91473-66-4Relevant academic research and scientific papers
Synthesis and anti-tumor activity of 2-amino-3-cyano-6-(1H-indol-3-yl)-4- phenylpyridine derivatives in vitro
Zhang, Fan,Zhao, Yanfang,Sun, Li,Ding, Lu,Gu, Yucheng,Gong, Ping
, p. 3149 - 3157 (2011/06/26)
A series of novel 2-amino-3-cyano-6-(1H-indol-3-yl)-4-phenylpyridine derivatives were synthesized and their cytotoxic activity against A549, H460, HT-29 and SMMC-7721 cell lines was evaluated in vitro. Among them, ten compounds (10, 11, 14, 16, 17, 26, 27, 29, 30 and 31) displayed excellent anti-tumor activity against different cell lines. The most promising compound 27 showed strong anti-tumor activity against A549, H460, HT-29 and SMMC-7721 cell lines with IC50 values of 22, 0.23, 0.65 and 0.77 nM, which were 2.6-, 83-, 1.1 × 103- and 2.0 × 103- fold more active than MX-58151 (IC50 values of 0.058, 0.019, 0.70 and 1.53 μM), respectively.
Molecular design of pyrazolo[3,4-d]pyridazines
Matiichuk,Potopnyk,Obushak
experimental part, p. 1352 - 1361 (2009/09/06)
Reactions of arenediazonium chlorides with ethyl 2-methyl-and 2-chloro-4-oxobutanoates gave, respectively, ethyl 2-(arylhydrazono)propanoates and chloro(arylhydrazono)acetates. Ethyl 2-(arylhydrazono)-propanoates reacted with the Vilsmeier-Haak reagent to give ethyl 1-aryl-4-formyl-1 H-pyrazole-3-carboxylates. Ethyl 1-aryl-4-acetyl-5-methyl-1H-pyrazole-3- carboxylates were obtained by reaction of chloro(arylhydrazono) acetates with acetylacetone. Reactions of the obtained pyrazole derivatives with hydrazine and methylhydrazine led to the formation of the corresponding 3,4-R 2 1 -6-R2-2-aryl-2,6-dihydro-7H-pyrazolo-[3,4-d]pyridazin-7- ones (R1, R2 = H, Me) which were subjected to alkylation and sulfurization.
N-Benzylindole-2-carboxylic acids: Potent functional antagonists of the CCR2b chemokine receptor
Kettle, Jason G.,Faull, Alan W.,Barker, Andy J.,Davies, D. Huw,Stone, Michael A.
, p. 405 - 408 (2007/10/03)
Screening of the corporate database led to the discovery of a novel series of N-benzylindole-2-carboxylic acid CCR2b chemokine receptor antagonists. These compounds demonstrate high affinity and functional inhibition of the CCR2b receptor. A discussion of
Geometrical Isomerism of Phenylhydrazones of α-Keto Esters. II. p-Substituted Phenylhydrazones of Ethyl Pyruvate and 2,4-Dinitrophenylhydrazones of Some α-Keto Esters
Ishibashi, Fumihide,Nashima, Takeo,Nishino, Junko,Kobayashi, Ikuko,Ichihara, Yoshinori,et al.
, p. 73 - 76 (2007/10/02)
Each geometrical isomer of various substituted phenylhydrazones of ethyl pyruvate and 2,4-dinitrophenylhydrazones of some α-keto esters was isolated in a pure state.Partial isomerizations of the E-isomers of the former hydrazones to the Z-isomers took place by keeping solutions of the hydrazones in organic solvents containing C, H, and Cl in the dark.An E- or Z-structure was assigned to each molecule on the basis of IR and 1H NMR spectra.In all cases, isomers with higher Rf -values on a silica gel TLC (using benzene as a developing solvent) involved an intramolecular hydrogen bonding between the imino hydrogen and the ester carbonyl oxygen.Thus, the Z-structure was assigned.An E-structure was assigned to other isomers with lower Rf-values.The present assignment is, thus, entirely the same as that proposed in a previous investigation.
