Co-reporter:Marine Z. C. Hatit, Ciaran P. Seath, Allan J. B. Watson, and Glenn A. Burley
The Journal of Organic Chemistry May 19, 2017 Volume 82(Issue 10) pp:5461-5461
Publication Date(Web):April 28, 2017
DOI:10.1021/acs.joc.7b00545
A method for conditional control of orthogonal sequential Cu-catalyzed azide−alkyne cycloaddition (CuAAC) reactions is reported. The inherent reactivity of an aromatic ynamine is controlled by a silyl protecting group that allows the selective CuAAC reaction of less reactive alkynes. Alternatively, the same protected ynamine undergoes selective CuAAC reaction via silyl deprotection in situ to give the ynamine click products. This allows complete orthogonal control of dialkyne systems and provides a unifying strategy for chemoselective CuAAC ligations in multialkyne/azide systems.
Co-reporter:Thomas A. Clohessy, Alastair Roberts, Eric S. Manas, Vipulkumar K. Patel, Niall A. Anderson, and Allan J. B. Watson
Organic Letters December 1, 2017 Volume 19(Issue 23) pp:6368-6368
Publication Date(Web):November 14, 2017
DOI:10.1021/acs.orglett.7b03214
Functionalized bicyclic amino-azaheterocycles are rapidly accessed in a one-pot cross-coupling/reduction sequence enabled by the use of COware. Incompatible reagents are physically separated in a single reaction vessel to effect two chemoselective transformations—Suzuki–Miyaura cross-coupling and heteroarene reduction. The developed method allows access to novel heterocyclic templates, including semisaturated Hedgehog and dual PI3K/mTOR inhibitors, which show enhanced physicochemical properties compared to their unsaturated counterparts.
Co-reporter:Lisa M. Miller, John M. Pritchard, Simon J. F. Macdonald, Craig Jamieson, and Allan J. B. Watson
Journal of Medicinal Chemistry April 27, 2017 Volume 60(Issue 8) pp:3241-3241
Publication Date(Web):January 30, 2017
DOI:10.1021/acs.jmedchem.6b01711
The RGD integrins are recognized therapeutic targets for thrombosis, fibrosis, and cancer, among others. Current inhibitors are designed to mimic the tripeptide sequence (arginine–glycine–aspartic acid) of the natural ligands; however, the RGD-mimetic antagonists for αIIbβ3 have been shown to cause partial agonism, leading to the opposite pharmacological effect. The challenge of obtaining oral activity and synthetic tractability with RGD-mimetic molecules, along with the issues relating to pharmacology, has left integrin therapeutics in need of a new strategy. Recently, a new generation of inhibitor has emerged that lacks the RGD-mimetic. This review will discuss the discovery of these non-RGD-mimetic inhibitors and the progress that has been made in this promising new chemotype.
Co-reporter:John J. Molloy;Thomas A. Clohessy;Craig Irving;Niall A. Anderson;Guy C. Lloyd-Jones
Chemical Science (2010-Present) 2017 vol. 8(Issue 2) pp:1551-1559
Publication Date(Web):2017/01/30
DOI:10.1039/C6SC04014D
We report the direct chemoselective Brown-type oxidation of aryl organoboron systems containing two oxidizable boron groups. Basic biphasic reaction conditions enable selective formation and phase transfer of a boronic acid trihydroxyboronate in the presence of boronic acid pinacol (BPin) esters, while avoiding speciation equilibria. Spectroscopic investigations validate a base-promoted phase-selective discrimination of organoboron species. This phenomenon is general across a broad range of organoboron compounds and can also be used to invert conventional protecting group strategies, enabling chemoselective oxidation of BMIDA species over normally more reactive BPin substrates. We also demonstrate the selective oxidation of diboronic acid systems with chemoselectivity predictable a priori. The utility of this method is exemplified through the development of a chemoselective oxidative nucleophile coupling.
Co-reporter:Lisa M. Miller, Willem-Jan Keune, Diana Castagna, Louise C. Young, Emma L. Duffy, Frances Potjewyd, Fernando Salgado-Polo, Paloma Engel García, Dima Semaan, John M. Pritchard, Anastassis Perrakis, Simon J. F. Macdonald, Craig JamiesonAllan J. B. Watson
Journal of Medicinal Chemistry 2017 Volume 60(Issue 2) pp:
Publication Date(Web):December 16, 2016
DOI:10.1021/acs.jmedchem.6b01597
Autotaxin (ATX) is a secreted enzyme responsible for the hydrolysis of lysophosphatidylcholine (LPC) to the bioactive lysophosphatidic acid (LPA) and choline. The ATX-LPA signaling pathway is implicated in cell survival, migration, and proliferation; thus, the inhibition of ATX is a recognized therapeutic target for a number of diseases including fibrotic diseases, cancer, and inflammation, among others. Many of the developed synthetic inhibitors for ATX have resembled the lipid chemotype of the native ligand; however, a small number of inhibitors have been described that deviate from this common scaffold. Herein, we report the structure–activity relationships (SAR) of a previously reported small molecule ATX inhibitor. We show through enzyme kinetics studies that analogues of this chemotype are noncompetitive inhibitors, and by using a crystal structure with ATX we confirm the discrete binding mode.
Co-reporter:Chao Xu;James W. B. Fyfe;Ciaran P. Seath;Steven H. Bennett
Chemical Communications 2017 vol. 53(Issue 65) pp:9139-9142
Publication Date(Web):2017/08/10
DOI:10.1039/C7CC05416E
A chemoselective tandem reaction of a multi-reactive, two electrophile + two nucleophile, system is reported. An allylation/cross-coupling process of a haloaryl aldehyde, an aryl BPin, and an allyl BPin can be controlled using a temperature gradient to overcome natural reactivity profiles and allow two sequential chemoselective C–C bond formations without intervention. This process offers efficient access to an array of functionalised products including pharmaceutical and natural product scaffolds.
Co-reporter:James W.B. Fyfe, Allan J.B. Watson
Chem 2017 Volume 3, Issue 1(Volume 3, Issue 1) pp:
Publication Date(Web):13 July 2017
DOI:10.1016/j.chempr.2017.05.008
Organoboron reagents have been synonymous with organic chemistry for over half a century and continue to see widespread application today; for example, classic reactions such as hydroboration and Suzuki-Miyaura cross-coupling are regularly practiced throughout the chemical community. In particular, applications of organoboron compounds have underpinned pharmaceutical and agrochemical development on both discovery and process scales for decades. Although it is noteworthy that these seminal reactions have stood the test of time, continually increasing pressure to improve efficiency in chemical synthesis demands innovation. Over the past few years, through an explosion in the number of new methods for the installation and manipulation of organoboron functional groups, as well as the understanding of their mechanistic operation, organoboron chemistry has risen to this challenge.Organoboron reagents are one of the most widely studied and applied classes of reagent throughout organic synthesis and catalysis. Not only are these reagents integral to many of the fundamental methods in the organic chemists toolbox, but they continue to be pivotal in the development of novel chemistries. This review covers selected advances in organoboron chemistry in recent years by focusing on both advances in methods for the installation of boron functional groups and the development of new methodologies based on organoboron reagents.Download high-res image (137KB)Download full-size image
Co-reporter:Kirsty L. Wilson, Jane Murray, Helen F. Sneddon, Katherine M.P. Wheelhouse, Allan J.B. Watson
Chem 2017 Volume 3, Issue 3(Volume 3, Issue 3) pp:
Publication Date(Web):14 September 2017
DOI:10.1016/j.chempr.2017.08.014
The chemical industry is under pressure to increase the sustainability of its operations. Key focus areas include the use of more resource-efficient bond-forming methods and replacements for hazardous solvents. In this Synergy article, we discuss the potential benefits of using sustainable solvents in academic method development.
Co-reporter:Marine Z. C. Hatit, Joanna C. Sadler, Liam A. McLean, Benjamin C. Whitehurst, Ciaran P. Seath, Luke D. Humphreys, Robert J. Young, Allan J. B. Watson, and Glenn A. Burley
Organic Letters 2016 Volume 18(Issue 7) pp:1694-1697
Publication Date(Web):March 22, 2016
DOI:10.1021/acs.orglett.6b00635
Aromatic ynamines or N-alkynylheteroarenes are highly reactive alkyne components in Cu-catalyzed Huisgen [3 + 2] cycloaddition (“click”) reactions. This enhanced reactivity enables the chemoselective formation of 1,4-triazoles using the representative aromatic ynamine N-ethynylbenzimidazole in the presence of a competing aliphatic alkyne substrate. The unique chemoselectivity profile of N-ethynylbenzimidazole is further demonstrated by the sequential click ligation of a series of highly functionalized azides using a heterobifunctional diyne, dispelling the need for alkyne protecting groups.
Co-reporter:Allan J. B. Watson and James R. Frost
Chemical Communications 2016 vol. 52(Issue 59) pp:9173-9177
Publication Date(Web):04 Jul 2016
DOI:10.1039/C6CC90302A
A graphical abstract is available for this content
Co-reporter:Ciaran P. Seath, Kirsty L. Wilson, Angus Campbell, Jenna M. Mowat and Allan J. B. Watson
Chemical Communications 2016 vol. 52(Issue 56) pp:8703-8706
Publication Date(Web):16 Jun 2016
DOI:10.1039/C6CC04554E
A one-pot cascade reaction for the synthesis of 2-BMIDA 6,5-bicyclic heterocycles has been developed using Cu(I)/Pd(0)/Cu(II) catalysis. 2-Iodoanilines and phenols undergo a Cu(I)/Pd(0)-catalyzed Sonogashira reaction with ethynyl BMIDA followed by in situ Cu(II)-catalyzed 5-endo-dig cyclization to generate heterocyclic scaffolds with a BMIDA functional group in the 2-position. The method provides efficient access to borylated indoles, benzofurans, and aza-derivatives, which can be difficult to access through alternative methods.
Co-reporter:Diana Castagna; David C. Budd; Simon J. F. Macdonald; Craig Jamieson
Journal of Medicinal Chemistry 2016 Volume 59(Issue 12) pp:5604-5621
Publication Date(Web):January 8, 2016
DOI:10.1021/acs.jmedchem.5b01599
The autotaxin–lysophophatidic acid (ATX–LPA) signaling pathway is implicated in a variety of human disease states including angiogenesis, autoimmune diseases, cancer, fibrotic diseases, inflammation, neurodegeneration, and neuropathic pain, among others. As a result, ATX–LPA has become of significant interest within both the industrial and the academic communities. This review aims to provide a concise overview of the development of novel ATX inhibitors, including the disclosure of the first ATX clinical trial data.
Co-reporter:Julien C. Vantourout, Robert P. Law, Albert Isidro-Llobet, Stephen J. Atkinson, and Allan J. B. Watson
The Journal of Organic Chemistry 2016 Volume 81(Issue 9) pp:3942-3950
Publication Date(Web):April 5, 2016
DOI:10.1021/acs.joc.6b00466
The Chan–Evans–Lam reaction is a valuable C–N bond forming process. However, aryl boronic acid pinacol (BPin) ester reagents can be difficult coupling partners that often deliver low yields, in particular in reactions with aryl amines. Herein, we report effective reaction conditions for the Chan–Evans–Lam amination of aryl BPin with alkyl and aryl amines. A mixed MeCN/EtOH solvent system was found to enable effective C–N bond formation using aryl amines while EtOH is not required for the coupling of alkyl amines.
Co-reporter:Calum W. Muir, Julien C. Vantourout, Albert Isidro-Llobet, Simon J. F. Macdonald, and Allan J. B. Watson
Organic Letters 2015 Volume 17(Issue 24) pp:6030-6033
Publication Date(Web):December 3, 2015
DOI:10.1021/acs.orglett.5b03030
Formal homologation of sp2-hybridized boronic acids is achieved via cross-coupling of boronic acids with conjunctive haloaryl BMIDA components in the presence of a suitably balanced basic phase. The utility of this approach to provide a platform for diversity-oriented synthesis in discovery medicinal chemistry is demonstrated in the context of the synthesis of a series of analogues of a BET bromodomain inhibitor.
Co-reporter:John J. Molloy, Robert P. Law, James W. B. Fyfe, Ciaran P. Seath, David J. Hirst and Allan J. B. Watson
Organic & Biomolecular Chemistry 2015 vol. 13(Issue 10) pp:3093-3102
Publication Date(Web):21 Jan 2015
DOI:10.1039/C5OB00078E
A modular synthesis of functionalised biaryl phenols from two boronic acid derivatives has been developed via one-pot Suzuki–Miyaura cross-coupling, chemoselective control of boron solution speciation to generate a reactive boronic ester in situ, and oxidation. The utility of this method has been further demonstrated by application in the synthesis of drug molecules and components of organic electronics, as well as within iterative cross-coupling.
Co-reporter:Diana Castagna, Emma L. Duffy, Dima Semaan, Louise C. Young, John M. Pritchard, Simon J. F. Macdonald, David C. Budd, Craig Jamieson and Allan J. B. Watson
MedChemComm 2015 vol. 6(Issue 6) pp:1149-1155
Publication Date(Web):08 May 2015
DOI:10.1039/C5MD00081E
Three novel series were generated in order to mimic the pharmacophoric features displayed by lead compound AM095, a lysophosphatidic acid (LPA1) receptor antagonist. Biological evaluation of this array of putative LPA1antagonists led us to the discovery of three novel series of inhibitors of the ectoenzyme autotaxin (ATX), responsible for LPA production in blood, with potencies in the range of 1–4 μM together with good (>100 μg mL−1) solubility.
Co-reporter:Diana Castagna, Emma L. Duffy, Dima Semaan, Louise C. Young, John M. Pritchard, Simon J. F. Macdonald, David C. Budd, Craig Jamieson and Allan J. B. Watson
MedChemComm 2015 vol. 6(Issue 8) pp:1575-1575
Publication Date(Web):07 Jul 2015
DOI:10.1039/C5MD90032H
Correction for ‘Identification of a novel class of autotaxin inhibitors through cross-screening’ by Diana Castagna et al., Med. Chem. Commun., 2015, 6, 1149–1155.
Co-reporter:Ciaran P. Seath;James W. B. Fyfe;John J. Molloy ;Dr. Allan J. B. Watson
Angewandte Chemie 2015 Volume 127( Issue 34) pp:10114-10117
Publication Date(Web):
DOI:10.1002/ange.201504297
Abstract
Control of boronic acid speciation is presented as a strategy to achieve nucleophile chemoselectivity in the Suzuki–Miyaura reaction. Combined with simultaneous control of oxidative addition and transmetalation, this enables chemoselective formation of two CC bonds in a single operation, providing a method for the rapid preparation of highly functionalized carbogenic frameworks.
Co-reporter:Ciaran P. Seath;James W. B. Fyfe;John J. Molloy ;Dr. Allan J. B. Watson
Angewandte Chemie International Edition 2015 Volume 54( Issue 34) pp:9976-9979
Publication Date(Web):
DOI:10.1002/anie.201504297
Abstract
Control of boronic acid speciation is presented as a strategy to achieve nucleophile chemoselectivity in the Suzuki–Miyaura reaction. Combined with simultaneous control of oxidative addition and transmetalation, this enables chemoselective formation of two CC bonds in a single operation, providing a method for the rapid preparation of highly functionalized carbogenic frameworks.
Co-reporter:James W. B. Fyfe;Elena Valverde;Ciaran P. Seath;Dr. Alan R. Kennedy;Dr. Joanna M. Redmond;Dr. Niall A. Anderson;Dr. Allan J. B. Watson
Chemistry - A European Journal 2015 Volume 21( Issue 24) pp:8951-8964
Publication Date(Web):
DOI:10.1002/chem.201500970
Abstract
Boronic acid solution speciation can be controlled during the Suzuki–Miyaura cross-coupling of haloaryl N-methyliminodiacetic acid (MIDA) boronic esters to enable the formal homologation of boronic acid derivatives. The reaction is contingent upon control of the basic biphase and is thermodynamically driven: temperature control provides highly chemoselective access to either BMIDA adducts at room temperature or boronic acid pinacol ester (BPin) products at elevated temperature. Control experiments and solubility analyses have provided some insight into the mechanistic operation of the formal homologation process.
Co-reporter:Fiona I. McGonagle, Helen F. Sneddon, Craig Jamieson, and Allan J. B. Watson
ACS Sustainable Chemistry & Engineering 2014 Volume 2(Issue 3) pp:523
Publication Date(Web):December 2, 2013
DOI:10.1021/sc4004532
The concept of molar efficiency is introduced as a new metric to enable assessment of reaction efficiency in discovery medicinal chemistry. Calculations from molar units enable cross-comparison of the broad range of transformations employed in discovery-phase medicinal chemistry research and is proposed to facilitate identification of more sustainable synthetic transformations.Keywords: Discovery medicinal chemistry; Metrics; reaction efficiency
Co-reporter:James W. B. Fyfe;Ciaran P. Seath ;Dr. Allan J. B. Watson
Angewandte Chemie 2014 Volume 126( Issue 45) pp:12273-12276
Publication Date(Web):
DOI:10.1002/ange.201406714
Abstract
Control of boronic acid solution speciation is presented as a new strategy for the chemoselective synthesis of boronic esters. Manipulation of the solution equilibria within a cross-coupling milieu enables the formal homologation of aryl and alkenyl boronic acid pinacol esters. The generation of a new, reactive boronic ester in the presence of an active palladium catalyst also facilitates streamlined iterative catalytic CC bond formation and provides a method for the controlled oligomerization of sp2-hybridized boronic esters.
Co-reporter:James W. B. Fyfe;Ciaran P. Seath ;Dr. Allan J. B. Watson
Angewandte Chemie International Edition 2014 Volume 53( Issue 45) pp:12077-12080
Publication Date(Web):
DOI:10.1002/anie.201406714
Abstract
Control of boronic acid solution speciation is presented as a new strategy for the chemoselective synthesis of boronic esters. Manipulation of the solution equilibria within a cross-coupling milieu enables the formal homologation of aryl and alkenyl boronic acid pinacol esters. The generation of a new, reactive boronic ester in the presence of an active palladium catalyst also facilitates streamlined iterative catalytic CC bond formation and provides a method for the controlled oligomerization of sp2-hybridized boronic esters.
Co-reporter:Donna S. MacMillan, Jane Murray, Helen F. Sneddon, Craig Jamieson and Allan J. B. Watson
Green Chemistry 2013 vol. 15(Issue 3) pp:596-600
Publication Date(Web):19 Dec 2012
DOI:10.1039/C2GC36900A
A range of alternative solvents have been evaluated within amidation reactions employing common coupling reagents with a view to identifying suitable replacements for dichloromethane and N,N-dimethylformamide.
Co-reporter:Fiona I. McGonagle, Donna S. MacMillan, Jane Murray, Helen F. Sneddon, Craig Jamieson and Allan J. B. Watson
Green Chemistry 2013 vol. 15(Issue 5) pp:1159-1165
Publication Date(Web):09 Apr 2013
DOI:10.1039/C3GC40359A
A range of alternative, more environmentally conservative solvents have been evaluated for use within the direct reductive amination reactions of aldehydes using borane-based reductants. The data generated has been used to develop a guide to facilitate replacement of less desirable chlorinated solvents, such as DCE, from these widely used synthetic processes.
Co-reporter:Calum W. Muir, Alan R. Kennedy, Joanna M. Redmond and Allan J. B. Watson
Organic & Biomolecular Chemistry 2013 vol. 11(Issue 20) pp:3337-3340
Publication Date(Web):26 Mar 2013
DOI:10.1039/C3OB40578H
4H-Quinolizin-4-ones are a unique class of heterocycle with valuable physicochemical properties and which are emerging as key pharmacophores for a range of biological targets. A tandem Horner–Wadsworth–Emmons olefination/cyclisation method has been developed to allow facile access to substituted 4H-quinolizin-4-ones encoded with a range of functional groups.
Co-reporter:Donna S. MacMillan, Jane Murray, Helen F. Sneddon, Craig Jamieson and Allan J. B. Watson
Green Chemistry 2012 vol. 14(Issue 11) pp:3016-3019
Publication Date(Web):02 Oct 2012
DOI:10.1039/C2GC36378J
Replacement of dichloromethane as the bulk medium within chromatographic purification has been evaluated with a broad range of molecules containing functionality common within Medicinal Chemistry programmes. Analysis of the data set has generated a set of general guidelines to assist in the selection of alternative solvents for CH2Cl2 as the bulk media in these ubiquitously employed processes.
Co-reporter:John J. Molloy, Robert P. Law, James W. B. Fyfe, Ciaran P. Seath, David J. Hirst and Allan J. B. Watson
Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 10) pp:NaN3102-3102
Publication Date(Web):2015/01/21
DOI:10.1039/C5OB00078E
A modular synthesis of functionalised biaryl phenols from two boronic acid derivatives has been developed via one-pot Suzuki–Miyaura cross-coupling, chemoselective control of boron solution speciation to generate a reactive boronic ester in situ, and oxidation. The utility of this method has been further demonstrated by application in the synthesis of drug molecules and components of organic electronics, as well as within iterative cross-coupling.
Co-reporter:Ciaran P. Seath, Kirsty L. Wilson, Angus Campbell, Jenna M. Mowat and Allan J. B. Watson
Chemical Communications 2016 - vol. 52(Issue 56) pp:NaN8706-8706
Publication Date(Web):2016/06/16
DOI:10.1039/C6CC04554E
A one-pot cascade reaction for the synthesis of 2-BMIDA 6,5-bicyclic heterocycles has been developed using Cu(I)/Pd(0)/Cu(II) catalysis. 2-Iodoanilines and phenols undergo a Cu(I)/Pd(0)-catalyzed Sonogashira reaction with ethynyl BMIDA followed by in situ Cu(II)-catalyzed 5-endo-dig cyclization to generate heterocyclic scaffolds with a BMIDA functional group in the 2-position. The method provides efficient access to borylated indoles, benzofurans, and aza-derivatives, which can be difficult to access through alternative methods.
Co-reporter:Calum W. Muir, Alan R. Kennedy, Joanna M. Redmond and Allan J. B. Watson
Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 20) pp:NaN3340-3340
Publication Date(Web):2013/03/26
DOI:10.1039/C3OB40578H
4H-Quinolizin-4-ones are a unique class of heterocycle with valuable physicochemical properties and which are emerging as key pharmacophores for a range of biological targets. A tandem Horner–Wadsworth–Emmons olefination/cyclisation method has been developed to allow facile access to substituted 4H-quinolizin-4-ones encoded with a range of functional groups.
Co-reporter:Allan J. B. Watson and James R. Frost
Chemical Communications 2016 - vol. 52(Issue 59) pp:NaN9177-9177
Publication Date(Web):2016/07/04
DOI:10.1039/C6CC90302A
A graphical abstract is available for this content
Co-reporter:John J. Molloy, Thomas A. Clohessy, Craig Irving, Niall A. Anderson, Guy C. Lloyd-Jones and Allan J. B. Watson
Chemical Science (2010-Present) 2017 - vol. 8(Issue 2) pp:NaN1559-1559
Publication Date(Web):2016/10/27
DOI:10.1039/C6SC04014D
We report the direct chemoselective Brown-type oxidation of aryl organoboron systems containing two oxidizable boron groups. Basic biphasic reaction conditions enable selective formation and phase transfer of a boronic acid trihydroxyboronate in the presence of boronic acid pinacol (BPin) esters, while avoiding speciation equilibria. Spectroscopic investigations validate a base-promoted phase-selective discrimination of organoboron species. This phenomenon is general across a broad range of organoboron compounds and can also be used to invert conventional protecting group strategies, enabling chemoselective oxidation of BMIDA species over normally more reactive BPin substrates. We also demonstrate the selective oxidation of diboronic acid systems with chemoselectivity predictable a priori. The utility of this method is exemplified through the development of a chemoselective oxidative nucleophile coupling.
![Ferrocene, [[[3-[4-[6-[[5-[1-[2-[methyl(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]ethyl]-1H-1,2,3-triazol-4-yl]-1-oxopentyl]amino]-1H-benzimidazol-1-yl]-1H-1,2,3-triazol-1-yl]propyl]amino]carbonyl]-](/data/chemimg/3721800/1887761-60-5.png)
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![SILANE, TRIMETHYL[[(4R)-4-PROPYL-1-CYCLOHEXEN-1-YL]OXY]-](http://img.cochemist.com/ccimg/717200/717101-53-6.png)
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![Silane, trimethyl[[(4R)-4-phenyl-1-cyclohexen-1-yl]oxy]-](http://img.cochemist.com/ccimg/152400/152387-04-7_b.png)
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![Silane, [[4-(1,1-dimethylethyl)-1-cyclohexen-1-yl]oxy]trimethyl-](http://img.cochemist.com/ccimg/20000/19980-19-9_b.png)
![Silane, trimethyl[(6-methyl-1-cyclohexen-1-yl)oxy]-](http://img.cochemist.com/ccimg/20000/19980-33-7.png)
![Silane, trimethyl[(6-methyl-1-cyclohexen-1-yl)oxy]-](http://img.cochemist.com/ccimg/20000/19980-33-7_b.png)
![Silane, trimethyl[[(4S)-4-(1-methylethyl)-1-cyclohexen-1-yl]oxy]-](http://img.cochemist.com/ccimg/100200/100190-37-2.png)
![Silane, trimethyl[[(4S)-4-(1-methylethyl)-1-cyclohexen-1-yl]oxy]-](http://img.cochemist.com/ccimg/100200/100190-37-2_b.png)
![Spiro[3H-indole-3,3'-pyrrolidin]-2(1H)-one, 1'-methyl-](http://img.cochemist.com/ccimg/66900/66859-18-5.png)
![Spiro[3H-indole-3,3'-pyrrolidin]-2(1H)-one, 1'-methyl-](http://img.cochemist.com/ccimg/66900/66859-18-5_b.png)
![Silane, [[(4S)-4-(1,1-dimethylethyl)-1-cyclohexen-1-yl]oxy]trimethyl-](http://img.cochemist.com/ccimg/100200/100190-34-9.png)
![Silane, [[(4S)-4-(1,1-dimethylethyl)-1-cyclohexen-1-yl]oxy]trimethyl-](http://img.cochemist.com/ccimg/100200/100190-34-9_b.png)
![1-[4-(2-HYDROXYPHENYL)PHENYL]ETHANONE](http://img.cochemist.com/ccimg/21900/21849-93-4.png)
![1-[4-(2-HYDROXYPHENYL)PHENYL]ETHANONE](http://img.cochemist.com/ccimg/21900/21849-93-4_b.png)
![Silane, trimethyl[[(4S)-4-methyl-1-cyclohexen-1-yl]oxy]-](http://img.cochemist.com/ccimg/100200/100190-39-4.png)
![Silane, trimethyl[[(4S)-4-methyl-1-cyclohexen-1-yl]oxy]-](http://img.cochemist.com/ccimg/100200/100190-39-4_b.png)
![(1S,2S)-2-ethyl-1-({[(3aS,6R,7aS)-6-ethyl-1-oxo-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]carbonyl}amino)cyclopropanecarboxylic acid](http://img.cochemist.com/ccimg/62300/62251-96-1.png)
![(1S,2S)-2-ethyl-1-({[(3aS,6R,7aS)-6-ethyl-1-oxo-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]carbonyl}amino)cyclopropanecarboxylic acid](http://img.cochemist.com/ccimg/62300/62251-96-1_b.png)
![Benzamide, N-[2-(benzoyloxy)ethyl]-](http://img.cochemist.com/ccimg/16200/16180-99-7.png)
![Benzamide, N-[2-(benzoyloxy)ethyl]-](http://img.cochemist.com/ccimg/16200/16180-99-7_b.png)
![Tricyclo[3.3.1.13,7]decane, 1-azido-](/data/chemimg/409500/24886-73-5.png)
![Tricyclo[3.3.1.13,7]decane, 1-azido-](/data/chemimg/409500/24886-73-5_b.png)
![2-{[(4-bromophenyl)acetyl]amino}benzamide](http://img.cochemist.com/ccimg/349500/349430-83-7.png)
![2-{[(4-bromophenyl)acetyl]amino}benzamide](http://img.cochemist.com/ccimg/349500/349430-83-7_b.png)
![Silane, [(2,6-dimethyl-1-cyclohexen-1-yl)oxy]trimethyl-](http://img.cochemist.com/ccimg/63600/63547-53-5.png)
![Silane, [(2,6-dimethyl-1-cyclohexen-1-yl)oxy]trimethyl-](http://img.cochemist.com/ccimg/63600/63547-53-5_b.png)
![N-[4-(trifluoromethyl)benzyl]propan-1-amine](http://img.cochemist.com/ccimg/90400/90390-13-9.png)
![N-[4-(trifluoromethyl)benzyl]propan-1-amine](http://img.cochemist.com/ccimg/90400/90390-13-9_b.png)
![1H-Indole, 1-[(4-methylphenyl)sulfonyl]-2-phenyl-](http://img.cochemist.com/ccimg/107800/107734-06-5.png)
![1H-Indole, 1-[(4-methylphenyl)sulfonyl]-2-phenyl-](http://img.cochemist.com/ccimg/107800/107734-06-5_b.png)
![2-[4-[4-[4-[[(1R)-1-(2-CHLOROPHENYL)ETHOXY]CARBONYLAMINO]-3-METHYL-1,2-OXAZOL-5-YL]PHENYL]PHENYL]ACETIC ACID](http://img.cochemist.com/ccimg/1228700/1228690-19-4.png)
![2-[4-[4-[4-[[(1R)-1-(2-CHLOROPHENYL)ETHOXY]CARBONYLAMINO]-3-METHYL-1,2-OXAZOL-5-YL]PHENYL]PHENYL]ACETIC ACID](http://img.cochemist.com/ccimg/1228700/1228690-19-4_b.png)
![Benzamide, N-[(4-methoxyphenyl)methyl]-4-methyl-](http://img.cochemist.com/ccimg/288200/288154-96-1.png)
![Benzamide, N-[(4-methoxyphenyl)methyl]-4-methyl-](http://img.cochemist.com/ccimg/288200/288154-96-1_b.png)
![Benzoic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, methyl ester](http://img.cochemist.com/ccimg/133700/133642-20-3.png)
![Benzoic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, methyl ester](http://img.cochemist.com/ccimg/133700/133642-20-3_b.png)
![Phenol, 4-benzo[b]thien-2-yl-](http://img.cochemist.com/ccimg/65600/65540-08-1.png)
![Phenol, 4-benzo[b]thien-2-yl-](http://img.cochemist.com/ccimg/65600/65540-08-1_b.png)
![[1,1'-Biphenyl]-4-aceticacid, methyl ester](http://img.cochemist.com/ccimg/59800/59793-29-2.png)
![[1,1'-Biphenyl]-4-aceticacid, methyl ester](http://img.cochemist.com/ccimg/59800/59793-29-2_b.png)
![Benzeneacetamide, N-[(4-methoxyphenyl)methyl]-](http://img.cochemist.com/ccimg/305900/305849-49-4.png)
![Benzeneacetamide, N-[(4-methoxyphenyl)methyl]-](http://img.cochemist.com/ccimg/305900/305849-49-4_b.png)
![Silane, trimethyl[[(4S)-4-propyl-1-cyclohexen-1-yl]oxy]-](http://img.cochemist.com/ccimg/269800/269744-82-3.png)
![Silane, trimethyl[[(4S)-4-propyl-1-cyclohexen-1-yl]oxy]-](http://img.cochemist.com/ccimg/269800/269744-82-3_b.png)
![2l5-1,3,2-Diazaphosphorin-2-amine,2-[(1,1-dimethylethyl)imino]-N,N-diethylhexahydro-1,3-dimethyl-](http://img.cochemist.com/ccimg/98100/98015-45-3.png)
![2l5-1,3,2-Diazaphosphorin-2-amine,2-[(1,1-dimethylethyl)imino]-N,N-diethylhexahydro-1,3-dimethyl-](http://img.cochemist.com/ccimg/98100/98015-45-3_b.png)
![3H-SPIRO[1-BENZOFURAN-2,4''-PIPERIDINE]](http://img.cochemist.com/ccimg/72000/71916-73-9.png)
![3H-SPIRO[1-BENZOFURAN-2,4''-PIPERIDINE]](http://img.cochemist.com/ccimg/72000/71916-73-9_b.png)
![2-Pyridinemethanamine,N-[(1R)-1-phenylethyl]-](http://img.cochemist.com/ccimg/157200/157160-17-3.png)
![2-Pyridinemethanamine,N-[(1R)-1-phenylethyl]-](http://img.cochemist.com/ccimg/157200/157160-17-3_b.png)
![SODIUM;2-[4-[4-[3-METHYL-4-[[(1R)-1-PHENYLETHOXY]CARBONYLAMINO]-1,2-OXAZOL-5-YL]PHENYL]PHENYL]ACETATE](http://img.cochemist.com/ccimg/1345700/1345614-59-6.png)
![SODIUM;2-[4-[4-[3-METHYL-4-[[(1R)-1-PHENYLETHOXY]CARBONYLAMINO]-1,2-OXAZOL-5-YL]PHENYL]PHENYL]ACETATE](http://img.cochemist.com/ccimg/1345700/1345614-59-6_b.png)
![[(3-chlorophenyl)hydrazono]malononitrile](http://img.cochemist.com/ccimg/600/555-60-2.png)
![[(3-chlorophenyl)hydrazono]malononitrile](http://img.cochemist.com/ccimg/600/555-60-2_b.png)
![Spiro[cyclopropane-1,3'-[3H]indol]-2'(1'H)-one](http://img.cochemist.com/ccimg/13900/13861-75-1.png)
![Spiro[cyclopropane-1,3'-[3H]indol]-2'(1'H)-one](http://img.cochemist.com/ccimg/13900/13861-75-1_b.png)
![3,5-Dichlorobenzyl 4-(3-oxo-3-(2-oxo-2,3-dihydrobenzo[d]oxazol-6-yl)propyl)piperazine-1-carboxylate](http://img.cochemist.com/ccimg/1144100/1144035-53-9.png)
![3,5-Dichlorobenzyl 4-(3-oxo-3-(2-oxo-2,3-dihydrobenzo[d]oxazol-6-yl)propyl)piperazine-1-carboxylate](http://img.cochemist.com/ccimg/1144100/1144035-53-9_b.png)
![[1,1'-Biphenyl]-4-amine, N,N,4'-trimethyl-](http://img.cochemist.com/ccimg/141100/141082-00-0.png)
![[1,1'-Biphenyl]-4-amine, N,N,4'-trimethyl-](http://img.cochemist.com/ccimg/141100/141082-00-0_b.png)
![Benzo[g]pteridine-2,4(1H,3H)-dione](http://img.cochemist.com/ccimg/500/490-59-5.png)
![Benzo[g]pteridine-2,4(1H,3H)-dione](http://img.cochemist.com/ccimg/500/490-59-5_b.png)
![1,3,2-Dioxaborolane,2-[(1E)-3,3-dimethyl-1-butenyl]-4,4,5,5-tetramethyl-](http://img.cochemist.com/ccimg/158000/157945-83-0.png)
![1,3,2-Dioxaborolane,2-[(1E)-3,3-dimethyl-1-butenyl]-4,4,5,5-tetramethyl-](http://img.cochemist.com/ccimg/158000/157945-83-0_b.png)
![2H-Indol-2-one, 3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylene]-1,3-dihydro-](/data/chemimg/3000/204005-46-9.png)
![2H-Indol-2-one, 3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylene]-1,3-dihydro-](/data/chemimg/3000/204005-46-9_b.png)
![Benzene, 1-bromo-4-[(1E)-2-bromoethenyl]-](http://img.cochemist.com/ccimg/115700/115665-77-5.png)
![Benzene, 1-bromo-4-[(1E)-2-bromoethenyl]-](http://img.cochemist.com/ccimg/115700/115665-77-5_b.png)
![2-Naphthalenol,1-[(S)-aminophenylmethyl]-](/data/chemimg/20700/219897-38-8.png)
![2-Naphthalenol,1-[(S)-aminophenylmethyl]-](/data/chemimg/20700/219897-38-8_b.png)
