scholarly journals Synthesis of novel 3-deoxy-3-C-triazolylmethyl-allose derivatives and evaluation of their biological activity

2012 ◽  
Vol 10 (2) ◽  
pp. 386-394 ◽  
Author(s):  
Jekaterina Rjabova ◽  
Vitālijs Rjabovs ◽  
Antonio Moreno Vargas ◽  
Elena Clavijo ◽  
Māris Turks
Keyword(s):  
Biological Activity ◽  
Biological Activities ◽  
Dipolar Cycloaddition ◽  
Molecular Scaffolds ◽  
New Compounds

AbstractRecently, monosaccharide-triazole conjugates have proved to possess a large variety of useful biological activities. This paper describes synthesis of a new series of 3-deoxy-3-C-triazolylmethyl-allose derivatives. These new compounds are obtained from acetonide-protected 3-deoxy-3-azidomethyl allose and commercial alkynes via Cu(I) catalyzed 1,3-dipolar cycloaddition. The obtained molecular scaffolds differ from those described earlier by the presence of a methylene linker (-CH2-) between the C(3) of allose and the triazole moiety. It was demonstrated that acetonide-protected monosaccharide, 3-deoxy-3-C-(4-phenyl-1H-1,2,3-triazol-1-yl)methyl-1,2:5,6-di-O-isopropylidene-α-d-allofuranose, inhibited α-L-fucosidase for 26% at 0.1 mM concentration, but a deprotected analog, 3-deoxy-3-C-(4-(4-tert-butylphenyl)-1H-1,2,3-triazol-1-yl)methyl-β-d-allofuranose, showed 15% inhibition of β-glucosidase at 1 mM concentration.

scholarly journals Biomimetic Approaches to the Synthesis of Natural Disesquiterpenoids: An Update

Plants ◽  
2021 ◽  
Vol 10 (4) ◽  
pp. 677
Author(s):  
Diego Caprioglio ◽  
Stefano Salamone ◽  
Federica Pollastro ◽  
Alberto Minassi
Keyword(s):  
Biological Activity ◽  
Secondary Metabolites ◽  
Total Synthesis ◽  
Small Group ◽  
Molecular Scaffolds ◽  
Natural Processes ◽  
Laboratory Conditions ◽  
New Compounds ◽  
Synthetic Target ◽  
Made In

Natural disesquiterpenoids represent a small group of secondary metabolites characterized by complex molecular scaffolds and interesting pharmacological profiles. In the last decade, more than 400 new disesquiterpenoids have been discovered and fully characterized, pointing out once more the “magic touch” of nature in the design of new compounds. The perfect blend of complex and unique architectures and biological activity has made sesquiterpene dimers an attractive and challenging synthetic target, inspiring organic chemists to find new and biomimetic approaches to replicate the efficiency and the selectivity of natural processes under laboratory conditions. In this work, we present a review covering the literature from 2010 to 2020 reporting all the efforts made in the total synthesis of complex natural disesquiterpenoids.

SYNTHESIS OF 3- (1,1-DIOXIDOTHIETAN-3-YL) -6-METHYLURACIL AND HYDRAZONE DERIVATIVES

2021 ◽  
pp. 181-189
Author(s):  
Melnikov A.S. ◽  
Meshcheryakova S.A.
Keyword(s):  
Biological Activity ◽  
Biological Activities ◽  
Antioxidant Properties ◽  
Statistical Processing ◽  
Biologically Active ◽  
High Biological Activity ◽  
Treatment And Prevention ◽  
Methods Of Synthesis ◽  
New Compounds ◽  
Derivatives Of

Uracil derivatives containing various N1, N3 substituents are characterized by various pharmacological and biological activities. Since the beginning of the XXI century, among them, new biologically active substances have been discovered that have pronounced antiparasitic, antibacterial, antioxidant properties. Known that modern methods of treatment and prevention of many diseases involve the inclusion of substances that have the ability to stimulate immune processes. Such compounds, in particular, include derivatives of nucleoside bases with high biological activity. Derivatives of 6-methyluracil containing a hydrazone system are widely studied in the treatment of Alzheimer's disease, antifungal, antiviral, antianginal, anti-eczema and other types of activity. The study of the alkylation of 6-methyluracil, which contains hydrazone systems in the role of pharmacophore fragments, is one of the topical trends in the synthesis of new chains of biologically active compounds. Purpose: For this purpose, we studied the alkylation of 6-methyl-3- (1,1-dioxidothietan-3-yl) pyrimidin-2,4 (1H, 3H)-dione with 1-chloropropan-2-one and the interaction of the resulting N1- 2-oxopropyl derivative with various hydrazines. Materials and Methods: The individuality of the new compounds was confirmed by the method of thin layer chromatography and determination of the melting point. The structure of the synthesized substances was confirmed by elemental analysis and NMR spectroscopy. Statistical data processing was carried out using variational analysis using the STATISTICA 8.0 software package. Student's test was chosen as a criterion for the representativeness of statistical processing. A preliminary analysis of toxicity and types of potential biological activity was carried out in silico using the resources of the Internet platform Way2Drag. Conclusions: Methods of synthesis have been developed and the most probable types of biological and pharmacological influence have been statistically processed, proceeding from the value of the probability of being active and the probability of inertness. Based on the analysis of data, modeled types of biological activity, some patterns of "structure-activity" are determined. In the conclusion, further directions of research are identified.

scholarly journals Design, Synthesis and Fungicidal Activity of Novel Strobilurin Analogues Containing Substituted N-phenylpyrimidin-2-amines

2009 ◽  
Vol 4 (9) ◽  
pp. 1934578X0900400
Author(s):  
Hui-Chao Li ◽  
Chang-Ling Liu ◽  
Bao-Shan Chai ◽  
Miao Li ◽  
Zhi-Nian Li ◽  
...  
Keyword(s):  
Biological Activity ◽  
Fungicidal Activity ◽  
Biological Activities ◽  
Design Synthesis ◽  
Strobilurin Fungicide ◽  
New Compounds

A series of novel compounds (5-8) was designed and synthesized by integrating the active pharmacophore of the N-phenylpyrimidin-2-amine fungicide with the structure of strobilurin fungicide. The rationale of this approach was to determine if these new compounds exhibit unique biological activity (selectivity and potency) compared with the commercial standards. The title compounds were prepared from 2-(phenylamino)pyrimidin-4-ols (3) by treatment with one equivalent of intermediates (4) containing strobilurin pharmacophores. 2-(Phenylamino)pyrimidin-4-ols (3) were in turn prepared from phenylguanidines (1) and substituted β-ketoesters (2). Biological activities evaluated in the greenhouse indicated that compounds 5a, 6a and 7a have good fungicidal activity at 25 mg/L, comparable with that of the commercial standards, cyprodinil and azoxystrobin.

scholarly journals Synthesis and Characterization of New Compounds Derived from Pyrrolidine-2-One and Evaluation of their Biological Activities

2020 ◽  
Vol 23 (4) ◽  
pp. 5-12
Author(s):  
Nadia A. Betti ◽  
◽  
Redha Ib. Hussain ◽  
Sahar Ab. Kadhem ◽  
Abdul Jabar Kh. Atia ◽  
...  
Keyword(s):  
Biological Activity ◽  
Mass Spectrum ◽  
Biological Activities ◽  
The Other ◽  
Synthesis And Characterization ◽  
E Coli ◽  
Ft Ir ◽  
New Compounds ◽  
Derivatives Of

New derivatives of pyrrolidine-2-one have been prepared by lactamization of -butyrolactone GBL with hydrazine hydrate (NH2NH2(80%)) to afford (1-aminopyrrolidin-2-one) which undergo many reactions to prepare the other derivatives. The prepared derivatives were determined by utilizing their FT-IR,1H-NMR and some by Mass spectrum. These derivatives were evaluated biologically against (Staphylococcus aureusand E. coli).Some of these derivatives exhibited good biological activity against one or both kind of bacteria while some exhibited no biological activity at all.

A common mechanism links activities of butyrate in the colon

2017 ◽  
Author(s):  
Mohit S. Verma ◽  
Michael J. Fink ◽  
Gabriel L Salmon ◽  
Nadine Fornelos ◽  
Takahiro E. Ohara ◽  
...  
Keyword(s):  
Stem Cells ◽  
Histone Deacetylases ◽  
Biological Activities ◽  
Short Chain Fatty Acids ◽  
Common Mechanism ◽  
Epithelial Stem Cells ◽  
Degree Of Unsaturation ◽  
Structure Activity ◽  
Starting Point ◽  
New Compounds

Two biological activities of butyrate in the colon (suppression of proliferation of colonic epithelial stem cells and inflammation) correlate with inhibition of histone deacetylases. Cellular and biochemical studies of molecules similar in structure to butyrate, but different in molecular details (functional groups, chain-length, deuteration, oxidation level, fluorination, or degree of unsaturation) demonstrated that these activities were sensitive to molecular structure, and were compatible with the hypothesis that butyrate acts by binding to the Zn<sup>2+</sup> in the catalytic site of histone deacetylases. Structure-activity relationships drawn from a set of 36 compounds offer a starting point for the design of new compounds targeting the inhibition of histone deacetylases. The observation that butyrate was more potent than other short-chain fatty acids is compatible with the hypothesis that crypts evolved (at least in part), to separate stem cells at the base of crypts from butyrate produced by commensal bacteria.

New Pyrrolo[1,2-b]pyridazine Derivatives by 1,3-Dipolar Cycloaddition of Mesoionic Oxazolopyridazinone

2008 ◽  
Vol 59 (11) ◽  
Author(s):  
Miron Teodor Caproiu ◽  
Florea Dumitrascu ◽  
Mino R. Caira
Keyword(s):  
Nmr Spectroscopy ◽  
Elemental Analysis ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Pyridazine Derivatives ◽  
New Compounds

New pyrrolo[1,2-b]pyridazine derivatives 8a-f were synthesized by 1,3-dipolar cycloaddition reaction between mesoionic 1,3-oxazolo[3,2-b]pyridazinium-2-oxides and diethyl or diisopropyl acetylenedicarboxylate as alkyne dipolarophiles. The structures of the new compounds were assigned by elemental analysis and NMR spectroscopy.

Current Advances in the Biological Activity of Polysaccharides in Dendrobium with Intriguing Therapeutic Potential

2018 ◽  
Vol 25 (14) ◽  
pp. 1663-1681 ◽  
Author(s):  
Chun-Ting Lee ◽  
Heng-Chun Kuo ◽  
Yung-Hsiang Chen ◽  
Ming-Yen Tsai
Keyword(s):  
Biological Activity ◽  
Therapeutic Potential ◽  
Biological Activities ◽  
Biological Effects ◽  
Herbal Medicines ◽  
Research Field ◽  
Protective Effects ◽  
Pharmacological Effects ◽  
The Family ◽  
Anti Tumor Activity

The polysaccharides in many plants are attracting worldwide attention because of their biological activities and medical properties, such as anti-viral, anti-oxidative, antichronic inflammation, anti-hypertensive, immunomodulation, and neuron-protective effects, as well as anti-tumor activity. Denodrobium species, a genus of the family orchidaceae, have been used as herbal medicines for hundreds of years in China due to their pharmacological effects. These effects include nourishing the Yin, supplementing the stomach, increasing body fluids, and clearing heat. Recently, numerous researchers have investigated possible active compounds in Denodrobium species, such as lectins, phenanthrenes, alkaloids, trigonopol A, and polysaccharides. Unlike those of other plants, the biological effects of polysaccharides in Dendrobium are a novel research field. In this review, we focus on these novel findings to give readers an overall picture of the intriguing therapeutic potential of polysaccharides in Dendrobium, especially those of the four commonly-used Denodrobium species: D. huoshanense, D. offininale, D. nobile, and D. chrysotoxum.

Click Reactions in Chemistry of Triterpenes - Advances Towards Development of Potential Therapeutics

2018 ◽  
Vol 25 (5) ◽  
pp. 636-658 ◽  
Author(s):  
Jan Pokorny ◽  
Lucie Borkova ◽  
Milan Urban
Keyword(s):  
Biological Activities ◽  
Synthetic Approach ◽  
Clinical Use ◽  
New Approach ◽  
Click Reactions ◽  
Drug Candidates ◽  
The Past ◽  
Low Toxicity ◽  
New Compounds ◽  
Potential Therapeutics

Triterpenoids are natural compounds with a large variety of biological activities such as anticancer, antiviral, antibacterial, antifungal, antiparazitic, antiinflammatory and others. Despite their low toxicity and simple availability from the natural resources, their clinical use is still severely limited by their higher IC50 and worse pharmacological properties than in the currently used therapeutics. This fact encouraged a number of researchers to develop new terpenic derivatives more suitable for the potential clinical use. This review summarizes a new approach to improve both, the activity and ADME-Tox properties by connecting active terpenes to another modifying molecules using click reactions. Within the past few years, this synthetic approach was well explored yielding a lot of great improvements of the parent compounds along with some less successful attempts. A large quantity of the new compounds presented here are superior in both activity and ADME-Tox properties to their parents. This review should serve the researchers who need to promote their hit triterpenic structures towards their clinical use and it is intended as a guide for the chemical synthesis of better drug candidates.

Naphthoquinone Derivatives Isolated from Plants: Recent Advances in Biological Activity

2020 ◽  
Vol 20 (19) ◽  
pp. 2019-2035
Author(s):  
Esmaeil Sheikh Ahmadi ◽  
Amir Tajbakhsh ◽  
Milad Iranshahy ◽  
Javad Asili ◽  
Nadine Kretschmer ◽  
...  
Keyword(s):  
Clinical Trials ◽  
Biological Activity ◽  
Small Molecules ◽  
Anticancer Activity ◽  
Clinical Significance ◽  
Phase Ii ◽  
Biological Activities ◽  
Phase Ii Clinical Trials ◽  
Naturally Occurring ◽  
The Subject

Naturally occurring naphthoquinones (NQs) comprising highly reactive small molecules are the subject of increasing attention due to their promising biological activities such as antioxidant, antimicrobial, apoptosis-inducing activities, and especially anticancer activity. Lapachol, lapachone, and napabucasin belong to the NQs and are in phase II clinical trials for the treatment of many cancers. This review aims to provide a comprehensive and updated overview on the biological activities of several new NQs isolated from different species of plants reported from January 2013 to January 2020, their potential therapeutic applications and their clinical significance.

Synthesis and Biological Activity of Hydrazones and Derivatives: A Review

2020 ◽  
Vol 20 (5) ◽  
pp. 342-368 ◽  
Author(s):  
Juliana de Oliveira Carneiro Brum ◽  
Tanos Celmar Costa França ◽  
Steven R. LaPlante ◽  
José Daniel Figueroa Villar
Keyword(s):  
Biological Activity ◽  
Medicinal Chemistry ◽  
Biological Activities ◽  
New Drugs ◽  
New Drug ◽  
Cancer Inflammation

Hydrazones and their derivatives are very important compounds in medicinal chemistry due to their reported biological activity for the treatment of several diseases, like Alzheimer’s, cancer, inflammation, and leishmaniasis. However, most of the investigations on hydrazones available in literature today are directed to the synthesis of these molecules with little discussion available on their biological activities. With the purpose of bringing lights into this issue, we performed a revision of the literature and wrote this review based on some of the most current research reports of hydrazones and derivatives, making it clear that the synthesis of these molecules can lead to new drug prototypes. Our goal is to encourage more studies focused on the synthesis and evaluation of new hydrazones, as a contribution to the development of potential new drugs for the treatment of various diseases.

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