175201-95-3Relevant articles and documents
A convenient approach to heterocyclic building blocks: Synthesis of novel ring systems containing a [5,6]pyrano[2,3-c]pyrazol-4(1H)-one moiety
Eller, Gernot A.,Holzer, Wolfgang
, p. 60 - 73 (2008/02/04)
Starting from commercially available educts, a straightforward synthetic route to new heterocyclic building blocks is exemplified with the one- or two-step synthesis of tri-, tetra-, or pentacyclic ring systems. Representatives of the following novel ring systems are prepared from 3-methyl-1-phenyl-2- pyrazolin-5-one and the corresponding o-haloarenecarbonyl chloride using calcium hydroxide in refluxing 1,4-dioxane: pyrimidino[4′,5′:5,6]pyrano[2, 3-c]pyrazol-4(1H)-one, thieno[3′,2′:5,6]pyrano[2,3c]pyrazol-4-(1H)- one, thieno[3′,4′:5,6]pyrano[2,3-c]pyrazol-4(1H)-one, thieno[3″,2″:4′,5′]thieno-[2′,3′:5,6] pyrano[2,3-c]pyrazol-4(1H)-one, [1,3]dioxolo[5′,6′][1] benzothieno[2′,3′:5,6]pyrano-[2,3-c]pyrazol-4(1H)-one, pyridazino[4′,3′:5,6]pyrano[2,3-c]pyrazol-4(1H)-one, and pyrazolo[4″,3″:5′,6′]pyrido[3′,4′:5,6] pyrano[2,3-c]pyrazol-6(9H)-one. While the latter two ring systems are directly obtained due to a spontaneous intramolecular substitution reaction, in the other reactions uncyclised 4-aroylpyrazol-5-ols are produced, which are cyclised into the target heterocycles in a subsequent synthetic step (i.e. treatment with NaH in DMF). Detailed NMR spectroscopic investigations (1H-, 13C-, 15N-) with the obtained compounds were undertaken to unambiguously prove the new structures.
New orally active PDE4 inhibitors with therapeutic potential
Ochiai, Hiroshi,Ishida, Akiharu,Ohtani, Tazumi,Kusumi, Kensuke,Kishikawa, Katuya,Obata, Takaaki,Nakai, Hisao,Toda, Masaaki
, p. 29 - 32 (2007/10/03)
Structural optimization of pyrazolopyridine derivative 2, which is one of the newly discovered chemical leads for PDE4 inhibitors from our in-house library, was carried out successfully. The process of discovery of new orally active PDE4 inhibitors, which
Discovery of new orally active phosphodiesterase (PDE4) inhibitors
Ochiai, Hiroshi,Ishida, Akiharu,Ohtani, Tazumi,Kusumi, Kensuke,Kishikawa, Katuya,Yamamoto, Susumu,Takeda, Hiroshi,Obata, Takaaki,Nakai, Hisao,Toda, Masaaki
, p. 1098 - 1104 (2007/10/03)
A series of 4-anilinopyrazolopyridine derivatives were synthesized and biologically evaluated as inhibitors of phosphodiesterase (PDE4). Chemical modification of 3, a structurally new chemical lead that was found in our in-house library, was focused on 1- and 3-substituents. Full details of the discovery of a new orally active chemical lead 5 are presented. Structure-activity relationship data, pharmacological evaluation, and the subtype selectivity study are also presented.
New orally active PDE4 inhibitors with therapeutic potential
Ochiai, Hiroshi,Ishida, Akiharu,Ohtani, Tazumi,Kusumi, Kensuke,Kishikawa, Katuya,Yamamoto, Susumu,Takeda, Hiroshi,Obata, Takaaki,Nakai, Hisao,Toda, Masaaki
, p. 4089 - 4100 (2007/10/03)
The design, synthesis, and biological evaluation of a series of pyrazolopyridines was carried out. Structural optimization of the aniline moiety of 4-anilinopyrazolopyridine derivative 3a, which is one of the newly discovered chemical leads for PDE4 inhib
