Design and Synthesis of a Biologically Active Antibody Mimic Based on an Antibody-Antigen Crystal Structure

1994 ◽  
Vol 116 (7) ◽  
pp. 2725-2733 ◽  
Author(s):  
M. L. Smythe ◽  
M. von Itzstein
Keyword(s):  
Crystal Structure ◽  
Biologically Active ◽  
Design And Synthesis

scholarly journals Design and synthesis of a novel 5-(aminomethylene)thiazolidine-2,4-dione derivatives as potent hepatitis-B virus polymerase inhibitors

2015 ◽  
Vol 10 (2) ◽  
pp. 271
Author(s):  
Wei-Guo Li ◽  
He-Qun Wang
Keyword(s):  
Hbv Dna ◽  
Biologically Active ◽  
Secondary Amines ◽  
Design And Synthesis ◽  
H Nmr ◽  
Viral Antigens ◽  
Polymerase Inhibitors ◽  
Potent Inhibition ◽  
B Virus ◽  
C Nmr

<p>A series of novel thiazolidinedione analogues (TZD) were designed and synthesized potent inhibitors of HBV capsid assembly. The synthesis of thiazolidine-2,4-dione derivatives (4a–4o), starting from the condensation of 5-(ethoxymethylene)thiazolidine-2,4-dione (1) with various secondary amines (3) derived from biologically active compounds. The newly synthesized TZD analogues 4a-4o were characterized by <sup>1</sup>H NMR, <sup>13</sup>C NMR, and MS and evaluated for their anti-HBV activity. Most of the compounds inhibited the expression of viral antigens at low concentration. Six compounds, 4g, 4h, 4l, 4m, 4n, and 4o, demonstrated potent inhibition of HBV DNA replication at submicromolar range. Of these five initial hits, compound 4o was the most active when compared with lamivudine.</p><p> </p><p> </p>

scholarly journals A Dendralenic C–H Acid

Synlett ◽  
2019 ◽  
Vol 30 (04) ◽  
pp. 433-436 ◽  
Author(s):  
Denis Höfler ◽  
Richard Goddard ◽  
Nils Nöthling ◽  
Benjamin List
Keyword(s):  
Crystal Structure ◽  
Acid Catalysis ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Design And Synthesis ◽  
Brönsted Acid ◽  
Bronsted Acid Catalysis

The design and synthesis of a strong, dendralenic C–H acid is described. Crystal structure analyses confirm the proposed structure. Despite the moderate stability of our motif, an application to Brønsted acid catalysis has been explored.

scholarly journals Phosphonate reagents and building blocks in the synthesis of bioactive compounds, natural products and medicines

2019 ◽  
Vol 91 (5) ◽  
pp. 811-838 ◽  
Author(s):  
Marian Mikołajczyk
Keyword(s):  
Building Block ◽  
Methyl Esters ◽  
Building Blocks ◽  
Biologically Active ◽  
Type I ◽  
Antiulcer Drug ◽  
Total Syntheses ◽  
Prostaglandin Analogues ◽  
Design And Synthesis ◽  
Neplanocin A

Abstract This account outlines the results obtained in the author’s laboratory on the application of phosphonates in the synthesis of various classes of biologically active cyclopentenones and cyclopentanones. In the first place two general methods for the synthesis of mono-, 1,2- and 1,4-dicarbonyl compounds are presented. The first is based on the use of α-phosphoryl sulfides in conjunction with the Horner reaction while in the second method the oxygenation reaction of α-phosphonate carbanion is a key step. The utility of these two approaches to 1,4-diketones as precursors of cyclopentenones was exemplified by the synthesis of dihydrojasmone and (Z)-jasmone. The use of simple phosphonates, α-phosphoryl sulfides and β- and γ-ketophosphonates as starting reagents in the synthesis of cyclopentanoid antibiotics (methylenomycin B, racemic desepoxy-4,5-didehydromethylenomycin, enantiomeric sarkomycins) is presented. The synthesis and reactivity of achiral 3-(phosphorylmethyl)cyclopent-2-enone and chiral diastereoisomeric camphor protected 3-(phosphorylmethyl)-4,5-dihydroxycyclopent-2-enones as building blocks is discussed as a platform for developing a new access to a variety of bioactive cyclopentenones. The utility and value of achiral phosphonate building block is demonstrated by the synthesis of racemic and enantiopure prostaglandin B1 methyl esters and enantiomeric phytoprostanes B1 type I and II. The range of biologically active compounds prepared from chiral diastereoisomeric cyclopentenone phosphonates is wider. Herein the total syntheses of the following target compounds are presented: enantiomeric isoterreins, natural (−)-neplanocin A and its unnatural (+)-enantiomer, anticancer prostaglandin analogues (enantiomers of TEI-9826, NEPP-11, iso-NEPP-11). The design and synthesis of racemic and four enantiopure stereoisomers of an antiulcer drug rosaprostol is also described.

scholarly journals Design and Synthesis of N-phenyl Phthalimides as Potent Protoporphyrinogen Oxidase Inhibitors

Molecules ◽  
2019 ◽  
Vol 24 (23) ◽  
pp. 4363
Author(s):  
Wei Gao ◽  
Xiaotian Li ◽  
Da Ren ◽  
Susu Sun ◽  
Jingqian Huo ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Enzyme Activity ◽  
Molecular Docking ◽  
Molecular Design ◽  
Design Strategy ◽  
Docking Studies ◽  
Activity Assay ◽  
Enzyme Activity Assay ◽  
Protoporphyrinogen Oxidase ◽  
Design And Synthesis

Protoporphyrinogen oxidase (PPO) has been identified as one of the most promising targets for herbicide discovery. A series of novel phthalimide derivatives were designed by molecular docking studies targeting the crystal structure of mitochondrial PPO from tobacco (mtPPO, PDB: 1SEZ) by using Flumioxazin as a lead, after which the derivatives were synthesized and characterized, and their herbicidal activities were subsequently evaluated. The herbicidal bioassay results showed that compounds such as 3a (2-(4-bromo-2,6-difluorophenyl) isoindoline-1,3-dione), 3d (methyl 2-(4-chloro-1,3-dioxoisoindolin-2-yl)-5-fluorobenzoate), 3g (4-chloro-2-(5-methylisoxazol-3-yl) isoindoline-1,3-dione), 3j (4-chloro-2-(thiophen-2-ylmethyl) isoindoline-1,3-dione) and 3r (2-(4-bromo-2,6-difluorophenyl)-4-fluoroisoindoline-1,3-dione) had good herbicidal activities; among them, 3a showed excellent herbicidal efficacy against A. retroflexus and B. campestris via the small cup method and via pre-emergence and post-emergence spray treatments. The efficacy was comparable to that of the commercial herbicides Flumioxazin, Atrazine, and Chlortoluron. Further, the enzyme activity assay results suggest that the mode of action of compound 3a involves the inhibition of the PPO enzyme, and 3a showed better inhibitory activity against PPO than did Flumioxazin. These results indicate that our molecular design strategy contributes to the development of novel promising PPO inhibitors.

2-Methacryloxytropone

2006 ◽  
Vol 62 (7) ◽  
pp. o2986-o2987 ◽  
Author(s):  
Kanji Kubo ◽  
Eriko Fukeda ◽  
Taisuke Matsumoto ◽  
Kazuhiko Endo ◽  
Akira Mori
Keyword(s):  
Crystal Structure ◽  
Dihedral Angle ◽  
Title Compound ◽  
Biologically Active

The title compound, 7-oxo-1,3,5-cycloheptatrien-1-yl 2-methyl-2-propenoate, C11H10O3, is known as an intermediate for the synthesis of biologically active polymers. In its crystal structure, the tropolone ring forms a dihedral angle of 69.76 (2)° with the ester plane, and intermolecular C—H...π and C—H...O interactions are observed.

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