14908-49-7Relevant academic research and scientific papers
Synthesis of phthalazinones via palladium(ii)-catalysed intramolecular oxidative C-H/C-H cross-coupling of N′-methylenebenzohydrazides
Matsuda, Takanori,Tomaru, Yuki,Matsuda, Yoshiya
supporting information, p. 2084 - 2087 (2013/04/23)
A palladium(ii)-catalysed intramolecular oxidative C-H/C-H cross-coupling of N′-methylenebenzohydrazides to phthalazin-1(2H)-ones has been developed. This cyclization is believed to mechanistically proceed via electrophilic ortho-palladation and subsequen
Syntheses and antitumor activities of N′1, N′3-dialkyl-N′1,N′3-di- (alkylcarbonothioyl) malonohydrazide: The discovery of elesclomol
Chen, Shoujun,Sun, Lijun,Koya, Keizo,Tatsuta, Noriaki,Xia, Zhiqiang,Korbut, Timothy,Du, Zhenjian,Wu, Jim,Liang, Guiqing,Jiang, Jun,Ono, Mitsunori,Zhou, Dan,Sonderfan, Andrew
, p. 5070 - 5076 (2013/09/12)
A series of N′1,N′3-dialkyl- N′1,N′3-di(alkylcarbonothioyl) malonohydrazides have been designed and synthesized as anticancer agents by targeting oxidative stress and Hsp70 induction. Structure-activity relationship (SAR) studies lead to the discovery of STA-4783 (elesclomol), a novel small molecule that has been evaluated in a number of clinical trials as an anticancer agent in combination with Taxol.
Synthesis, characterization, and tuberculostatic activity of novel 2-(4-nitrobenzoyl)hydrazinecarbodithioic acid derivatives
Gobis, Katarzyna,Foks, Henryk,Augustynowicz-Kopec, Ewa,Napiorkowska, Agnieszka,Szczesio, Malgorzata,Olczak, Andrzej,Glowka, Marek L.
scheme or table, p. 607 - 617 (2012/08/07)
A series of novel S-esters of 2-(4-nitrobenzoyl) hydrazinecarbodithioic acid and S,S'-diesters of (4-nitrobenzoyl)carbonohydrazonodithioic acid were synthesized by reaction of 4-nitrobenzohydrazide and N-methyl- 4-nitrobenzohydrazide with carbon disulfide and alkyl halides in the presence of triethylamine. Novel 5-(4-nitrophenyl)- 1,3,4-oxadiazoles were also obtained. The structures were confirmed by IR, NMR, and mass spectroscopy, and by elemental analysis. All the compounds obtained were screened in vitro for their tuberculostatic activity. Promising preliminary results were obtained for some of the compounds. The crystal structure of the most active compound was determined. The Author(s) 2012.
An efficient synthesis of substituted hydrazides
Benstead, David J.,Hulme, Alison N.,McNab, Hamish,Wight, Paul
, p. 1571 - 1574 (2007/10/03)
Routes for the selective synthesis of 1-, or 2-substituted hydrazides, and 1,2-disubstituted hydrazides are reported. These routes proceed via cyanoborohydride reduction of stable acyl hydrazone intermediates. Georg Thieme Verlag Stuttgart.
Synthesis and antitumor activity of methyltriazene prodrugs simultaneously releasing DNA-methylating agents and the antiresistance drug O 6-benzylguanine
Wanner, Martin J.,Koch, Melle,Koomen, Gerrit-Jan
, p. 6875 - 6883 (2007/10/03)
Active resistance of tumor cells against DNA alkylating agents arises by the production of high levels of the DNA repair protein O6- alkylguanine-DNA alkyltransferase (AGT). This resistance during treatment with, for example, the anticancer agent temozolomide can be reversed by administration of O6-benzylguanine, a purine that transfers its benzyl group to AGT and irreversibly inactivates it. Stimulated by the favorable therapeutic properties of temozolomide we designed and synthesized DNA-methylating triazenes built on the anti-resistance benzylguanine ring system. The condensation reaction between 2-nitrosopurines and acylhydrazines proved to be very suitable to prepare acylated methyltriazenes. Fine-tuning of the release rate of both the methylating agent (diazomethane) and of O6-benzylguanine was accomplished by variation of the hydrolysis-sensitive acyl substituent in 5. Hydrolysis studies were performed with 1H NMR and revealed that the p-nitrophenyl substituted triazene 26 showed an optimal hydrolysis rate (t 1/2 = 23 min) and almost 100% selectivity for the desired fragmentation route. In vitro antitumor studies in the 60 human tumor cell line panel of the National Cancer Institute confirmed the superior properties ofp-nitrophenyl-protected methyl triazene 26, showing mean IC50 values of 10 μM. compared to 100 μM for temozolomide. In analogy with temozolomide, triazene 26 showed however low preference for each of the cancer subpanels, with IC50 values between 8 and 14 μM.
