Chemistry for Pharmacy Students : General, Organic and Natural ...

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Contents Preface ix 1 Introduction 1 1.1 Role of chemistry in modern life 1 1.2 Physical properties of drug molecules 3 2 Atomic structure and bonding 17 2.1 Atoms, elements and compounds 17 2.2 Atomic structure: orbitals and electronic configurations 18 2.3 Chemical bonding theories: formation of chemical bonds 21 2.4 Electronegativity and chemical bonding 27 2.5 Bond polarity and intermolecular forces 28 2.6 Significance of chemical bonding in drug–receptor interactions 31 3 Stereochemistry 35 3.1 Stereochemistry: definition 36 3.2 Isomerism 36 3.3 Significance of stereoisomerism in determining drug action and toxicity 53 3.4 Synthesis of chiral molecules 55 3.5 Separation of stereoisomers: resolution of racemic mixtures 56 3.6 Compounds with stereocentres other than carbon 57 3.7 Chiral compounds that do not have a tetrahedral atom with four different groups 57 4 Organic functional groups 59 4.1 Organic functional groups: definition and structural features 60 4.2 Hydrocarbons 61 4.3 Alkanes, cycloalkanes and their derivatives 61 4.4 Alkenes and their derivatives 103 4.5 Alkynes and their derivatives 108 4.6 Aromatic compounds and their derivatives 112 4.7 Heterocyclic compounds and their derivatives 143 4.8 Nucleic acids 170 4.9 Amino acids and peptides 179 4.10 Importance of functional groups in determining drug actions and toxicity 184 4.11 Importance of functional groups in determining stability of drugs 188 5 Organic reactions 191 5.1 Types of organic reaction 191 5.2 Radical reactions: free radical chain reactions 192 5.3 Addition reactions 197 5.4 Elimination reactions: 1,2-elimination or b-elimination 223
viii CONTENTS 5.5 Substitution reactions 232 5.6 Hydrolysis 260 5.7 Oxidation–reduction reactions 264 5.8 Pericyclic reactions 278 6 Natural product chemistry 283 6.1 Introduction to natural product drug discovery process 283 6.2 Alkaloids 288 6.3 Carbohydrates 303 6.4 Glycosides 319 6.5 Terpenoids 331 6.6 Steroids 352 6.7 Phenolics 359 Index 371
Page 2 and 3: Chemistry for Pharmacy Students Gen
Page 4: This book is dedicated to pharmacy
Page 9 and 10: x PREFACE countries. Therefore, the
Page 12 and 13: 1 Introduction Learning objectives
Page 14 and 15: Whatever the source is, chemistry i
Page 16 and 17: 1.2 PHYSICAL PROPERTIES OF DRUG MOL
Page 18 and 19: Each acid has a conjugate base, and
Page 20 and 21: 1.2 PHYSICAL PROPERTIES OF DRUG MOL
Page 22 and 23: CH3CH3 ðEthaneÞ !CH3NH2 ðMethyla
Page 24 and 25: takes place. K a ¼ K eq½H2OŠ ¼
Page 26: Recommended further reading RECOMME
Page 29 and 30: 18 CH2 ATOMIC STRUCTURE AND BONDING
Page 46 and 47: 3 Stereochemistry Learning objectiv
Page 48 and 49: dimensional orientation of the hydr
Page 50 and 51: H H H H H H H H H H H C 3 Butane Am
Page 52 and 53: Again, in reality, cyclohexane is n
Page 54 and 55: not chiral. With achiral molecules,
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3.2 ISOMERISM 45 When we have a pai
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( ). This D and L system is common
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HO H 4 1 2COOH CH2OH 3 (R)-2,3-Dihy
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Geometrical isomers H H H H Cl Cl C
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3.3 SIGNIFICANCE OF STEREOISOMERISM
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H H * * (+)-Limonene (in orange) (
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3.7 CHIRAL COMPOUNDS THAT DO NOT HA
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4 Organic functional groups Learnin
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ðContinuedÞ Name General structur
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4.3 ALKANES, CYCLOALKANES AND THEIR
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drawn as solid wedges, and those po
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CH4 + 2 O2 CO2 + 2 H2O CH3CH2CH + 2
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Reactivity of alkyl halides RHC CH2
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Alkanes can be prepared from alkyl
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H OH OH H i. BH3 .THF H2O, H2SO4 or
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Nomenclature of thiols The nomencla
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H2C CH2 CH3CH CH2 CH3CH2CH CH2 O O
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Nomenclature of amines Aliphatic am
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aldehydes and ketones, followed by
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O C2H5 C 4.3 ALKANES, CYCLOALKANES
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earlier, alcohols can be prepared f
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Aliphatic dicarboxylic acids are na
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aldehydes (see Section 5.7.11), ozo
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4.3.14 Acid chlorides The functiona
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Preparation of acid anhydrides Anhy
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Reactions of esters Esters are less
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espectively (see Section 5.5.5). Th
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eagent or organolithium produces ke
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unsaturated groups are called the v
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Alkenes are obtained from selective
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equires two hybrid orbitals to bond
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addition reactions, e.g. hydrogenat
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4.6 AROMATIC COMPOUNDS AND THEIR DE
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form two doughnut-shaped clouds of
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the overlap of a p orbital on the s
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electrons from the ring through the
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CH 2 Br Bromomethylbenzene 4.6.10 P
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A number of other reactions can als
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Physical properties of aniline 4.6
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From chlorobenzene Treatment of chl
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4.7 HETEROCYCLIC COMPOUNDS AND THEI
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4.7 HETEROCYCLIC COMPOUNDS AND THEI
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4.7.4 PYRROLE, FURAN AND THIOPHENE:
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Furan is synthesized by decarbonyla
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N H S + HNO 3 + HNO 3 Acetic anhydr
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dipole moment of pyridine is 1.57 D
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N Cl 2-Chloropyridine Br N OMe 4-Br
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R' R NH 2 O + R'' O X Base R' R O H
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for isoxazole, pyrazole and isothia
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A number of drug molecules contain
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4.7.9 Purine Purine contains a pyri
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4.7.10 Quinoline and isoquinoline 4
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MeO MeO MeO MeO NH 2 β-Phenylethyl
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at room temperature, and posseses a
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In the nucleotides, while the heter
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4.8.2 Structure of nucleic acids Pr
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Sugar _ phosphate backbone O O P O
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Transcription: synthesis of RNA 4.8
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sample is obtained from a crime sce
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AVK (one letter). The ends of a pep
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Carbon CO 2 + H 2 O 4.9 AMINO ACIDS
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4.10 IMPORTANCE OF FUNCTIONAL GROUP
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4.10 IMPORTANCE OF FUNCTIONAL GROUP
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Certain functional groups in drug m
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192 CH5 ORGANIC REACTIONS Reaction
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194 CH5 ORGANIC REACTIONS H C 3 H +
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196 CH5 ORGANIC REACTIONS brominati
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198 CH5 ORGANIC REACTIONS General r
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200 CH5 ORGANIC REACTIONS Electroph
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202 CH5 ORGANIC REACTIONS addition
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204 CH5 ORGANIC REACTIONS Br. + Br.
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206 CH5 ORGANIC REACTIONS CH3CH CH2
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208 CH5 ORGANIC REACTIONS Hydrobora
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210 CH5 ORGANIC REACTIONS p bond, a
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212 CH5 ORGANIC REACTIONS Mechanism
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214 CH5 ORGANIC REACTIONS Addition
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216 CH5 ORGANIC REACTIONS molecule
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218 CH5 ORGANIC REACTIONS O R C Y Y
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220 CH5 ORGANIC REACTIONS condition
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222 CH5 ORGANIC REACTIONS Aldol con
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224 CH5 ORGANIC REACTIONS remove th
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226 CH5 ORGANIC REACTIONS formation
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230 CH5 ORGANIC REACTIONS Stereoche
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232 CH5 ORGANIC REACTIONS E1 versus
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234 CH5 ORGANIC REACTIONS solvent i
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236 CH5 ORGANIC REACTIONS configura
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238 CH5 ORGANIC REACTIONS the base,
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242 CH5 ORGANIC REACTIONS The react
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244 CH5 ORGANIC REACTIONS Conversio
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250 CH5 ORGANIC REACTIONS Conversio
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252 CH5 ORGANIC REACTIONS Preparati
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254 CH5 ORGANIC REACTIONS Nucleophi
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256 CH5 ORGANIC REACTIONS In the ca
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258 CH5 ORGANIC REACTIONS Cl 2 , Fe
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260 CH5 ORGANIC REACTIONS Step 3. L
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262 CH5 ORGANIC REACTIONS : O: R C
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264 CH5 ORGANIC REACTIONS water. Th
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268 CH5 ORGANIC REACTIONS work-up.
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270 CH5 ORGANIC REACTIONS (C5H5NH +
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272 CH5 ORGANIC REACTIONS OH Cyclop
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274 CH5 ORGANIC REACTIONS hydride s
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276 CH5 ORGANIC REACTIONS 5.7.20 Re
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280 CH5 ORGANIC REACTIONS Cyclic co
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282 CH5 ORGANIC REACTIONS with a mi
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284 CH6 NATURAL PRODUCT CHEMISTRY 6
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286 CH6 NATURAL PRODUCT CHEMISTRY t
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288 CH6 NATURAL PRODUCT CHEMISTRY L
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290 CH6 NATURAL PRODUCT CHEMISTRY C
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292 CH6 NATURAL PRODUCT CHEMISTRY O
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294 CH6 NATURAL PRODUCT CHEMISTRY p
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296 CH6 NATURAL PRODUCT CHEMISTRY I
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298 CH6 NATURAL PRODUCT CHEMISTRY T
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300 CH6 NATURAL PRODUCT CHEMISTRY P
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302 CH6 NATURAL PRODUCT CHEMISTRY M
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304 CH6 NATURAL PRODUCT CHEMISTRY a
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306 CH6 NATURAL PRODUCT CHEMISTRY h
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308 CH6 NATURAL PRODUCT CHEMISTRY H
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314 CH6 NATURAL PRODUCT CHEMISTRY 6
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316 CH6 NATURAL PRODUCT CHEMISTRY g
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322 CH6 NATURAL PRODUCT CHEMISTRY T
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324 CH6 NATURAL PRODUCT CHEMISTRY k
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326 CH6 NATURAL PRODUCT CHEMISTRY S
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328 CH6 NATURAL PRODUCT CHEMISTRY B
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330 CH6 NATURAL PRODUCT CHEMISTRY h
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332 CH6 NATURAL PRODUCT CHEMISTRY (
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334 CH6 NATURAL PRODUCT CHEMISTRY G
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344 CH6 NATURAL PRODUCT CHEMISTRY S
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346 CH6 NATURAL PRODUCT CHEMISTRY P
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350 CH6 NATURAL PRODUCT CHEMISTRY B
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352 CH6 NATURAL PRODUCT CHEMISTRY i
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354 CH6 NATURAL PRODUCT CHEMISTRY I
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360 CH6 NATURAL PRODUCT CHEMISTRY s
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362 CH6 NATURAL PRODUCT CHEMISTRY N
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364 CH6 NATURAL PRODUCT CHEMISTRY c
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368 CH6 NATURAL PRODUCT CHEMISTRY F
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370 CH6 NATURAL PRODUCT CHEMISTRY R
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372 INDEX Amino sugar 304, 305, 317
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374 INDEX Closed shell configuratio
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376 INDEX Friedel-Crafts alkylation
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378 INDEX Lincomycin 318 Linum usit
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380 INDEX Polymerization 106, 110 P
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382 INDEX Sulphanilamide 140 Sulpha
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