Hu, Wen-Jing,Zhao, Xiao-Li,Ma, Ming-Liang,Guo, Fang,Mi, Xian-Qiang,Jiang, Biao,Wen, Ke
-
supporting information; experimental part
p. 1448 - 1454
(2012/04/11)
-
- New SmCG phases in a hydrogen-bonded bent-core liquid crystal featuring a branched siloxane terminal group
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In this study, we synthesized three analogous bent-core molecules, a hydrogen-bonded complex and a covalent-bonded compound with branched siloxane units (H-SiO and C-SiO, respectively) and a hydrogen-bonded complex with an alkyl unit (H-Alk), and investigated the effects of the hydrogen bonding and branched siloxane terminal units on their mesomorphic properties. The covalent-bonded compound C-SiO and the hydrogen-bonded complex H-Alk exhibited typical SmCP phases; in contrast, the hydrogen-bonded complex H-SiO exhibited a series of general tilt smectic (SmCG) phases with highly ordered layer structures (i.e., SmCG2PF-USmCG2P A-SmCG2PF-SmCGPF upon cooling). During the SmCG-type phase transition process, a 2D-modulated ribbon structure transferred into highly ordered layers via undulated layers, as the hydrogen-bonding strength increased with reduced temperatures. As the SmCG domains were aligned under dc electric fields, a gradual decrease in the leaning angle from ca. 60° to 50° (while the tilt angle kept at ca. 31°) could be determined by in situ wide-angle X-ray scattering (WAXS). Combined with Fourier transform infrared and Raman spectroscopic data, our results suggest that the change in the leaning angle was governed by the competition of the hydrogen bonds and microsegregation of siloxane units within the bilayer structure of the hydrogen-bonded complex H-SiO. In addition, the ferroelectric-(antiferroelectric)-ferroelectric transitions proven by the switching current responses in the SmCG-type phases of H-SiO reveal that the polar switching occurred through collective rotations around the long axis of H-SiO. Therefore, novel SmCG phases with a series of highly ordered 2D-structures were induced by the effects of the hydrogen bonding and branched terminal siloxane unit in the bent-core hydrogen-bonded LC complex H-SiO.
- Chen, Wei-Hong,Chuang, Wei-Tsung,Jeng, U-Ser,Sheu, Hwo-Shuenn,Lin, Hong-Cheu
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supporting information; experimental part
p. 15674 - 15685
(2011/11/28)
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- Smectic-layer alignments of surface-modified gold nanoparticles in the nanocomposite induced by a hydrogen-bonded bent-core liquid crystalline host under electric fields
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Packing tips: The layer spacing of 5.5 nm (see TEM image) of the nanocomposite VPy-SiA/AuNPs-S (5 wt %) under DC/AC electric fields perfectly matches the d spacing of 5.5 nm obtained by in situ XRD measurements under a DC electric field. TEM images revealed that the well-organized packing of layers of surface-modified gold NPs could be induced in the nanocomposite under electric fields. Copyright
- Chen, Wei-Hong,Chang, Yi-Ting,Lee, Jey-Jau,Chuang, Wei-Tsung,Lin, Hong-Cheu
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supporting information; experimental part
p. 13182 - 13187
(2012/02/02)
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- Chemoselective bromodeboronation of organotrifluoroborates using tetrabutylammonium tribromide: Application in (Z)-dibromoalkene syntheses
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(Chemical Equation Presented) Tetrabutylammonlum trlbromlde (TBATB) has been found to be a unique bromodeboronatlon reagent for organotrlf luoroborates. When compared to previously reported bromodeboronatlon methods, the mild and metal-free reaction conditions tolerate a wider range of functional groups. High reglo- and chemoselectlvlty are observed In the presence of both unsaturated carbon-carbon bonds and aldehyde functional groups. An efficient synthetic route to (Z)-dlbromoalkenes from terminal alkynes has been developed using the TBATB-medlated bromodeboronatlon as a key step.
- Yao, Min-Liang,Reddy, Marepally Srinivasa,Li, Yong,Walfish, Ingrid,Blevins, David W.,Kabalka, George W.
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supporting information; experimental part
p. 700 - 703
(2010/04/02)
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- The biomimetic synthesis and first characterization of the (+)- and (-)-isocentrolobines, 2,6-cis- and 2,6-trans-disubstituted tetrahydro-2H-pyrans
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The four stereoisomers of the novel title compounds were prepared by oxidative cyclization of their enantiomerically pure diarylheptanoid precursors by means of the straightforward biomimetic approach presented in the preceding article. The isocentrolobin
- Rogano, Frank,Froidevaux, Georges,Rueedi, Peter
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experimental part
p. 1299 - 1312
(2010/09/12)
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- Highly sensitive and selective "turn-on" calcium cation sensing from a dendronic terthiophene tetraethylene glycol (TEG) molecule
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A molecule consisting of a branched or dendronic terthiophene with tetraethylene glycol moiety (3T5O) was synthesized for highly sensitive and selective calcium ion detection in solution. The sulfur atoms of the terthiophene dendron moiety contribute to t
- Park, Yushin,Apodaca, Dahlia C.,Pullen, Jonathan,Advincula, Rigoberto C.
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experimental part
p. 13084 - 13094
(2011/02/27)
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- Synthesis and dopaminergic activity of some E-3-(piperidin-1-yl)-1-(4-substituted phenyl)prop-2-en-1-one derivatives
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A convenient route for the synthesis of some 2-propen-1-one derivatives with E isomeric configuration is described. The activity of the synthesized compounds was evaluated through behavioral studies of apomorphine-induced licking in animal models. It was demonstrated that most of the synthesized compounds showed moderate activity in inhibition of lickings, among which 6a, was the most active compound at 30 mg/kg.
- Sakhteman, Amirhossein,Foroumadi, Alireza,Sharifzadeh, Mohammad,Amanlou, Masoud,Rayatnia, Farhoud,Shafiee, Abbas
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scheme or table
p. 6908 - 6913
(2009/12/24)
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- DERIVATIVES OF 3-(2-HYDROXY-5-METHYPHENYL)-N,N-DIISOPROPYL-3-PHENYLPROPYLAMINE AND METHODS OF USE THEREOF
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This invention relates to novel derivatives of tolterodine, 5-hydroxymethyl tolterodine, fesoterodine and pharmaceutically acceptable salts thereof. This invention also provides compositions comprising a compound of this invention and the use of such comp
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Page/Page column 26
(2009/11/29)
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- Counterattack mode differential acetylative deprotection of phenylmethyl ethers: Applications to solid phase organic reactions
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A counterattack protocol for differential acetylative cleavage of phenylmethyl ether has been developed. The phenylmethyl moiety is liberated as benzyl bromide that is isolated and reused providing advantages in terms of waste minimization/utilization and atom economy. The applicability of this methodology has been extended for solid phase organic reactions with the feasibility of reuse of the solid support.
- Chakraborti, Asit K.,Chankeshwara, Sunay V.
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supporting information; experimental part
p. 1367 - 1370
(2009/07/04)
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- Oligomeric benzylsulfonium salts: Facile benzylation via high-load ROMP reagents
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(Chemical Equation Presented) The development of high-load, oligomeric benzylsulfonium salts, generated via ring-opening metathesis polymerization, and their utility in facile benzylations of various nucleophiles is reported. These oligomeric sulfonium salts exist as free-flowing powders and are stable at room temperature. After the benzylation event, purification is attained via simple dry load/filtration, followed by solvent removal to deliver products in excellent yield and purity.
- Zhang, Mianji,Flynn, Daniel L.,Hanson, Paul R.
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p. 3194 - 3198
(2008/02/04)
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- COMPOUNDS AND COMPOSITIONS AS PPAR MODULATORS
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The invention provides compounds, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with the activity of the Peroxisome Proliferator-Activated Receptor (PPAR) families.
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Page/Page column 32
(2010/11/27)
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- Synthesis of dictyomedins using phosphazene base catalyzed diaryl ether formation
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Dictyomedins isolated from dictyostelium cellular slime molds were synthesized by using diaryl ether derivatives as key intermediates for the cyclization to dibenzofuran followed by palladium catalyzed intramolecular biaryl formation.
- Ebisawa, Masaru,Ueno, Masahiro,Oshima, Yoshiteru,Kondo, Yoshinori
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p. 8918 - 8921
(2008/03/14)
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