16735-28-7Relevant articles and documents
Pyrrolo[2,1-d][1,2,3,5]tetrazine-4(3H)-ones, a new class of azolotetrazines with potent antitumor activity
Diana, Patrizia,Barraja, Paola,Lauria, Antonino,Montalbano, Alessandra,Almerico, Anna Maria,Dattolo, Gaetano,Cirrincione, Girolamo
, p. 2371 - 2380 (2003)
Pyrrolo[2,1-d][1,2,3,5]tetrazinones 10a-o, compounds that hold the deaza skeleton of the antitumor drug temozolomide, were prepared by reaction of 2-diazopyrroles 9 and isocyanates. Such a synthetic route represents, among those leading to azolotetrazinones reported so far, the only possible one since attempts to cyclize to the title ring system 2-amino-1-carbamoylpyrroles 11 or the mono substituted 2-triazenopyrrole 12 failed. Compounds 10 were screened at the National Cancer Institute (NCI) for their activity against a panel of about 60 human tumor cell lines. Most of them possess remarkable antineoplastic activity having GI50 values in the low micromolar or sub-micromolar range and reaching, in the case of compound 10d, nanomolar concentrations. The most sensitive cell lines were MDA-N and MDA-MB-435 of the breast sub-panel, and SR, K-562, HL60 (TB) and CCRF-CEM of the leukaemia sub-panel. SAR evaluation and COMPARE computations indicate, for compounds 10, a mechanism of action different from that of temozolomide.
Chemistry of indoles carrying a basic function. Part VII. A new aspect of Stobbe reaction
Moldvai, István,Temesvári-Major, Eszter,Incze, Mária,Platthy, Tünde,Gács-Baitz, Eszter,Szántay, Csaba
, p. 309 - 319 (2007/10/03)
While performing Stobbe reactions of a succinic diester derivative (1) different routes were found leading to different indole derivatives (2-5) depending on the reaction conditions applied, thus widening the scope and limitation of this useful procedure. Simpler pyrrolidine (13) and piperidine derivatives (14, 15) were also achieved through application of the intramolecular Stobbe reaction.
Indium as a reducing agent: Reduction of oximes
Harrison,Moody,Pitts
, p. 1601 - 1602 (2007/10/03)
α-Oximino carbonyl compounds can be selectively reduced to the corresponding N-acetyl amine with indium powder, acetic anhydride and acetic acid in THF.