Abstract
A series of N-benzyl-N-(2-haloethyl)amines have been synthesized for comparison of possible antineoplastic properties with those of the corresponding N-bis(2-chloroethyl)amines. Conversion of 3,4-dichlorobenzoylaziridine (II) with HCl or HBr to, respectively, amides IIIa and IIIb followed by a diborane reduction sequence yielding amines IVa and IVb outlines the synthetic methods employed. Several N-2-iodoethylamides of the type illustrated by structure IIIc were prepared from the corresponding aziridine amide employing HI or from a N-2-chloroethylamide precursor using NaI in acetone. Reaction between the N-2-iodoethylamides and diborane (in tetrahydrofuran) at approximately 60° for 2 hr or at room temperature (overnight) was shown to cause virtually complete hydrogenolysis of the C-I bond. Presently available biological results indicate the N-(2-chloroethyl)-benzylamines to be considerably less active than the corresponding N-bis(2-chloroethyl)benzylamines.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 692-696 |
| Number of pages | 5 |
| Journal | Journal of Medicinal Chemistry |
| Volume | 10 |
| Issue number | 4 |
| State | Published - 1967 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Antineoplastic agents. XVIII. N-(2-haloethyl)benzylamines. / Pettit, George; Gupta, S. K.; Whitehouse, P. A.
In: Journal of Medicinal Chemistry, Vol. 10, No. 4, 1967, p. 692-696.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Antineoplastic agents. XVIII. N-(2-haloethyl)benzylamines
AU - Pettit, George
AU - Gupta, S. K.
AU - Whitehouse, P. A.
PY - 1967
Y1 - 1967
N2 - A series of N-benzyl-N-(2-haloethyl)amines have been synthesized for comparison of possible antineoplastic properties with those of the corresponding N-bis(2-chloroethyl)amines. Conversion of 3,4-dichlorobenzoylaziridine (II) with HCl or HBr to, respectively, amides IIIa and IIIb followed by a diborane reduction sequence yielding amines IVa and IVb outlines the synthetic methods employed. Several N-2-iodoethylamides of the type illustrated by structure IIIc were prepared from the corresponding aziridine amide employing HI or from a N-2-chloroethylamide precursor using NaI in acetone. Reaction between the N-2-iodoethylamides and diborane (in tetrahydrofuran) at approximately 60° for 2 hr or at room temperature (overnight) was shown to cause virtually complete hydrogenolysis of the C-I bond. Presently available biological results indicate the N-(2-chloroethyl)-benzylamines to be considerably less active than the corresponding N-bis(2-chloroethyl)benzylamines.
AB - A series of N-benzyl-N-(2-haloethyl)amines have been synthesized for comparison of possible antineoplastic properties with those of the corresponding N-bis(2-chloroethyl)amines. Conversion of 3,4-dichlorobenzoylaziridine (II) with HCl or HBr to, respectively, amides IIIa and IIIb followed by a diborane reduction sequence yielding amines IVa and IVb outlines the synthetic methods employed. Several N-2-iodoethylamides of the type illustrated by structure IIIc were prepared from the corresponding aziridine amide employing HI or from a N-2-chloroethylamide precursor using NaI in acetone. Reaction between the N-2-iodoethylamides and diborane (in tetrahydrofuran) at approximately 60° for 2 hr or at room temperature (overnight) was shown to cause virtually complete hydrogenolysis of the C-I bond. Presently available biological results indicate the N-(2-chloroethyl)-benzylamines to be considerably less active than the corresponding N-bis(2-chloroethyl)benzylamines.
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M3 - Article
VL - 10
SP - 692
EP - 696
JO - Journal of Medicinal Chemistry
JF - Journal of Medicinal Chemistry
SN - 0022-2623
IS - 4
ER -