Cutting-Edge Organic Synthesis and Chemical Biology of Bioactive Molecules

2019 ◽  
2020 ◽  
Vol 7 (1) ◽  
pp. 23-39 ◽  
Author(s):  
Kantharaju Kamanna ◽  
Santosh Y. Khatavi

Multi-Component Reactions (MCRs) have emerged as an excellent tool in organic chemistry for the synthesis of various bioactive molecules. Among these, one-pot MCRs are included, in which organic reactants react with domino in a single-step process. This has become an alternative platform for the organic chemists, because of their simple operation, less purification methods, no side product and faster reaction time. One of the important applications of the MCRs can be drawn in carbon- carbon (C-C) and carbon-heteroatom (C-X; X = N, O, S) bond formation, which is extensively used by the organic chemists to generate bioactive or useful material synthesis. Some of the key carbon- carbon bond forming reactions are Grignard, Wittig, Enolate alkylation, Aldol, Claisen condensation, Michael and more organic reactions. Alternatively, carbon-heteroatoms containing C-N, C-O, and C-S bond are also found more important and present in various heterocyclic compounds, which are of biological, pharmaceutical, and material interest. Thus, there is a clear scope for the discovery and development of cleaner reaction, faster reaction rate, atom economy and efficient one-pot synthesis for sustainable production of diverse and structurally complex organic molecules. Reactions that required hours to run completely in a conventional method can now be carried out within minutes. Thus, the application of microwave (MW) radiation in organic synthesis has become more promising considerable amount in resource-friendly and eco-friendly processes. The technique of microwaveassisted organic synthesis (MAOS) has successfully been employed in various material syntheses, such as transition metal-catalyzed cross-coupling, dipolar cycloaddition reaction, biomolecule synthesis, polymer formation, and the nanoparticle synthesis. The application of the microwave-technique in carbon-carbon and carbon-heteroatom bond formations via MCRs with major reported literature examples are discussed in this review.


2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Shi Cao ◽  
Wei Hong ◽  
Ziqi Ye ◽  
Lei Gong

AbstractThe direct and selective C(sp3)-H functionalization of cycloalkanes and alkanes is a highly useful process in organic synthesis owing to the low-cost starting materials, the high step and atom economy. Its application to asymmetric catalysis, however, has been scarcely explored. Herein, we disclose our effort toward this goal by incorporation of dual asymmetric photocatalysis by a chiral nickel catalyst and a commercially available organophotocatalyst with a radical relay strategy through sulfur dioxide insertion. Such design leads to the development of three-component asymmetric sulfonylation involving direct functionalization of cycloalkanes, alkanes, toluene derivatives or ethers. The photochemical reaction of a C(sp3)-H precursor, a SO2 surrogate and a common α,β-unsaturated carbonyl compound proceeds smoothly under mild conditions, delivering a wide range of biologically interesting α-C chiral sulfones with high regio- and enantioselectivity (>50 examples, up to >50:1 rr and 95% ee). This method is applicable to late-stage functionalization of bioactive molecules, and provides an appealing access to enantioenriched compounds starting from the abundant hydrocarbon compounds.


2014 ◽  
Vol 9 (5) ◽  
pp. 1070-1074
Author(s):  
Ramesh Prasad Pandey ◽  
Ho Jeong Kwon ◽  
Jong Seog Ahn ◽  
Hiroyuki Osada ◽  
Jae Kyung Sohng

2020 ◽  
Author(s):  
Abdul Aziz Ali

Among nitrogen-containing heterocyclic compounds, 1,2,3-triazoles are privileged structure motif and received a great deal of attention in academics and industry. Even though absent in nature, 1,2,3-triazoles have found broad applications in drug discovery, organic synthesis, polymer chemistry, supramolecular chemistry, bioconjugation, chemical biology, fluorescent imaging, and materials science. Therefore, the development of facile and straightforward methodology for the synthesis of 1,2,3-triazoles is of noteworthy interest. In this study, emphasis will be given to numerous synthetic approaches for the synthesis of 1,2,3-triazoles, especially the popular click chemistry approach. Furthermore, several biological activities of this promising heterocycle will also be discussed.


ChemInform ◽  
2016 ◽  
Vol 47 (9) ◽  
pp. no-no
Author(s):  
Maximillian T. W. Lee ◽  
Antoine Maruani ◽  
Vijay Chudasama

ChemInform ◽  
2009 ◽  
Vol 40 (28) ◽  
Author(s):  
M. Hamadouche ◽  
M. Belkheira ◽  
D. El Abed

2014 ◽  
Vol 70 (a1) ◽  
pp. C1005-C1005
Author(s):  
Melissa Ignacio ◽  
Aaron Smith ◽  
Dmitriy Soldatov

Short peptides are ecologically friendly and non-toxic molecules, so they can be safely utilized in green chemistry processes or incorporated in pharmaceuticals and food additives. It has been shown that some dipeptides can form crystals that incorporate other molecules through intermolecular hydrogen bonding and van der Waals interactions[1]. The utilization of such dipeptides for solid state organic synthesis or storage and stabilization of bioactive molecules would be of great practical interest, but the principles that define the successful combinations are not clear. In order to identify what factors lead to complementary pairs of a dipeptide and a second component, a series of leucine-containing dipeptides was screened against 40 organic solvents and solids. Direct or solvent-assisted grinding was used followed by PXRD analysis. It was found that each dipeptide was able to form new phases with some of the utilized reactive and bioactive molecules. The Figure illustrates three experimental powder patterns in the 5-35 2θ degree range. The dipeptide leucyl-valine (1) and the second component 5-acetylsalicylamide (2) combine to form a new crystalline phase (3). After screening was complete, a series of crystallizations was performed and several crystals comprised of both a dipeptide and another molecule have been isolated and studied. A number of structural motifs were observed, although a layered architecture with the second component included in the interlayer space prevailed.


2010 ◽  
Vol 6 ◽  
pp. 1219-1228 ◽  
Author(s):  
Yuya A Lin ◽  
Benjamin G Davis

Olefin metathesis has emerged as a powerful tool in organic synthesis. The activating effect of an allylic hydroxy group in metathesis has been known for more than 10 years, and many organic chemists have taken advantage of this positive influence for efficient synthesis of natural products. Recently, the discovery of the rate enhancement by allyl sulfides in aqueous cross-metathesis has allowed the first examples of such a reaction on proteins. This led to a new benchmark in substrate complexity for cross-metathesis and expanded the potential of olefin metathesis for other applications in chemical biology. The enhanced reactivity of allyl sulfide, along with earlier reports of a similar effect by allylic hydroxy groups, suggests that allyl chalcogens generally play an important role in modulating the rate of olefin metathesis. In this review, we discuss the effect of allylic chalcogens in olefin metathesis and highlight its most recent applications in synthetic chemistry and protein modifications.


2008 ◽  
Vol 47 (30) ◽  
pp. 5496-5499
Author(s):  
Christian P. R. Hackenberger ◽  
Hermann A. Wegner ◽  
Andreas Zumbuehl

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