Review of Organic Functional Groups. Introduction to Medical Organic Chemistry

158 Pages·16.567 MB·English

by  Lemke T.L.

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UI'PINCOIT WllLIAMS & WILKINS
FOYE'S PRINCIPLES of MEDICINAL
CHEMISTRY, Fifth Edition
David A. Williams, PhD and Thomas L. Lemke, PhD
ThiS text offers a contemporary account
01 the various drug classes and the prin
cipies determining a drug molecule's aetion
when it enters the cell.
Featuring full caverage on:
• Biochemistry, pharmacology, molecular
biology, and medicinal chemistry
• Molecular modeling
• Pharmaceutical biotechnology
• Biopharmaceutical properties 01 drug
substances
boIlW" ....
L~
• Approaches to anti-AIOS agents
• Drugs presently used, sorne in clinical
trials, and drugs that were lead sub
2(}(}l/I, 114 pagesll,211
stances for research and development.
iIIusrrations/O·683·30737· ,
New ro this cdition:
• Table 01 Contents organized logically by body system
• Text comprises three major parts: Part 1: Principies 01 Discovery; Part 11:
Pharmacodynamic Agents; and Part 111: Recent Advances in Drug Discovery
• Case Studies. Hot Topies and sidebar5 broa den discussions beyond
the classroom.
IT'S EASV TO ORDER!
CAll TOll FREE: 1-800-638-3030 (Outside the U.S., call301-223-23001
FAX: [phone] ONl1NE: lWW.com
Or, purchase directJy from your local health science bookstore.
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•
LJI'PlNOJII WlLU• •M S6 Wlu:.1N:S
I
A3H95522:::J lEMKEC2AD BlSlKE H3PHH955
Review of Organic
Functional Groups
Introduction to Medicinal Organic Chemistry
T hJ.. . On_
""
EL/lror. Davif/ B. TroIj
J.
Maoog/ng Edit()r. Matt/¡ew H¡wber
Marl.:elillg Manager: Sallumlll(l Smith
Productlotl EL/itor. Jenn/fer Ajd/o
Deslgncr: Doug Smock
Compositor. Manj/aml Com1JO!1ilion
Pr/nter: Ron. lAmlldl!J & Sans-Crawlord.wJlle
e
Cop)Tight 2003 Lippincott WiJliams & \\r¡[kins
351 "'es! Camden Street
Bahimorc. MI) 21201
S30 Walnul Strt.'t.'1
Phlladelphia, PA 19106
AII ri~hls reserved. This book is protL'Ctet[ by cop)Tight. No part of this book may be repro
cluectl in any fonu or by any mean!, including photocopying, or ulilized by any inforrnalion
§loragtJ and relrieval s)'stem without ..... riUen p<:nllission rmm the copyright 0I\11cr.
The publisher is nol rcsponsihle (as a matleror prodlld líahility, negligenL"e. or otllCl"\\ioo) ror
tln)' inJul)' resulting from an)' material contained herein. This publication conlains information
retaling 10 general principlesof medical care thal should not be construed as specif"ic instruc
tions for indÍ\idllal patients. Manufacturers' proclllct informaliOll and package inoom shollld
be revie"wed for current infonnation. induding contraindications, dosages. aOO precautions.
Printer/ in tlu: Uuitet/ States 01 AmcriaJ
First Edilion, 1983
Second Editlon, 1987
Third Edition. 1992
Ubnuy of Congress Catllloging-in-Publiclltion Dnrn
Lemke. Thomas L.
Rcview of organic runctional groups: introduction to medicinal organic chemislryl
L. Lcmke.-4th ed.
Thoma.~
p.;
Cnl.
Indudcs inde~.
ISBN 0-7817-4381-8
1. I'harmace1ltical chemisll)·. 2. Chcmistl)', Organic. l. TItle.
fDNLM: L Chemisll)'. Organic. 2. Chemistl)'. Pharmacelltical. QV 744 L554t 2(03)
HS403.L.3972003
615'3-<lc21
2003051692
Tite publishcn 11(1-00 "UllÚ t'vt'"j efTon to lmee tlu: copyright IlOlt/cf"$ lorborrowetl matcr/al.
1I ¡hey IIflL'e iuatl-ooncutly ove,.{OOketl ally, I"elj !ViII be plea$etl lO IIUlkc l/u: 1l~$$fIry
fl1T(1ngcmCIIIs al 11u: finll aplXlrlllllUy.
To purchase additional copies oflhis book. can out custorncr serdce departmcnt al (800) 638-
3030 or fa¡¡ ordcrs lo [phone]. Inlcmational CIlslomcrs soouM C".ul [phone].
Vi,i' U""incoll Wilfio,... ¿- Wilki,... on ,he ',,'ernd: hllp:/lwtcu:.l..W\Y.com. LippinooU
\\r¡niams & Wilkil1.'l cmlomer oon'ice are :wailablc f mili 8:30 mn t06:00 pm, EST.
representati\"l~s
04 05 06 07 08
2 .3 4 5 6 7 8 9 10
e
;.pvrlghted material
his book has been prepare<! with the intent Ihal il may be use<! as a self·
¡:mce<! review of organic funetional groups. If Ihe mate'rial covered in Ihis
book were lo be presented in a conventional classroom setting, il would
require 14 lo 16 fonnal lecture houn. \Vith this in mind, you should no!
attemp! to cover all of the material in one sitting. A slow, leisurely pace will great·
Iy incrC:lSe yOllr comprehension and decrease Ihe number of retum visils lo the
mll!erial. You should stop lo review any section Ihal you do not complelely lInder·
sland. Adde<! lo this edition of Ihe book is an electronic sel of queslions designe<!
around each chapler. The questions are follo\\'OO by a detailed explanation of Ihe
correct unS\ver. EncloSf!<! with this book is an Electronic World)(x)k CD·Rom com·
pose<! of problem seis corresponding lo each of the organic f\lI1ctional grollps
(Chaplers 2-15 and 17). Each problem sel is followed by anS\vers lo the questions
and a detailed diSCllssion explaining the process leading to Ihe anS\\'ers. If do
}'OU
nol understand an answer or Ihe process leading lo the answer, retum to the appro
priale section of the book and review thal section again.
OBJECTIVES
The following outline is a general review of Ihe functional groups common lo
organic chemistry. It is Ihe objective of this book to review Ihe general topies of
nomenclature. physica! properties (with specific emphasis place<! on \\f'J.ler and
lipid solubility), chemical properties (Ihe stability lack of stability of a function·
Of
al group lo nonnal environmental conrntions, referred lo as in vitro stability), and
metabolism (tlle stability of lack of stability of a fun<.tional group in the body,
referred lo as in vivo stability). There \vill be no attempt to co\'er synthesis, nor will
great emphasis be place<! on chemieaJ reactions except when Ihey relate<! lo the
physical or chemical slability and mechanistic action of drugs. 111is review is meant
lo provide background material for Ihe fonnal pharmacy courses in medicinal
chemistry. The objectÍ\'Cs are presenle<! in Ihe follO\ving manner lo aid in focusing
attenlion on the expected learning outcomes.
Upon successful completion of the book. tbe following goals will have been
attaine<!:
• TIle sludenl \vill be able lo dmw a chemieal struclure of simple organic
molecules gi\'en a common 'or officiaJ chemical name. With more complex
polyfunctional molecules, the student \vill be able lo idenlif)' Ihe functional
groups b>iven the chemical slructure.
-
• The studenl will be abJe 10 predicI Ihe solubility of a chemical in:
l. Aqueous acid
2. \Valer
3. Aqueous base
• 111e studenl will be able lo predict and 5how, with chemical struclures, Ihe
chcmical instabilitíes of cach organic functional group under conditions
appropriate lo a substance ··setting on ¡he shelf,fl by which is meant condi
lions such as air, lighl. aqueous a(:id or b.'lse, and
he~lt.
• The sludenl will be able 10 predict and sho\\', wilh chcmical structures, Ihe
melabolislll of each organic functional group.
To help Ihese skills. Ihe infornmtion is presenled in lhe following
yOll m¡L~ler
order:
• Nomenclature
1. ComlllOIl
2. Official (JUPAC)
• Physic(I{-Chemic(I{ Prvperlies
l . Ph)'sic-dl properties-relalcd lo waler and lipid solubility
2. Chemical properties in slability or reactivity of functional groups
\~ho
on the sheJr
w
• Metabofism
Chemical properties in vi\'o--slabilily or reactivity of functional groups Win
the bodyfl
RECOMMENDED PREPARATION
To nm.>ámize leaming and lo perspectivtl in ¡he study of the book, il would
prO\~de
be helpful lo read certain background material. It is highly recommende<! thal a
textbook on general organic chemistry be reviewed and consulted as a referente
book while using this book. Pay special attentíon lo Ihe se<..'tions on nomenclature
and ph)'sical-chemical properties.
e ;.pvrlghted material
his book would nol llave been possible withoul the encoumgement and
input of colleagues al my own inslitution and frorn medicinal chernists
throughout the Uniled States. 111e idea for Ihe text originated from a late
night disclIssion al a Medicinal Symposiulll bul carne lo fruition because
of support fmm SmilhKline Corporalion and sludenls al Ihe University of Houston
College of Pharmucy. Continuous suggestions have come from Ihose faculty who
actually make use of the book and Ihis has led lo the changes which are found in
previOllS edilions as well as this edition of Ihe book. 1 wOllld especially like lo Ihank
Dr. Louis WilIiams for his timely commenls. And Ihe real joy comes fmm sludenls,
sorne of whom are nO\\! my colleagues, who infonnally lell me of the beneflts they
have gained fmm Ihis hook.
1 mus! also acknowledge the excellent staIT. p<'l51 and presenl, al L\V\V who have
made Ihi5 pmject seem more Hke an academic undertaking mther than a commer
dal pnx:ess. Many of Ihe slaff members 1 have only mel electronically or via phone
collversaliolls. bul their (."Onlribulions have led lo a more readable texto1 would Hke
lo speciflcally acknowledge Donna Balado for her (lasl support and David B. Troy
for making this eclition harpen. The continuous support al L\V\V has come fmm
J.
managing edilor Matthew Hallber. Without Matfs pmhlem-solving ability and
encouragement. 1 am certain thal Ihis eclition would have been a labor of work
mther Ihan joyo Finally. a very SpecilU Ihank lo my wife Pal for (lutting up wilJ¡
}'OU
the IlOurs oflime pul ¡nlo Ihe lext.
T.L. L.
. .
Copyrighted malerial
Introductlon , ,
lit
, """ , , , ,
Water So!ublLlty and ehemica! Bondlns . .. ..... .. ... . 1
1
• Van der Waals Attract;on (Forces) , , , , , , , , , , , , , , , , , " , " , , , ,1
• Dipole-Dipole Bonding (Hydrogen Bond) , , , , , , , , , . , , , , , , , , ' , ,2
• lonicAttraction ".",." . " .. "."""" "" " " , ", 3
• lon·Di leBondin " .. , .....
" . ",."""." ,. "."., ,4
A!kanes (e,H" , ,) .... .. .... ... .... .. .... . . . . . . .6
2
3 A!kenes (e, H, .,) ... . . . . . . . . . . .... . . . . ... . .. .. .. 11
• Cycloalkanes: Alkene lsomers , .. " .. " .. , ... , .. , ........ 14
" Aromatlc Hydrocarbons . . . . . . . . . . .. . . ,. ,.,., .. , .16
5 Halogenated Hydrocarbons . . . . . . . , . . . ,., .,." . , .19
6 Aleohols ... . . . ...... . ... , ... . . , . , . ",, ' , ' , '
,21
Phenols ,., .. ",.,., .. ,.,. , . ,. , . . . , .. ,., . . . .2 5
8 Ethers . . . . . . .... . . . . .. . . . . ... .. . . .. ........ .3 0
A!deh des and Ketones . .. ........... .. ..... . . . .3 3
Amines " , , 3B
10
• Quaternary Ammonium Salts .. , .. . ... , ... , ..... , ' , , . , , , ,46
11 (a[boxyUe Acids ., . . . . . .. . .. . . . , . . . . . . . , .. . . . .4 8
Funcllona! Derlvatives 01 earboxyllc Aclds . .. ..... .. . .5 6
12
• Este!} """" . " ... ,.,."" " "., ... , .. , .. , ... , .. ,56
• Amides ",.""., .. " .. ,."., .... " .. , .. " . .... , .. ,59
• Carbonates, Carbamates. and Ureas , ....... , . , ... . , , . , , . , ,62
• Amidines and Guanidines .. , .. . . . . . .. , ... . ...... , ...... 64
Sulfonie Aclds and Sulfonamides .. . .. , . . . ",.", . .6 6
1)
• Sulfonic Adds ".".",.", . " .. "." .. "." .. , . . " .. 66
• Sulfonamides .................. , .. , ... . .. .. . , . . , . .. ,66
e
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