103788-65-4Relevant articles and documents
Synthesis of substituted oxazoles from N-benzyl propargyl amines and acid chlorides
Wachenfeldt, Henrik V.,Paulsen, Filip,Sundin, Anders,Strand, Daniel
, p. 4578 - 4585 (2013/07/26)
The reaction between N-benzylpropargylamines and acid chlorides at elevated temperatures provides efficient, direct access to a variety of di- and tri-substituted oxazoles. The versatility of this reaction is explored and 21 examples are demonstrated. The usefulness of the methodology is showcased through the short and efficient formal syntheses of medicinally relevant drugs aleglitazar and romazarit. The reaction between N-benzylpropargylamines and acid chlorides at elevated temperatures gives oxazoles in up to 99 % yield. Twenty-one examples are demonstrated varying the substitution at all positions of the heterocycle. Copyright
Synthesis and antimicrobial evaluation of 3-methanone-6-substituted- benzofuran derivatives
Liu, Jingbao,Jiang, Faqin,Jiang, Xizhen,Zhang, Wei,Liu, Jingjing,Liu, Wenlu,Fu, Lei
experimental part, p. 879 - 886 (2012/09/10)
Seventeen benzofuran derivatives were synthesized and screened for their antibacterial activities against Escherichia coli, Staphylococcus aureus, Methicillin-resistant S. aureus, Bacillus subtilis, and Pseudomonas aeruginosa. Seven of them have showed excellent antibacterial activities compared to the positive controls (Cefotaxime and Sodium Penicillin). The substitutions at C-6 and C-3 positions of these derivatives were found to greatly impact on the antibacterial activity and strains specificity, respectively. Specifically, compounds bearing a hydroxyl group at C-6 (5a, 5b, 5c and 12) offered excellent antibacterial activities against all five above-mentioned strains (MIC 80 = 0.78-12.5 ug/mL), and those with imine (15) and (3, 4, 5-trimethoxyphenyl) methanone (7e), respectively, at C-3 position showed selective activity against S. aureus among five tested strains with great MIC80 values (3.12-12.5 ug/mL).
Design and synthesis of Oxime ethers of β-oxo-γ-phenylbutanoic acids as PPAR a and -γ dual agonists
Han, Hee Oon,Koh, Jong Sung,Kim, Seung Hae,Park, Ok Ku,Kim, Kyoung-Hee,Jeon, Sang Kweon,Hur, Gwong-Cheung,Yim, Hyeon Joo,Kim, Geun Tae
, p. 1979 - 1982 (2012/08/14)
Oxime ethers of p-oxo-y-phenylbutanoic acids were prepared to develop more effective PPAR a and y dual agonists. Among them, compound 11k exhibited potent in vitro activities with EC50 of 2.5 nM and 3.3 nM in PPAR a and y, respectively. It showed better g
Design, synthesis and antimicrobial activity of chiral 2-(substituted- hydroxyl)-3-(benzo[d]oxazol-5-yl)propanoic acid derivatives
Zhang, Wei,Liu, Wenlu,Jiang, Xizhen,Jiang, Faqin,Zhuang, Hao,Fu, Lei
experimental part, p. 3639 - 3650 (2011/11/05)
Chiral 2-(substituted-hydroxyl)-3-(benzo[d]oxazol-5-yl)propanoic acid derivatives were synthesized and their antibacterial activities were evaluated against fungus, Gram-negative and Gram-positive bacteria. In general, these compounds showed in vitro acti
(S)-3-(4-(2-(5-Methyl-2-phenyloxazol-4-yl)ethoxy)phenyl)-2-(piperazin-1-yl)propanoic acid compounds: Synthesis and biological evaluation of dual PPARα/γ agonists
Zhou, Xinbo,Chen, Wei,Xu, Cheng,Fan, Shiyong,Xie, Yunde,Zhong, Wu,Wang, Lili,Li, Song
scheme or table, p. 2605 - 2608 (2010/06/17)
A series of novel, potent PPARα/γ dual agonists were synthesized and appraised. The most potent analogue, compound 2b demonstrated EC50 value of 0.012 ± 0.002 and 0.032 ± 0.01 μM, respectively, for hPPARα and hPPARγ in transactivation assay. Additionally, compound 2b demonstrated good glucose and lipid lowering effect in genetic diabetic (db/db) mice.
Aleglitazar, a new, potent, and balanced dual PPARα/γ agonist for the treatment of type II diabetes
Benardeau, Agnes,Benz, Joerg,Binggeli, Alfred,Blum, Denise,Boehringer, Markus,Grether, Uwe,Hilpert, Hans,Kuhn, Bernd,Maerki, Hans Peter,Meyer, Markus,Puentener, Kurt,Raab, Susanne,Ruf, Armin,Schlatter, Daniel,Mohr, Peter
scheme or table, p. 2468 - 2473 (2010/03/24)
Design, synthesis, and SAR of novel α-alkoxy-β-arylpropionic acids as potent and balanced PPARαγ coagonists are described. One representative thereof, Aleglitazar ((S)-2Aa), was chosen for clinical development. Its X-ray structure in complex with both receptors as well as its high efficacy in animal models of T2D and dyslipidemia are also presented.
Design and synthesis of oxime ethers of α-acyl-β-phenylpropanoic acids as PPAR dual agonists
Oon Han, Hee,Hae Kim, Seung,Kim, Kyoung-Hee,Hur, Gwong-Cheung,Joo Yim, Hyeon,Chung, Hee-Kyung,Ho Woo, Sung,Dong Koo, Ki,Lee, Chang-Seok,Sung Koh, Jong,Tae Kim, Geun
, p. 937 - 941 (2007/10/03)
Oxime ethers of α-acyl-β-phenylpropanoic acids were prepared to apply as PPARα and γ dual agonists. Among them, compound 11l proved to exhibit potent in vitro activities with EC50 of 19 and 13 nM in PPARα and γ, respectively. It showed better g
TYROSINE DERIVATIVES SUBSTITUTED BY N-PHENYLACRYLOYL AS AGONISTS OF HPPAR ALPHA AND HPPAR GAMA
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Page/Page column 10, (2008/06/13)
The present invention relates to a compound of formula I, racemates, optically active isomers, or pharmaceutically acceptable salts or solvates thereof, and a pharmaceutical composition comprising the compound, the various radicals in the formula I are the same as defined in the claims. The present invention also relates to a process for preparing the compound of formula I and use of said compound in the preparation of a medicament for the treatment of hyperglycemia, dyslipidemia, type II diabetes mellitus including associated diabetic dyslipidemia
Substitued A-Piperazingly Phenylpropionic Acid Derivatives As Hppar Alpha And/Or Hppar Gamma Agonists
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Page/Page column 8, (2008/06/13)
The present invention relates to a compound of formula I, racemates, optically active isomers, or pharmaceutically acceptable salts or solvates thereof, and a pharmaceutical composition comprising the compound, the various radicals in the formula I are the same as defined in the claims. The present invention also relates to a process for preparing the compound of formula I and use of said compound in the preparation of a medicament for the treatment of hyperglycemia, dyslipidemia, type II diabetes mellitus including associated diabetic dyslipidemia
Process development and scale-up of AG035029
Saenz, James,Mitchell, Mark,Bahmanyar, Sami,Stankovic, Nebojsa,Perry, Michael,Craig-Woods, Bridgette,Kline, Billie,Yu, Shu,Albizati, Kim
, p. 30 - 38 (2012/12/26)
A practical process for the synthesis of PPARγ agonist AG035029 was developed which involved six steps along the longest linear path. The process development utilized automated technology and computational chemistry extensively to accelerate the speed of
