New di-(beta-chloroethyl)-alpha-amides on N-(meta-acylamino-benzoyl)- D,L-aminoacid supports with antitumoral activity.
In order to obtain new compounds with antitumoural action the N-(meta-acylaminobenzoyl)-alpha-acylaminobenzoyl)-alpha-aminoacids 4-9 were prepared. These compounds were subsequently converted into the corresponding Delta(2)-oxazolin-5-ones 10-15, which in turn were submitted to a ring opening reaction with di-(beta-chloroethyl)amine to afford the peptide supported N-mustards 16-21, which showed low toxicity and cytostatic activity similar to that of sarcolisine against the Ehrlich ascite and Walker 253 carcinosarcoma.
Sunel
Valeriu
V
Department of Organic Chemistry and Biochemistry, Faculty of Chemistry, Al. I. Cuza University, Iasi, 11 B-dul Carol I, 700506, Romania.
Popa
Marcel
M
Desbrières
Jacques
J
Profire
Lenuta
L
Otilia
Pintilie
P
Catalina
Lionte
L
D000478:Alkylation / Q000187:drug effects; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001565:Benzoates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D011522:Protons; D051381:Rats; D017208:Rats, Wistar; D013055:Spectrophotometry, Infrared
D000577:Amides; D000596:Amino Acids; D000970:Antineoplastic Agents; D001565:Benzoates; D011522:Protons