Reaxys in Education and Research at ETH Zurich

Dr.  Jozica  Dolenc,  ETH  Zurich,  Chemistry  |  Biology |  Pharmacy Information  Center

Reaxys in  Education  and Research  at  ETH  Zurich

Agenda

• ETH  Zurich  and  the  Chemistry  |  Biology |  Pharmacy Information  Center

• Reaxys in  Education

• Reaxys in  Research  

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 2

ETH  Zurich  at  a  Glance

Reaxys   in  Education   and  Research   at  ETH  Zurich    |    Dr.  Jozica  Dolenc    |    10.  12.   2015 3

Founded  in  1855

One  of  the  leading  international  universities  for  technology  and  natural  sciences  • THE  World  University  Ranking:  No.  9  (2015/16)• QS  World  University  Ranking:  No.  9  (2015/16)• Academic  Ranking  of  World  Universities:  No.  20  (2015)

Place  of  study,  research  and  employment  for  approximately  29’000  people  from  over  110  different  countries• 18’616  students• 498  professors• 8’143  staff  members

Nobel  Prize  Laureates:  21  

ETH  Zurich:  Organization

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 4

Chemistry  |  Biology |  Pharmacy Information  Center

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 5

Joined  facility  of  the  Department  of  Chemistry  and  Applied  Biosciences  and  the  Department  of  Biology  

Scientific   information  skill  center  supporting  students  and  researchers• Information  resources:  databases  &  tools• Awareness  • Education  &  training• Information  consulting  &  retrieval• Library  services• Place  to  study

Team  of  10  members  (information  consultants  for  biology,  chemistry  andpharmacy,  library  professionals)• Head:  Dr.  Oliver  Renn

Chemistry  |  Biology |  Pharmacy Information  Center

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 6

www.infozentrum.ethz.ch

Databases  and  Tools

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 7

Databases  and  Tools

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 8

Reaxys in  Education

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 9

Reaxys trainings  are  integrated  into  • Five  undergraduate  lab  courses

Organic  Compounds:  Synthesis  and  Properties(Inorganic  and  Organic  Chemistry  I)

Searching  for  Organic  Compounds  (Organic  Chemistry  for  Students  of  Biology,Pharmaceutical  Sci.  and  Health  Sci.  &  Techn.)

Searching  for  Organometallic  and   InorganicCompounds  (Inorganic  and  Organic  Chemistry  II)

Searching  for  Information  on  Polymers  (Practical  Laboratory  Course   for  Materials  Science  Students)

Chemical  Engineering  Case  Studies

• A  course  for  chemistry  and  life  sciences  PhD  studentsScientific  Information  Retrieval  &  Management   in  Life  Sciences  and  Chemistry

Questions Most  Often Asked by UndergraduateStudents

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 10

• How  can  I  synthesize a  given  compound

• How  can  I  characterize the  compound  (melting  point,  IR  spectra,…)

• How  toxic is  the  compound  (reagents),  how  dangerous  is  the  experimental  procedure

How Do  You Think  Undergraduate Students UsuallyStart  a Reaxys Search?

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 11

Students Choose...

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 12

Main  reasons:

• Drawing  the  molecule  is  time  consuming  and  you  have  to  know  its  chemical  structure

• Chemical  names  are  often  complicated  and  not  unique

1.     Ask  Reaxys,  the  well  known  Google-­like  search  bar  

2. Create  Structure  Template  from  Name

3. Structure  editor

Example 1Synthesis  of Cobalt  (III)  acetylacetonate

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 13

• Co(acac)2

• Molecular  formula:  C15H21CoO6

Inorganic   and   Organic   Chemistry  II:  Searching   for  Organometallic   and   Inorganic   Compounds  

Example 1Ask Reaxys

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 14

Example 1Preparations

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 15

Example 1Exclude Patents

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 16

Example 1Sort by Reactant Availability or Filter  by Document Type

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   201517

or

Example 1Characterization,  Physical Data

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 18

Example 1Physical Data,  Spectra

Reaxys   in  Education   and  Research   at  ETH  Zurich    |    Dr.  Jozica  Dolenc    |    10.  12.   201519

Example 1Reaxys Report

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 20

Example 2Synthesis  of (1,1'-­bis(diphenylphosphino)ferrocene)palladium(II)  dichloride

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 21

• PdCl2(dppf)

• Molecular  formula:  C34H28P2FePdCl2

Natalja Früh &  Raffael HuberLaboratory   of   Inorganic   Chemistry,  ETH  Zurich

Example 2Ask Reaxys

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 22

Example 2Molecular Formula

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 23

Example 2Preparations

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 24

Example 2Exclude Patents

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 25

Example 2Synthesis  of 1,1'-­bis-­(diphenylphosphino)ferrocene

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 26

Reaxys in  Research

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 27

Coffee  Lectures• 10-­minute  presentations  about  databases,  

tools  and  services

• Given  in  blocks  of  three  weeks,  three  days  a  week

• Free  coffee  or  tea  is  always  available

Research  Group  Menu  Card  Seminars• Tailored  seminars  for  research  groups  

• The  research  groups  can  create  their  own  Information  Menu  by  choosing  an  Entrée,  Main  Course,  Dessert,  and  Special  from  our  Research  Group  Menu  Card

Questions  Most  Often  Asked  by  Researchers

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 28

• How  can  I  best  define  my  substructure?

• Can  I  search  for  compounds  that  have  a  specific  property?

• Can  I  do  a  batch  query  in  Reaxys?

How Do  You Think  Researchers  Usually Start  a ReaxysSearch?

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 29

Researchers  Choose ...  

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 30

Main  reasons:

• Researchers  know  their  molecules  very  well  (incl.  CAS  registry  number)

• Substructure  search  and  precise  reaction  searches  are  possible  using  the  structure  editor  

CAS  registry  number or  Structure  editor,  depending  on  the  question  asked

Example 3Searching for Bioactive Derivatives  of Epothilone A

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 31

Epothilone A    is  a  natural  product  with  known  cancer  cell  inhibitory  activity

• Microtubule-­binding  agent

Goal:  Epothilone A  structure  optimization  for  development  of  new  chemotherapeutic  drugs

• Structural  variations  around  the  epoxide  ring• Changes  in  the  size  and  flexibility  of  the  

C9-­C11 segment• Variations  at  C3• Variations  in  the  thiazole ring

Example 3Substructure Search

32Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015

Example 3Substructure Search

33

Example 3Searching for Bioactive Derivatives  of Epothilone A

34

Example 3

35

Epothilone AEpothilone A

Epothilone A  aziridine(12S,13S,15S)-­cyclopropylepothilone A

Epothilone E

Example 3Pharmcological Effects

36

Example 4Density Data  for a  Large  Set  of Compounds

Batch  querying

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 37Pascal  MerzLaboratory   of  Physical  Chemistry,  ETH  Zurich

Example 4Density Data  for a  Large  Set  of Compounds

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 38

Example 4Density Data  for a  Large  Set  of Compounds

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 39

Example 4Density Data  for a  Large  Set  of Compounds

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Reaxys is  a  Strong  and  Solid  Database

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 41

• Excellent  data  quality  and  coverage

• Data  is  clearly  presented

• Simple  and  intuitive  interface

• Advanced  search  options  for  those  who  want  more

Working  with  Reaxys is  fun!

Thank  You  for  Your  Attention

Reaxys in  Education   and Research   at  ETH  Zurich |    Dr.  Jozica  Dolenc    |    10.  12.   2015 42

dolenc@chem.ethz.ch