cas 14548-39-1, 6-Bromoindanone | Articles data

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Light-Modulated Self-Blockage of a Urea Binding Site in a Stiff-Stilbene Based Anion Receptor
Anion binding to a receptor based on stiff-stilbene, which is equipped with a urea hydrogen bond donating group and a phosphate or phosphinate hydrogen bond accepting group, can be controlled by light. In one photoaddressable state (E isomer) the urea binding site is available for binding, while in the other (Z isomer) it is blocked because of an intramolecular interaction with its hydrogen bond accepting motif. This intramolecular interaction is supported by DFT calculations and 1H NMR titrations reveal a significantly lower anion binding strength for the state in which anion binding is blocked. Furthermore, the molecular switching process has been studied in detail by UV/Vis and NMR spectroscopy. The presented approach opens up new opportunities toward the development of photoresponsive anion receptors.
de Jong, Jorn,Feringa, Ben L.,Wezenberg, Sander J.
p. 3306 - 3310
(2019)
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Synthesis and antitumor activity of aza-brazilan derivatives containing imidazolium salt pharmacophores
The synthesis of a series of novel aza-brazilan derivatives containing imidazolium salt pharmacophores is presented. The biological activity of such imidazolium salts was further evaluated in vitro against a panel of human tumor cell lines. The results suggest that the electron-withdrawing group on the aza-brazilan moiety, substituted 5,6-dimethyl-benzimidazole ring and substitution of the imidazolyl-3-position with a 4-methylbenzyl group were essential for modulating the cytotoxic activity. Compounds 55 and 39, bearing a 4-methylbenzyl substituent at position-3 of 5,6-dimethyl-benzimidazole, were found to be the most potent compounds with IC50 values of 0.52-1.30 μM and 0.56-1.51 μM against four human tumor cell lines investigated. Particularly, compound 57 exhibited inhibitory activity against the MCF-7 cell line with an IC50 value of 0.35 μM and was 56-fold more sensitive than DDP. Moreover, compound 55 inhibited cell proliferation through inducing G0/G1 cell cycle arrest and apoptosis in SMMC-7721 cells.
Huang, Mingqin,Duan, Shengzu,Ma, Xueqiong,Cai, Bicheng,Wu, Dongmei,Li, Yan,Li, Liang,Zhang, Hongbin,Yang, Xiaodong
supporting information
p. 1027 - 1036
(2019/06/27)

LIQUID CRYSTAL COMPOUND, LIQUID CRYSTAL COMPOSITION, AND LIQUID CRYSTAL DISPLAY DEVICE
PROBLEM TO BE SOLVED: To provide a liquid crystal compound, a liquid crystal composition, and a liquid crystal device using the compound or the composition. SOLUTION: The liquid crystal compound is represented by formula (I). In formula (I), R1 represents H, an alkyl having 1 to 10 carbon atoms, or the like; R2 represents an alkenyl having 2 to 10 carbon atoms or a fluoroalkenyl having 2 to 10 carbon atoms and one or two non-adjacent -CH2- in R2 is replaced by -O- or an ether having 2 to 10 carbon atoms; A1 to A4 each independently represent a formula below, where R3 independently represents H or a halogen; Z1 to Z3 each independently represents a sing bond, -CH2-, -CH2O-, -OCH2-, -CF=CF-, -COO-, -OCO-, -CF2O-, -OCF2-, -C≡C-, -CH=CH-, or the like; and n and m each independently represent 0 or 1. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0057

(2016/10/07)

Recyclable Hypervalent-Iodine-Mediated Dehydrogenative α,β′-Bifunctionalization of β-Keto Esters under Metal-Free Conditions
We have developed a method for recyclable hypervalent-iodine-mediated direct dehydrogenative α,β′- bifunctionalization of β-ketoesters and β-diketones under metal-free conditions, which affords a straightforward way to synthesize benzo-fused 2,3-dihydrofurans. This efficient, mild method, which has a wide substrate scope and good functional-group tolerance, was used for the multistep synthesis of the protected aglycone of a naturally occurring phenolic glycoside. A mechanism involving Michael addition to an enone intermediate and subsequent oxidative cyclization is proposed.
Duan, Ya-Nan,Cui, Li-Qian,Zuo, Lin-Hong,Zhang, Chi
supporting information
p. 13052 - 13057
(2015/09/07)

Synthesis of 1,3-diketones from 3-(4-R-phenyl)propionic acids
Self-acylation of 3-(4-R-phenyl)propionic acids (R = H, Br, 1-adamantyl) in trifluoroacetic anhydride catalyzed by trifluoromethanesulfonic acid provides a simple and efficient synthesis of 1,3-diketones. Indan-1-ones formed in the first step undergo acylation to give the corresponding 2-(3-phenyl-1-oxopropyl) indan-1-ones as the major products. One-pot synthesis of polysubstituted pyrazoles directly from 3-(4-R-phenyl)propionic acids is described.
Kim,Shokova,Tafeenko,Kovalev
p. 464 - 468
(2014/06/10)

Non-conventional methodologies in the synthesis of 1-indanones
1-Indanones have been successfully prepared by means of three different non-conventional techniques, namely microwaves, high-intensity ultrasound and a Q-tube reactor. A library of differently substituted 1-indanones has been prepared via one-pot intramolecular Friedel-Crafts acylation and their efficiency and "greenness" have been compared.
Oliverio, Manuela,Nardi, Monica,Costanzo, Paola,Cariati, Luca,Cravotto, Giancarlo,Giofre, Salvatore Vincenzo,Procopio, Antonio
p. 5599 - 5610
(2014/06/10)

(CF3CO)2O/CF3so3H-mediated synthesis of 1,3-diketones from carboxylic acids and aromatic ketones
A very simple and convenient reaction for 1,3-diketone preparation from carboxylic acids and aromatic ketones in TFAA/TfOH system is described. When the β-phenylpropionic acids were used as starting materials, they initially gave 1-indanones and then underwent further acylation with the formation of 2-(β-phenylpropionyl)-1-indanones as the main reaction products. In addition, the application of the proposed protocol allowed for the synthesis of selected polysubstituted pyrazoles in a one-pot procedure directly from acids and ketones.
Kim, JungKeun,Shokova, Elvira,Tafeenko, Victor,Kovalev, Vladimir
p. 2270 - 2278
(2014/12/11)

AROMATIC KETONE SYNTHESIS WITH AMIDE REAGENTS AND RELATED REACTIONS
A method of preparing an aryl carbonyl or aryl thiocarbonyl compound, comprises reacting an N-(nitroaryl)-amide or N-(nitroaryl)-thioamide with an aromatic ring, with a superacid catalyst, to produce the aryl carbonyl or aryl thiocarbonyl compound. The superacid is present in an amount of at most 8 equivalents in proportion to the N-(nitroaryl)-amide or N-(nitroaryl)-thioamide. A method of preparing aryl amide or aryl thioamide, comprises reacting an N-(nitroaryl)-carbamide or N-(nitroaryl)-thiocarbamide with an aromatic ring, with a superacid catalyst, to produce the aryl amide or aryl thioamide.
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Paragraph 0038-0039

(2013/10/22)

Catalytic asymmetric cross-dehydrogenative coupling: Activation of C-H bonds by a cooperative bimetallic catalyst system
A cooperative bimetallic catalyst system was applied in the catalytic asymmetric cross-dehydrogenative coupling of β-ketoesters and xanthene. Various optically active xanthene derivatives bearing a quaternary stereogenic carbon center were obtained in moderate to good yields (up to 90%) with excellent enantioselectivities (up to 99% ee). Meanwhile, a transition-state model was proposed to explain the origin of the asymmetric induction.
Cao, Weidi,Liu, Xiaohua,Peng, Ruixue,He, Peng,Lin, Lili,Feng, Xiaoming
supporting information
p. 3470 - 3472
(2013/05/23)

Friedel-crafts acylation with amides
Friedel-Crafts acylation has been known since the 1870s, and it is an important organic synthetic reaction leading to aromatic ketone products. Friedel-Crafts acylation is usually performed with carboxylic acid chlorides or anhydrides, while amides are generally not useful substrates in these reactions. Despite being the least reactive carboxylic acid derivative, we have found a series of amides capable of providing aromatic ketones in good yields (55-96%, 17 examples). We propose a mechanism involving diminished C-N resonance through superelectrophilic activation and subsequent cleavage to acyl cations.
Raja, Erum K.,Deschepper, Daniel J.,Nilsson Lill, Sten O.,Klumpp, Douglas A.
experimental part
p. 5788 - 5793
(2012/07/30)

INHIBITORS OF BETA-SECRETASE
The present invention is directed to a compound represented by the following structural formula or a pharmaceutically acceptable salt thereof. Pharmaceutical compositions and method of use of the compounds are also described.
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Page/Page column 77

(2010/10/03)

BICYCLO-SUBSTITUTED PYRAZOLON AZO DERIVATIVES, PREPARATION PROCESS AND PHARMACEUTICAL USE THEREOF
The bicyclo-substituted pyrazolon-azo derivatives of formula (I) or pharmaceutical acceptable salts, hydrates or solvates thereof, methods for their preparation, pharmaceutical compositions containing the same and their use as a therapeutic agent, especially as thrombopoietin (TPO) mimetics and their use as agonists of thrombopoietin receptor are disclosed. The definition of substituents in formula (I) are the same as defined in the description.
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Page/Page column 58

(2010/10/19)

7-PIPERIDINOALKYL-3,4-DIHYDROQUINOLONE DERIVATIVE
To provide a novel compound, a pharmaceutically acceptable salt or a hydrate thereof useful for preventing or treating for depression, anxiety disorders (such as generalized anxiety disorder, posttraumatic stress disorder, panic disorder, obsessive-compulsive disorder or social anxiety disorder), attention deficit disorder, mania, manic-depressive illness, schizophrenia, mood disorders, stress, sleep disorders, attacks, memory impairment, cognitive impairment, dementia, amnesia, delirium, obesity, eating disorder, appetite disorder, hyperphagia, bulimia, cibophobia, diabetes, cardiovascular diseases, hypertension, dyslipidemia, myocardial infarction, movement disorder (such as Parkinson's disease, epilepsy, convulsion or tremor), drug abuse, drug addiction or sexual dysfunction, based on a melanin-concentrating hormone receptor (MCH receptor) antagonistic action. SOLUTION A compound, a pharmaceutically acceptable salt or a hydrate thereof represented by the formula (I).
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Page/Page column 43

(2010/04/27)

SUBSTITUTED FLUOROETHYL UREAS AS ALPHA 2 ADRENERGIC AGENTS
Therapeutic compounds, and methods, compositions, and medicaments related thereto are disclosed herein.
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Page/Page column 20

(2008/12/04)

Efficient synthesis of halo indanones via chlorosulfonic acid mediated Friedel-Crafts cyclization of aryl propionic acids and their use in alkylation reactions
Several halo indanones were synthesized from benzyl Meldrum's acid derivatives in two steps. Although several Lewis acids are effective for the Friedel-Crafts ring-closing reaction on more electron-rich arenes, in the case of the electron-deficient arenes this chemistry is not efficient. Here it is reported that chlorosulfonic acid (used as solvent) is an efficient reagent for cyclization of electron-withdrawing arenes. These molecules are potentially useful for subsequent alkylation reactions. The selective alkylation of 5,7-dibromo indanone is demonstrated using Pd-catalyzed Grignard coupling to provide monoalkylated indanone in good yield.
Sharma, Anil K.,Subramani, Amutha V.,Gorman, Christopher B.
p. 389 - 395
(2007/10/03)

The discovery and synthesis of novel adenosine receptor (A2A) antagonists
In high throughput screening of our file compounds, a novel structure 1 was identified as a potent A2A receptor antagonist with no selectivity over the A1 adenosine receptor. The structure-activity relationship investigation using 1 as a template lead to identification of a novel class of compounds as potent and selective antagonists of A2A adenosine receptor. Compound 26 was identified to be the most potent A2A receptor antagonist (Ki = 0.8 nM) with 100-fold selectivity over the A1 adenosine receptor.
Matasi, Julius J.,Caldwell, John P.,Hao, Jinsong,Neustadt, Bernard,Arik, Leyla,Foster, Carolyn J.,Lachowicz, Jean,Tulshian, Deen B.
p. 1333 - 1336
(2007/10/03)

DISUBSTITUTED CHALCONE OXIMES HAVING RARγ RETINOID RECEPTOR ANTAGONIST ACTIVITY
Compounds of the formula where the variables have the values described in the specification are antagonists of RARγ retinoid receptors.
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Page/Page column 27-28

(2008/06/13)

TRICYCLIC PYRAZOLE KINASE INHIBITORS
Compounds of the present invention are useful for inhibiting protein tyrosine kinases. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.
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Page/Page column 55

(2008/06/13)

Fused tricyclic compounds as inhibitors of 17beta-hydroxysteroid dehydrogenase 3
Fused tricyclic compounds, methods of using such compounds in the treatment of hormone sensitive diseases such as prostate cancer, and pharmaceutical compositions containing such compounds.
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Page/Page column 22

(2010/02/14)

Indanylidenes. 1. Design and synthesis of (E)-2-(4,6-difluoro-1-indanylidene)acetamide, a potent, centrally acting muscle relaxant with antiinflammatory and analgesic activity
The design of rigid cyclic analogues derived from cinnamamide 1, (E)-N-cyclopropyl-3-(3-fluorophenyl)prop-2-enamide, and β-methylcinnamamide 2, (E)-N-cyclopropyl-3-(3-fluorophenyl)but-2-enamide, has led to the discovery of the potent, centrally acting muscle relaxant (E)-2-(4,6-difluoro-1-indanylidene)acetamide, 17. Compound 17 also possesses potent antiinflammatory and analgesic activity. This paper describes the synthesis and the muscle relaxant, antiinflammatory, and analgesic structure-activity relationships of 17 and 67 of its analogues. Compound 17 has been taken into phase I clinical trials.
Musso, David L.,Cochran, Felicia R.,Kelley, James L.,McLean, Ed W.,Selph, Jeffrey L.,Rigdon, Greg C.,Orr, G. Faye,Davis, Ronda G.,Cooper, Barrett R.,Styles, Virgil L.,Thompson, James B.,Hall, William R.
p. 399 - 408
(2007/10/03)

Stereochemical and mechanistic aspects of dioxygenase-catalysed benzylic hydroxylation of indene and chromane substrates
Toluene dioxygenase (TDO)-catalysed benzylic hydroxylation of indene substrates (8, 16 and 17), using whole cell cultures of Pseudomonas putida UV4, was found to yield inden-1-ol (14 and 223) and indan-1-one bioproducts (15 and 23). The formation of these bioproducts is consistent with the involvement of carbon-centred radical intermediates. TDO-catalysed oxidation of indenes 8 and 16 also gave cis-diols 13 and 18 respectively. TDO and naphthalene dioxygenase (NDO), used as both whole-cell preparation and as purified enzymes, were found to catalyse the benzylic hydroxylation of chromane 30, deuteriated (±)-chromane 30D and enantiomers (4S)-30D and (4R)-30D to yield (4R)- and (4S)-chroman-4-ols 31/31D respectively. The mechanism of benzylic hydroxylation of chromane 30/30D involves the stereoselective abstraction of a pro-R (with TDO) or a pro-S (with NDO) hydrogen atom at C-4 and a marked preference for retention of configuration.
Boyd, Derek R.,Sharma, Narain D.,Bowers, Nigel I.,Boyle, Rosemary,Harrison, John S.,Lee, Kyoung,Bugg, Timothy D.H.,Gibson, David T.
p. 1298 - 1307
(2007/10/03)

Indenyl compounds for the polymerization of olefins
Indenyl compound of formula (1) wherein: M is a transition metal from the lanthanides or from group 3, 4, 5 or 6 of the Periodic System of Elements, Q is an anionic ligand to M, k is the number of Q groups, R is a bridging group and Z and X are substituents, wherein R contains at least one sp2-hybridized carbon atom that is bonded to the indenyl group at the 2-position with the exclusion of Ti(deshydronorbiphenacene) dichloride.
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Example II

(2010/01/30)

Synthesis of new C3h and C3v truxene derivatives
Palladium-catalyzed cross coupling of 2,7,12-tribromotruxene with organostannanes and boronic acids leads to 2,7,12-trisubstituted truxenes. 5,10,15-Tdarylated and trialkynylated truxene derivatives are obtained by the reaction of truxenone with aryl Grignard reagents or an alkynyllithium, followed by reduction of the tertiary alcohols with Et3SiH or BF3. syn-5,10,15-Triarylated derivatives were obtained by the base-catalyzed isomerization of the anti derivatives.
Go?mez-Lor, Berta,De Frutos, O?scar,Ceballos, Pla?cido A.,Granier, Thierry,Echavarren, Antonio M.
p. 2107 - 2114
(2007/10/03)

2-AMINOINDANS AS SELECTIVE DOPAMINE D3 LIGANDS
Compounds and their pharmaceutically acceptable salts suitable for treating central nervous system disorders associated with the dopamine D3 receptor activity of Formula I: wherein R 1 and R 2 are independently H, C 1-8 alkyl or C 1-8 alkylAryl; X is CH 2 R. sub.3 or NHSO 2 R 4 ; Y is hydrogen, CH 2 R 3, NHSO. sub. 2 R 4, CONR 1 R 2, SO 2 NR 1 R 2, SO 2 CH. sub.3, halogen, OSO 2 CF 3, SCH 3 or OCH 3 ; R 3 is NHSO 2 R 4, SO 2 R 4, CONR 1 R 2 or Aryl; and R. sub.4 is NR 1 R 2, C 1-C 8 alkyl, Aryl or C 1-C. sub.8 alkylAryl.
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(2008/06/13)

1-arylsulphonyl, arylcarbonyl and arylthiocarbonyl pyridazino derivatives and methods of preparation
1-Arylsulphonyl, arylcarbonyl and arylthiocarbonyl pyridazino derivatives and processes for making said derivatives are described. The novel derivatives are non-steroidal heterocyclic compounds which act as selective progestins and/or antiprogestins having a high in-vitro affinity for either the uterine, breast or bone progestin receptor. As such, the non-steroidal heterocyclic derivatives are useful in contraception, menopause, osteoporosis or endometriosis.
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(2008/06/13)

A convenient synthesis of mono- and polyhalogenated benzocyclanones
Benzocyclanones were mono- or dihalogenated on the aromatic ring with elemental halogen or N-halosuccinimide without solvent in an aluminum chloride slurry in good yield. This process is the most direct method for the synthesis of 5- or 7-halo, or 5,7-dihalotetralones and can be extended to indan-1-ones and benzocycloheptan-1-ones as well as to trihalogenated and to mixed halogenated products.
Cornelius,Combs
p. 2777 - 2788
(2007/10/02)

Synthesis of Biological Markers in Fossil Fuels. 2. Synthesis and 13C NMR Studies of Substituted Indans and Tetralins
Unambiguous syntheses of all possible methyl, ethyl, n-propyl, and n-butyl derivatives of indan and tetralin were developed using the Kumada coupling procedure involving the reaction of aryl or vinyl halides with Grignard reagents in the presence of nickel(II) chloride.An analysis of the 13C NMR spectra of these compounds was also completed.
Adamczyk, Maciej,Watt, David S.,Netzel, Daniel A.
p. 4226 - 4237
(2007/10/02)

Hydrocarbures arylaliphatiques. Partie VII. Orientation dans la reaction de bromation de benzocyclenes bi- et tricycliques superieurs
The bromination of 1,2,3-trimethylbenzene, and bi- and tricyclic fused ring systems (i.e. indan, tetralin, benzosuberan, 2a,3,4,5-tetrahydroacenaphthen and higher homologues) is described in this paper.This work is part of a research project studying the ring size influence of peri-fused semi-aromatic ring system on benzene reactivity.This study was started in a first step on acetylation and was continued on bromination.Forthcoming studies (now underway) concern the kinetic measurement of protodesilylation of univocal silyl derivatives.The synthesis of the starting bromo derivatives used for this latter study is described here.These bromides were used for the attribution via NMR spectroscopy of the electrophile reaction site in the direct bromination of the fused ring unsymmetrical systems (the reactive sites are obvious in symmetrical molecules). Thus, meta substitution is predominant in the case of tetraline and benzosuberan, but ortho substitution is relatively more important in tetralin.In 1,2,3-trimethylbenzene and the fused tricyclic compounds, substitution takes place in an ortho position respective to the substituent or the ring system, the meta position being totally deactivated.In the special case of a five-membered ring, the ortho position this ring is always non reactive.The reactivity differences between these compounds are explained by hyper conjugation and the stabilities of the transition states.
Gruber, Rene,Cagniant, Denise,Cagniant, Paul
p. 96 - 104
(2007/10/02)