132682-22-5Relevant articles and documents
Utilization of L-serine in an oxime olefin cycloaddition route to a functionalized asymmetric pyrrolidine, a selective α-glucosidase inhibitor
Hassner, Alfred,Falb, Eliezer,Nudelman, Abraham,Albeck, Amnon,Gottlieb, Hugo E.
, p. 2397 - 2400 (1994)
A new route for asymmetric aza-sugar analogs starting with L-serine and utilizing an intramolecular oxime olefin cycloaddition has been successfully developed. A member of this family of branched chain sugar amino di(hydroxymethyl) pyrrolidines (1 and 2) exhibits selective inhibition of α-glucosidase, while no inhibition of β-glucosidase was detected.
Versatile approach for the synthesis of novel seven-membered iminocyclitols via ring-closing metathesis dihydroxylation reaction
Lin, Chang-Ching,Pan, Yi-Shin,Patkar, Laxmikant N.,Lin, Hsiu-Mei,Tzou, Der-Lii M.,Subramanian, Thangaiah,Lin, Chun-Cheng
, p. 3259 - 3267 (2004)
Seven-membered iminocyclitols with diverse diastereomers were prepared starting with D- and L-serines and employing ring-closing olefin metathesis and dihydroxylation reaction sequence. The iminocyclitols were assayed for glycosidase inhibition and compound 20 was found to be a competitive inhibitor for β-glucosidase with Ki 26.3μM.
Enhanced enantiocontrol in catalytic metal carbene transformations with dirhodium(II) tetrakis, Rh2(4S-MEOX)4
Doyle, Michael P.,Dyatkin, Alexey B.,Protopopova, Marina N.,Yang, Chien I.,Miertschin, Charla S.,et al.
, p. 163 - 170 (1995)
The synthesis, spectral characteristics, and X-ray structures for dirhodium(II) tetrakis, Rh2(4S-MEOX)4, and the related dirhodium(II) tetrakis, Rh2(4S-THREOX)4, are reported.Comparison is made between these 2-oxooxazolidin-ligated dirhodium(II) catalysts for metal carbene transformations and those with comparable 2-oxopyrrolidine ligands, especially dirhodium(II) tetrakis, Rh2(5S-MEPY)4.Structure-selectivity comparisons reveal that Rh2(4S-MEOX)4 provides higher enantiocontrol and, in some cases, higher diastereocontrol than Rh2(5S-MEPY)4 in intramolecular carbon-hydrogen insertion reactions of sterically demanding diazoacetates and diazoacetamides and is the catalyst of choice for highly enantioselective diazodecomposition of adamantyl diazoacetates and N-(tert)butyldiazoacetamides.The structurally analogous Rh2(4S-THREOX)4 is nearly identical with Rh2(4S-MEOX)4 in its overall effect on selectivity.The net advantage of Rh2(4S-MEOX)4 lies in its wider openness for metal carbene transformations.
Metal-Free Selective Modification of Secondary Amides: Application in Late-Stage Diversification of Peptides
Adebomi, Victor,Sriram, Mahesh,Streety, Xavier,Raj, Monika
supporting information, p. 6189 - 6193 (2021/08/01)
Here we solve a long-standing challenge of the site-selective modification of secondary amides and present a simple two-step, metal-free approach to selectively modify a particular secondary amide in molecules containing multiple primary and secondary amides. Density functional theory (DFT) provides insight into the activation of C-N bonds. This study encompasses distinct chemical advances for late-stage modification of peptides thus harnessing the amides for the incorporation of various functional groups into natural and synthetic molecules.
HETERCYCLIC COMPOUNDS FOR THE TREATMENT OF DISEASE
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Paragraph 0023, (2018/12/13)
Described herein are heterocyclic compounds, compositions, and methods for their use for treatment of disease.
NOVEL BENZODIOXANE-PIPERIDINE DERIVATIVES AND THEIR THERAPEUTIC APPLICATIONS FOR TREATING NEUROPSYCHIATRIC DISORDERS
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Paragraph 1234; 1277-1280, (2015/12/05)
The present invention concerns benzodioxane-piperidine with general formula I: wherein notably: R1 represents one or more identical or different substituent(s) on the benzene ring, each independently representing a hydrogen or halogen atom, or a C1-4 alkyl group, or a C1-4 alkoxy group or a C1-4 hydroxyalkyl group or a C1-4 alkylcarbonyl or an alkoxycarbonyl group or an OH group or an SO2R group with R alkyl, or a CN group, or a CF3 group, or an OCF 3 group; n=1, 2 or 3;m=0 or 1, andR2 represents one or more identical or different substituent(s) on the oxazolidinone or morpholinone ring, each independently representing: a hydrogen atom, a C1-4 alkyl group, or a C1-4 alkoxy group, or a C1-4 hydroxyalkyl group, or an alkylcarbonyl group, or an alkoxycarbonyl group, or an alkoxyphenyl group.
Synthesis of tryptophans by Lewis acid promoted ring-opening of aziridine-2-carboxylates: Optimization of protecting group and Lewis acid
Tirotta, Ilaria,Fifer, Nathan L.,Eakins, Julia,Hutton, Craig A.
, p. 618 - 620 (2013/02/23)
The preparation of tryptophan derivatives through the Lewis acid promoted substitution of aziridine carboxylates with indole was found to be accompanied by a ring-expansion reaction to generate an oxazolidinone byproduct. The ratio of tryptophan to oxazol
A ferrocenyl-DHIPOH/Cu(OAc)2 complex for diastereo- and enantioselective catalysis of the 1,4-addition of glycine derivatives to alkylidene malonates
Shi, Yu-Hua,Wang, Zheng,Hu, Bin,Wang, Ming,Fossey, John S.,Deng, Wei-Ping
supporting information; experimental part, p. 6010 - 6013 (2012/01/04)
A planar chiral ferrocene derivative Fc-DHIPOH served as an excellent N,O- chiral ligand for asymmetric copper catalyzed 1,4-addition of glycine derivatives to alkylidene malonates. The corresponding 1,4-adducts were obtained in high yields with excellent enantioselectivities up to 95% ee.
Fluorogenic peptide substrates for serine and threonine phosphatases
Xue, Fengtian,Seto, Christopher T.
supporting information; experimental part, p. 1936 - 1939 (2010/07/06)
Figure presented A new fluorescent assay for Ser/Thr protein phosphatases has been developed. Hydrolysis of a phosphoSer residue liberates the Ser hydroxyl group, which induces a cyclization reaction on the N-terminal carbamate and releases a fluorescent reporter. Sequence selectivity is observed using several peptide substrates against alkaline phosphatase (ALP), bacteriophage protein phosphatase (-PPase), and vaccinia H1 related phosphatase (VHR). These studies suggest that the assay could be a useful tool for profiling the substrate specificities of medicinally important phosphatases.
Efficient regio- And stereoselective formation of azocan-2-ones via 8-endo cyclization of α-carbamoyl radicals
Fang, Xinqiang,Liu, Kun,Li, Chaozhong
supporting information; experimental part, p. 2274 - 2283 (2010/05/01)
The iodine-atom-transfer 8-endo cyclization of α-carbamoyl radicals was investigated experimentally and theoretically. With the aid of Mg(CIO 4)2 and a bis(oxazoline) ligand, N- ethoxycarbonylsubstituted N-(pent-4-enyl)-2-iodoalkanamides underwent 8-endo cyclization leading to the formation of only the corresponding 3,5-trans-substituted azocan-2-ones in excellent yields. Similarly, the BF 3·OEt2/H2O-promoted reactions of N-ethoxycarbonyl-N-(2-allylaryl)-2-iodoalkanamides afforded exclusively the benzazocanone products with a 3,5-cis configuration in high yields. The bidentate chelation of substrate radicals not only significantly improved the efficiency of cyclization but also resulted in the change of stereochemistry of azocanone products from 3,8-iransto 3,8-cis. Theoretical calculations at the UB3LYP/6-31G* level revealed that the cyclization of N-carbonyl- substituted α-carbamoyl radicals occurs via the E-conformational transition states without the presence of a Lewis acid. On the other hand, the cyclization proceeds via the Z-conformational transition states when the substrates form the bidentate chelation with a Lewis acid. In both cases, the 8-endo cyclization is always fundamentally preferred over the corresponding 7-exo cyclization. The complexed radicals having the more rigid conformations also allow the better stereochemical control in the iodine-atom-abstraction step. To further understand the reactivity of a-carbamoyl radicals, the competition between the 8-endo and 5-exo cyclization was also studied. The results demonstrated that the 8-endo cyclization is of comparable rate to the corresponding 5-exo cyclization for a-carbamoyl radicals with fixed Z-conformational transition states. As a comparison, the 8-endo mode is fundamentally preferred over the 5-exo mode in the cyclization of NH-amide substrates because the latter requires the Z-conformational transition states, whereas the former proceeds via the more stable E-conformational transition states.
