- Treatment method of by-product after enzymatic resolution of gamma-lactam
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The invention provides a treatment method of a by-product after enzymatic resolution of gamma-lactam. The treatment method comprises the following steps of carrying out racemization catalytic reactionon the by-product (+)1-amino-4-formate-2-cyclopentene,
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Paragraph 0014-0017
(2021/02/10)
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- Access to 1′-Amino Carbocyclic Phosphoramidite to Enable Postsynthetic Functionalization of Oligonucleotides
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We report a synthesis of a carbocyclic, abasic RNA phosphoramidite decorated with an amino functionality. The building block was efficiently incorporated into an RNA oligonucleotide in a site-specific manner, followed by deprotection to a free amino group
- Rydzik, Anna M.,Balk, Regina,Koegler, Martin,Steinle, Tobias,Riether, Doris,Gottschling, Dirk
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supporting information
p. 6735 - 6739
(2021/09/11)
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- Diastereoselective Diboration of Cyclic Alkenes: Application to the Synthesis of Aristeromycin
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The Pt-catalyzed diboration of cyclic alkenes is extended to unsaturated heterocycles and bicyclic compounds and can be accomplished in a diastereoselective fashion. The optimal procedures, substrate scope, and diastereoselectivity were investigated, and examples employing both homogeneous and heterogeneous catalysis were examined. Lastly, application to the construction of the nucleoside analog (±)-aristeromycin was conducted.
- Vendola, Alex J.,Allais, Christophe,Dechert-Schmitt, Anne-Marie R.,Lee, James T.,Singer, Robert A.,Morken, James P.
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supporting information
p. 2863 - 2867
(2021/05/05)
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- Pyrimido triazole compound and medical application thereof (by machine translation)
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The present invention relates to a compound of general (I) or a hydrate thereof or a pharmaceutically acceptable salt, thereof, a hydrate thereof or a pharmaceutically acceptable salt thereof, a pharmaceutical composition containing the same or a pharmaceutically acceptable salt thereof, and use, of the compound or a pharmaceutically acceptable salt thereof in the manufacture of a medicament . The medicament is for anti-platelet aggregation and treatment of related diseases such as antithrombotic . (by machine translation)
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Paragraph 0043; 0045-0047
(2020/05/30)
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- Substituent and solvent effects in the 1,3-dipolar cycloadditions for synthesis of anti-influenza agent peramivir and its analog
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Influenza remains a health problem to humans. Peramivir is a FDA approved anti-influenza drug targeting the virus neuraminidase. The (3 + 2) cycloaddition reaction of 2-ethylbutanenitrile oxide with the cyclopentene dipolarophile derived from Vince lactam is a key step in the conventional synthesis of peramivir. Our study showed that conducting the (3 + 2) cycloaddition reactions with either aliphatic or aromatic nitrile oxide in hexane solution provided high percentage of the desired regioisomer, and the N-substituent having electron-withdrawing property is also beneficial to the regioselectivity. This study also demonstrated an alternative synthetic pathway of (?)-peramivir and the analog having a phenyl group in place of the 3-pentyl moiety.
- Chen, Chien-Liang,Chiu, Tzu-Wei,Chen, Yung-Wen,Fang, Jim-Min
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p. 4458 - 4470
(2019/07/03)
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- CHEMOKING RECEPTOR ANTAGONISTS
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Disclosed herein are chemokine receptor antagonists of formula (I) wherein G1, X1, X2, and X3 are as defined in the specification. Compositions comprising such compounds; and methods for treating conditions and disorders using such compounds and compositions are also described.
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Page/Page column 155
(2013/03/26)
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- Syntheses and evaluation of fluorinated conformationally restricted analogues of GABA as potential inhibitors of GABA aminotransferase
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Inhibition of γ-aminobutyric acid aminotransferase (GABA-AT) could raise the concentration of GABA, an inhibitory neurotransmitter in the human brain, and could have therapeutic applications for a variety of neurological diseases including epilepsy. Four fluorine-containing analogues of GABA with conformations restricted by a cyclohexane ring system were designed and synthesized, but unlike some of their five-membered ring counterparts, minimal inhibition of GABA-AT was observed. It is likely that the rigid chair conformation of these compounds cannot be accommodated well in the enzyme's active site.
- Wang, Zhiyong,Silverman, Richard B.
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p. 2242 - 2252
(2007/10/03)
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- Ruthenium-catalyzed rom-RCM of cyclopentene-yne. concise synthesis of a pyrrolizidine derivative
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ROM-RCM (Ring-Opening Metathesis and Ring-Closing Metathesis) of cyclopentene-yne having an ester moiety was demonstrated using first- and second-generation Grubbs' catalysts. When the reaction of cycloalkene-yne was carried out in the presence of 5 mol %
- Wakamatsu, Hideaki,Sato, Yoshihiro,Fujita, Reiko,Mori, Miwako
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- PRODUCTION METHOD FOR CIS-1-AMINO-4-HYDROXYMETHYL-2-CYCLOPENTENE OR ITS SALT
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PROBLEM TO BE SOLVED: To provide a method capable of producing cis-1-amino-4-hydroxymethyl-2-cyclopentene or its salt with high selectivity and a high yield by using inexpensive reactants easily handleable. SOLUTION: Cis-1-amino-4-hydroxymethyl-2-cyclopentene represented by formula (II) or its salt is produced by mixing a cis-4-amino-2-cyclopentene-1-carboxylic ester salt represented by general formula (I) (wherein R1 is an optionally substituted alkyl, cycloalkyl, alkenyl, alkynyl, aryl, or aralkyl group; and A is an inorganic or organic acid residue) with a metal boron hydride complex compound under the condition that the stoichiometric ratio of the amount of the metal boron hydride complex compound to the amount of the cis-4-amino-2-cyclopentene-1-carboxylic ester salt is 1-10. COPYRIGHT: (C)2006,JPOandNCIPI
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Page/Page column 15
(2010/02/14)
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- Process for preparing (-)-(1S, 4R) N-protected 4-amino-2-cyclopentene-1-carboxylate esters
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The invention relates to a process for preparing (?)-(1S,4R) N protected 4-amino-2-cylcopentene-1-carboxylate esters represented by the formula (I) wherein R1 and R2 are as described within the specification.
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- Systematic structure-based design and stereoselective synthesis of novel multisubstituted cyclopentane derivatives with potent antiinfluenza activity
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The design and synthesis of novel, orally active, potent, and selective inhibitors of influenza neuraminidase differing structurally from existing neuraminidase inhibitors are described. X-ray crystal structures of complexes of neuraminidase with known five- and six-membered ring inhibitors revealed that potent inhibition of the enzyme is determined by the relative positions of the interacting inhibitor substituents (carboxylate, glycerol, acetamido, hydroxyl) rather than by the absolute position of the central ring. This led us to design potential neuraminidase inhibitors in which the cyclopentane ring served as a scaffold for substituents (carboxylate, guanidino, acetamido, alkyl) that would interact with the four binding pockets of the neuraminidase active site at least as effectively as those of the established six-membered ring inhibitors such as DANA (2), zanamivir (3), and oseltamivir (4). A mixture of the isomers was prepared initially. Protein crystallography of inhibitor - enzyme complexes was used to screen mixtures of isomers in order to identify the most active stereoisomer. A synthetic route to the identified candidate 50 was developed, which featured (3 + 2) cycloaddition of 2-ethylbutyronitrile oxide to methyl (1S,4R)-4[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylate (43). Structures of the synthetic compounds were verified by NMR spectroscopy using nuclear Overhauser effect methodology. Two new neuraminidase inhibitors discovered in this work, 50 and 54, have IC50 values vs neuraminidase from influenza A and B of 50 values are comparable or superior to those for zanamivir and oseltamivir, agents recently approved by the FDA for treatment of influenza. The synthetic route used to prepare 50 and 54 was refined so that synthesis of pure active isomer 54, which has five chiral centers, required only seven steps from readily available intermediates. Further manipulation was required to prepare deoxy derivative 50. Because the activities of the two compounds are comparable and 54 [RWJ-270201 (BCX-1812)] is the easier to synthesize, it was selected for further clinical evaluation.
- Chand,Montgomery,Kotian,Dehghani,El-Kattan,Lin,Hutchison,Babu,Bantia,Elliott
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p. 4379 - 4392
(2007/10/03)
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- An approach to a carbocyclic analogue of cyclic adenosine 5'-diphosphate ribose. The synthesis and bisphosphorylation of N1-[(1S,3R)-3-(hydroxymethyl)cyclopent-1-yl]inosine
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The synthesis of N1-[(1S,3R)-3-(hydroxymethyl)cyclopent-1-yl]inosine (11) via a cyclocondensation route is reported. Regioselective bisphosphorylation of the primary 5'-hydroxyl groups leads to a carbocyclic, inosine analogue of seco adenosine 5'-diphosphate ribose(3).
- Fortt, Simon M.,Potter, Barry V. L.
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p. 5371 - 5374
(2007/10/03)
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- Lipase-catalyzed resolution of 2-azabicyclo[2.2.1]hept-5-en-3-ones
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The lipase-catalyzed asymmetric resolution of 2-azabicyclo[2.2.1]hept-5-en-3-ones is reported; non-racemic chiral 2-azabicyclo[2.2.1]hept-5-en-3-ones were obtained conveniently by lipase-catalyzed enantioselective transesterification or hydrolysis of N-hydroxymethyl-2-azabicyclo[2.2.1]hept-5-en-3-one or N-acyloxymethyl-2-azabicyclo[2.2.1]hept-5-en-3-one.
- Nakano, Hiroto,Iwasa, Kazuto,Okuyama, Yuko,Hongo, Hiroshi
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p. 2381 - 2386
(2007/10/03)
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- Biocatalytical Transformations. IV. Enantioselective Enzymatic Hydrolyses of Building Blocks for the Synthesis of Carbocyclic Nucleosides
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Enantiomerically pure alkyl (1S,4R)- and (1R,4S)-4-acetamido-cyclopent-2-ene-carboxylates are obtained from their corresponding racemates by hydrolysis with PLE or the lipase from Candida cylindracea.
- Csuk, Rene,Doerr, Petra
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p. 269 - 276
(2007/10/02)
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