scholarly journals Design and Synthesis of Fused Pyridine Building Blocks for Automated Library Generation

ChemMedChem ◽  
2020 ◽  
Author(s):  
Helena Mora‐Radó ◽  
Werngard Czechtizky ◽  
María Méndez ◽  
Joseph P. A. Harrity

1995 ◽  
Vol 98 (1) ◽  
pp. 483-490
Author(s):  
J. L. M. van Nunen ◽  
A. P. H. J. Schenning ◽  
R. J. H. Hafkamp ◽  
C. F. van Nostrum ◽  
M. C. Feiters ◽  
...  


2015 ◽  
Vol 112 (27) ◽  
pp. 8187-8192 ◽  
Author(s):  
Michael D. Hardy ◽  
Jun Yang ◽  
Jangir Selimkhanov ◽  
Christian M. Cole ◽  
Lev S. Tsimring ◽  
...  

Cell membranes are dynamic structures found in all living organisms. There have been numerous constructs that model phospholipid membranes. However, unlike natural membranes, these biomimetic systems cannot sustain growth owing to an inability to replenish phospholipid-synthesizing catalysts. Here we report on the design and synthesis of artificial membranes embedded with synthetic, self-reproducing catalysts capable of perpetuating phospholipid bilayer formation. Replacing the complex biochemical pathways used in nature with an autocatalyst that also drives lipid synthesis leads to the continual formation of triazole phospholipids and membrane-bound oligotriazole catalysts from simpler starting materials. In addition to continual phospholipid synthesis and vesicle growth, the synthetic membranes are capable of remodeling their physical composition in response to changes in the environment by preferentially incorporating specific precursors. These results demonstrate that complex membranes capable of indefinite self-synthesis can emerge when supplied with simpler chemical building blocks.



2008 ◽  
Vol 130 (6) ◽  
pp. 1833-1835 ◽  
Author(s):  
Farid Nouar ◽  
Jarrod F. Eubank ◽  
Till Bousquet ◽  
Lukasz Wojtas ◽  
Michael J. Zaworotko ◽  
...  


2019 ◽  
Vol 91 (5) ◽  
pp. 811-838 ◽  
Author(s):  
Marian Mikołajczyk

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.



Molecules ◽  
2020 ◽  
Vol 25 (24) ◽  
pp. 5917
Author(s):  
Yang Pan ◽  
Shogo Morisako ◽  
Shinobu Aoyagi ◽  
Takahiro Sasamori

Divalent silicon species, the so-called silylenes, represent attractive organosilicon building blocks. Isolable stable silylenes remain scarce, and in most hitherto reported examples, the silicon center is stabilized by electron-donating substituents (e.g., heteroatoms such as nitrogen), which results in electronic perturbation. In order to avoid such electronic perturbation, we have been interested in the chemistry of reactive silylenes with carbon-based substituents such as ferrocenyl groups. Due to the presence of a divalent silicon center and the redox-active transition metal iron, ferrocenylsilylenes can be expected to exhibit interesting redox behavior. Herein, we report the design and synthesis of a bis(ferrocenyl)silirane as a precursor for a bis(ferrocenyl)silylene, which could potentially be used as a building block for redox-active organosilicon compounds. It was found that the isolated bis(ferrocenyl)siliranes could be a bottleable precursor for the bis(ferrocenyl)silylene under mild conditions.





2019 ◽  
Vol 10 ◽  
pp. 1217-1227 ◽  
Author(s):  
Giulia Tuci ◽  
Andree Iemhoff ◽  
Housseinou Ba ◽  
Lapo Luconi ◽  
Andrea Rossin ◽  
...  

The rational design and synthesis of covalent triazine frameworks (CTFs) from defined dicyano-aryl building blocks or their binary mixtures is of fundamental importance for a judicious tuning of the chemico-physical and morphological properties of this class of porous organic polymers. In fact, their gas adsorption capacity and their performance in a variety of catalytic transformations can be modulated through an appropriate selection of the building blocks. In this contribution, a set of five CTFs (CTF1–5) have been prepared under classical ionothermal conditions from single dicyano-aryl or heteroaryl systems. The as-prepared samples are highly micro-mesoporous and thermally stable materials featuring high specific surface area (up to 1860 m2·g−1) and N content (up to 29.1 wt %). All these features make them highly attractive samples for carbon capture and sequestration (CCS) applications. Indeed, selected polymers from this series rank among the CTFs with the highest CO2 uptake at ambient pressure reported so far in the literature (up to 5.23 and 3.83 mmol·g−1 at 273 and 298 K, respectively). Moreover, following our recent achievements in the field of steam- and oxygen-free dehydrogenation catalysis using CTFs as metal-free catalysts, the new samples with highest N contents have been scrutinized in the process to provide additional insights to their complex structure–activity relationship.



2020 ◽  
Vol 16 ◽  
pp. 2314-2321
Author(s):  
Elizabeth A Margolis ◽  
Rebecca J Keyes ◽  
Stephen D Lockey ◽  
Edward E Fenlon

The thread–link–cut (TLC) approach has previously shown promise as a novel method to synthesize molecular knots. The modular second-generation approach to small trefoil knots described herein involves electrostatic interactions between an electron-rich bis-macrocyclic host compound and electron-deficient guests in the threading step. The bis-macrocyclic host was synthesized in eight steps and 6.6% overall yield. Ammonium and pyridinium guests were synthesized in 4–5 steps. The TLC knot-forming sequence was carried out and produced a product with the expected molecular weight, but, unfortunately, further characterization did not produce conclusive results regarding the topology of the product.



ChemInform ◽  
2007 ◽  
Vol 38 (4) ◽  
Author(s):  
Jacilynn A. Brant ◽  
Yunling Liu ◽  
Dorina F. Sava ◽  
Derek Beauchamp ◽  
Mohamed Eddaoudi


Synlett ◽  
2019 ◽  
Vol 30 (20) ◽  
pp. 2209-2215 ◽  
Author(s):  
Ke Du ◽  
Andrew C.-H. Sue

Rim-differentiated pillar[5]arenes (P[5]s) are intriguing macrocyclic molecular platforms with C 5-symmetry, but their conventional statistical syntheses suffer from low yields and laborious separation. Our group recently reported a ‘pre-oriented’ protocol that results in highly selective production of C 5-symmetric P[5]s among four constitutional isomers. Subsequently, we devised a more general divergent synthetic route starting with a common P[5] precursor with rim differentiation, followed by a series of high-yielding reactions that permit successive transformations of both rims freely. As a result, a variety of rim-differentiated P[5]s can be made to order in gram-scale quantities. This total solution not only populates the list of C 5-symmetric P[5]s, but also enables further design and synthesis of assorted five-fold organic building blocks towards complex supramolecular architectures.



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