Fundamentals of Medicinal Chemistry

Table 7.6 Some examples of the classes and compounds of anti-cancer agents that act by alkylation of

nucleic acids. It is emphasized that this table only lists some of the classes of alkylating compound that are

active against cancers

Class (based on) Examples Active against

Nitrogen mustard

R

Cl

Cl

N

Melphalan

Dacarbazine

Busulphan

Carmustine

Temozolomide

Carboplatin

Trimenlamol

N

N

H

CONH 2

NN CH^3

CH 3

N

HOOCCHCH 2

NH 2

Cl

Cl

N

ClCH 2 CH 2 NHCONCH 2 CH 2 Cl

N

O

O

H 3 C S O

O

O

S

O

O CH^3

H 2 NOC

N

N

N

N

N

CH 3

O

Pt

H 3 N

H 3 N

O

O

O

O

N

N

N

CH 3

CH 3

CH 3

CH 2 OH

CH 2 OH

HOCH 2

Multiple myeloma, ovarian and

breast carcinoma.

Triazeneimidazoles

N

N

H

N

N

N

Wide range including

malignant lymphomas,

malanomas and sarcomas.

Alkyl dimethanesulphonates

RO 2 SOCH 2 CH 2 CH 2 CH 2 OSO 2 R

Granulocytic leukaemia.

Nitrosoureas –NHCON(NO)– Active against cancers of the

brain and cerebrospinal fluid.

Imidazotetrazinones

N

N

N

N

N

O

Melanoma and brain tumours.

Platinum complexes

Pt

Testicular and ovarian cancers.

Carbinolamines –NR– CHOH– Ovarian cancer.

DRUGS THAT TARGET NUCLEIC ACIDS 153