61490-28-6Relevant articles and documents
Synthesis and biological evaluation of enantiomerically pure glyceric acid derivatives as LpxC inhibitors
Tangherlini, Giovanni,Torregrossa, Tullio,Agoglitta, Oriana,K?hler, Jens,Melesina, Jelena,Sippl, Wolfgang,Holl, Ralph
, p. 1032 - 1044 (2016)
Inhibitors of the UDP-3-O-[(R)-3-hydroxymyristoyl]-N-acetylglucosamine deacetylase (LpxC) represent a promising class of novel antibiotics, selectively combating Gram-negative bacteria. In order to elucidate the impact of the hydroxymethyl groups of diol (S,S)-4 on the inhibitory activity against LpxC, glyceric acid ethers (R)-7a, (S)-7a, (R)-7b, and (S)-7b, lacking the hydroxymethyl group in benzylic position, were synthesized. The compounds were obtained in enantiomerically pure form by a chiral pool synthesis and a lipase-catalyzed enantioselective desymmetrization, respectively. The enantiomeric hydroxamic acids (R)-7b (Ki = 230 nM) and (S)-7b (Ki = 390 nM) show promising enzyme inhibition. However, their inhibitory activities do not substantially differ from each other leading to a low eudismic ratio. Generally, the synthesized glyceric acid derivatives 7 show antibacterial activities against two Escherichia coli strains exceeding the ones of their respective regioisomes 6.
1,3(R):4,6(R)-Di-O-benzylidene-D-mannitol
Xiao, Yingxin,Voll, Ronald J.,Billodeaux, Damon R.,Fronczek, Frank R.,Younathan, Ezzat S.
, p. 582 - 583 (2000)
The title compound, C20H22O6, has crystallographic twofold symmetry. The central six-C-atom chain has an extended conformation similar to that of D-mannitol, with two independent C-C-C-C torsion angles of 165.69 (14) and 177.60(12)°. The 1,3-dioxane ring has a chair conformation. All chiral centers have the R configuration.
A Direct Method for the Efficient Synthesis of Benzylidene Acetal at Room Temperature
Reddy, Narra Rajashekar,Kumar, Rashmi,Baskaran, Sundarababu
supporting information, p. 1548 - 1552 (2019/01/09)
For the first time, a metal-free direct method has been developed for the efficient synthesis of benzylidene acetal at room temperature using Dowex 50WX8 as a solid acid catalyst and Cl3CCN as a novel water scavenger. At room temperature, a wide variety of aryl and α,β-unsaturated aldehydes react readily with functionalized 1,2- and 1,3-diols to furnish the corresponding acetals in very good yields. Labile functional groups, like N-Boc, N-Cbz, -OTBDMS, -OBn, -N3 and acetonide are found to be stable under the reaction conditions. The versatility of this method is further demonstrated with carbohydrate substrates and optically active diols.
D-Mannitol-derived novel chiral thioureas: Synthesis and application in asymmetric Henry reactions
Liu, Miaoxi,Ji, Nan,Wang, Li,Liu, Peng,He, Wei
supporting information, p. 999 - 1004 (2018/02/23)
Five novel thioureas have been obtained through multi-step reactions from D-Mannitol as starting material and applied as catalysts in the asymmetric Henry reaction. Using catalyst 7a, (1S,2R)-2-nitro-1-phenylpropan-1-ol containing two chiral centers was o
Synthesis of novel, azasugar-modified anthraquinone derivatives and their cytotoxicity
Zhang, Ping-Zhu,Yang, Hai-Long,Li, Cui-Cui,Xia, Zhi-Chao,Wang, Xiao-Man,Wei, Hua,Rong, Rui-Xue,Cao, Zhi-Ran,Wang, Ke-Rang,Chen, Hua,Li, Xiao-Liu
, p. 1057 - 1059 (2014/08/18)
A series of novel, azasugar-modified 2-monosubstituted, 2,6- and 2,7-bissubstituted anthraquinone derivatives have been synthesized by the nucleophilic substitution of N-alkylamino azasugar with mono-, bis(2-chloroacetamido)anthraquinones. Their cytotoxic activities against HeLa and MCF-7 cells were preliminarily evaluated and compound 9a with mono-azasugar pendant at 2-position showed similar activity to the control drug (Cisplatin).
Synthesis of enantiopure bis-aziridines, bis-epoxides, and aziridino-epoxides from d-mannitol
Sureshkumar, Devarajulu,Maity, Susama,Chandrasekaran, Srinivasan
, p. 10162 - 10170 (2007/10/03)
A practical synthesis of enantiopure bis-aziridines 11 and 15, bis-epoxides 12 and 17, and aziridino-epoxides 27 and 30 is reported using inexpensive d-mannitol as the starting material. The key transformation involves the reductive cleavage of bis-benzyl
Synthesis of mono- and disaccharide analogs of moenomycin and lipid II for inhibition of transglycosylase activity of penicillin-binding protein 1b
Garneau, Sylvie,Qiao, Lei,Chen, Lan,Walker, Suzanne,Vederas, John C.
, p. 6473 - 6494 (2007/10/03)
Three types of mono- and disaccharides as well as some chaetomellic acid A analogs were synthesized and evaluated for inhibitory activity against the E. coli transglycosylase PBP1b. Three types of mono- and disaccharides 3a,b, 4a-c, 5, and some chaetomell
Studies on the formation of a tricyclic C2-symmetric sulfide
Winn, Caroline L.,Goodman, Jonathan M.
, p. 7091 - 7093 (2007/10/03)
Attempts to synthesise chiral sulfide 1 from the dimesylate precursor 5, via a cyclisation reaction using sodium sulfide in dimethyl sulfoxide, led to the unexpected formation of an unsymmetrical furan derivative 8. Studies were made into the effect of changing the leaving group, and changing the solvent of reaction. The desired compound could be synthesized in good yields from the xanthate 9 using a radical-mediated procedure.
