105459-05-0Relevant articles and documents
Efficient synthesis of 4′-cyclopropylated carbovir analogues with use of ring-closing metathesis from glycolate
Liu, Lian Jin,Yoo, Jin Cheol,Hong, Joon Hee
, p. 1186 - 1196 (2008)
The first synthetic route of novel 4′-cyclopropylated carbovir analgues is described. The construction of cyclopropylated quaternary carbon at 4′-position of carbocyclic nucleosides was successfully made via sequential Johnson's orthoester rearrangement and ring-closing metathesis (RCM) starting from ethyl glycolate. Synthesized compounds 15 and 16 showed moderate antiviral activity without any cytotoxicity up to 100 μmol. Copyright Taylor & Francis Group, LLC.
Biosynthesis of porphyrins and related macrocycles. Part 53.1'2 Stereochemical studies on the enzymic formation of hydroxymethylbilane, the precursor of uroporphyrinogen III
Schauder, Jean-Roch,Jendrezejewski, Stefan,Neidhart, Werner L.,Hart, Graham J.,Battersby, Alan R.
, p. 2691 - 2698 (1999)
A new synthesis of porphobilinogen 1 (PBG) is described that allows the preparation of (11R)-[1l-3H1]PBG la and its (1 lS)Tenantiomer Ib. Their enantiomeric purities are determined by degradation of their immediate synthetic precursors by way of 3H-labelled glycines to yield two samples of 3H-labelled glycolic acid 16. The enzyme glycolate oxidase, known to remove HK stereospecifically from the methylene group of glycolic acid in forming glyoxylic acid 17, is then used to assay the configurations of these two samples. Each 3H-labelled PBG la and Ib is converted by hydroxymethylbilane synthase into hydroxymethylbilane 5a and 5b. Methods are devised for the isolation of this labile product from water and for its subsequent degradation to two further samples of glycolic acid. These are assayed enzymically to prove that there is overall retention of configuration as the aminomethyl carbon of PBG 1 enzymically affords the hydroxymethyl centre of the bilane 5. Thus, the two covalent bonds that are formed in this whole process must both involve reactions with retention of configuration or both with inversion. The significance of these results is discussed. The Royal Society of Chemistry 1999.
Hydrophilic azaspiroalkenes as robust bioorthogonal reporters
An, Peng,Wu, Hsuan-Yi,Lewandowski, Tracey M.,Lin, Qing
, p. 14005 - 14008 (2018)
Two hydrophilic spiroalkenes, azaspiro[2.3]hex-1-ene and azaspiro[2.4]hept-1-ene, were designed and synthesized. Compared to the previously reported spiro[2.3]hex-1-ene, the azaspiroalkenes exhibited greater water solubility and reactivity as dipolarophiles in the photoinduced tetrazole-alkene cycloaddition reaction. In addition, an azaspiro[2.3]hex-1-ene-containing amino acid, AsphK, was found to be charged by an engineered pyrrolysyl-tRNA synthetase into proteins via amber codon suppression in E. coli as well as in mammalian cells.
Preparation method of abacavir hydroxyacetate
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Paragraph 0041-0044; 0047-0050; 0053-0056, (2020/07/21)
The invention discloses a preparation method of abacavir hydroxyacetate. The abacavir hydroxyacetate is a compound shown as a formula I, and the preparation method comprises the following steps c, b-cor a-b-c in the following synthesis route which is shown in the specification, wherein R1 is an alcoholic hydroxyl protecting group. In the step a, a compound as shown in a formula V and R1Cl are subjected to substitution reaction to obtain a compound as shown in a formula IV. In the step b, a compound shown as a formula II is obtained by esterification reaction of a compound shown as a formula III and the compound shown as the formula IV. In the step c, the compound shown in the formula II is subjected to hydrolysis reaction under an acidic condition to obtain a compound shown in a formula I. Each step of reaction in the whole route has the advantages of simplicity in operation, low production cost, mild reaction conditions, easiness in separation and purification of products and high reaction yield, the purity of the prepared abacavir hydroxyacetate is higher than 99.6%, the content of single impurity is lower than 0.1%, and the abacavir hydroxyacetate is easy for large-scale production.
A fluorogenic probe using a catalytic reaction for the detection of trace intracellular zinc
Takashima, Ippei,Inoue, Yohei,Matsumoto, Nobuyuki,Takagi, Akira,Okuda, Kensuke
supporting information, p. 13327 - 13330 (2020/11/10)
Labile zinc plays various roles in cells at low concentrations which most fluorescent probes are not able to detect. Here we report a cephem-based probe which coordinates to zinc and zinc-bound water cleaves the scaffold and releases the fluorophore. In addition, the zinc is recycled and reacts with multiple probes, amplifying the signal. This signal amplification system is useful for the detection of intracellular zinc at low concentrations and has potential for further development of probes with a similar molecular design. This journal is
Hydrophilic carbonate type antibody drug conjugate
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Paragraph 0166-0168, (2020/04/29)
The invention provides a hydrophilic carbonate type antibody drug conjugate or a pharmaceutically acceptable salt thereof. The hydrophilic carbonate type antibody drug conjugate or the pharmaceutically acceptable salt thereof provided by the invention can be used for effectively releasing drugs in a tumor weakly acidic microenvironment to obtain a better in-vivo drug effect on tumors, and can be used for obtaining very good in-vivo PK under high DAR.
PRODRUGS OF FUSED-BICYCLIC C5aR ANTAGONISTS
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Paragraph 0391, (2019/10/23)
The present disclosure provides, inter alia, Compounds of Formulae IA, IB, IC, IIA, IIB and IIC or pharmaceutically acceptable salts thereof that are modulators of the C5a receptor. Also provided are pharmaceutical compositions and methods of use including the treatment of diseases or disorders involving pathologic activation from C5a and non-pharmaceutical applications.
Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation
Mills, L. Reginald,Graham, Joshua M.,Patel, Purvish,Rousseaux, Sophie A. L.
supporting information, p. 19257 - 19262 (2019/12/02)
Herein, we report a Ni-catalyzed reductive coupling for the synthesis of benzonitriles from aryl (pseudo)halides and an electrophilic cyanating reagent, 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions. A variety of medicinally relevant benzonitriles can be made in good yields. Addition of NaBr to the reaction mixture allows for the use of more challenging aryl electrophiles such as aryl chlorides, tosylates, and triflates. Mechanistic investigations suggest that NaBr plays a role in facilitating oxidative addition with these substrates.
Dess-Martin periodinane oxidative rearrangement for preparation of α-keto thioesters
Sanichar, Randy,Carroll, Ciaran,Kimmis, Ryan,Reiz, Bela,Vederas, John C.
supporting information, p. 593 - 597 (2018/02/09)
A Dess-Martin Periodinane (DMP) mediated oxidative rearrangement reaction was uncovered. The reaction proceeds via oxidation of a β-hydroxy thioester to a β-keto thioester, followed by an α-hydroxylation and then further oxidation to form a vicinal thioester tricarbonyl. This product then rearranges, extruding CO2, to form an α-keto product. The mechanism of the rearrangement was elucidated using 13C labelling and analysis of the intermediates as well as the products of the reaction. This efficient process allows for easy preparation of α-keto thioesters which are potential intermediates in the synthesis of pharmaceutically important heterocyclic scaffolds such as quinoxalinones.
COMPOUNDS FOR MODULATING AQUAPORINS
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Page/Page column 53, (2017/12/08)
The invention relates to compounds of formula (I) pharmaceutical compositions thereof and methods for modulating aquaporin 9.
