- Preparation method of (-) - Cytoxazone and (+) -4 - epi-Cytoxazone
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The preparation method of (-) - Cytoxazone and (+) -4 - epi-Cytoxazone takes D - p-hydroxyphenylglycine as a raw material, the intermediate 2 is obtained through methyl esterification reaction under catalysis of thionyl chloride, and then the amino is protected with Boc anhydride to obtain the intermediate 3. The compound 4 is obtained by using potassium carbonate as a base and reacting with methyl iodide under reflux conditions. The methyl ester was reduced with sodium borohydride/lithium chloride to give the primary alcohol compound 5. An intermediate IBX is then obtained with 6 primary alcohol, then reacted with acetone cyanohydrin SN2 to give intermediate 7, and the intermediate 8 is obtained by reacting with the methanol solution of hydrogen chloride to obtain two five-membered ring compound compounds 9 and 10, respectively, with sodium borohydride to obtain (-) - Cytoxazone and its isomers (+) -4 - epi-Cytoxtoxtoxtoxol, respectively.
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Paragraph 0090-0094
(2021/11/14)
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- Compound, pharmaceutically acceptable salt thereof and medical application thereof
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The invention belongs to the field of medicines, and particularly relates to a compound shown as a formula I or medicinal salt thereof. The invention also relates to application of the compound or themedicinal salt thereof in selectively inhibiting LF activity, resisting anthrax toxin toxicity and preventing or treating anthracnose.
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Paragraph 0243-0247
(2020/07/24)
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- Intermediate of RORgamma inhibitor and preparation method thereof
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The invention belongs to the technical field of drugs, in particular to an intermediate of a RORgamma inhibitor and a preparation method thereof. The intermediate is as shown in a formula (I). The method has the advantages of being easily available in raw material, concise in process, economic and environment-friendly, high in yield and the like. The formula is as shown in the description.
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Paragraph 0161; 0162; 0163; 0164; 0165
(2019/04/27)
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- ((S)-3-Mercapto-2-methylpropanamido)acetic acid derivatives as metallo-β-lactamase inhibitors: Synthesis, kinetic and crystallographic studies
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The emergence and global spread of metallo-β-lactamase (MBL) mediated resistance to almost all β-lactam antibacterials poses a serious threat to public health. Since no clinically useful MBL inhibitors have been reported, there is an urgent need to develop new potent broad-spectrum MBL inhibitors effective against antibacterial resistance. Herein, we synthesized a set of 2-substituted ((S)-3-mercapto-2-methylpropanamido) acetic acid derivatives, some of which displayed potent inhibition with high ligand efficiency to the clinically relevant MBL subtypes, Verona Integron-encoded MBL (VIM)-2 and New Delhi MBL (NDM)-1. Kinetic studies revealed that the inhibitors are not strong zinc chelators in solution, and they bind reversibly to VIM-2 but dissociate very slowly. Crystallographic analyses revealed that they inhibit VIM-2 via chelating the active site zinc ions and interacting with catalytically important residues. Further cell- and zebrafish-based assays revealed that the inhibitors slightly increase susceptibility of E. coli cells expressing VIM-2 to meropenem, and they have no apparent toxicity to the viability of HEK293T cells and the zebrafish embryogenesis.
- Liu, Sha,Jing, Li,Yu, Zhu-Jun,Wu, Chengyong,Zheng, Yongxiang,Zhang, En,Chen, Qiang,Yu, Yamei,Guo, Li,Wu, Yong,Li, Guo-Bo
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p. 649 - 660
(2018/02/10)
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- NOVEL ANTIESTROGENIC HETEROCYCLIC COMPOUNDS
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The present invention provides novel heterocyclic compounds of Formula I wherein A, B, E, ring Z, Y, L, ring X, D, m, n, R7 and R8 are as defined in the specification as estrogen receptor antagonists/degraders. The compound of Formula I can be used for the treatment of cancers mediated by estrogen receptors. (Formula I ).
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Page/Page column 64; 65
(2018/08/20)
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- Electronic effects of aryl-substituted bis(oxazoline) ligands on the outcome of asymmetric copper-catalysed C-H insertion and aromatic addition reactions
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The effect of the modification of bis(oxazoline) ligands on the outcome of copper-catalysed C-H insertion and aromatic addition reactions is described. In general, these reactions display minimum sensitivity in terms of enantiocontrol to variation of the electronic properties of the aryl moiety of the ligand however, some influence is observed for C-H insertions employing naphthyl-substituted bis(oxazolines) and for aromatic addition reactions of biphenyl diazo ketone substrates. The synthesis of the modified bis(oxazolines), which include four novel structures, is also described.
- Slattery, Catherine N.,O'Keeffe, Sarah,Maguire, Anita R.
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p. 1265 - 1275
(2013/11/19)
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- A multikilogram-scale synthesis of (R)-methyl 2-[(1r,4R)-4-(tert-butoxy- carbonylamino)cyclohexyl]-2-(2-nitrophenylsulfonamido)acetate - A doubly protected building block with three points of variation
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A robust and scalable synthesis of (R)-methyl 2-[(1r,4R)-4-(tert- butoxycarbonylamino)cyclohexyl]-2-(2-nitrophenylsulfon-amido)acetate is reported. This serves as a scaffold for the preparation of trans-substituted aminocyclohexanes. The key synthetic step is the reduction of d-4-hydroxyphenylglycine, or a protected equivalent, to achieve the required regiochemistry across the cyclohexyl ring. Georg Thieme Verlag Stuttgart · New York.
- Carr, Gregory,Butterworth, Sam,Walker, Phil,Reck, Folkert,Geng, Bolin,Pandarinathan, Lakshmipathi
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experimental part
p. 875 - 880
(2012/05/19)
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- Synthesis and bioactivity of some 2-oxo-5-aryl-3-hydrazone and 2-oxo-5-aryl-4-hydrazone pyrrolidine derivatives
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2-Aryl-4,5-dioxopyrrolidine-3-carboxylate and 5-aryl-2,4-dioxopyrrolidine- 3-carboxylate derivatives were successfully synthesized via carbonyl-based multiple component reaction and Dieckmann cyclization, respectively. Successive functional group transformations which include decarboxylation and hydrazonation afforded 2-oxo-5-aryl-3-hydrazone and 2-oxo-5-aryl-4-hydrazone derivatives. Compound 3d exhibited activity against human histiocytic lymphoma (U937) and neuroblastoma (SH-SY5Y) cell lines while compound 6 showed neuroprotective ability from oxidative stress medium induced with H2O2.
- Mohammat, Mohd Fazli,Najim, Nigar,Mansor, Nurul Shulehaf,Sarman, Sharil,Shaameri, Zurina,Zain, Mazatulikhma Mat,Hamzah, Ahmad Sazali
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experimental part
p. 429 - 438
(2011/12/05)
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- Synthesis of hydroxyphenylglycine-derived novel poly(silylenevinylenephenyleneethynylene)s
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The hydrosilylation polymerization of d-(-)-p-hydroxyphenylglycine-derived diethynyl monomers 1p and 1m with dihydrosilanes Si1 and Si2 was carried out using RhI(PPh3)3 as a catalyst to give optically active novel poly(silylenevinylenephenyleneethynylene)s [(E)-poly(1p-Si1), (E)-poly(1p-Si2), (E)-poly(1m-Si1), (E)-poly(1m-Si2), and (Z)-poly(1p-Si1)] with number-average molecular weights ranging from 2800 to 17,000 in 41-92% yields. Polymers having (E)- and (Z)-olefin moieties were obtained, wherein the (E)-/(Z)-ratios depended on the reaction conditions. The UV-vis absorption edge of (E)-poly(1p-Si1) was positioned at a wavelength longer than that of (Z)-poly(1p-Si1), indicating that (E)-vinylene-linkage extends the conjugation more largely than the (Z)-counterpart. This was also confirmed by fluorescence spectroscopy. Alkaline hydrolysis of ester moieties of these polymers gave the corresponding polymers having carboxy groups. The (E)-polymers showed different solubility in hydrophobic solvents before and after hydrolysis, but the non-hydrolyzed and hydrolyzed (Z)-polymers exhibited the same solubility.
- Ueda, Tokiko,Shiotsuki, Masashi,Sanda, Fumio
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experimental part
p. 3570 - 3579
(2012/05/20)
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- Diketopiperazine supramolecule derived from hydroxyphenylglycine
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A diketopiperazine (DKP) having long alkyl chains was synthesized from D-p-hydroxyphenylglycine, and the formation of supramolecules was examined. The 1H NMR and UV-vis spectroscopic measurements and molecular modeling have suggested that the D
- Ohta, Yosuke,Terada, Kayo,Masuda, Toshio,Sanda, Fumio
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experimental part
p. 1477 - 1483
(2009/12/24)
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- Novel antibacterial agents
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This invention relates to novel multibinding compounds (agents) that are antibacterial agents. The multibinding compounds of the invention comprise from 2-10 ligands covalently connected by a linker or linkers, wherein each of said ligands in their monovalent (i.e., unlinked) state have the ability to bind to a an enzyme involved in cell wall biosynthesis and metabolism, a precursor used in the synthesis of the bacterial cell wall and/or the bacterial cell surface thereby interfere with the synthesis and/or metabolism of the cell wall. In particular the multibinding compounds of the invention comprise from 2-10 ligands covalently connected by a linker or linkers, wherein each of said ligands has a ligand domain capable of binding to penicillin binding proteins, a transpeptidase enzyme, a substrate of a transpeptidase enzyme, a beta-lactamase enzyme, pencillinase enzyme, cephalosporinase enzyme, a transglycoslase enzyme, or a transglycosylase enzyme substrate; Preferably, the ligands are selected from the beta lactam or glycopeptide class of antibacterial agents.
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Page/Page column 85-86
(2008/06/13)
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- Syntheses of amino alcohols and chiral C2-symmetric bisoxazolines derived from O-alkylated R-4-hydroxyphenylglycine and S-tyrosine
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Chiral C2-symmetric bisoxazolines 1b-f and 2b,c, derived from 4′-O-alkylated R-4-hydroxyphenylglycine or S-tyrosine, were prepared. As intermediates, a series of chiral amino alcohols possessing substituted phenolic groups was prepared and fully characterized.
- Caplar, Vesna,Raza, Zlata,Katalenic, Darinka,Zinic, Mladen
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- Stereoselective synthesis of (-)-cytoxazone and (+)-5-epi-cytoxazone
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A novel, stereo selective synthesis of (-)-cytoxazone 1a and stereoselective synthesis of (+)-5-epi-cytoxazone 1b were achieved via stereoselective Grignard addition of vinylmagnesium bromide on N-Boc aldehyde obtained from p-hydroxy-D-phenylglycine 2 followed by cyclization of N-Boc alcohol 6, ozonolysis and reduction to get (+)-5-epi-cytoxazone. Compound 6 underwent mitsunobu conditions, deprotection of ester followed by cyclization of N-Boc alcohol to get (-)-cytoxazone.
- Ravi Kumar,Bhaskar,Madhan,Venkateswara Rao
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p. 2907 - 2916
(2007/10/03)
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- Total synthesis of the amaryllidaceae alkaloid (+)-plicamine and its unnatural enantiomer by using solid-supported reagents and scavengers in a multistep sequence of reactions
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A sequence of polymer-supported reagents and scavengers was used to promote the synthetic transformations in the first total synthesis of (+)-plicamine (1), a member of the amaryllidaceae alkaloid family, starting from L-4-hydroxyphenylglycine (see scheme).
- Baxendale, Ian R.,Ley, Steven V.,Piutti, Claudia
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p. 2194 - 2197
(2007/10/03)
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- Total synthesis of the amaryllidaceae alkaloid (+)-plicamine using solid-supported reagents
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In this report we describe in full the total synthesis of the amaryllidaceae alkaloid (+)-plicamine 1 including a model compound study. In both cases the compounds were prepared using solid-supported reagents and scavengers in multi-step sequences of reactions to give materials which required no conventional purification but could be carried on to the next synthetic step.
- Baxendale, Ian R,Ley, Steven V,Nessi, Marcella,Piutti, Claudia
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p. 6285 - 6304
(2007/10/03)
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