Chemical Nomenclature

Abstract

Here we present information on the naming convention of various organic chemicals and common moieties used by medicinal chemists. We also included figures of typical five-membered, six-mem-bered and bicyclic heterocyclic rings.

Contents

12.1 General Nomenclature for Organic Compounds 201

12.1 GENERAL NOMENCLATURE FOR ORGANIC COMPOUNDS

General prefix for a carbon chain of any length: alkGeneral suffix for a functional group moiety: -yl

Table12.L Prefixes based C1: meth- C4: but- C7: hept- C10: dec-on length of carbon cham C2: eth- C5: pent- C8: oct-

Table12.2. Suffixesbased Single bond (saturated) on carbon saturation Double bond

Triple bond -yne

S.C. Khojasteh et al., Drug Metabolism and Pharmacokinetics 201 Quick Guide, DOI 10.1007/978-1-4419-5629-3_12, © Springer Science+Business Media, LLC 2011

Table 12.3. Suffixes and prefixes for common functional groups

Functional group Suffix

Prefix

Acyl Aldehyde Alcohol Amide Carboxylic acid Carboxylic acid salt or ester Ketone Nitrile

-one -nitrile

Acyl-None Hydroxyl-None None None

Keto- or oxo-Cyano-

Table 12.4. Prefixes for heteroatoms

Element

Nitrogen (N) Oxygen (O) Sulfur (S) Phosphorous (P)

Valence

Prefix

Aza-Oxa-Thia-Phospha-

Table 12.5. Common suffixes for nitrogen-containing and non-nitrogen-containing heterocycles

Saturated Unsaturated

Table 12.5. Common suffixes for nitrogen-containing and non-nitrogen-containing heterocycles

Saturated Unsaturated

Ring size

with N

without N

with N

without N

3

-iridine

-irane

-irine

-irene

4

-etidine

-etane

-ete

-ete

5

-olidine

-olane

-ole

-ole

6

-inine

-inane (-ane)

-ine

-ine

Note that if the ring contains some degree of unsaturation, the prefixes dihydro- or tetrahydro- are added accordingly.

H

H ;

: H

H :

• H

Ö

o

Cr

Ô \-NH

j i (_ //N : V—N

Pyrrolidine

Pyrrole ;

; Pyrazolidine

Imidazolidine

; 1,2,3-Triazole

Ô

Ô

: \ NH

\—N :

: N—N

Tetrahydrofuran

Furan ;

■ Pyrazoline

Imidazoline !

'' 1,2,4-Triazole

Gn

: N—N

Tetrahydrothiophene

Thiophene ;

; Pyrazole

Imidazole ;

; Tetrazole

tx g-Lactam Oxazolidine-2-one Oxazolidine-2,4-dione Figure 12.1. Five-membered heterocyclic rings.

Oxazole Isoxazole ;

: Oxadiazole Two N for A-D

Thiazole Isothiazole ;

Hydantoin u u

Piperidine

Pyridine .N

Piperazine

Pyrazine N

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