67199-66-0Relevant articles and documents
Synthesis of batracylin and its N-sulfonamido analogues in [b-3C-im][NTf2] ionic liquid
Tseng, Ming-Chung,Lai, Peng-Yeh,Shi, Lin,Li, Hsin-Yi,Tseng, Min-Jen,Chu, Yen-Ho
, p. 2629 - 2633 (2014/04/03)
Starting with commercial and inexpensive reagents, a high-yielding chemical process carried out in [b-3C-im][NTf2] ionic liquid was achieved to afford the synthesis of batracylin and its N-sulfonamido analogues. Among all compounds synthesized, compounds 1, 11, and 14 exhibit potent inhibitory activity against human topoisomerase 1 (hTop1).
A concise and cascade synthesis of batracylin and substituted isoindolo-[1,2- b ]quinazolin-12(10 H)-ones
Shankar,Wagh, Manoj Balu,Madhubabu,Vembu,Kumar, U. K. Syam
, p. 844 - 848 (2011/06/21)
A concise, highly convergent, and practical synthesis of the clinical-phase anticancer agent batracylin in a two-stage process in excellent yield is described. The B and C rings of this tetracyclic heterocycle are constructed by cascade cyclization of 5-nitro-2-aminobenzyl alcohol with 2-cyanomethyl benzoate in trifluoroacetic acid in good yield in a single-pot reaction. A plausible mechanism for the cascade reaction is also proposed. As part of these studies, a range of batracylin derivatives with different substituents on the C and D rings are synthesized. Georg Thieme Verlag Stuttgart.
Synthesis and cytotoxic activity of conjugates of muramyl and normuramyl dipeptides with batracylin derivatives
Dzierzbicka, Krystyna,Trzonkowski, Piotr,Sewerynek, Przemys?aw,My?liwski, Andrzej
, p. 978 - 986 (2007/10/03)
The synthesis of MDP (muramyl dipeptide) or nor-MDP (normuramyl dipeptide) conjugates modified at the peptide part with batracylin (BAT) or batracylin derivatives is described. Batracylin was synthesized by our modified method (Scheme 3). The synthesis of BAT via this modified route now appears to be feasible on a multigram scale. Preliminary screening data obtained at the National Cancer Institute (NCI, Bethesda, MD) have revealed that the conjugates did not expose any cytotoxic activity even at 10-4-10-8 M or μg/mL. During tests performed at Medical University of Gdansk, Poland, two analogues 11c and 11e reduced the proliferation of Ab melanoma cells in vitro compared with batracylin alone (Table 2, Figure 1).
Synthesis and pharmacological evaluation of isoindolo[1,2-b]quinazolinone and isoindolo[2,1-a]benzimidazole derivatives related to the antitumor agent batracylin
Meegalla,Stevens,McQueen,Chen,Yu,Liu,Barrows,LaVoie
, p. 3434 - 3439 (2007/10/02)
The synthesis and pharmacological activity of isoindolo[1,2-b]quinazolin- 12(10H)-ones and isoindolo[2,1-a]benzimidazoles related to batracylin are described. The acute toxicity of batracyclin has been associated with the formation of its N-acetyl metabolite which is a potent inducer of unscheduled DNA synthesis in rat hepatocytes. The desamino derivative and the 8-aza analog of batracylin retained the ability to inhibit topoisomerase II but did not induce unscheduled DNA synthesis. While less active than batracylin, these analogs were cytotoxic to CCRF CEM leukemia cells. The isoindolo[2,1- a]benzimidazole derivatives were inactive as topoisomerase II inhibitors and, in general, failed to exhibit comparable antitumor activity or to induce unscheduled DNA synthesis.
A Comparison of the Reactions of Some Ethyl N-Arylcarbamates with Those of the Corresponding Acetanilides. II Amidomethylation with N-Hydroxymethylphthalimide
Rosevear, Judi,Wilshire, John F. K.
, p. 339 - 353 (2007/10/02)
The reactions of some ethyl N-arylcarbamates and of the corresponding acetanilides towards 1 equiv. of N-hydroxymethylphthalimide in concentrated sulfuric acid at 50 deg C have been compared with one another.In the case of certain para-substituted compoun
