SEARCHING THE CHEMICAL LITERATURE ASSIGNMENT
Use Scifinder Scholar to answer the following questions. Consult the GT library website regarding
access. You should work alone on this assignment.
1. Pharmaceutical chemistry – finding compounds, starting from Wikipedia
The HCl salt of 2-dimethylaminoethyl (4-chlorophenoxy)acetate goes by a number of trade
names. The text of the Wikipedia entry for Centrophenxoine is shown below. NOTE that
Wikipedia completely misses the fact that this pharmaceutical is the HCl salt!
Centrophenoxine (also called Meclofenoxate, and formerly sold under the brand name Lucidril) is a
drug used to treat the symptoms of senile dementia and Alzheimer's Disease. It is a compound of two
biochemicals: dimethylaminoethanol (DMAE) and parachlorophenoxyacetate (pCPA). DMAE is a
natural substance, found especially in fish, and also produced in the human brain. pCPA is a synthetic
compound that resembles a variety of plant hormones called auxins.
Like DMAE, it is a precursor to the neurotransmitter acetylcholine and may increase levels of this
chemical in the CNS. It also increases cellular membrane phospholipids which is considered by some to
be an important antiaging effect. It has been clinically shown to improve memory, have a mentally
stimulating effect, and improve general cognition.[citation needed]
It is also used off-label as a nootropic, often combined with a racetam drug such as piracetam. A typical
nootropic dose is 250-3,000 mg taken in 1 or more doses.
Provide the following information by using the “Explore Substances” function in SciFinderScholar
Start the search by using a substance identifier (use a common name)
(i)
Provide the complete citations for the following:
(a) The first paper in English to report the synthesis of the compound (the HCl salt)
From the publications in which the compound is reported, restrict your search to those in
which theprepartion is described, then sort by year
(b) The most highly cited paper which reports the synthesis (in any language)
(c) Provide the citation for the papers which provide a detailed synthetic procedure for the
preparation of the 4-bromo analog which is available in the Georgia Tech library.
(ii)
Provide the registry numbers for the following compounds:
(a) the free amine
(b) the HCl salt
(c) the HBr salt
Many compounds which are active on the central nervous system are amines which contain a 4chlrophenyl group (these two features help such molecules bond to receptors of neurotransmitters).
Your research advisor in medical school has asked you to explore the effect of other substituents on the
ring, in any single position (ortho, meta, para) in addition to the acetate ester side chain. Once you have
the substance record, click on the structure and select “Explore by Chemical Structure”. Do a Chemical
Structure search: Restrict the aliphatic parts of the molecule (CH3, CH2, and CH) by using the “Short” tool
(click on the “Short” tool, click on CH3, and then click on the carbon atoms you want fixed as methyl
groups, repeat to fix the methylenes). Then place hydrogen on the ring positions that you do not what
to bear a substitutent. Be careful to search only for the free amines (not salts); and consider the results
of the searches carefully (compounds retrieved for which there are zero referenecnes have not been
made!)
(iii)
How many analogs of the free base (not salts) have been reported with a single
substituent…
(a) … in the ortho position? How many of these are commercially available?
(b) … in the meta position? How many of these are commercially available?
(c) … in the para position? How many of these are commercially available?
(iv)
How many analogs of the free base are commercially available that have two substituents
on the ring (in addition to the acetate ester)?
2. Following up on a seminar
At a conference you attend a talk on polymer brushes. The presenter makes reference to a
great recent review article on the subject by “Bill Britain”. You jot down his name, but are not
sure of the spelling (Britain – as in “Great”? Briton – as in the people of Britain? Britten – as in
Benjamin, the composer? etc) Upon your return to the lab you figure that you should find the
review and share it with your advisor. Upon reading the article you become interested in the
subject and wish to pursue graduate studies with Prof. “Britain (sp?)”.
(i) What is the full citation of his most highly cited review article published since 2005?
(ii) How many times has this review been cited?
(iii)Where does “Britain (sp?)” work now?
Given your answer to (iii), you figure that you should look further afield for possible Ph.D.
research advisors working in this area.
(iv) Who are the five most productive authors on this topic in the U.S., and what are their
current affiliations?
(v) How many papers does Dr. Collard have on this topic? (it’s not many, we are new to the
field)
3. A Quickie
What is the melting point of the following compound?
CHEM 2802, Sp10
HW – Literature searching
NAME: NAME
1 i (a) paper citation:
ANSWER
1 i (b) paper citation:
ANSWER
1 i (c) paper citation:
ANSWER
1 ii (a) RN
1 ii (a) RN
1 ii (a) RN
ANSWER
ANSWER
ANSWER
1 iii (a) # ortho
1 iii (a) # meta
1 iii (a) # para
ANSWER
ANSWER
ANSWER
2 (i) paper citation
ANSWER
2 (ii) times cited
2(iii) Home institution
ANSWER
ANSWER
2 (iv) Five authors (last names)
ANSWER
ANSWER
ANSWER
ANSWER
ANSWER
2 (v) # papers
3 mp
ANSWER
ANSWER °C
1 iv # commercial
disubstituted
ANSWER