scholarly journals 4-Amino-2-butyl-7-methoxycarbonylthiazolo[4,5-c]quinoline

Molbank ◽  
10.3390/m1305 ◽  
2021 ◽  
Vol 2021 (4) ◽  
pp. M1305
Author(s):  
Peter G. Larson ◽  
David M. Ferguson

4-Amino-imidazo-, oxazolo-, and thiazoloquinolines are key structural scaffolds in the design of nucleoside base analogs for use as therapeutic agents. Current strategies for arriving at diverse substitutions at the C6–C9 positions of the thiazolo- and oxazoloquinolines, however, are limited due to difficulties in arriving at the thiazoloquinoline-5N-oxide intermediate using electron deficient aromatic systems. Here, we demonstrate a synthetic route to obtain substituted thiazoloquinolines with electron-withdrawing groups at the C7 position. The target compound, 4-amino-2-butyl-7-methoxycarbonylthiazolo[4,5-c]quinoline, is obtained in eight steps using a 7-bromo surrogate as a precursor to the successful generation of the N-oxide intermediate, and final transformation via Pd-mediated C7-acylation.

Author(s):  
Cosmas Chinweike Eze ◽  
Mercy Amarachukwu Ezeokonkwo ◽  
Benjamin Ebere Ezema ◽  
Abraham Efeturi Onoabedje ◽  
David Izuchukwu Ugwu

: Coumarin, sulphonamide and amide scaffolds exhibit diverse pharmacological features and constitute an important class of therapeutic agents. In this review, we have discussed the synthesis, biological properties, and SAR of coumarins containing sulphonamide or amide group in the last seven years. Many reviews on the therapeutic activities of coumarins, sulphonamides, and amides have been published, hence the authors focused on coumarin-linked sulphonamide or amide scaffolds. The review provides information on the synthetic route to new coumarins containing sulphonamide or amide groups with improved pharmacological properties.


2011 ◽  
Vol 2011 ◽  
pp. 1-8
Author(s):  
Jamie B. Côté ◽  
Tan D. Quach ◽  
Andrey P. Demenev ◽  
David S. Garvey ◽  
Judd M. Berman

An optimized synthetic route to prepare ring-locked retinoid 1a has been developed. We fully describe a purification protocol that provides isomerically pure 1a in support of on-going proof of concept studies for the development of therapeutic agents to treat human ADRP. Additionally, we have found that isomerically pure 1a can be stored in amber vials under argon at −20°C for use over time (up to six months) without degradation. Thus, enabling 1a to be an accessible and valuable biological tool.


2019 ◽  
Vol 43 (11-12) ◽  
pp. 480-485
Author(s):  
Caijiao Wu ◽  
Qifan Zhou ◽  
Dake Song ◽  
Hui Li ◽  
Changshun Bao ◽  
...  

A practical synthetic route to pimavanserin tartrate, in which the target compound was obtained with 99.84% purity and in 46% total yield via a 5-step synthesis starting from 4-hydroxybenzaldehyde and (4-fluorophenyl)methanamine, is reported. The main advantages of the route include inexpensive starting materials, mild reaction conditions and an acceptable overall yield.


2018 ◽  
Vol 14 ◽  
pp. 856-860 ◽  
Author(s):  
Bettina Riedl ◽  
Walther Schmid

Synthetic approaches towards N-acetylgalactosamine (GalNAc) have been attracting considerable interest since this compound is known for its pivotal role in cell–cell interaction and receptor induced cell signaling. Herein, we present a synthetic route in which two of the four stereogenic centers present in the target compound are derived from enantiopure tartaric acid being selectively converted to epoxy alcohols. The key step is the Pd-catalyzed, stereo- and regioselective epoxide opening and subsequent nucleophilic substitution of an azide functionality. This approach enables the synthesis of the naturally D- and unnaturally L-configured GalNAc, as well as both enantiomers of the largely unknown N-acetylidosamine (IdoNAc).


2009 ◽  
Vol 62 (6) ◽  
pp. 546 ◽  
Author(s):  
Ligong Liu ◽  
Ken D. Johnstone ◽  
Jon K. Fairweather ◽  
Keith Dredge ◽  
Vito Ferro

An improved synthetic route to α(1→3)/α(1→2)-linked mannooligosaccharides has been developed and applied to a more efficient preparation of the potent anti-angiogenic sulfated pentasaccharide, benzyl Manα(1→3)-Manα(1→3)-Manα(1→3)-Manα(1→2)-Man hexadecasulfate, using only two monosaccharide building blocks. Of particular note are improvements in the preparation of both building blocks and a simpler, final deprotection strategy. The route also provides common intermediates for the introduction of aglycones other than benzyl, either at the building block stage or after oligosaccharide assembly. The anti-angiogenic activity of the synthesized target compound was confirmed via the rat aortic assay.


2011 ◽  
Vol 343-344 ◽  
pp. 1236-1241
Author(s):  
Yong En Guo ◽  
Jing Cao ◽  
Cai Ju Zhou ◽  
Shao Peng Wen ◽  
Ya Mei Zhang ◽  
...  

Salvianolic acid B has many important pharmacological activities. A novel synthetic route of methyl acrylate derivative—an important intermediate to synthesize salvianolic acid B, was designed, and the target compound was prepared in seven steps of reactions with 2-bromo-3-hydroxy-4-methoxybenzaldehyde as major starting material. Its and other four important unreported intermediates’ structures were characterized by IR, 1H NMR, MS, etc.


2014 ◽  
Vol 50 (86) ◽  
pp. 13100-13102 ◽  
Author(s):  
Antonio Fernández ◽  
Esteban Alvarez ◽  
Ramón Alvarez-Manzaneda ◽  
Rachid Chahboun ◽  
Enrique Alvarez-Manzaneda

A short synthetic sequence for the preparation of merosesquiterpenes with a benzoxanthene skeleton starting from (−)-sclareol is reported. The D ring of the target compound is obtained through a Diels–Alder cycloaddition.


Reactions ◽  
2011 ◽  
Author(s):  
Peter Atkins

In this final reaction I am going to show you in the broadest of outlines how chemists build the equivalent of a cathedral. That is, how they synthesize a complicated molecule from scratch. The aim of a synthesis is to take a reasonably readily available laboratory chemical and process it—add bits on, take things off, close rings of atoms, open rings, build flying buttresses, and so on—until the target compound has been made. You could take the view that you should really start from absolute scratch, from the elements themselves, typically hydrogen, carbon, nitrogen, and oxygen, and build the molecule from those. However, that would be a waste of time and not crucial to the demonstration of the synthetic route because it is possible to argue that there are already plenty of methods for synthesizing the simple starting materials from scratch, and the real challenge is to build the intricate molecule. That is rather like accepting that a contractor can supply windows, bricks, and beams when constructing a real house and that it isn’t necessary to go all the way back to the sand, clay, and iron ore from which they are made to demonstrate that the house can be built literally from the ground up. Of course, the starting materials in a modern chemical synthesis might seem a bit recondite, but be assured that they are reasonably acceptable and purchasable from suppliers of laboratory reagents or easily made from what they do supply. Now for the particular cathedral on which I intend to focus. That scourge of humanity, malaria (‘bad air’), was introduced into the New World in the fifteenth century and soon wrought the havoc that had for long, and still, afflicts millions. The natives there found that an extract of the bark of the quina-quina tree, in due course to be classified as Cinchona Officinalis, was an effective cure, in particular having saved the life of the Countess of Cinchona. In due course the active component, quinine, was identified and extracted.


2020 ◽  
Vol 7 (4) ◽  
pp. 159-168
Author(s):  
M. S. Dzyurkevich ◽  
N. V. Shtyrlin ◽  
Y. G. Shtyrlin

In this work we describe the transformation of synthetic route of the antiepileptic drug candidate Sumepirin starting from discovery stage. Initial method included six step process requiring two steps of purification using colon chromatography and has poor overall yield of target compound. The process developed is convenient, scalable, technological and meet the most of conditions of green chemistry. The overall yield was increased up to 62.5% in four steps without colon chromatography purification which allows to obtain the target compound with purity of 99.5+% which is especially important for the active ingredient.


2020 ◽  
Vol 56 (65) ◽  
pp. 9332-9335
Author(s):  
Sandra Estalayo-Adrián ◽  
Salvador Blasco ◽  
Sandra A. Bright ◽  
Gavin J. McManus ◽  
Guillermo Orellana ◽  
...  

Two new water-soluble amphiphilic Ru(ii) polypyridyl complexes were synthesised and their photophysical and photobiological properties evaluated; both complexes showed a rapid cellular uptake and phototoxicity against HeLa cervical cancer cells.


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