146605-64-3Relevant articles and documents
A divergent synthetic pathway for pyrimidine-embedded medium-sized azacycles through an N-quaternizing strategy
Choi, Yoona,Kim, Heejun,Park, Seung Bum
, p. 569 - 575 (2019)
Medium-sized heterocycles have recently received significant attention because of their potential roles as modulators of protein-protein interactions, but their molecular diversity and synthetic availability are still inadequate to meet the demand. To address these issues, we developed a new divergent synthetic pathway for skeletally distinct pyrimidine-containing medium-sized azacycles. We introduced N-quaternized pyrimidine-containing polyheterocycles as novel key intermediates for diversity-generating reactions via selective bond cleavages or migrations and prepared 14 discrete core skeletons in an efficient manner. The skeletal diversity of the resulting molecular frameworks was confirmed by chemoinformatic analysis.
A convenient synthesis of pyrazolidine and 3-amino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one
Boros,Bouvier,Randhawa,Rabinowitz
, p. 613 - 616 (2001)
A convenient four-step synthesis of the aminobicyclopyrazolone hydrochloride 1·HCl was achieved starting from di-tert-butyl hydrazodiformate (8). The route entails cyclization of 8 with 1,3-dibromopropane under phase transfer conditions followed by deprotection of 1,2-di-tert-butoxycarbonylpyrazolidine (9) to give pyrazolidine hydrochloride (2·HCl). Cyanoacetylation of the latter and ring closure of the resulting cyanoacetyl pyrazolidine (7) gave 1·HCl. This novel synthesis circumvents distillation of pyrazolidine (2) and flash chromatography to provide the hydrochloride of 1 in 35-46% overall yields compared to 6% yield for the patent procedure.
Substituted Pyrazalones
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Page/Page column 30, (2010/04/23)
The invention is related to compounds of formula (I) as antagonists of the TGFβ family type I receptors, Alk5 and/or AIk 4, compositions and methods of use. The compounds of formula (I) can be employed in the prevention and/or treatment of diseases such a
Development of cyclic hydrazine and hydrazide type organocatalyst-mechanistic aspects of cyclic hydrazine/hydrazide-catalyzed diels-alder reactions
Suzuki, Ichiro,Hirata, Ai,Takeda, Kei
scheme or table, p. 851 - 863 (2009/12/01)
Some hydrazines and hydrazides were prepared and screened for their catalytic efficiencies in Diels-Alder reactions. 1H-NMR studies and ab initio calculations revealed that catalytic efficiencies of these catalysts are greatly dependent on the release of the catalysts from the Diels-Alder adducts.
Biginelli reactions catalyzed by hydrazine type organocatalyst
Suzuki, Ichiro,Iwata, Yukari,Takeda, Kei
, p. 3238 - 3241 (2008/09/21)
Pyrazolidine dihydrochloride can be used in the acceleration of Biginelli reactions between urea, ethyl acetoacetate and various aldehydes to provide DHPMs in good to excellent yields.
Synthesis, biological evaluation and structural determination of β-aminoacyl-containing cyclic hydrazine derivatives as dipeptidyl peptidase IV (DPP-IV) inhibitors
Ahn, Jin Hee,Shin, Mi Sik,Jun, Mi Ae,Jung, Sun Ho,Kang, Seung Kyu,Kim, Kwang Rok,Rhee, Sang Dal,Kang, Nam Sook,Kim, Sun Young,Sohn, Sang-Kwon,Kim, Sung Gyu,Jin, Mi Sun,Lee, Jie Oh,Cheon, Hyae Gyeong,Kim, Sung Soo
, p. 2622 - 2628 (2008/02/11)
Inhibitors of dipeptidyl peptidase IV (DPP-IV) have been shown to be effective treatments for type 2 diabetes. A series of β-aminoacyl-containing cyclic hydrazine derivatives were synthesized and evaluated as DPP-IV inhibitors. One member of this series, (R)-3-amino-1-(2-benzoyl-1,2-diazepan-1-yl)-4-(2,4,5-trifluorophenyl)but an-1-one (10f), showed potent in vitro activity, good selectivity and in vivo efficacy in mouse models. Also, the binding mode of compound 10f was determined by X-ray crystallography.
NOVEL CATHEPSIN C INHIBITORS AND THEIR USE
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Page/Page column 21-22, (2010/11/23)
The invention is directed to novel cathepsin C inhibitors and their use in the treatment of diseases mediated by the cathepsin C enzyme. Specifically, the invention is directed to compounds according to Formula (I): wherein X and n are defined below, and
Synthesis and evaluation of pyrazolidine derivatives as dipeptidyl peptidase IV (DP-IV) inhibitors
Ahn, Jin Hee,Kim, Jin Ah,Kim, Hye-Min,Kwon, Hyuk-Man,Huh, Sun-Chul,Rhee, Sang Dal,Kim, Kwang Rok,Yang, Sung-Don,Park, Sung-Dae,Lee, Jae Mok,Kim, Sung Soo,Cheon, Hyae Gyeong
, p. 1337 - 1340 (2007/10/03)
A new series of pyrazolidine derivatives was synthesized and evaluated for their ability to inhibit dipeptidyl peptidase IV (DP-IV). Compound 9i was the most active in this series, exhibited IC50 value of 1.56 μM and ED50 value of 80
Synthesis, molecular modeling and biological evaluation of aza-proline and aza-pipecolic derivatives as FKBP12 ligands and their in vivo neuroprotective effects
Wilkinson, Douglas E.,Thomas IV, Bert E.,Limburg, David C.,Holmes, Agnes,Sauer, Hansjorg,Ross, Douglas T.,Soni, Raj,Chen, Yi,Guo, Hong,Howorth, Pamela,Valentine, Heather,Spicer, Dawn,Fuller, Mike,Steiner, Joseph P.,Hamilton, Gregory S.,Wu, Yong-Qian
, p. 4815 - 4825 (2007/10/03)
Nonimmunosuppressant ligands, exemplified by GPI 1046 (1), for the peptidyl-prolyl isomerase FKBP12 have been found to unexpectedly possess powerful neuroprotective and neuroregenerative effects in vitro and in vivo. We have extensively explored the thera
