54642-23-8Relevant academic research and scientific papers
Alkyl chain substituted 1,9-pyrazoloanthrones exhibit prominent inhibitory effect on c-Jun N-terminal kinase (JNK)
Prasad, Karothu Durga,Trinath, Jamma,Biswas, Ansuman,Sekar, Kanagaraj,Balaji, Kithiganahalli N.,Guru Row, Tayur N.
supporting information, p. 4656 - 4662 (2014/06/24)
N-Alkyl substituted pyrazoloanthrone derivatives were synthesized, characterized and tested for their in vitro inhibitory activity over c-Jun N-terminal kinase (JNK). Among the tested molecules, a few derivatives showed significant inhibitory activity against JNK with minimal off-target effect on other mitogen-activated protein kinase (MAP kinase) family members such as MEK1/2 and MKK3,6. These results suggested that N-alkyl (propyl and butyl) bearing pyrazoloanthrone scaffolds provide promising therapeutic inhibitors for JNK in regulating inflammation associated disorders. This journal is
Regioselective synthesis of 1-alkyl- Or 1-aryl-1H-indazoles via copper-catalyzed cyclizations of 2-haloarylcarbonylic compounds
Vina, Dolores,Del Olmo, Esther,Lopez-Perez, Jose L.,Feliciano, Arturo San
, p. 525 - 528 (2007/10/03)
A general method for the one-step regioselective synthesis of 1-alkyl- or 1-aryl-1H-indazoles from ortho-halogenated alkanoylphenones, benzophenones, and arylcarboxylic acids, via copper-catalyzed amination, was developed by using 0.2% mol of CuO in the p
N-tert-butoxycarbonyl-N-substituted hydrazines in S(N)Ar displacements. Synthetic pathways to N-1-substituted anthrapyrazoles, aza-anthrapyrazoles and aza-benzothiopyranoindazoles
Oliva, Ambrogio,Ellis, Michael,Fiocchi,Menta, Ernesto,Krapcho, A. Paul
, p. 47 - 55 (2007/10/03)
The synthesis of several N-tert-butoxycarbonyl(Boc)-protected-N- substituted hydrazines has been accomplished. The use of these protected hydrazines in S(N)Ar substitutions leads to products in which the most nucleophilic nitrogen displaces the leaving group. Treatment of these compounds with trifluoroacetic acid readily removes the Boc-protecting group and the intermediates readily undergo cyclizations to yield N-1-substituted aza-benzothiopyranoindazoles, anthrapyrazoles and aza-anthrapyrazoles. Side chain buildup was employed in the synthesis of several aza-anthrapyrazoles.
Formation of N-N and N-C Bond-Cleavage Products in Displacements with N,N-Disubstituted Hydrazines on 1-Halo- or 1,4-Dihaloanthracene-9,10-diones
Krapcho, A. Paul,Avery, Kenneth L.
, p. 5927 - 5929 (2007/10/02)
The displacements of 1-halo- and 1,4-dihaloanthracene-9,10-diones by N,N-disubstituted hydrazines have been studied.These reactions proceed via N-N bond cleavages of the hydrazine to yield products with the regiospecific incorporation of an N,N-disubstituted amino group.In addition, pyrazoles which arise from intermediates which undergo N-C bond cleavage are also formed.The ratio of the N-N to N-C cleavage products is dependent on the reaction solvent, temperature, structure of the hydrazine, and the nature of the leaving group being displaced from the anthracene-9,10-dione.For example, treatment of 1a with N,N-dimethylhydrazine in pyridine or dimethyl sulfoxide (DMSO) leads to 3a:2c ratios of 6 and 3, respectively.Compound 1e under comparable reaction conditions gives 3a:2c product ratios of 49 and 4, respectively.The dichloro dione 1c with N,N-dimethylhydrazine in pyridine or DMSO leads predominantly to 3b in 76percent and 72percent yields, respectively, with relatively little pyrazole 2d.The more reactive difluoro dione 1h on reaction with N,N-dimethylhydrazine in pyridine leads to N-N bond-cleavage products 3c (48percent) and 3d (40percent).Treatment of 1e with 1-piperidinamine in pyridine yields 3f.The results will be discussed.
