scholarly journals 6’-Amino-5,7-Dibromo-2-Oxo-3’-(Trifluoromethyl)-1’H-Spiro[Indoline-3,4’-Pyrano[2,3-c]Pyrazole]-5’-Carbonitrile

Molbank ◽  
10.3390/m1309 ◽  
2021 ◽  
Vol 2022 (1) ◽  
pp. M1309
Author(s):  
Yuliya E. Ryzhkova ◽  
Varvara M. Kalashnikova ◽  
Michail N. Elinson
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Biological Activity ◽  
Infrared Spectroscopy ◽  
Sodium Acetate ◽  
Multicomponent Reactions ◽  
Structural Diversity ◽  
Synthetic Methods ◽  
Environmentally Benign ◽  
Complex Molecules ◽  
Synthetic Target

The multicomponent reactions are environmentally benign synthetic methods of building-up of complex molecules and several levels of structural diversity for diverse applications. Spirooxindoles are an important synthetic target possessing extended biological activity and drug discovery applications. In this communication, the multicomponent transformation of 5,7-dibromoisatin, malononitrile, and 5-(trifluoromethyl)-2,4-dihydro-3H-pyrazol-3-one in EtOH at reflux in the presence of sodium acetate was carefully investigated to give 6’-amino-5,7-dibromo-2-oxo-3’-(trifluoromethyl)-1’H-spiro[indoline-3,4’-pyrano[2,3-c]pyrazole]-5’-carbonitrile in excellent yield. The structure of the new compound was established by means of elemental analysis, mass and nuclear magnetic resonance, and infrared spectroscopy.

A Review on Onychine and its Analogs: Synthesis and Biological Activity

2020 ◽  
Vol 17 (1) ◽  
pp. 3-22
Author(s):  
Claudia R.B. Gomes ◽  
Marcus V.N. de Souza ◽  
Victor Facchinetti
Keyword(s):  
Biological Activity ◽  
Multicomponent Reactions ◽  
Diels Alder ◽  
Synthetic Methods ◽  
Reaction Conditions ◽  
Low Concentrations ◽  
Wide Range ◽  
Intramolecular Cyclizations ◽  
Synthetic Approaches ◽  
Operational Simplicity

Background: Onychine is a 4-azafluorenone alkaloid isolated from the Annonaceae family, in low concentrations. Onychine and its analogs exhibit a wide range of pharmacological activities such as antifungal, antibacterial, anticancer, and antimalarial. Because of the high bioactivity of some 4-azafluorenone derivatives, several synthetic methods have been developed for their procurement. Objective: Considering the importance of these alkaloids, we aim to present the main synthetic approaches to onychines and its derivatives and the biological activity of some 4-azafluorenones. Methods: The most prominent methodologies for the synthesis of onychines were reviewed. Results: In this work, we cover many synthetic approaches for the synthesis of onychine and 4-azafluorenone derivatives including intramolecular cyclizations, multicomponent reactions, microwave-assisted multicomponent reactions, Diels-alder reactions, among others. Moreover, we also review the biological activity of 4-azafluorenones. Conclusion: 4-azafluorenones have risen as prominent structures in medicinal chemistry; however, most of the time, access to new derivatives involves toxic catalysts, harsh reaction conditions, and long-step procedures. Therefore, the development of new synthetic routes with more operational simplicity, simple purification procedure, good yields, and low environmental impact, is desirable.

Consecutive multicomponent reactions for the synthesis of complex molecules

2019 ◽  
Vol 17 (33) ◽  
pp. 7632-7650 ◽  
Author(s):  
Sanjun Zhi ◽  
Xiaoming Ma ◽  
Wei Zhang
Keyword(s):  
Multicomponent Reactions ◽  
Structural Diversity ◽  
Complex Molecules ◽  
Molecular Complexity ◽  
Synthetic Efficiency

Consecutive multicomponent reactions (MCRs) combine two or more MCRs to achieve high synthetic efficiency, product structural diversity, and molecular complexity.

scholarly journals 1,3-Dimethyl-3′,5-diphenyl-1,5-dihydro-2H,5′H-spiro[furo[2,3-d]pyrimidine-6,4′-isoxazole]-2,4,5′(3H)-trione

Molbank ◽  
10.3390/m1317 ◽  
2022 ◽  
Vol 2022 (1) ◽  
pp. M1317
Author(s):  
Yuliya E. Ryzhkova ◽  
Varvara M. Kalashnikova ◽  
Fedor V. Ryzhkov ◽  
Michail N. Elinson
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Infrared Spectroscopy ◽  
Magnetic Resonance ◽  
Elemental Analysis ◽  
Sodium Acetate ◽  
Room Temperature ◽  
Halogen Atom ◽  
Ring Closure ◽  
Leaving Group ◽  
Intramolecular Ring

Michael addition–halogenation–intramolecular ring-closing (MHIRC) reactions are processes in which a halogen atom as a leaving group can attach to substrates or reactants during the reaction, which then undergoes intramolecular ring closure. In this communication the MHIRC transformation of 4-benzylidene-3-phenylisoxazol-5(4H)-one and 1,3-dimethylbarbituric acid in the presence of N-bromosuccinimide and sodium acetate in EtOH at room temperature was carefully investigated to give novel 1,3-dimethyl-3′,5-diphenyl-1,5-dihydro-2H,5′H-spiro[furo[2,3-d]pyrimi- dine-6,4′-isoxazole]-2,4,5′(3H)-trione in a good yield. The structure of the new compound was confirmed by the results of elemental analysis as well as mass, nuclear magnetic resonance, and infrared spectroscopy.

Marine Alkaloid Pityriacitrin and Its Analogues: Discovery, Structures, Synthetic Methods and Biological Properties

2020 ◽  
Vol 20 ◽  
Author(s):  
Shaoyong Ke ◽  
Tingting Xu ◽  
Yong Min ◽  
Zhongyi Wan ◽  
Ziwen Yang ◽  
...  
Keyword(s):  
Biological Activity ◽  
Mechanism Of Action ◽  
Structural Diversity ◽  
Structural Features ◽  
Biological Properties ◽  
Research Interest ◽  
Synthetic Methods ◽  
Biological Functions ◽  
Marine Alkaloid ◽  
Novel Drugs

: Pityriacitrin is a natural marine alkaloid with the typical β-carboline scaffold, and which has been demonstrated to exhibit diverse biological functions. Especially, the special structural features for pityriacitrin lead to the increasing research interest and the emergence of versatile derivatives, and many pityriacitrin analogues have been isolated or synthesized over past decades. The structural diversity and evolved biological activity of this natural alkaloids can offer opportunities for the development of highly potential novel drugs with new mechanism of action, and so the aim of this brief review is to describe the discovery, synthesis and biological properties of natural pityriacitrin and its derivatives, as well as the isolation source.

scholarly journals Multicomponent Synthesis of Dimethyl 2-(2,4-Diamino-3- cyano-5H-chromeno[2,3-b]pyridin-5-yl)malonate

Molbank ◽  
10.3390/m1308 ◽  
2021 ◽  
Vol 2022 (1) ◽  
pp. M1308
Author(s):  
Yuliya E. Ryzhkova ◽  
Oleg I. Maslov ◽  
Michail N. Elinson
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Infrared Spectroscopy ◽  
Magnetic Resonance ◽  
Organic Synthesis ◽  
Multicomponent Reactions ◽  
Room Temperature ◽  
Low Cost ◽  
Multicomponent Synthesis ◽  
Dimethyl Malonate ◽  
Efficient Construction

Dimethyl sulfoxide (DMSO) is widely used as a solvent in organic synthesis and in pharmacology because of its low cost, stability, and non-toxicity. Multicomponent reactions are a powerful synthetic tool for the rapid and efficient construction of complicated molecular frameworks. In this communication, the multicomponent transformation of salicylaldehyde, malononitrile dimer, and dimethyl malonate in DMSO at room temperature was carefully investigated to give dimethyl 2-(2,4-diamino-3-cyano-5H-chromeno[2,3-b]pyridin-5-yl)malonate with good yield. The structure of the new compound was established by means of elemental analysis and mass, nuclear magnetic resonance, and infrared spectroscopy.

Metal-, and Organocatalyst-Free One-Pot Assembly of Chiral Aza-Tricyclic Molecules: Creating Six Contiguous Stereocenters from 2-D-Structures and an Amino Acid

2020 ◽  
Author(s):  
Dung Do
Keyword(s):  
Amino Acid ◽  
Chemical Space ◽  
Structural Diversity ◽  
Therapeutic Agents ◽  
Chiral Molecules ◽  
One Pot ◽  
Complex Molecules ◽  
Chiral Catalyst ◽  
Chiral Complex ◽  
Free Process

<p>Chiral molecules with their defined 3-D structures are of paramount importance for the study of chemical biology and drug discovery. Having rich structural diversity and unique stereoisomerism, chiral molecules offer a large chemical space that can be explored for the design of new therapeutic agents.<sup>1</sup> Practically, chiral architectures are usually prepared from organometallic and organocatalytic processes where a transition metal or an organocatalyst is tailor-made for desired reactions. As a result, developing a method that enables rapid assembly of chiral complex molecules under metal- and organocatalyst-free condition represents a daunting challenge. Here we developed a straightforward route to create a chiral 3-D structure from 2-D structures and an amino acid without any chiral catalyst. The center of this research is the design of a <a>special chiral spiroimidazolidinone cyclohexadienone intermediate</a>, a merger of a chiral reactive substrate with multiple nucleophillic/electrophillic sites and a transient organocatalyst. <a>This unique substrate-catalyst (“subcatalyst”) dual role of the intermediate enhances </a><a>the coordinational proximity of the chiral substrate and catalyst</a> in the key Aza-Michael/Michael cascade resulting in a substantial steric discrimination and an excellent overall diastereoselectivity. Whereas the “subcatalyst” (hidden catalyst) is not present in the reaction’s initial components, which renders a chiral catalyst-free process, it is strategically produced to promote sequential self-catalyzed reactions. The success of this methodology will pave the way for many efficient preparations of chiral complex molecules and aid for the quest to create next generation of therapeutic agents.</p>

Diversity-Oriented Synthetic Approaches for Furoindoline: A Review

2019 ◽  
Vol 16 (3) ◽  
pp. 342-368 ◽  
Author(s):  
Ramandeep Kaur ◽  
Yagyesh Kapoor ◽  
Sundeep K. Manjal ◽  
Ravindra K. Rawal ◽  
Kapil Kumar
Keyword(s):  
Rheumatoid Arthritis ◽  
Cancer Cachexia ◽  
Biological Activities ◽  
Ring System ◽  
Synthetic Methods ◽  
Structural Units ◽  
Current Article ◽  
Tetrahydropyranyl Ether ◽  
Synthetic Approaches ◽  
Synthetic Target

The furo [2,3-b] indoline ring system is one of the most important structural units in various natural products. It has been known to have inherent biological activities and is utilized as a synthetic target for a number of natural compounds; therefore, this has contributed to a great demand for the growth of synthetic methods for this ring system. Most important compounds with furoindoline ring system are physovenine, madindoline A and B and makomotindoline etc. These compounds are well known to exhibit biological activity against different diseases such as glaucoma, cancer, cachexia, Castleman’s disease, rheumatoid arthritis, etc. The current article focuses on various synthetic approaches for furoindoline containing compounds and essential furoindoline moiety, such as oxindole-5-O-tetrahydropyranyl ether route etc., and various other diastereoand enantio- controlled approach in a very concise way.

Isoselenocyanates: Synthesis and Their Use for Preparing Selenium-Based Heterocycles

Synthesis ◽  
2021 ◽  
Author(s):  
Stefan H. Bossmann ◽  
Raul Neri
Keyword(s):  
Biological Activity ◽  
Infectious Diseases ◽  
Cancer Cells ◽  
Multicomponent Reactions ◽  
Oxidative Cyclization ◽  
Biologically Active ◽  
Organoselenium Compounds ◽  
X Ray ◽  
Synthetic Work

AbstractIsoselenocyanates (ISCs) are a class of organoselenium compounds that have been recognized as potential chemotherapeutic and chemopreventative agents against cancer(s) and infectious diseases. ISC compounds are chemically analogous to their isosteric relatives, isothiocyanates (ITCs); however, they possess increased biological activity, such as enhanced cytotoxicity against cancer cells. ISCs not only serve as significant products, but also as precursors and essential intermediates for a variety of organoselenium compounds, such as selenium-containing heterocycles, which are biologically active. While syntheses of ISCs have become less difficult to accomplish, the syntheses of selenium-containing heterocycles are often difficult due to the use of highly toxic selenium reagents. Because of this, ISCs can serve as versatile reagents for the preparation of these heterocycles. In this review, the classical and recent syntheses of ISCs will be discussed, along with notable and recent synthetic work employing ISCs to access novel selenium-containing heterocycles.1 Introduction1.1 Selenium and Health2 Isoselenocyanates2.1 Preparation of Isoselenocyanates3 Selenium-Containing Heterocycles3.1 Notable Synthetic Work3.2 Recent Synthetic Work3.2.1 Synthesis of N-(3-Methyl-4-phenyl-3H-selenazol-2-ylidene)benzamide­ Derivatives3.2.2 Synthesis and X-ray Studies of Diverse Selenourea Derivatives3.2.3 Synthesis of Heteroarene-Fused [1,2,4]Thiadiazoles/Selenadiazoles via Iodine-Promoted [3+2] Oxidative Cyclization3.2.4 2-Amino-1,3-selenazole Derivatives via Base-Promoted Multicomponent Reactions4 Conclusion

Ring-Opening Polymerization of Lactide Using Aluminum Salen-Type Initiators

2014 ◽  
Vol 915-916 ◽  
pp. 713-716
Author(s):  
Qing Zhang ◽  
Jing Tian ◽  
Zhi Qi Cao ◽  
Ru Xia Xu ◽  
Zhen Zhen Sun ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Infrared Spectroscopy ◽  
Reaction Time ◽  
Magnetic Resonance ◽  
Schiff Bases ◽  
Reaction Temperature ◽  
Ring Opening ◽  
Ring Opening Polymerization ◽  
Resonance Spectroscopy ◽  
Aluminum Complex

In this investigation, Schiff bases aluminum complex was synthesized and used as the initiator in the polymerization of D,L-lactide. The aluminum complex was characterized by infrared spectroscopy (IR), and nuclear magnetic resonance spectroscopy (NMR). The influences of different factors, including reaction time, reaction temperature, and the ratio of D, L-lactide/Al3+ on the synthesis of polylactide were described. The results showed that Schiff bases aluminum complex could be successfully applied in the ring opening polymerization. The optimum condition of the ring opening polymerization of D,L-lactide, which included D,L-lactide/Al3+ (mol/mol) ratio of 250, reaction temperature of 120 °C, and reaction time of 16 hours.

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