61496-24-0Relevant academic research and scientific papers
Design, synthesis, and evaluation of indeno[2,1-c]pyrazolones for use as inhibitors against hypoxia-inducible factor (HIF)-1 transcriptional activity
Fuse, Shinichiro,Kadonosono, Tetsuya,Kizaka-Kondoh, Shinae,Kuchimaru, Takahiro,Nakamura, Hiroyuki,Sato, Shinichi,Suzuki, Kensuke,Ueda, Hiroki
supporting information, (2019/11/26)
HIF-1 is regarded as a promising target for the drugs used in cancer chemotherapy, and creating readily accessible templates for the development of synthetic drug candidates that could inhibit HIF-1 transcriptional activity is an important pursuit. In this study, indeno[2,1-c]pyrazolones were designed as readily available synthetic inhibitors of HIF-1 transcriptional activity. Nine compounds were synthesized in 4–5 steps from commercially available starting materials. In evaluations of the ability to inhibit the hypoxia-induced transcriptional activity of HIF-1, compound 3c showed a higher level compared with that of known inhibitor, YC-1. The compound 3c suppressed HIF-1α protein accumulation without affecting the levels of HIF-1α mRNA.
METHYL-1H-PYRAZOLE ALKYLAMINE COMPOUNDS HAVING MULTIMODAL ACTIVITY AGAINST PAIN
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Page/Page column 124; 126, (2016/07/05)
The present invention relates to compounds having dual pharmacological activity towards both the sigma (σ) receptor, and the μ-opiod receptor and more particularly to methyl-1H-pyrazole alkylamine compounds having this pharmacological activity, to process
Regioselective Halo- and Carbodesilylation of (Trimethylsilyl)-1-methylpyrazoles
Effenberger, Franz,Krebs, Andreas
, p. 4687 - 4695 (2007/10/02)
The isomeric 3-, 4-, and 5-(trimethylsilyl)- as well as the 3,4-, 3,5-, and 4,5-bis(trimethylsilyl)-1-methylpyrazoles (2, 7, 3, 5, 9, and 10, respectively) are obtained by methylation of the corresponding (trimethylsilyl)-1H-pyrazoles or by silylation of Grignard or lithio derivatives of appropriate 1-methylpyrazoles with chlorotrimethylsilane. 5 and 10 are halodesilylated regioselectively by Br2 or ICl in the 4-position, yielding 13 and 15.With addditional bromine, these monobromo compounds suffer exclusively bromodesilylation to give 3,4- and 4,5-dibromo-1-methylpyrazole (14 and 16, respectively).These findings are in accord with the electrophilic substitution reactivity indices for 1-methylpyrazole (8) and with ipso-directing influence of the Me3Si group.The reaction of 5 with I2, unexpectedly, attacks preferentially at the 3-position.Regioselective carbodesilylation in the 5-position is observed in the fluoride-catalyzed reactions of 3, 9, and 10 with carbon electrophiles.The high regiospecificity of this reaction is rationalized in terms of carbanion stabilization at the individual pyrazole positions.
