the long and winding road to chemical information
DESCRIPTION
8th German Conference on Chemoinformatics, Goslar, 12.11.2012 (Award address for the Gmelin-Beilstein-Denkmünze of the Gesellschaft Deutscher Chemiker)TRANSCRIPT
The Long and Winding Road toChemical Information
Engelbert Zass (retd.)
Chemistry Biology PharmacyInformation Center
ETH Zurich
8093 Zürich, Switzerland
Dedicated to the Memory of
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Dr. Ursula Schoch-Grübler Prof. Dr. Reiner Luckenbach1949 – 2011 1941 – 2011
Beilstein ⇒ Reaxys
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Beilstein: Handbook ⇐ Excerption
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Beilstein: Handbook ⇒ Database
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1994
2009
1988
1991
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The Long and Winding Road to
Chemical Information
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Robert Burns
Woodward
1917-1979
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330 publications,including 100 patents
3rd Europ. Symp. Vitamin B12 and Intrinsic Factor
Zürich, March 1979
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Vitamin B12
Total Synthesis:
R.B. Woodward
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Heterocycles 82, 63-86 (2010)
Publications by A. Eschenmoser
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SciFinder: Molecular Formula
• Manganese(II)sulfate
MnO4S ⇒ H2O4S . Mn
• Iron(II)formiate
CHFeO2 ⇒ CH2O2 . ½ Fe
• Berylliumphosphate
Be3O8P2 ⇒ Be . 2/3 H3O4P
but:
• Sodium ClorideCl Na (Cl . Na gives different result)
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Ca3(PO4)2 • 3 H2O
SciFinder: Claims and Hype
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Essentially correct and true (relatively speaking)
Hype and dangerous insinuation !
SciFinder: Preparation of a Compound
• Search via:
1. Get Reaction: Product
(CASREACT)
2. Additional Reactions
(CASREACT ⇒ CAplus)
3. Registry Role Matrix (Patents, Nonpatents)
(Registry ⇒ CAplus)
4. Get References – Limit results to: Preparation
(CAplus)
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Preparation of Lidocaine (27.6.2009)
• Reaxys
23 refs. 1946-2008
• SciFinder Web
– CASREACT: 4 refs. 1984-2009
– CAplus: 109 refs. 1948-2009
only 45 relevant !
CHMINF-L
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Steroids with Data in Literature
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all carbon skeleton, any bonds, any substitution, no anellated rings
Properties: Data, Spectra
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SciFinder:
Dipole Moments for
Aminoquinolines
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Reaxys:
Dipole Moments for
Aminoquinolines
Dipole Moments of
Aminoquinolines and Aminoacridines
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cis-Hydroxylation: SciFinder / Reaxys
Reagenz Reaxys SciFinder
H2O2 / Molybdenum tungsten hydroxide oxide phosphate 7
H2O2 / Tricarbonyl(η5-cyclopentadienyl)(phenylethynyl)molybdenum 1
H2O2 / fac-Trichloro(1,4,7-trimethyl-1,4,7-triazacyclononane)ruthenium 1
H2O2 / Ruthenium(1+), aqua(octahydro-1,4,7-trimethyl-1H-1,4,7-triazonine-
κN1,κN4,κN7)bis(2,2,2-trifluoroacetato-κO)-, (OC-6-33)-, 2,2,2-trifluoroacetate (1:1)
1 3
H2O2 1 1
B2Cl4 / H2O2 1
H2O2 / Tris-µ-oxobis[(1,4,7-trimethyl-1,4,7-triazacyclononane)manganese(IV)]
hexafluorophosphate
1 1
KMnO4 10 1
Methyltriphenylphosphonium permanganate 1
N-methylmorpholineoxide / OsO4 1 2
K2OsO4 / OsO4 1
K3Fe(CN)6 / K2OsO4 1 1
I2 / AgOAc 1 1
cis-Hydroxylation: SciFinder
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Chemical Information: State of the Art
• Neither «new» nor «old» sources arecomprehensible or reliable enoughon an individual basis
⇒ one source is usually not enough !
• The traditional strenght of «old» sourcesis partially negated by the complexity oftheir content (data structure)
⇒ improve databases (not only interfaces)
Improve Education & Support
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The Past: "Must Use" Brands
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Present: Many "Equal" Brands
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Dendrobine Total Syntheses (4/2012)
• Total relevant references: 43 (1965-2012)
– SciFinder 38 of 54 (10 excl.)
– Reaxys 13 of 14 (none excl.)
– Web of Knowledge 20 of 22 (none excl.)
– Scopus 18 of 19 (none excl.)
– Google Scholar 18 of 18 (1 excl.: grant)
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Databases: Problems and Dangers
2°Literature (A&I, Handbooks) =endangered species ?
• (Relatively) complex interfaces
• Too many sources needed
• Too many differences between sources
• Problematic legacies
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(Cost) Effort / Utility ratio not obvious enough
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Remedies
• To Producers & Specialists:
– Meta Data about Sources
– Exchange & Feedback of Experience
• To Users:
– Support
– Education & Training
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Meta Data: Gmelin, CASREACT
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