- Chiral Bifunctional Metalloporphyrin Catalysts for Kinetic Resolution of Epoxides with Carbon Dioxide
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Chiral binaphthyl-strapped Zn(II) porphyrins with triazolium halide units were synthesized as bifunctional catalysts for kinetic resolution of epoxides with CO2. Several catalysts were screened by changing the linker length and nucleophilic counteranions, and the optimized catalyst accelerated the enantioselective reaction at ambient temperature to produce optically active cyclic carbonates and epoxides.
- Maeda, Chihiro,Mitsuzane, Mayato,Ema, Tadashi
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supporting information
p. 1853 - 1856
(2019/03/11)
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- Chiral Macrocyclic Organocatalysts for Kinetic Resolution of Disubstituted Epoxides with Carbon Dioxide
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Among chiral macrocycles 1 synthesized, 1m with the 3,5-bis(trifluoromethyl)phenylethynyl group was the best organocatalyst for the enantioselective synthesis of cyclic carbonates from disubstituted or monosubstituted epoxides and CO2. The X-ray crystal structure of 1m revealed a well-defined chiral cavity with multiple hydrogen-bonding sites that is suitable for the enantioselective activation of epoxides. A catalytic cycle proposed was supported by DFT calculations.
- Ema, Tadashi,Yokoyama, Maki,Watanabe, Sagiri,Sasaki, Sota,Ota, Hiromi,Takaishi, Kazuto
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supporting information
p. 4070 - 4073
(2017/08/15)
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- Synthesis and biological evaluation of 1-(2-hydroxy-3-phenyloxypropyl) piperazine derivatives as T-type calcium channel blockers
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To obtain selective and potent inhibitor for T-type calcium channel by ligand based drug design, 2-hydroxy-3-phenoxypropyl piperazine derivatives were synthesized and evaluated for in vitro activities. Compound 6m and 6q showed high selectivity over hERG
- Park, Jung-Eun,Ji, Wan Keun,Jang, Jae Wan,Pae, Ae Nim,Choi, Keehyun,Choi, Ki Hang,Kang, Jahyo,Roh, Eun Joo
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supporting information
p. 1887 - 1890
(2013/04/10)
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- Enantioselective α-hydroxylation of β-keto esters catalyzed by chiral S-timolol derivatives
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A screen of aryloxy aminopropanol organocatalysts derived from the β-blocker inhibitor S-timolol determined the most active catalyst of asymmetric α-hydroxylation of β-keto esters. (R)-1-(tert-butylamino)- 3-(3,4,5-trimethoxyphenoxy) propan-2-ol (3k) was the most effective derivative, enantioselectively catalyzing α-hydroxylation of β-keto esters using tert-butyl hydroperoxide as the oxidant in hexane to afford the corresponding products in excellent yield and with good enantioselectivity (up to 96% yield, 88% ee).
- Cai, Yuanchun,Lian, Mingming,Li, Zhi,Meng, Qingwei
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experimental part
p. 7973 - 7977
(2012/09/21)
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- Development of β-amino alcohol derivatives that inhibit toll-like receptor 4 mediated inflammatory response as potential antiseptics
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Toll-like receptor 4 (TLR4) induced proinflammatory signaling has been directly implicated in severe sepsis and represents an attractive therapeutic target. Herein, we report our investigations into the structure-activity relationship and preliminary drug metabolism/pharmacokinetics study of β-amino alcohol derivatives that inhibit the TLR4 signaling pathway. Lead compounds were identified from in vitro cellular examination with micromolar potency for their inhibitory effects on TLR4 signaling and subsequently assessed for their ability to suppress the TLR4-induced inflammatory response in an ex vivo whole blood model. In addition, the toxicology, specificity, solubility, brain-blood barrier permeability, and drug metabolism of several compounds were evaluated. Although further optimizations are needed, our findings lay the groundwork for the future drug development of this class of small molecule agents for the treatment of severe sepsis.
- Chavez, Sherry A.,Martinko, Alexander J.,Lau, Corinna,Pham, Michael N.,Cheng, Kui,Bevan, Douglas E.,Mollnes, Tom E.,Yin, Hang
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p. 4659 - 4669
(2011/09/15)
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- An unusual (R)-selective epoxide hydrolase with high activity for facile preparation of enantiopure glycidyl ethers
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A novel epoxide hydrolase (BMEH) with unusual (R)-enantioselectivity and very high activity was cloned from Bacillus megaterium ECU1001. Highest enantioselectivities (E>200) were achieved in the bioresolution of ortho-substituted phenyl glycidyl ethers and para-nitrostyrene oxide. Worthy of note is that the substrate structure remarkably affected the enantioselectivities of the enzyme, as a reversed (S)-enantiopreference was unexpectedly observed for the ortho-nitrophenyl glycidyl ether. As a proof-of-concept, five enantiopure epoxides (>99% ee) were obtained in high yields, and a gram-scale preparation of (S)-ortho-methylphenyl glycidyl ether was then successfully performed within a few hours, indicating that BMEH is an attractive biocatalyst for the efficient preparation of optically active epoxides. Copyright
- Zhao, Jing,Chu, Yan-Yan,Li, Ai-Tao,Ju, Xin,Kong, Xu-Dong,Pan, Jiang,Tang, Yun,Xu, Jian-He
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experimental part
p. 1510 - 1518
(2011/08/03)
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- Discovery, synthesis, and biological evaluation of piperidinol analogs with anti-tuberculosis activity
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Direct anti-tuberculosis screening of commercially available compound libraries identified a novel piperidinol with interesting anti-tuberculosis activity and drug like characteristics. To generate a structure activity relationship about this hit a 22 mem
- Sun, Dianqing,Scherman, Michael S.,Jones, Victoria,Hurdle, Julian G.,Woolhiser, Lisa K.,Knudson, Susan E.,Lenaerts, Anne J.,Slayden, Richard A.,McNeil, Michael R.,Lee, Richard E.
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experimental part
p. 3588 - 3594
(2009/10/10)
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- Jacobsen-type enantioselective hydrolysis of aryl glycidyl ethers. 31P NMR analysis of the enantiomeric composition of oxiranes
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The enantioselective partial hydrolysis of a number of racemic aryl glycidyl ethers in the presence of chiral Co(salen)-catalyst was studied. The enantiomeric composition of the isolated (R)-aryl glycidyl ethers was analyzed by 31P NMR using optically active substituted 2-chloro-1,3,2- dioxaphospholanes. A synthesis of β-adrenoblocking agents (S)-toliprolol and (S)-moprolol based on the simultaneously obtained (S)-3-aryloxypropane-1,2- diols was proposed.
- Bredikhin,Strunskaya,Novikova,Azancheev,Sharafutdinova,Bredikhina
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p. 213 - 218
(2007/10/03)
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- Analogs of the dopamine D4 receptor ligand FAUC 113 with planar- and central-chirality
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By employing yeast enzymes, natural amino acids and the Jacobsen's catalyst as sources of chirality, we have synthesized pyrazolo[1,5-a]pyridine derivatives with central- and planar-chirality as analogs of the dopamine D4 receptor ligand FAUC 113. In vitro binding experiments displayed enhanced D2 and D3 affinity for both enantiomers of the [2.2]paracyclophane 3. The C-methylpiperazine (R)-4a revealed excellent D4 selectivity.
- Loeber, Stefan,Ortner, Birgit,Bettinetti, Laura,Huebner, Harald,Gmeiner, Peter
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p. 2303 - 2310
(2007/10/03)
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- Enantioselective ring opening of epoxides with trimethylsilyl azide (TMSN3) in the presence of β-cyclodextrin: An efficient route to 1,2-azido alcohols
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The ring opening of epoxides with nucleophiles such as TMSN3 and isopropylamine takes place enantioselectively in the presence of β- cyclodextrin under extremely mild conditions and the azido alcohols and amino alcohols are formed as (S)-isomers. (C) 1999 Published by Elsevier Science Ltd.
- Kamal, Ahmed,Arifuddin,Rao, Maddamsetty V.
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p. 4261 - 4264
(2007/10/03)
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- CsF in organic synthesis. Regioselective nucleophilic reactions of phenols with oxiranes leading to enantiopure β-blockers
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The two modes of the paths in the reaction of oxiranes with phenols are completely controlled by CsF. Glycidyl nosylate undergoes exclusive substitution at the C1 position whereas the ring-opening (C-3 attack) occurs with epichlorohydrin, glycidol, and 1,2-epoxyalkanes. These reactions provide convenient access to enantiopure β-blockers.
- Kitaori, Kazuhiro,Furukawa, Yoshiro,Yoshimoto, Hiroshi,Otera, Junzo
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p. 14381 - 14390
(2007/10/03)
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