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

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Chemistry for Pharmacy Students General, Organic and Natural Product Chemistry Satyajit D. Sarker University of Ulster, Coleraine, Northern Ireland, UK Lutfun Nahar University of Ulster, Coleraine, Northern Ireland, UK
Copyright #2007 John Wiley & Sons Ltd, The Atrium, Southern Gate, Chichester, West Sussex PO19 8SQ, England Telephone (þ44) 1243 779777 Email (for orders and customer service enquiries): cs-books@wiley.co.uk Visit our Home Page on www.wiley.com All Rights Reserved. No part of this publication may be reproduced, stored in a retrieval system or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning or otherwise, except under the terms of the Copyright, Designs and Patents Act 1988 or under the terms of a licence issued by the Copyright Licensing Agency Ltd, 90 Tottenham Court Road, London W1T 4LP, UK, without the permission in writing of the Publisher. Requests to the Publisher should be addressed to the Permissions Department, John Wiley & Sons Ltd, The Atrium, Southern Gate, Chichester, West Sussex PO19 8SQ, England, or emailed to permreq@wiley.co.uk, or faxed to (þ44) 1243 770620. Designations used by companies to distinguish their products are often claimed as trademarks. All brand names and product names used in this book are trade names, service marks, trademarks or registered trademarks of their respective owners. The Publisher is not associated with any product or vendor mentioned in this book. This publication is designed to provide accurate and authoritative information in regard to the subject matter covered. It is sold on the understanding that the Publisher is not engaged in rendering professional services. If professional advice or other expert assistance is required, the services of a competent professional should be sought. Other Wiley Editorial Offices John Wiley & Sons Inc., 111 River Street, Hoboken, NJ 07030, USA Jossey-Bass, 989 Market Street, San Francisco, CA 94103-1741, USA Wiley-VCH Verlag GmbH, Boschstrasse 12, D-69469 Weinheim, Germany John Wiley & Sons Australia Ltd, 42 McDougall Street, Milton, Queensland 4064, Australia John Wiley & Sons (Asia) Pte Ltd, 2 Clementi Loop #02-01, Jin Xing Distripark, Singapore 129809 John Wiley & Sons Canada Ltd, 6045 Freemont Blvd. Mississauga, ONT, L5R 4J3, Canada Wiley also publishes its books in a variety of electronic formats. Some content that appears in print may not be available in electronic books. Anniversary Logo Design: Richard J. Pacifico Library of Congress Cataloging-in-Publication Data Sarker, Satyajit D. Chemistry for pharmacy students: general, organic, and natural product chemistry / Satyajit D. Sarker, Lutfun Nahar. p.; cm. Includes bibliographical references. ISBN 978-0-470-01780-7 (cloth : alk. paper) 1. Chemistry–Textbooks. I. Nahar, Lutfun, Ph. D. II. Title. [DNLM: 1. Chemistry, Pharmaceutical. 2. Chemistry. QV 744 S517c 2007] QD31.3.S377 2007 540–dc22 2007017895 British Library Cataloguing in Publication Data A catalogue record for this book is available from the British Library ISBN 978-0-470-01780-7 (HB) 978-0-470-01781-4 (PB) Typeset in 11/14pt Times by Thomson Digital Printed and bound in Great Britain by Antony Rowe Ltd., Chippenham, Wilts This book is printed on acid-free paper responsibly manufactured from sustainable forestry in which at least two trees are planted for each one used for paper production.
Page 4: This book is dedicated to pharmacy
Page 7 and 8: viii CONTENTS 5.5 Substitution reac
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
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Again, in reality, cyclohexane is n
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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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