- Efficient and eco-friendly synthesis of iodinated aromatic building blocks promoted by iodine and hydrogen peroxide in water: A mechanistic investigation by mass spectrometry
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The reaction of aromatic and heteroaromatic compounds with molecular iodine in the presence of aqueous hydrogen peroxide using water without any co-solvent at 50 °C for 24 h produced versatile iodinated organic molecules with potential application in organic synthesis and medicine in very good yields. In addition, a mechanistic investigation for the iodination process was carried out by mass spectrometry.
- Gallo, Rafael D.C.,Ferreira, Irlon M.,Casagrande, Gleison A.,Pizzuti, Lucas,Oliveira-Silva, Diogo,Raminelli, Cristiano
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Read Online
- Complexes featuring N-heterocyclic carbenes with bowl-shaped wingtips
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Three imidazolium salts having their two N-substituents equipped with remote calix[4]arenyl termini have been synthesised and converted into N-heterocyclic carbene (NHC) complexes of the type [PdCl2(NHC)(pyridine)]. An X-ray diffraction study c
- Almallah, Hamzé,Nos, Mélodie,Ayzac, Virgile,Brenner, Eric,Matt, Dominique,Gourlaouen, Christophe,Jahjah, Mohamad,Hijazi, Akram
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Read Online
- Base-Mediated Generation of Ketenimines from Ynamides: [3+2] Annulation with Azaallyl Anions
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Under basic conditions and heat, ynamides can serve as precursors to ketenimines, whose synthetic potential is often hampered by their difficulty of access. Herein, we report that they can undergo a [3+2] cycloaddition with 2-azaallyl anions, obtained from benzylimines under the same reaction conditions. This reaction between two highly reactive intermediates, both generated in situ from bench stable starting materials, gives access to various nitrogen-rich heterocycles. The reaction usually proceeds with excellent diastereoselectivity, in favor of the cis adduct. Deuteration experiments and DFT calculations helped rationalize the regio- and stereoselectivity of the process as well as the formation of side products. (Figure presented.).
- D'Hollander, Agathe C. A.,Romero, Eugénie,Vijayakumar, Kamsana,Le Houérou, Camille,Retailleau, Pascal,Dodd, Robert H.,Iorga, Bogdan I.,Cariou, Kevin
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supporting information
p. 2903 - 2908
(2021/04/21)
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- NAMPT MODULATORS
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Provided are compounds of Formula (II) or a pharmaceutically acceptable salt thereof, wherein R1, R2, R3, R4, R5, R6, and p are as defined herein. Also provided is a pharmaceutically acceptable composition comprising a compound of Formula (II), or a pharmaceutically acceptable salt thereof. Also provided are methods of using a compound of Formula (II), or a pharmaceutically acceptable salt thereof.
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Paragraph 0228
(2021/08/13)
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- Mild deprotection of the: N-tert -butyloxycarbonyl (N -Boc) group using oxalyl chloride
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We report a mild method for the selective deprotection of the N-Boc group from a structurally diverse set of compounds, encompassing aliphatic, aromatic, and heterocyclic substrates by using oxalyl chloride in methanol. The reactions take place under room temperature conditions for 1-4 h with yields up to 90percent. This mild procedure was applied to a hybrid, medicinally active compound FC1, which is a novel dual inhibitor of IDO1 and DNA Pol gamma. A broader mechanism involving the electrophilic character of oxalyl chloride is postulated for this deprotection strategy. This journal is
- Awuah, Samuel G.,George, Nathaniel,Ofori, Samuel,Parkin, Sean
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p. 24017 - 24026
(2020/07/23)
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- Selective Janus Kinase 2 (JAK2) Pseudokinase Ligands with a Diaminotriazole Core
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Janus kinases (JAKs) are non-receptor tyrosine kinases that are essential components of the JAK-STAT signaling pathway. Associated aberrant signaling is responsible for many forms of cancer and disorders of the immune system. The present focus is on the d
- Liosi, Maria-Elena,Krimmer, Stefan G.,Newton, Ana S.,Dawson, Thomas K.,Puleo, David E.,Cutrona, Kara J.,Suzuki, Yoshihisa,Schlessinger, Joseph,Jorgensen, William L.
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p. 5324 - 5340
(2020/06/10)
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- Direct Transformation of Arylamines to Aryl Halides via Sodium Nitrite and N-Halosuccinimide
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A one-pot universal approach for transforming arylamines to aryl halides via reaction with sodium nitrite (NaNO2) and N-halosuccinimide (NXS) in DMF at room temperature under metal- and acid-free condition is described. This new protocol that is complementary to the Sandmeyer reaction, is suggested to involve the in situ generation of nitryl halide induce nitrosylation of aryl amine to form the diazo intermediate which is halogenated to furnish the aryl halide.
- Mukhopadhyay, Sushobhan,Batra, Sanjay
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p. 14622 - 14626
(2018/09/21)
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- A para-C–H Functionalization of Aniline Derivatives via In situ Generated Bulky Hypervalent Iodinium Reagents
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A practical para-C-H functionalization of aniline derivatives has been developed using an in situ generated bulky hypervalent iodinium reagent. Para-iodo, bromo, chloro, nitro, trifluormethyl aniline derivatives can be obtained efficiently, in many cases in 10 min in a transition metal-free manner. Medicinal chemicals or intermediates can be purified without column chromatography or recrystallization, which significantly reduces the waste and simplifies the work-up process.
- Tian, Chao,Yao, Xu,Ji, Weizhe,Wang, Qian,An, Guanghui,Li, Guangming
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supporting information
p. 5972 - 5979
(2018/11/23)
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- Multicomponent Oxidative Trifluoromethylation of Alkynes with Photoredox Catalysis: Synthesis of α-Trifluoromethyl Ketones
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The direct oxidative addition of CF3 and H2O to alkynes was achieved with photoredox catalysis to obtain α-trifluoromethyl ketones via rapid enol-keto tautomerization. The reaction exhibits high functional group tolerance and regioselectivity. Heterocycles of various sizes containing CF3 were synthesized from the α-CF3-substituted diketones obtained through the protocol, thereby demonstrating the versatile applicability of the method. Mechanistic studies of the reaction with isotopes provided insight into the reaction pathway.
- Malpani, Yashwardhan R.,Biswas, Bishyajit Kumar,Han, Hong Sik,Jung, Young-Sik,Han, Soo Bong
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supporting information
p. 1693 - 1697
(2018/04/16)
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- Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature
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Despite the wide use of aryl radicals in organic synthesis, current methods to prepare them from aryl halides, carboxylic acids, boronic acids, and diazonium salts suffer from limitations. Aryl triflates, easily obtained from phenols, are promising aryl radical progenitors but remain elusive in this regard. Inspired by the single electron transfer process for aryl halides to access aryl radicals, we developed a simple and efficient protocol to convert aryl triflates to aryl radicals. Our success lies in exploiting sodium iodide as the soft electron donor assisted by light. This strategy enables the scalable synthesis of two types of important organic molecules, i.e., aryl boronates and aryl iodides, in good to high yields, with broad functional group compatibility in a transition-metal-free manner at room temperature. This protocol is anticipated to find potential applications in other aryl-radical-involved reactions by using aryl triflates as aryl radical precursors.
- Liu, Wenbo,Yang, Xiaobo,Gao, Yang,Li, Chao-Jun
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supporting information
p. 8621 - 8627
(2017/07/06)
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- Efficient and expeditious chemoselective BOC protection of amines in catalyst and solvent-free media
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A green and eco-friendly route for the almost quantitative BOC protection of a large variety of aliphatic and aromatic amines, amino acids, and amino alcohols is reported in catalyst and solvent-free media under mild reaction conditions. The products were confirmed by 1H, 13C NMR, IR spectroscopy, and in some cases, elemental analysis. This protocol does not require any water quenches, solvent separations, and purification steps, such as recrystallization and column chromatography.
- Viswanadham, Balaga,Mahomed, Abdul S.,Friedrich, Holger B.,Singh, Sooboo
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p. 1355 - 1363
(2017/02/15)
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- Excited-State Intramolecular Proton-Transfer Properties of Three Tris(N-Salicylideneaniline)-Based Chromophores with Extended Conjugation
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The synthesis and photophysical properties of three tris(N-salicylideneaniline) (TSA) compounds containing 1,3,5-triarylbenzene, -tristyrylbenzene, and -tris(arylethynyl)benzene core units are reported. The TSA compounds underwent efficient excited-state
- Jagadesan, Pradeepkumar,Whittemore, Tyler,Beirl, Toni,Turro, Claudia,McGrier, Psaras L.
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supporting information
p. 917 - 925
(2017/02/05)
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- Pyrazolo[3,4-c]pyridine derivative
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The invention relates to a pyrazolo[3,4-c]pyridine derivative. The invention relates to a compound represented by a formula (I), a tautomer thereof, an optical isomer thereof or a pharmaceutically acceptable salt thereof, wherein the formula (I) is shown in the description, and Z, X, RNc, RNd, RNe and RNf are defined according to the claim 1. The invention further relates to the pharmaceutical composition contain the compound. The invention further relates to use of the compound or the pharmaceutical composition in preparing a drug for preventing and/or treating a disease which inhibits positive influence of an Xa factor, particularly use in preparing the drug for preventing and/or treating the disease which inhibits positive influence of the Xa factor under the condition of low hemorrhage risk.
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Paragraph 0242; 0243; 0244
(2016/10/08)
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- Highly ortho-Selective Chlorination of Anilines Using a Secondary Ammonium Salt Organocatalyst
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An organocatalytic, highly facile, efficient, and regioselective ortho-chlorination of anilines is described. A secondary ammonium chloride salt has been employed as the catalyst and the reaction can be conducted at room temperature without protection from air and moisture. In addition, the reaction is readily scalable and the catalyst can be recycled and reused. This catalytic protocol has been applied to the efficient synthesis of a highly potent c-Met kinase inhibitor. Mechanistic studies revealed that unique structural features of the secondary ammonium chloride salt are important for both the catalysis and regioselectivity of the electrophilic ortho-chlorination.
- Xiong, Xiaodong,Yeung, Ying-Yeung
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supporting information
p. 16101 - 16105
(2016/12/26)
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- Ultrasound-promoted rapid and efficient iodination of aromatic and heteroaromatic compounds in the presence of iodine and hydrogen peroxide in water
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A rapid and efficient ultrasound-promoted protocol for iodination of aromatic and heteroaromatic compounds, using molecular iodine in the presence of aqueous hydrogen peroxide in water without any cosolvent, has produced versatile iodinated organic molecules with potential application in organic synthesis and medicine in short reaction times and good to excellent yields. Copyright
- Ferreira, Irlon M.,Casagrande, Gleison A.,Pizzuti, Lucas,Raminelli, Cristiano
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supporting information
p. 2094 - 2102
(2014/07/07)
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- INHIBITORS OF THE MITF MOLECULAR PATHWAY
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Provided herein are compounds of the formula (IV) as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful as MITF inhibitors, MITF pathway inhibitors and for the treatment of cancer.
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Paragraph 00189
(2015/01/09)
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- A universal procedure for the [18F]trifluoromethylation of aryl iodides and aryl boronic acids with highly improved specific activity
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Herein we describe a valuable method for the introduction of the [18F]CF3 group into arenes with highly improved specific activity by the reaction of [18F]trifluoromethane with aryl iodides or aryl boronic acids. This [su
- Vanderborn, Dion,Sewing, Claudia,Herscheid,Windhorst, Albert D.,Orru, Romano V. A.,Vugts, Danielle J.
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supporting information
p. 11046 - 11050
(2015/03/30)
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- LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS
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Compounds, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or diagnose diseases, disorders, or conditions associated with one or more of the lysophosphatidic acid receptors are provided.
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Paragraph 0965; 0966
(2014/07/23)
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- A peptide based two component white light emitting system
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A peptide based two component white light emitting system has been designed and developed on the basis of a co-assembly of a PDI containing peptide system as an acceptor and a stilbene containing peptide system as a donor in organic solvents.
- Maiti, Dibakar Kumar,Banerjee, Arindam
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supporting information
p. 6909 - 6911
(2013/07/26)
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- A synthetic amino acid residue containing a new oligopeptide-based photosensitive fluorescent organogel
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A synthetic amino acid (with a stilbene residue in the main chain) containing a tripeptide-based organogelator has been discovered. This peptide-based synthetic molecule 1 self-assembles in various organic solvents to form an organogel. The gel has been thoroughly characterized by using various microscopic techniques including field-emission scanning electron microscopy (FESEM), atomic force microscopy (AFM), X-ray diffraction (XRD), UV-visible and fluorescence spectroscopy, and rheology. Morphological investigations using FESEM and AFM show a nanofibrillar network structure. Interestingly, the organogel is photoresponsive and a gel-sol transition occurred by irradiating the gel with UV light of 365 nm for 2 h as shown by the UV and fluorescence study. This photoresponsive fluorescent gel holds promise for new peptide-based soft materials with interesting applications. Copyright
- Maiti, Dibakar Kumar,Banerjee, Arindam
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supporting information
p. 113 - 120
(2013/02/26)
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- Preparation of phenylethylbenzamide derivatives as modulators of DNMT3 activity
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DNA-methyltransferases (DNMTs) are a class of epigenetic enzymes that catalyze the transfer of a methyl moiety from the methyl donor S-adenosyl-l-methionine onto the C5 position of cytosine in DNA. This process is dysregulated in cancers and leads to the hypermethylation and silencing of tumor suppressor genes. The development of potent and selective inhibitors of DNMTs is of utmost importance for the discovery of new therapies for the treatment of cancer. We report herein the synthesis and DNMT inhibitory activity of 29 analogues derived from NSC 319745. The effect of selected compounds on the methylation level in the MDA-MB-231 human breast cancer cell line was evaluated using a luminometric methylation assay. Molecular docking studies have been conducted to propose a binding mode for this series.
- Kabro, Anzhelika,Lachance, Hugo,Marcoux-Archambault, Iris,Perrier, Valerie,Dore, Vicky,Gros, Christina,Masson, Veronique,Gregoire, Jean-Marc,Ausseil, Frederic,Cheishvili, David,Laulan, Nathalie Bibens,St-Pierre, Yves,Szyf, Moshe,Arimondo, Paola B.,Gagnon, Alexandre
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p. 1562 - 1570
(2013/12/04)
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- One-pot synthesis of cyclic triamides with a triangular cavity from trans-stilbene and diphenylacetylene monomers
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(Chemical Equation Presented) Base-promoted self-condensation reactions of trans-stilbene and diphenylacetylene monomers bearing 4-alkylamino and 4′-methoxycarbonyl groups were investigated. Reactions of N-propyl monomers under pseudohigh-dilution conditions (a THF solution of monomer was added dropwise to a THF solution of LiHMDS) afforded the corresponding cyclic triamides in good yields. X-ray crystallographic analysis showed that these cyclic triamides possessed an almost equilateral triangle structure with a cavity surrounded by tilted benzene rings.
- Yokoyama, Akihiro,Maruyama, Takurou,Tagami, Kei,Masu, Hyuma,Katagiri, Kosuke,Azumaya, Isao,Yokozawa, Tsutomu
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supporting information; experimental part
p. 3207 - 3210
(2009/05/11)
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- CHEMICAL COMPOUNDS
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Compounds of formula (I) and their pharmaceutically acceptable salts are described: Formula (I). Processes for their preparation, pharmaceutical compositions containing them, their use as medicaments and their use in the treatment of bacterial infections are also described.
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Page/Page column 59
(2010/11/23)
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- 4′-Alkoxyl substitution enhancing the anti-mitotic effect of 5-(3′,4′,5′-substituted)anilino-4-hydroxy-8-nitroquinazolines as a novel class of anti-microtubule agents
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Mitosis inhibitors are powerful anticancer drugs. Based on a novel anti-microtubule agent of 5-(4′-methoxy)anilino-4-hydroxy-8-nitroquinazoline, a series of 5-(3′,4′,5′-substituted)anilino-4-hydroxy-8- nitroquinazolines were designed and synthesized to investigate the effect of the substitution on the inhibitory activity against mitotic progression of tumor cells. The large alkoxyl substitution on the 4′-position of 5-anilino ring is beneficial for the potency. The 5-(3′,4′,5′-trimethoxy)anilino-8-nitroquinazoline (1h) displays an overwhelming activity in arresting the cells at the G2/M phase, providing a promising new template for further development of potent microtubule-targeted anti-mitotic drugs.
- Jin, Yi,Zhou, Zu-Yu,Tian, Wei,Yu, Qiang,Long, Ya-Qiu
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p. 5864 - 5869
(2007/10/03)
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- Novel pentafluorosulfanyl compounds
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The present invention provides the compounds of formula I-A their pharmaceutically acceptable salts or esters, enantiomeric forms, diastereoisomers and racemates, the preparation of the above-mentioned compounds, pharmaceutical compositions containing th
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Page/Page column 15
(2010/02/13)
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- BIARYL COMPOUNDS HAVING ANTI-INFECTIVE ACTIVITY
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Aromatic compounds exemplified by exhibit antimicrobial activity.
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Page/Page column 24
(2008/06/13)
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- AZOLE COMPOUNDS
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The present invention provides a compound represented by the formula (I) wherein R1 is a hydrogen atom, a halogen atom, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group, an optionally substituted hydroxy group, an optionally substituted thiol group or an optionally substituted amino group, A is an optionally substituted cyclic amino group or -NR2-W-D wherein R2 is a hydrogen atom or an alkyl group, W is a bond or a divalent acyclic hydrocarbon group, and D is an optionally substituted cyclic group, an optionally substituted amino group or an optionally substituted acyl group, B is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, X is an oxygen atom, a sulfur atom or an optionally substituted nitrogen atom, and Y is a bond or a divalent acyclic hydrocarbon group, or a salt thereof, which is useful for the prophylaxis or treatment of diabetic neuropathy and the like.
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- A New Generation of N-Aryl-N′-(1-alkyl-2-chloroethyl)ureas as Microtubule Disrupters: Synthesis, Antiproliferative Activity, and β-Tubulin Alkylation Kinetics
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New N-aryl-N′-2-chloroethylureas (CEUs) with enhanced cytotoxicity were developed as antimitotic agents potentially useful in cancer chemotherapy. Highly potent CEUs were obtained by introduction of a branched alkylating chain, the N′-(1-methyl-2-chloro)e
- Mounetou, Emmanuelle,Legault, Jean,Lacroix, Jacques,Gaudreault, René C.
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p. 5055 - 5063
(2007/10/03)
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- Rational design, synthesis and structure-Activity relationships of a cyclic succinate series of TNF-α converting enzyme inhibitors. Part 1: Lead identification
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Rational design based on the broad spectrum MMP inhibitor CGS 27023A led to the identification of a novel series of cyclic succinate TACE inhibitors. As a mixture of two enantiomers, the lead compound 17b exhibited potent enzyme activity (IC50=
- Xue, Chu-Biao,He, Xiaohua,Roderick, John,Corbett, Ronald L.,Duan, James J.-W.,Liu, Rui-Qin,Covington, Maryanne B.,Newton, Robert C.,Trzaskos, James M.,Magolda, Ronald L.,Wexler, Ruth R.,Decicco, Carl P.
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p. 4293 - 4297
(2007/10/03)
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- Analine derivatives as OSC inhibitors
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The present invention relates to compounds of formula (I) wherein U, Y, V, W, L, X, A1, A2, A3, A4, A5 and A6 are as defined in the description and claims and pharmaceutically acceptable salts and/or pharmaceutically acceptable esters thereof. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with 2,3-oxidosqualene-lanosterol cyclase such as hypercholesterolemia, hyperlipemia, arteriosclerosis, vascular diseases, mycoses, parasite infections, gallstones, tumors and/or hyperproliferative disorders, and/or treatment and/or prophylaxis of impaired glucose tolerance and diabetes.
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- Heterocyclic substituted aniline calcium channel blockers
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The present invention provides compounds that block calcium channels having the Formula I shown below. STR1The present invention also provides methods of using the compounds of Formula I to treat stroke, cerebral ischemia, head trauma, epilepsy, asthma, amyotrophic lateral sclerosis, or pain and to pharmaceutical compositions that contain the compounds of Formula I.
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- The discovery of [1-(4-Dimethylamino-benzyl)-piperidin-4-yl]-[4-(3,3-dimethylbutyl)-phenyl]-(3-methyl-but-2-enyl)-amine, an N-type Ca+2 channel blocker with oral activity for analgesia
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Our drug discovery efforts for N-type calcium channel blockers in the 4-piperidinylaniline series led to the discovery of an orally active analgesic agent 26. 1-[4-Dimethylamino-benzyl)-piperidin-4-yl]-[4-(3,3-dimethyl-butyl)-phenyl]-(3-methyl-but-2-enyl)-amine (26) showed high affinity to functionally block N-type calcium channels (IC50=0.7 μM in the IMR32 assay) and exhibited high efficacy in the anti-writhing analgesia test with mice (ED50=12 mg/kg by po and 4 mg/kg by iv). In this report, the rationale for the design, synthesis, biological evaluation, and pharmacokinetics of this series of blockers is described. Copyright (C) 2000 Elsevier Science Ltd.
- Hu, Lain-Yen,Ryder, Todd R.,Rafferty, Michael F.,Taylor, Charles P.,Feng, M. Rose,Kuo, Be-Sheng,Lotarski, Susan M.,Miljanich, George P.,Millerman, Elizabeth,Siebers, Krista M.,Szoke, Balazs G.
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p. 1203 - 1212
(2007/10/03)
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- Biphenyl substituted dipeptide analogs promote release of growth hormone
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There are disclosed certain compounds identified as substituted dipeptide analogs which promote the release of growth hormone in humans and animals. This property can be utilized to promote the growth of food animals to render the production of edible meat products more efficient, and in humans, to increase the stature of those afflicted with a lack of a normal secretion of natural growth hormone. Growth promoting compositions containing such substituted dipeptide analogs as the active ingredient thereof are also disclosed.
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- (4-alkoxypyran-4-yl) substituted arylalkylaryl-, aryalkenylaryl-, and aryalkynylarylurea inhibitors of 5-lipoxygenase
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Compounds of the structure STR1 wherein W is selected from STR2 where Q is oxygen or sulfur, R6 and R7 are hydrogen or alkyl, or R6 and R7, together with the nitrogen atoms to which they are attached, define a r
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- TRANS-1,4-DIALKOXYCYCLOHEXYL SUBSTITUTED ARYLALKYLARYL- ARYLALKENYLARYL-, AND ARYLALKYNYLARYLUREA INHIBITORS OF 5-LIPOXYGENASE
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Compounds of stracture where W is selected from the group consisting of where Q is oxygen or sulfur, R7 and R8 are independently selected from hydrogen and alkyl, or R7 and R8, together with the nitrogen atoms to which they are attached, define a radical
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- (4-ALKOXYPYRAN-4-YL) SUBSTITUTED ARYLALKYLARYL-, ARYLALKENYLARYL-, AND ARYLALKYNYLARYLUREA INHIBITORS OF 5-LIPOXYGENASE
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Compounds of the structure wherein W is selected from where Q is oxygen or sulfur, R6 and R7 are hydrogen or alkyl, or R6 and R7, together with the nitrogen atoms to which they are attached, define a radical of formulaR8 is selected from hydrogen, alkyl,
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