University of Puthisastra

Department of Pharmacy

Therapeutic chemistry or Medicinal

Chemistry

Chapter 1: Heterocyclic Compounds

Lecturer : Tan Chantrea , MSc Ph

Number of credit : 3
Number of hour : 45h

Academic year :2021-2022

 Heterocyclic Compounds

Objectives
• Able to nomenclature of heterocyclic compound
• Know the interest of heterocyclic compound that present in
chemical structure of drugs

Content

1. Definition
2. Nomenclature of heterocyclic compound
3. Heterocyclic & Therapeutic agents
 Heterocyclic Compounds
I.Definition
Cyclic compounds having as ring members atoms of at least one different
elements(nitrogen, oxygen, and sulfur) “The IUPAC Gold Book”.

➔ Nomenclature of heterocyclic compound :

1) The Hantzsch-Widman Nomenclature.
2) Common Names
3) The Replacement Nomenclature
 Heterocyclic Compounds
II.Nomenclature of heterocyclic compound
1. The Hantzsch-Widman Nomenclature ( IUPAC)
➔ The Hantzsch-Widman nomenclature is based on
- the type (Z) of the heteroatom;
- the ring size (n) Oxygen→ Oxa

- The nature of the ring, whether it is saturated or unsaturated.

➔ Applies to monocyclic three-to-ten-membered ring heterocycles
1. Type of the heteroatom : indicated by a prefix Ring size : 3 with
saturated → irane
2. Ring size (n) : indicated by stem
3. Degree of unsaturation of the ring

3 of Nitrogen with indication

of location → 1,3,5-triaza

Ring size :6 with

N-nonsaturated→ ine

Nitrogen→ Aza

Ring size : 3 with N-saturated

→ iridine
 Heterocyclic Compounds
II.Nomenclature of heterocyclic compound
1. The Hantzsch-Widman Nomenclature ( IUPAC)
Hantzch-Widman stems to ring of 3-10 atomes Heteroatom

Rings without Nitrogen Rings with Nitrogen Oxygen→Oxa

Ring size Hete: Sulfur → Thia
Unsatd Satd Unsatd Satd Sulfur→Thia
Ring 4 satd→etane
3 irene irane irine iridine Selenium→Selena

4 ete etane ete etidine Nitrogen→Aza Thia + etane →Thietane

5 ole olane ole olidine Phosphorus→Phospha

6 ine/ininea aneb/inane ine ane Arsenic→Arsa

7 epine epane epine epane Antimony→Stibs

Hete: Oxygen → Oxa

8 ocine ocane ocine ocane Bismuth→Bisma
Nitrogen→Aza
9 onine onane onine onane Lead→Plumba
Ring 5 N-Unsatd→ole
10 cine ecane ecine ecane Mercury→Mercura

a: Rings containing P ,As, Sb< or B as element of last priority Oxa + Aza + ole → 1,2 oxazole
B: Rings containing O ,S,Se or Te as element of last priority
 Heterocyclic Compounds
II.Nomenclature of heterocyclic compound
1. The Hantzsch-Widman Nomenclature ( IUPAC)
Hantzch-Widman stems to ring of 3-10 atomes Heteroatom
Hete: Nitrogen → Aza
Rings without Nitrogen Rings with Nitrogen Oxygen→Oxa Ring 4 unsatd→ ete
Ring size
Unsatd Satd Unsatd Satd Sulfur→Thia N. of Unsated 1 (max: 2)
→ 2,3 dihydro
3 irene irane irine iridine Selenium→Selena
2,3 dihydro + Aza + ete →
4 ete etane ete etidine Nitrogen→Aza 2,3 dihydroazete

5 ole olane ole olidine Phosphorus→Phospha

6 ine/ininea aneb/inane ine ane Arsenic→Arsa

7 epine epane epine epane Antimony→Stibs

8 ocine ocane ocine ocane Bismuth→Bisma Hete: Sulfur → Thia

Nitrogen→Aza
9 onine onane onine onane Lead→Plumba Ring 6N-Unsatd(Max )→ine
And C6 present free H
10 cine ecane ecine ecane Mercury→Mercura
a: Rings containing P ,As, Sb< or B as element of last priority
B: Rings containing O ,S,Se or Te as element of last priority
1 Thia + 2,5 Diaza + ine + Free H atC6 → 6Hydro-1,2,5 thiadiazine
 Heterocyclic Compounds
II.Nomenclature of heterocyclic compound
1. The Hantzsch-Widman Nomenclature ( IUPAC)

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…………………... …………………... …………………...

…………………... …………………... …………………...

…………………... …………………...
…………………...
 Heterocyclic Compounds
II.Nomenclature of heterocyclic compound
2. Common Names
5-membered heterocycles with one or two heteroatoms

6-membered heterocycles with one or two heteroatoms

 Heterocyclic Compounds
II.Nomenclature of heterocyclic compound
2. Common Names
Fused heterocycles

Three-membered rings Four-membered rings

β-lactam
Fosfomycin oxetanocin
Thiotepa
Mitomycin C
 Heterocyclic Compounds
II.Nomenclature of heterocyclic compound
3. The Replacement Nomenclature
➔ Names of monocyclic hetero compounds may be formed by prefixing + their
locants, to the name of the corresponding hydrocarbon

Cyclopenta-1,3 diene
Sila-2-4 pentadiene

Benzene
Silabenzene
1-Thia-4-aza-2,6-disilacyclohexane
 Heterocyclic Compounds
III.Heterocyclic & Therapeutic agents
➔ Bioactive Furans, Pyrroles,Thiophenes (Five-membered
rings)

Nitrofurantoin

Ascorbic acid Nicotine

 Heterocyclic Compounds
III.Heterocyclic & Therapeutic agents
➔ Bioactive Pyridines (Six-membered rings)

Nicotine sulphapyridine
 Heterocyclic Compounds
III.Heterocyclic & Therapeutic agents
➔ Bioactive Quinolines/Isoquinolines
 Heterocyclic Compounds
III.Heterocyclic & Therapeutic agents
➔ Indoles – Bioactive Indoles

Ondansetron
 References
- An introduction to medicinal chemistry , 5th edition;
GRAHAM L.PATRICK
- Basic Principles of Drug discovery and Development
,ELSEVIER,2015.
- Foye’s Principles of Medicinal chemistry ,7th
edition,Thomas L.Lemke
- Organic Medical and Pharmaceutical chemistry , 12th, John
M.Beale,Jr.