391871-69-5Relevant academic research and scientific papers
Iridium-catalyzed enantioselective hydrogenation of α,β- unsaturated carboxylic acids with tetrasubstituted olefins
Song, Song,Zhu, Shou-Fei,Li, Yu,Zhou, Qi-Lin
, p. 3722 - 3725 (2013/08/23)
A highly efficient asymmetric hydrogenation of α,β-unsaturated carboxylic acids with tetrasubstituted olefin catalyzed by chiral spiro iridium complexes has been developed for the preparation of chiral α-substituted carboxylic acids in excellent enantioselectivities (up to 99% ee).
Access to functionalized steroid side chains via modified Julia olefination
Izgu, Enver Cagri,Burns, Aaron C.,Hoye, Thomas R.
supporting information; scheme or table, p. 703 - 705 (2011/04/26)
Various functionalized steroidal side chains were conveniently accessed by a modified Julia olefination strategy using a common sulfone donor and an appropriate α-branched aldehyde acceptor. For the coupling of these hindered classes of reaction partners (and in contrast to typically observed trends), the benzothiazolyl(BT)-sulfone anion gave superior outcomes compared to the phenyltetrazolyl(PT)-sulfone anion.
DIAZONAMIDE ANALOGS WITH IMPROVED SOLUBILITY
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Page/Page column 18; 30, (2009/07/10)
Diazonamide A analogs, and the salts, esters and conjugates thereof, having improved aqueous solubility are provided. Also provided are pharmaceutical compositions, and methods for preparing and using such compounds and compositions for the treatment of proliferative diseases.
A practical total synthesis of hapalosin, a 12-membered cyclic depsipeptide with multidrug resistance-reversing activity, by employing improved segment coupling and macrolactonization
Palomo, Claudio,Oiarbide, Mikel,Garcia, Jesus M.,Gonzalez, Alberto,Pazos, Raquel,Odriozola, Jose M.,Banuelos, Patricia,Tello, Monica,Linden, Anthony
, p. 4126 - 4134 (2007/10/03)
A practical total synthesis of hapalosin, a compound with multidrug resistance-reversing activity, has been carried out using an unprecedented macrolactonization strategy. One of the features of the new approach is the straightforward and fully stereocont
Asymmetric synthesis of β-hydroxy acid via stereoselective dirhodium(II)-catalyzed C-H insertion of α-alkoxydiazoketone
Yakura, Takayuki,Tanaka, Takeshi,Ikeda, Masazumi,Uenishi, Jun'ichi
, p. 471 - 473 (2007/10/03)
A new methodology for the asymmetric synthesis of β-hydroxy acid was developed. Dirhodium(II)-catalyzed C-H insertion of α-alkoxydiazoketone (3), which was prepared from primary alkyl halide (1) and readily available chiral α-hydroxy acid (2), gave stereo
Synthesis and anti-Helicobacter pylori activity of pyloricidin derivatives. I. Structure-activity relationships on the terminal peptidic moiety
Hasuoka, Atsushi,Nishikimi, Yuji,Nakayama, Yutaka,Kamiyama, Keiji,Nakao, Masafumi,Miyagawa, Ken-Ichiro,Nishimura, Osamu,Fujino, Masahiko
, p. 322 - 336 (2007/10/03)
The novel natural antibiotics pyloricidin A, B and C possess potent and highly selective antibacterial activity against Helicobacter pylori. In order to investigate the structure activity relationships for the terminal peptidic moiety, a series of pyloricidin B and pyloricidin C derivatives, bearing various amino acids in the moiety, were prepared and evaluated for their anti-H. pylori activity. The derivatives bearing α-D-, β- and γ-amino acids or peptidemimetics showed drastically decreased activity. On the other hand, the derivatives with α-L-amino acids were found to maintain the activity. Among the derivatives prepared in this work, the allyglycine derivative 2s showed the most potent anti-H. pylori activity, with an MIC value of less than 0.006 μg/ml against H. pylori NCTC11637, which is 60-fold greater than the activity of the lead compound pyloricidin C.
Development of new hydroxamate matrix metalloproteinase inhibitors derived from functionalized 4-aminoprolines
Natchus,Bookland,De,Almstead,Pikul,Janusz,Heitmeyer,Hookfin,Hsieh,Dowty,Dietsch,Patel,Garver,Gu,Pokross,Mieling,Baker,Foltz,Peng,Bornes,Strojnowski,Taiwo
, p. 4948 - 4963 (2007/10/03)
A series of hydroxamates was prepared from an aminoproline scaffold and tested for efficacy as matrix metalloproteinase (MMP) inhibitors. Detailed SAR for the series is reported for five enzymes within the MMP family, and a number of inhibitors, such as compound 47, display broad-spectrum activity with sub-nanomolar potency for some enzymes. Modifications of the P1′ portion of the molecule played a key role in affecting both potency and selectivity within the MMP family. Longer-chain aliphatic substituents in this region of the molecule tended to increase potency for MMP-3 and decrease potency for MMP-1, as exemplified by compounds 48-50, while aromatic substituents, as in compound 52, generated broad-spectrum inhibition. The data is rationalized based upon X-ray crystal data which is also presented. While the in vitro peroral absorption seemed to be less predictable, it tended to decrease with longer and more hydrophilic substituents. Finally, a rat model of osteoarthritis was used to evaluate the efficacy of these compounds, and a direct link was established between their pharmacokinetics and their in vivo efficacy.
A HIGHLY EFFECTIVE ASYMMETRIC SYNTHESIS OF α-HYDROXY ACIDS BY ALKYLATION OF CHIRAL N-(BENZYLOXYACETYL)-TRANS-2,5-BIS(METHOXYMETHOXYMETHYL)PYRROLIDINE
Enomoto, Masayuki,Ito, Yoshio,Katsuki, Tsutomu,Yamaguchi, Masaru
, p. 1343 - 1344 (2007/10/02)
Alkylation of lithiated N-(benzyloxyacetyl)-trans-2,5-bis(methoxymethoxymethyl)-pyrrolidine proceeded with high stereoselectivity (>96percent de) and subsequent transformations of the alkylated products gave synthetically useful α-benzyloxy acids or α-hydroxy acids of high enantiomeric purity.
