- Biarylhydrazine compounds and their adducts and applications in the preparation of antitumor drugs
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The present invention discloses a biarylhydrazine compound and its application in the preparation of antitumor drugs, the structure of the arylhydrazine compound as shown in formula I, the adduct is a biarylhydrazine compound on the hydrazine group plus benzyloxycarbonyl glycyl prolyl. The anticancer activity of the biarylhydrazine compounds of the present invention is superior to that of the existing positive control drug procarbazine; its Z-GP adduct can significantly reduce in vitro toxicity and in vivo toxicity to normal cells, and can be excised by FΑP-α enzyme specific hydrolysis in vivo (Z-GP) to release hydrolysate products; its Z-GP adduct can significantly inhibit tumor growth in tumor-bearing nude mice and reduce toxicity to non-target organs.
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Paragraph 0058; 0064; 0065; 0103-0107
(2022/03/27)
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- Divergent Synthesis of 1H-Indazoles and 1H-Pyrazoles from Hydrazones via Iodine-Mediated Intramolecular Aryl and sp3 C–H Amination
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A divergent intramolecular C–H amination of hydrazones has been developed employing molecular iodine (I2) as the sole oxidant. The required hydrazone substrates were readily obtained by condensation of hydrazines with the corresponding ketones.
- Wei, Wei,Wang, Zhen,Yang, Xikang,Yu, Wenquan,Chang, Junbiao
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p. 3378 - 3387
(2017/10/09)
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- An efficient transition-metal-free synthesis of 1H-indazoles from arylhydrazones with montmorillonite K-10 under O2 atmosphere
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An efficient transition-metal-free synthetic method of 1H-indazoles has been developed. The reaction of arylhydrazones in the presence of montmorillonite K-10 in 1,2-dichlorobenzene at 130 °C afforded 1H-indazoles in good yields most likely via a sequenti
- Yu, Jin,Lim, Jin Woo,Kim, Su Yeon,Kim, Jimin,Kim, Jae Nyoung
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supporting information
p. 1432 - 1436
(2015/03/04)
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- Mild method for the synthesis of 1H-indazoles through oxime-phosphonium ion intermediate
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The synthesis of 1H-indazoles from o-aminobenzoximes is achieved via N-N bond formation using triphenylphosphine, I2, and imidazole. Selective formation of oxime-phosphonium ion intermediate in the presence of the amino group is the driving for
- Paul, Saurav,Panda, Subhankar,Manna, Debasis
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supporting information
p. 2480 - 2483
(2014/05/06)
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- Synthesis of indazoles and azaindazoles by intramolecular aerobic oxidative C-N coupling under transition-metal-free conditions
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A transition-metal-free oxidative C-N coupling method has been developed for the synthesis of 1H-azaindazoles and 1H-indazoles from easily accessible hydrazones. The procedure uses TEMPO, a basic additive, and dioxygen gas as the terminal oxidant. This reaction demonstrates better reactivity, functional group tolerance, and broader scope than comparable metal catalyzed reactions. A transition-metal-free oxidative C-N coupling method has been developed for the synthesis of 1H-azaindazoles and 1H-indazoles from easily accessible hydrazones (see scheme). The procedure uses TEMPO, a basic additive, and dioxygen gas as the terminal oxidant. This reaction demonstrates better reactivity, functional group tolerance, and broader scope than comparable metal catalyzed reactions. TEMPO=2,2,6,6-tetramethyl-1-piperidinyloxy.
- Hu, Jiantao,Xu, Huacheng,Nie, Pengju,Xie, Xiaobo,Nie, Zongxiu,Rao, Yu
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supporting information
p. 3932 - 3938
(2014/04/17)
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- Nickel-catalyzed N-arylation of benzophenone hydrazone with bromoarenes
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A nickel-catalyzed method for the cross-coupling of benzophenone hydrazone with aryl bromides is described. The use of a simple Ni(ii)/NHC catalyst leads to the arylated hydrazones in good or acceptable yields. This protocol provides a simple, convenient alternative to the synthesis of arylhydrazines.
- Wu, Wei,Fan, Xin-Heng,Zhang, Li-Peng,Yang, Lian-Ming
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p. 3364 - 3367
(2014/01/06)
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- Method of forming a carbon-heteroatom bond
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The present invention relates to a method of creating a carbon-heteroatom bond, and preferably a carbon-nitrogen bond, by reacting a leaving group-bearing unsaturated compound and a nucleophilic compound. In particular, the invention relates to the creation of a carbon-nitrogen bond, using a method involving the arylation of nitrogenous organic derivatives; the inventive method consists in creating a carbon-heteroatom bond by reacting a leaving group-bearing unsaturated compound and a nucleophilic compound introducing a heteroatom which can be substituted for the leaving group, thereby creating a carbon-heteroatom bond, in the presence of a palladium-based catalyst, optionally a ligand. The invention is characterized in that the reaction takes place in the presence of an effective quantity of a metal hydroxide or ammonium hydroxide which is associated with an alcohol-type solvent.
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Page/Page column 24
(2009/07/25)
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- Hydrazinocarbonyl-thieno[2,3-C]pyrazoles, Process for Preparing Them, Compositions Containing Them and Use Thereof
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The present invention concerns hydrazinocarbonyl-thieno[2,3-c]pyrazoles of formula (I): wherein R1, R3, R4, are R5 are as defined in the disclosure; their preparation method, compositions containing the same and their use for the treatment of pathological conditions, in particular as anticancer agents.
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Page/Page column 36
(2008/12/06)
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- Efficient and convenient method for the synthesis of N-arylhydrazones using a palladium-catalyzed bond-forming reaction
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A highly effective, convenient, and reproducible industrial process for palladium-catalyzed carbon-nitrogen cross coupling has been developed and applied on a large scale. Thus various functionalized N-arylhydrazones have been easily prepared and well cha
- Mauger, Christelle,Mignani, Gerard
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p. 1123 - 1129
(2007/10/03)
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- Industrial-scale palladium-catalyzed coupling of aryl halides and amines - A personal account
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The palladium-catalyzed coupling of amines and aryl halides or aryl alcohol derivatives has matured from an exotic small-scale transformation into a very general, efficient and robust reaction during the last ten years. This article reports several applications of this method from an industrial vantage point, including ligand synthesis, synthesis of arylpiperazines, arylhydrazines and diarylamines. Much emphasis in placed on issues of scale-up and safety to underline the potential of C-N couplings as solutions for industrial-scale synthetic problems.
- Buchwald, Stephen L.,Mauger, Christelle,Mignani, Gerard,Scholz, Ulrich
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- The synthesis of important pharmaceutical building blocks by palladium-catalyzed coupling reaction: access to various arylhydrazines
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Various arylhydrazones have been successfully synthesized via a highly efficient palladium-catalyzed cross-coupling reaction between aryl halides and benzophenone hydrazone. All the reaction parameters have been studied and coupling products were obtained
- Mauger, Christelle,Mignani, Gerard
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p. 773 - 782
(2007/10/03)
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- Tandem hydroformylation/Fischer indole synthesis: A novel and convenient approach to indoles from olefins
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(Matrix presented) A novel one-pot synthesis of indole systems via tandem hydroformylation/Fischer indole synthesis starting from olefins and arylhydrazines is described. This tandem procedure leads directly to 3-substituted indoles if unsubstituted phenylhydrazine is used and to 3,5- respectively 3,7-disubstituted indoles if para- or ortho-substituted arylhydrazines are used.
- Koehling, Petra,Schmidt, Axel M.,Eilbracht, Peter
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p. 3213 - 3216
(2007/10/03)
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- A palladium-catalyzed method for the preparation of indoles via the Fischer indole synthesis
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A Pd-catalyzed method for the preparation of N-aryl benzophenone hydrazones 4 is described. The use of a Pd/BINAP-based catalyst provides hydrazones 4 in good yields. Using 0.1 mol % of a Pd/9,9-dimethyl-4,5- bis(diphenylphosphino)xanthene (Xantphos) cata
- Wagaw, Seble,Yang, Bryant H.,Buchwald, Stephen L.
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p. 10251 - 10263
(2007/10/03)
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