1483-24-5Relevant 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.
Insertion and fragmentation of 2-ferrocenylmethylidene-1, 3-diketones upon their reactions with N-methylhydrazine
Klimova, Elena I.,Vazquez Lopez, Eduardo A.,Martinez Mendoza, Juan M.,Ramirez, Lena Ruiz,Alamo, Marcos Flores,Backinowsky, Leon V.
experimental part, p. 484 - 491 (2009/08/17)
(Chemical Equation Presented) Reactions of 2-ferrocenylmethylidene-1,3- diketones (1a-c) with methylhydrazine afford mainly insertion products (～40-58%), viz., 1-(N′-acyl-N′-methylhydrazino)-1-ferrocenyl-2- acylethanes (7a-d), together with lesser amounts
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.
INDOLE COMPOUND AND MEDICINAL USE THEREOF
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Page 56, (2010/02/08)
An indole compound represented by the formula (1) wherein each symbol is as defined in the specification, a pharmaceutically acceptable salt thereof or a prodrug thereof is useful as a therapeutic agents for diabetes having an HLGPa inhibitory activity.
Use of N-acyl or N-alkyloxycarbonyl-aminotetrachlorophthalimides for the preparation of alkylhydrazines via the mitsunobu protocol
Pinto, Maria-Fatima,Brosse, Nicolas,Jamart-Gregoire, Brigitte
, p. 3603 - 3610 (2007/10/03)
N-acyl and N-alkyloxycarbonyl tetrachloro-aminophthalimides which are best acidic partners in the Mitsunobu reaction and more easily dephthaloylated than their unsubstituted analogs can be used efficiently for the preparation of 1,1-substituted hydrazines.
New Synthesis of 1,1-Substituted Hydrazines by Alkylation of N-Acyl- or N-alkyloxycarbonylaminophthalimide Using the Mitsunobu Protocol
Brosse, Nicolas,Pinto, Maria-Fatima,Jamart-Gregoire, Brigitte
, p. 4370 - 4374 (2007/10/03)
N-acyl- and N-alkoxycarbonylaminophthalimides are prepared using a convenient reaction and are efficiently used as acid partners in Mitsunobu reaction. This reaction allows them to be alkylated by primary, secondary or benzyl groups. Comparison of the reactivities and pKa values of these N-substituted aminophthalimides suggest that the success of the Mitsunobu reaction in this case seems to be governed more by steric than by electronic effects. A final dephthaloylation step results in an efficient method for the preparation of 1,1-substituted hydrazines.
NEW SYNTHETIC "TRICKS". FROM ALIPHATIC AMINES AND AMIDES TO AZIDES AND/OR HOW TO CONVERT RNHCOR' INTO RNHCOR" AVOIDING DRASTIC HYDROLYSES
Garcia, Jordi,Vilarrasa, Jaume
, p. 341 - 342 (2007/10/02)
Controlled reduction of N-alkyl-N-nitrosoamides to hydrazides followed by nitrosation and fragmentation affords azides in 80percent overall yields, under mild conditions.This simple idea is the basis of methods for the conversion of alkylamines and N-alkylamides to alkyl azides, of RNHCOR' into RNHCOR" or RN(COR''')2, and of lactames into ω-azido esters or ω-azido acids.
