cas 138500-85-3, 4-(Bromomethyl)benzeneboronic acid pinacol ester

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Synthesis and Automated Labeling of [18F]Darapladib, a Lp-PLA2 Ligand, as Potential PET Imaging Tool of Atherosclerosis
Atherosclerosis and its associated clinical complications are major health issues in industrialized countries. Lipoprotein-associated phospholipase A2 (Lp-PLA2) was demonstrated to play an important role in atherogenesis and to be a
Guibbal, Florian,Meneyrol, Vincent,Ait-Arsa, Imade,Diotel, Nicolas,Patché, Jessica,Veeren, Bryan,Bénard, Sébastien,Gimié, Fanny,Yong-Sang, Jennyfer,Khantalin, Ilya,Veerapen, Reuben,Jestin, Emmanuelle,Meilhac, Olivier
p. 743 - 748
(2019)
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A Persulfide Donor Responsive to Reactive Oxygen Species: Insights into Reactivity and Therapeutic Potential
Persulfides (RSSH) have been hypothesized as critical components in sulfur-mediated redox cycles and as potential signaling compounds, similar to hydrogen sulfide (H2S). Hindering the study of persulfides is a lack of persulfide-donor compounds
Powell, Chadwick R.,Dillon, Kearsley M.,Wang, Yin,Carrazzone, Ryan J.,Matson, John B.
p. 6324 - 6328
(2018)
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A General Strategy Toward Highly Fluorogenic Bioprobes Emitting across the Visible Spectrum
A general approach toward highly fluorogenic probes across the visible spectrum for various analytes offers significant potential for engineering a wide range of bioprobes with diverse sensing and imaging functions. Here we show a facile and general strategy that involves introducing a new fluorogenic mechanism in boron dipyrromethene (BODIPY) dyes, based on the principle of stimuli-triggered dramatic reduction in the electron-withdrawing capabilities of the meso-substituents of BODIPYs. The fluorogenic mechanism has been demonstrated to be applicable in various BODIPYs with emission maxima ranging from green to far red (509, 585, and 660 nm), and the synthetic strategy allows access to a panel of highly fluorogenic bioprobes for various biomolecules and enzymes (H2O2, H2S, and protease) via introducing specific triggering motifs. The potency of the general design strategy is exemplified by its application to develop a mitochondria-targeting far-red probe capable of imaging of endogenous H2O2 in living cells.
Chen, Haoliang,He, Xiujing,Su, Meihui,Zhai, Wenhao,Zhang, Hao,Li, Changhua
p. 10157 - 10163
(2017)
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Inhibition of RANTES/CCR1-mediated chemotaxis by cosalane and related compounds
The anti-HIV agent cosalane and several of its analogues inhibited RANTES-induced migration of human monocytes, but they did not inhibit migration induced by MIP1α or MIP1β. RANTES-induced migration of single receptor CCR1-HEK transfectants was also inhib
Howard,Dong, Hui Fang,Oppenheim, Joost J.,Insaf, Shabana,Santhosh, Kalpathy C.,Paul, Gitendra,Cushman, Mark
p. 59 - 62
(2001)
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A Two-Photon Ratiometric Sensing Platform Based on Solid-State Luminescent Benzocoumarin: Application to Prolonged Bioimaging of Hydrogen Peroxide
Fluorescent probes provide essential tools for studying biological systems. For the prolonged imaging of cellular analytes, the fast clearance of small-molecular probes and products is a matter of concern in the quantitative analysis. Activatable probes that produce insoluble products inside cells can be used for prolonged imaging, but those with ratiometric imaging capability are rare. We disclose a novel sensing platform that is capable of prolonged imaging, in addition to ratiometric signaling for reliable quantitative analysis. Specifically, 3-(pyridin-4-yl)-8-(pyrrolidin-1-yl)-2H-benzo[g]chromen-2-one and its pyridinium salt as a product/probe couple constitute the ratiometric sensing platform. As the former dye produces highly emissive insoluble nanoaggregates inside cells, a fluorescent probe in the latter form enables prolonged imaging of the target analyte in cells as well as in tissue by two-photon microscopy.
Rim Kim, Hye,Sarkar, Sourav,Han Ahn, Kyo
(2022/01/22)

A synthetic route to 1-(4-boronobenzyl)-1H-pyrrole
The synthesis of 1-(4-boronobenzyl)-1H-pyrrole was investigated using three different routes. Two key routes that involved the introduction of the boronate group protected as the pinacol ester, failed, due to deprotection problems. The route involving the
D’Silva, Claudius
p. 655 - 659
(2021/02/26)

DRUG AND GENE THERAPY TO TREAT HIGH MYOPIA AND OTHER OCULAR DISORDERS WITH ENLARGED EYE GLOBES
This invention relates to a treatment of various eye conditions relating to eye enlargement. The conditions can be treated by inhibiting an upstream protein within the said biological pathway or by increasing the expression of a downstream receptor within
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(2021/12/29)

Thiourea-Mediated Halogenation of Alcohols
The halogenation of alcohols under mild conditions expedited by the presence of substoichiometric amounts of thiourea additives is presented. The amount of thiourea added dictates the pathway of the reaction, which may diverge from the desired halogenation reaction toward oxidation of the alcohol, in the absence of thiourea, or toward starting material recovery when excess thiourea is used. Both bromination and chlorination were highly efficient for primary, secondary, tertiary, and benzyl alcohols and tolerate a broad range of functional groups. Detailed electron paramagnetic resonance (EPR) studies, isotopic labeling, and other control experiments suggest a radical-based mechanism. The fact that the reaction is carried out at ambient conditions, uses ubiquitous and inexpensive reagents, boasts a wide scope, and can be made highly atom economic, makes this new methodology a very appealing option for this archetypical organic reaction.
Mohite, Amar R.,Phatake, Ravindra S.,Dubey, Pooja,Agbaria, Mohamed,Shames, Alexander I.,Lemcoff, N. Gabriel,Reany, Ofer
p. 12901 - 12911
(2020/11/26)

Camptothecin derivative and applications thereof
The invention provides a camptothecin derivative and applications in preparation of antitumor drugs, wherein the camptothecin derivative has the following general formula (I). According to the invention, the MTT experiment results show that the camptothecin derivative has cytotoxicity only under ROS conditions, and has low cytotoxicity in a ROS-free culture solution; and based on high ROS concentration in tumor tissue, the anti-tumor medicine prepared from the camptothecin derivative has the advantage of low toxicity.
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Paragraph 0060-0063

(2020/05/01)

RADIOLABELED DARAPLADIB AND ANALOGS THEREOF AND THEIR USE AS IMAGING COMPOUNDS
The present inventors have developed new radiolabeled Darapladib and analogs thereof which can be used for the specific detection of vulnerable atherosclerotic plaques by targeting lipoprotein-associated phospholipase A2 (Lp-PLA2) which is a biomarker of
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(2019/04/26)

Fructose-sensitive thermal transition behaviour of boronic ester-bearing telechelic poly(2-isopropyl-2-oxazoline)
Boronic ester-bearing telechelic poly(2-isopropyl-2-oxazoline) (B-PiPrOx-B) exhibited a hydrophilic-hydrophobic phase transition near human-body temperature in aqueous media. The thermal transition temperature of B-PiPrOx-B changed notably upon addition o
Lee, Jiyoung,Park, Jong Min,Jang, Woo-Dong
p. 3343 - 3346
(2019/04/02)

BODIPY-based high-sensitivity fluorescent probe and synthesis method and application thereof
The invention relates to a BODIPY-based high-sensitivity fluorescent probe and a synthesis method and application thereof. A structural general formula of the probe is shown as (I), wherein Trigger is stimulant triggering groups, R1 and R2 are groups for regulating and controlling fluorescent transmission wavelength of the probe and introducing organelle targeting, and R1 and R2 are defined in the description. By the probe, detection of different substrates can be realized without changing mother nucleus structure of the probe by only changing different Trigger groups. In addition, according to different needs on wavelength and targeting, the mother nucleus structure of the probe can be quickly modified. By changing R1 and R2, maximum fluorescent emission wavelength of the probe can be changed, and the probe can target mitochondrion to realize detection of active substances in the mitochondrion. The probe has good biocompatibility, thereby being applicable to detecting biological systems. Application value of the fluorescent probe in the aspect of detecting bioactive molecules and protease over-expressed in inflammatory or tumor tissue has potential social benefit and economic benefit.
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(2018/03/24)

AIE BIOPROBES EMITTING RED OR YELLOW FLUORESCENCE
The present subject matter relates to red emitting mitochondria-targeted aggregation induced emission (AIE) probes as an indicator for membrane potential and mouse sperm activity. The present subject matter relates to AIE-active fluorescent probes for reactive oxygen species (ROS) detection and related biological applications, such as inflammation imaging and glucose assay, as well as the preparation and application of red fluorescent AIEgens.
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(2017/02/09)

Photoswitchable azobenzene-appended iridium(III) complexes
Iridium(iii) cyclometalated complexes have been used as models to study the effect that extended conjugation and substitution pattern has on the photochromic behavior of azobenzene-appended 2-phenylpyridyl (ppy) ligands. For this purpose four azobenzene-containing ppy ligands were synthesized. With these ligands, nine iridium(iii) complexes containing up to three appended azobenzenes were synthesized. Analysis of their photochromic behaviour by means of UV-vis and 1H-NMR spectroscopy permitted us to conclude that the light-induced trans-to-cis isomerization of the azobenzene was strongly inhibited upon coordination to the Ir(iii) cation when the electronic conjugation was extended along the whole ligand. The use of an aliphatic spacer unit (either -CH2- or -OCH2-) between the azobenzene and the ppy fragment of the ligand sufficed to disrupt the electronic communication, and obtain photochromic organometallic complexes.
Pérez-Miqueo,Altube,García-Lecina,Tron,McClenaghan,Freixa
p. 13726 - 13741
(2016/09/09)

Synthesis of Pinacolylboronate-Substituted Stilbenes and their application to the synthesis of boron capped polyenes
A series of novel 4,4,5,5-tetramethyl-2-(4-substitutedstyrylphenyl)-1,3,2 dioxaborolane derivatives has been synthesized. 4-(4,4,5,5-tetramethyl-1,3,2-dioxaboratophenyl)-methyl triphenylphosphonium bromide (4) was treated with 3 equiv of tBuONa, various a
Das, Bhaskar C.,Mahalingam, Sakkarapalayam M.,Das, Sasmita,Hosmane, Narayan S.,Evans, Todd
p. 51 - 59
(2015/12/18)

Reactions of difluorocarbene with organozinc reagents
Reactions of difluorocarbene with benzyl and alkylzinc halides leading to fluorinated organozinc species have been described. The generated α-difluorinated organozinc reagents are reasonably stable in solution and can be quenched with external electrophiles (iodine, bromine, proton), affording compounds containing the CF2 fragment.
Levin, Vitalij V.,Zemtsov, Artem A.,Struchkova, Marina I.,Dilman, Alexander D.
p. 917 - 919
(2013/03/28)

DETECTION OF HYDROGEN PEROXIDE
The present invention provides compounds of formula (I), (II) or (III) wherein R1and R11are boronic acid or a borate ester useful for detection of hydrogen peroxide and methods of using same.
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Paragraph 0086

(2013/03/26)

LABELING COMPOUND FOR PET
A labeling compound of the present invention includes a structure represented by formula (1) wherein X1 is 11CH3, CH218F, CF218F, 18F, 76Br or 124/sup
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(2012/05/20)

Design and synthesis of boron containing potential pan-RAR inverse agonists
We designed and successfully synthesized the compounds 5 and 8 as potential pan-RAR (retinoic acid receptor) agonists. These two compounds were designed based on an existing pan-RAR agonist (BMS493). We synthesized compound 5, in which the carboxylic acid
Das, Bhaskar C.,Tang, Xiang-Ying,Evans, Todd
scheme or table
p. 1316 - 1318
(2012/04/04)

NOVEL LIPOGENIC INHIBITORS AND USES THEREOF
The present invention provides resveratrol-based boron-containing analog! methods of use thereof in treatment of dyslipidemias and cancer.
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(2012/09/10)

Design, synthesis and biological study of pinacolyl boronate-substituted stilbenes as novel lipogenic inhibitors
A pilot library of novel 4,4,5,5-tetramethyl-2-(4-substitutedstyrylphenyl)- 1,3,2 dioxaborolane derivatives has been synthesized. 4-(4,4,5,5-Tetramethyl-1, 3,2-dioxaboratophenyl)-methyl triphenylphosphonium bromide 3 was treated with various aldehydes in the presence of 3 equiv of tBuONa in DMF, and stirred at room temperature for 4-6 h to yield the corresponding boron-containing stilbene derivatives in 71-94% yields. Several of them, including BF102 and BF175, have the lipogenesis inhibitory effect by suppressing lipogenic gene expression in mammalian hepatocytes. Further, BF102 also inhibits cholesterol biosynthesis by suppressing HMG-CoA reductase gene expression in hepatocytes. Interestingly, our preliminary in vivo data suggests that BF102 has no significant toxicity in mice at the highest possible dose we can administered. Thus, BF102 is a potential lead for the next generation of lipid-lowering drugs.
Das, Bhaskar C.,Zhao, Xiaoping,Tang, Xiang-Ying,Yang, Fajun
scheme or table
p. 5638 - 5641
(2011/10/12)

Caged mitochondrial uncouplers that are released in response to hydrogen peroxide
Caged versions of the most common mitochondrial uncouplers (proton translocators) have been prepared that sense the reactive oxygen species (ROS) hydrogen peroxide to release the uncouplers 2,4-dinitrophenol (DNP) and carbonylcyanide p-trifluoromethoxyphenylhydrazone (FCCP) from caged states with second order rate constants of 10 (±0.8) M-1 s-1 and 64.8 (±0.6) M-1 s-1, respectively. The trigger mechanism involves conversion of an arylboronate into a phenol followed by fragmentation. Hydrogen peroxide-activated uncouplers may be useful for studying the biological process of ageing.
Quin, Caroline,Robertson, Linsey,McQuaker, Stephen J.,Price, Nicholas C.,Brand, Martin D.,Hartley, Richard C.
experimental part
p. 2384 - 2389
(2010/05/18)

A modular approach to catalytic synthesis using a dual-functional linker for Click and Suzuki coupling reactions
The stable benzylazido-boronate ester 1 is presented as an example of a dual-functional linker that allows the synthetically valuable boronate motif to be clicked onto other molecules under mild conditions. The utility of the azido-boronate motif as a modular building block is demonstrated in the rapid synthesis of drug-like structures employing sequential catalytic azide-alkyne cycloaddition and Suzuki coupling reactions.
White, James R.,Price, Gareth J.,Schiffers, Stefanie,Raithby, Paul R.,Plucinski, Pawel K.,Frost, Christopher G.
supporting information; experimental part
p. 3913 - 3917
(2010/08/22)

Towards control of dendrimer properties by reversible exchange of termini: Synthesis and characterization of diverse porphyrin dendrimers
Porphyrin dendrimers with boronic ester, aldehyde, and pyridil termini were synthesized and fully characterized. These dendrimers have the potential to change their physical and chemical properties by reversible alteration of the reactive terminal groups.
Shema-Mizrachi, Meital,Aharoni, Anna,Iliashevsky, Olga,Lemcoff
scheme or table
p. 1 - 8
(2010/04/05)

Design and synthesis of novel pinacolylboronate containing combretastatin 'antimitotic agent' analogues
We developed a procedure to synthesize pinacolyl boronate containing stilbene derivatives and used this procedure to synthesize boron-containing combretastatin analogues. The key step involves the Wittig reaction of the ylide 4-(4,4,5,5-tetramethyl-1,3,2-
Das, Bhaskar C.,Mahalingam, Sakkarapalayam M.,Evans, Todd
body text
p. 3031 - 3034
(2009/10/04)

Supramolecular assemblies of polyaniline through cooperative bundling by a palladium-complex-appended synthetic cross-linker
A synthetic cross-linker (1) bearing two binding sites for imine moieties in polyaniline has been used to organize polyaniline emeraldine base (EB) or polyaniline emeraldine salt (ES) into aligned assemblies. Complex 1 exhibited highly cooperative binding
Kaseyama, Takahiro,Takebayashi, Shinji,Wakabayashi, Rie,Shinkai, Seiji,Kaneko, Kenji,Takeuchi, Masayuki
experimental part
p. 12627 - 12635
(2010/06/16)

Efficient synthesis of valsartan, a nonpeptide angiotensin II receptor antagonist
A highly efficient and convergent approach to the synthesis of the angiotensin II receptor antagonist valsartan (1), one of the most important agents used in antihypertensive therapy today, is described. Directed ortho-metalation of 4-bromotoluene provides the key boronic acid intermediate 11 which was subjected to palladium-catalyzed Suzuki coupling. This method overcomes many of the drawbacks associated with the previously reported syntheses. The saponification of the methyl ester in valsartan was realized in a convenient and economical manner, which is more suitable for industrial production. Georg Thieme Verlag Stuttgart.
Zhang, Chen,Zheng, Guojun,Fang, Lijing,Li, Yulin
p. 475 - 477
(2007/10/03)

METHOD FOR THE PRODUCTION OF LOSARTAN
The invention relates to a novel method for the production of losartan, an imidazol derivative with the chemical name 2-n-butyl-4-chloro-5-hydroxymethyl-1-{[2'-(1H-tetrazol-5-yl)biphenyl-4-]methyl}imidazol and the pharmacologically active salts thereof. The invention also relates to novel intermediate products which are suitable for the production of losartan, and to novel methods for the production of intermediate compounds which are suitable for the production of losartan. One aspect of the invention is a method for the production of a compound of general formula (I), which can arise as an intermediate step in the inventive representation of losartan.
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(2008/06/13)

Five-membered heterocycles having biphenylsulfonyl substitution, with sulfonylcyanamide side chain, compositions containing them, and methods of using them
Five-membered heterocycles having biphenylsulfonyl substitution, process for their preparation, their use as a medicament or diagnostic, and medicament comprising them. Compounds of the formula I in which the symbols have the meanings indicated in the claims, have outstanding antiarrhythmic properties and exhibit a cardioprotective component. They can preventively inhibit or greatly decrease the pathophysiological processes in the formation of ischemically induced damage, in particular in the elicitation of ischemically induced cardiac arrhythmias. Moreover, they have a potent inhibitory action on the proliferation of cells.
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(2008/06/13)

Synthesis of some para-functionalized phenylboronic acid derivatives
Straightforward preparations of para-, carboxy-, hydroxymethyl- and bromo methyl phenylboronic acid derivatives from para-formyl-phenylboronic acid as a common precursor are presented.
De Filippis, Arnault,Morin, Christophe,Thimon, Christian
p. 2669 - 2676
(2007/10/03)