Antineoplastic agents. XVIII. N-(2-haloethyl)benzylamines

George Pettit, S. K. Gupta, P. A. Whitehouse

Research output: Contribution to journalArticle

12 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)692-696
Number of pages5
JournalJournal of Medicinal Chemistry
Volume10
Issue number4
StatePublished - 1967

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Benzylamines
nornitrogen mustard
Amides
Antineoplastic Agents
Amines
Hydrogenolysis
Acetone
Temperature
diborane

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 journalArticle

Pettit, G, Gupta, SK & Whitehouse, PA 1967, 'Antineoplastic agents. XVIII. N-(2-haloethyl)benzylamines', Journal of Medicinal Chemistry, vol. 10, no. 4, pp. 692-696.
Pettit, George ; Gupta, S. K. ; Whitehouse, P. A. / Antineoplastic agents. XVIII. N-(2-haloethyl)benzylamines. In: Journal of Medicinal Chemistry. 1967 ; Vol. 10, No. 4. pp. 692-696.
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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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