Seminars & lectures in
MEDICINAL CHEMISTRY I
(summer semester of the 2nd
year of study)
●your teachers:
●doc. PharmDr. Oldřich Farsa,PhD. (7 times)
●Mgr. Aleš Kroutil (ones)
●PharmDr. Tomáš Goněc, PhD. (3 times)
Seminars in Medicinal Chemistry (MC)
●in seminar room at the basement of Pharmacy Pavilion (door No. 37)
●
every Tuesday 7.30 – 8.12 (except May 1st
and 8th
which are state holidays);
seminars are compulsory!
●presentations: 29 topics randomly taken from both general and special MC
●lenght of presentation at least 15 min; discussion and teacher's evaluation will
follow
•topics will be balloted and presented according to the alphabetic order of
students in the list; 3 topics per one seminar
•every presentation will be created and presented in *.ppt (PowerPoint), *.pdf
(Adobe Reader) or *.odp (OpenOffice.org Impress) formates
•every particular presentation will be evaluated by the teacher and will given 0
– 10 marks, accuracy, integrity, contemporarity, comprehensibility and lucidity
will be the evaluation criteria
• a student with 7 marks or more will pass the seminars successfully otherwise
he/she will write an additional test from the whole matter of seminars
•seminars will be closed by the final credit test
Requiremnts on a structure of a presentation
(with exception of topic History of MC)
● basic characterization of activity of compounds in a particular
group
● common structure or structures of compounds (if possible)
● SAR = (qualitative) structure-activity relationships: structural
fragments which are essential for the activity, additional
moieties or substituents and how they influence the activity
● mechanism of action
● significant chemical properties (namely those which are
important for activity, application or stability
● overview of basic compounds with their INN (and/or USAN,
BAN) names
● list of used literature resouces
Instruments for drawing of structure formulas
● Structural formula editors are strongly recommended for structural
formulas instead of common graphic programs or simple copying of
structures as pictures
● Freeware structural formulas editors
● ACD ChemSketch: version 12 now actual – download from
www.acdlabs.com after registration
– supports several structural formulas formates
– enables „translation“ of SMILES codes (text files which encode
chemical structure in one line) into formulas
– OLE function: inserting of formulas directly from within
presentation editor: Insert – Object – (OLE Object) – ACD
ChemSketch; after finishing the structure File – Update - Close
and return to app name
● ISIS Draw: popular, but download and support discontinued (the last
version 2.5), replaced with Symyx Draw, which is not fully integrated
into all the presentation editors
● ChemDraw: payed professional editor, installed on some computers in
computer room in opposite of this seminar room
Where to find particular information?
● recommended literature (listed thereinafter)
● data bases:
● ChemId Plus at chem.sis.nlm.nih.gov (provided by U.S. National
Library of Medicine), freely accessible, enables searching of
biologically active compounds by chemical, INN (USAN, BAN …)
or trade name or CAS number, or by chemical structure or
substructure
– possibility of transfer of structures into structural formulas (and
presentations) editors by means of SMILES codes, molfiles or
directly into ISIS Draw by means of Chime utility
– linked with Medline, FDA and other data bases
● Medline at http://www.ncbi.nlm.nih.gov/pubmed/ (provided by
U.S. National Library of Medicine), freely accessible, enables
searching of medical journals including those from the field of MC,
gives abstracts
– links to many fulltexts; some of them accessible by means of
University subscription of particular journals or freely
Where to find particular information? (Data bases continued)
● Web of Knowledge – payed data base of article abstracts from
renowned journals from all the filelds of science provided by Thomson
Reuters accesible at http://apps.webofknowledge.com or via
http://sis.vfu.cz/eiz/placene/
● Reaxys Data Base – searchable chemical data base originated from
Beilstein's Handbook of Organic Chemistry available from within
University network at https://www.reaxys.com or via
http://sis.vfu.cz/eiz/placene/
● search by structures, chemical names, CAS or similar BRN (now
Reaxys Nos) numbers, physical properties and many other
● links to full texts of articles
Where to find particular information? (Data bases continued)
● SciFinder – a data base form of Chemical Abstracts (CA), the oldest
chemical referate journal of the world
● published by American Chemical Society
● CA Service, which is part of its Editorial Board, has been giving
the unique CAS numbers to all known (and described)
compounds
● search by structures, chemical names, CAS numbers, physical
properties, author names and many other
● links to full texts of articles including patents
● not freely accessible; limited number of accesses at the
University only
Recommended literature
Printed books in English suitable for your study available in the Central
University Library at the Study and Information Centre
● activated ISIC as a reader's identity card needed
● Basic literature:
● Ashutosh Kar: Medicinal Chemistry. Third edition. Anshan, Tunbridge
Wells, UK, 2006
● Complementary
● Camille Georges Wermuth: The practice of Medicinal Chemistry. Third
Edition, Elsevier, 2008
Recommended literature - continued
Resources in English available via faculty network in electronic form at
http://sis.vfu.cz/eiz/e-books/ebooklist.html:
● Basic:
– János Fischer, C. Robin Ganelin (eds.): Analogue-based Drug Discovery.
ISBN: 3-527-31257-9. Willey-VCh, Weinheim, 2006
● further refered as Fischer 2006
– Camille G. Wermuth: The Practice of Medicinal Chemistry (Second Edition).
ISBN: 978-0-12-744481-9. Elsevier, 2003
● Complementary:
– R.S. Vardanyan and V.J. Hruby: Synthesis of Essential Drugs. ISBN: 978-0-
444-52166-8. Elsevier, 2006
– Rick Ng: Drugs: From Discovery to Approval, Second Edition. ISBN: 978-0-
470403587. John Wiley & Sons, Inc., 2009
● further refered as Rick 2009
– Walter Sneader: Drug Discovery. A History. ISBN 978-0-471-89979-2.
John Wiley & Sons, Inc., 2005
● further refered as Sneader 2005
– James Devillers: Neural Networks in QSAR and Drug Design. ISBN: 978-0-
12-213815-7. Elsevier, 1996
Topics of your choice for your presentations, their scheduled dates and recommended
literature
1. Platinum Antineoplastics (Fischer 2006 Chapter 19 pp. 385-394; Kelland L.,
Nature Reviews/Cancer 7, 573 – 583 (2007))
2. Anti-HIV Drugs (Mehellou Y., De Clerq E., J. Med. Chem. 53, 521 – 538 (2010)
3. History of Medicinal Chemistry (Rick 2009 Appendix 1 pp. 391 – 397;
Sneader 2005)
4. New Drugs for Insomnia (Hardeland R., Neuropsychiatric Disease and
Treatment 2009:5 341–354)
5. Drugs for Cytomegalovirus Diseases (Biron K. K., Antiviral Research 71
(2006) 154–163; Mercorelli B. et al., Rev. Med. Virol. 2008; 18: 177–210)
6. Opioid Receptors Ligands(Fischer 2006 Chapter 14 pp. 259-296)
7. H1
-Antihistamines (Fischer 2006 Chapter 21 pp. 401 - 418)
8. Stigmines (Fischer 2006 Chapter 15 pp. 277 - 295)
9. Bisphosphonates (Fischer 2006 Chapter 18 pp. 371 - 384)
10. Statins (Fischer 2006 Chapter 7 pp. 137 - 155)
11. Dihydropyridines (Edraki N. et al., Drug Discovery Today 14, 1058 – 1066
(2009) )
12. Potential Drugs acting on H3
-Histamine Receptor (Berlin M. et al., J. Med.
Chem. 54, 26 – 53 (2011))
13. Anti-ageing drugs (Kapoor V. K. et al., Drug Discovery Today 14, 899 – 903
(2009))
14. H2
-Receptor Histamine Antagonists (Fischer 2006 Chapter 4 pp. 69 - 80)
15. Organic nitrates for coronary heart disease
Resource: János Fischer, C. Robin Ganelin (eds.): Analogue-based Drug Discovery.
ISBN: 3-527-31257-9. Willey-VCh, Weinheim, 2006, chapter 10 pp. 247-268
available in electronic form at http://sis.vfu.cz/eiz/e-books/ebooklist.html
16. Proton pump inhibitors. Resource: János Fischer, C. Robin Ganelin (eds.):
Analogue-based Drug Discovery. ISBN: 3-527-31257-9. Willey-VCh, Weinheim,
2006, chapter 3 pp. 115-136 available in electronic form at
http://sis.vfu.cz/eiz/e-books/ebooklist.html
17. Calcium antagonists. Resource: János Fischer, C. Robin Ganelin (eds.):
Analogue-based Drug Discovery. ISBN: 3-527-31257-9. Willey-VCh, Weinheim,
2006, chapter 7 pp. 181-192 available in electronic form at
http://sis.vfu.cz/eiz/e-books/ebooklist.html
18. Clozapine and its analogues for treatment of schizophrenia. Resource:
János Fischer, C. Robin Ganelin (eds.): Analogue-based Drug Discovery. ISBN:
3-527-31257-9. Willey-VCh, Weinheim, 2006, chapter 13 pp. 297-313.
available in electronic form at http://sis.vfu.cz/eiz/e-books/ebooklist.html
19. Antibacterial quinolones. Resource: János Fischer, C. Robin Ganelin (eds.):
Analogue-based Drug Discovery. ISBN: 3-527-31257-9. Willey-VCh, Weinheim,
2006, chapter 17 pp. 315-370 available in electronic form at
http://sis.vfu.cz/eiz/e-books/ebooklist.html
20. Selective Beta-Adrenergic Receptor Blocking Agents. Resource: János Fischer, C. Robin
Ganelin (eds.): Analogue-based Drug Discovery. ISBN: 3-527-31257-9. Willey-VCh,
Weinheim, 2006, chapter 8 pp. 193-226 available in electronic form at
http://sis.vfu.cz/eiz/e-books/ebooklist.html
21. Biologic therapeutics: monoclonal antibodies which target EGFR. Resource:
Friedländer E., Barok M., Szöllosi J., Vereb G.: ErbB-directed immunotherapy:
Antibodies in current practice and promising new agents. Immunology Letters 116,
126 (2008)
22. Biologic therapeutics: Antibody-based therapeutics which were aims of interest
in 2011. Resource: Reichert J. M.: Antibody-based therapeutics to watch in 2011.
mAbs 3,76 (2011)
23. Drugs for treatment of MRSA infections. Resource: Angelo Pan, Silvia Lorenzotti,
Alessia Zoncada: Registered and Investigational Drugs for the Treatment of
Methicillin-Resistant Staphylococcus aureus Infection. Recent Patents on AntiInfective
Drug Discovery, 3, 10-33 (2008)
24. Pegylated interferones α in therapy. Resource: Bruno R., Sacchi P., Cima S.,
Maiocchi L., Novati S., Filice G., Fagiuoli S.: Comparison of peginterferon
pharmacokinetic and pharmacodynamic profiles. Journal of Viral Hepatitis 19, Suppl.
1, 33 (2012); doi:10.1111/j.1365-2893.2011.01519.x
25. Peptide and non-peptide hematopoietic growth factors. Resource: Steensma D.
P.: Hematopoietic growth factors in myelodysplastic syndromes. Seminars in
Oncology, 38, 635 (2011)
26. GLP-1 receptor agonists in the treatment of diabetes. Resouce: Madsbad S.,
Kielgast U., Asmar M., Deacon C. F., Torekov S. S., Holst J. J.: An overview of onceweekly
glucagon-like peptide-1 receptor agonists—available efficacy and safety
data and perspectives for the future. Diabetes, Obesity and Metabolism 13, 394
(2011).
27. Small molecule tyrosine kinase inhibitors in treatment of cancer. Resource: Roy V.,
Perez E.A.: Beyond trastuzumab: small molecule tyrosine kinase inhibitors
in HER-2-positive breast cancer. Oncologist. 14, 1061-9 (2009)
28. Insulin analogues. Resource: Sheldon B., Russell-Jones D., Wright J.: Insulin
analogues: an example of applied medical science. Diabetes, Obesity and Metabolism, 11,
5, (2009)
29. Chemistry of drugs for treatment of attention deficit and hyperactivity disorders.
Resource: Helmut Buschmann, José Luis Díaz, Jörg Holenz, Antonio Párraga, Antoni
Torrens, José Miguel Vela (eds.): Antidepressants, Antipsychotics, Anxiolytics: From
Chemistry and Pharmacology to Clinical Application. Part 4: Attention Deficit and
Hyperactivity Disorders. Chapter 4.4.: Jörg Holenz, José Luis Díaz and Helmut
Buschmann: Chemistry. 1183 – 1196. Wiley VCh, 2007;
http://onlinelibrary.wiley.com/doi/10.1002/9783527619337.ch19/pdf
30. Antituberculotics. Resource: Lynn G. Dover, Geoffrey D. Coxon: Current Status and
Research Strategies in Tuberculosis Drug Development. J. Med. Chem. 2011, 54, 6157–
6165; available at pubs.acs.org/jmc or via dx.doi.org/10.1021/jm200305q
31. Angiotensin-converting enzyme (ACE) inhibitors as antihypertensive agents. Resource:
Analogue-based Drug Discovery. ISBN: 3-527-31257-9. Willey-VCh, Weinheim, 2006,
chapter 9 pp. 169-179
available in electronic form at http://sis.vfu.cz/eiz/e-books/ebooklist.html
32. Angiotensin receptor blockers as antihypertensive agents. Resource: Analogue-based
Drug Discovery. ISBN: 3-527-31257-9. Willey-VCh, Weinheim, 2006, chapter 8 pp.
157-168; available in electronic form at
http://sis.vfu.cz/eiz/e-books/ebooklist.html