scholarly journals A New Method for the Synthesis of 2-Substituted Benzoxazoles from 2-Nitrophenol Derivatives and Aldehydes  

2021 ◽  
Vol 31 (3) ◽  
pp. 43-46
Keyword(s):  
Biological Activities ◽  
Catalyst System ◽  
Biologically Active ◽  
New Method ◽  
Redox Catalyst ◽  
High Pressure High Temperature ◽  
One Step ◽  
High Yields ◽  
Strong Acids ◽  
Single Reaction

Benzoxazole derivatives are one of the compounds with many interesting biological activities. Conventional methods are often performed under complex conditions using strong acids, expensive metal catalysts, requiring high pressure, high temperature, and under microwave irradiation. In this study, we reported a new method of benzoxazole synthesis with redox catalyst using FeCl3.6H2O and sulfur. This is a suitable, efficient, readily available and environmentally friendly catalyst system for redox and condensation reactions in one step at 100 oC. Applying this new method, we have synthesized eight 2-arylbenzoxazole derivatives with high yields (calculated according to 2-nitrophenol). This research is an important step forward in the synthesis of biologically active compounds containing the benzoxazole framework from readily available starting materials in a single reaction.

Synthetic Routes for 1,4-disubstituted 1,2,3-triazoles: A Review

2019 ◽  
Vol 23 (8) ◽  
pp. 860-900 ◽  
Author(s):  
Chander P. Kaushik ◽  
Jyoti Sangwan ◽  
Raj Luxmi ◽  
Krishan Kumar ◽  
Ashima Pahwa
Keyword(s):  
Solid Phase ◽  
Click Reaction ◽  
Biological Activities ◽  
Triazole Ring ◽  
Copper Catalysts ◽  
Biologically Active ◽  
Pharmaceutical Chemistry ◽  
Biological Targets ◽  
Synthetic Routes ◽  
High Yields

N-Heterocyclic compounds like 1,2,3-triazoles serve as a key scaffolds among organic compounds having diverse applications in the field of drug discovery, bioconjugation, material science, liquid crystals, pharmaceutical chemistry and solid phase organic synthesis. Various drugs containing 1,2,3-triazole ring which are commonly available in market includes Rufinamide, Cefatrizine, Tazobactam etc., Stability to acidic/basic hydrolysis along with significant dipole moment support triazole moiety for appreciable participation in hydrogen bonding and dipole-dipole interactions with biological targets. Huisgen 1,3-dipolar azide-alkyne cycloaddition culminate into a mixture of 1,4 and 1,5- disubstituted 1,2,3-triazoles. In 2001, Sharpless and Meldal came across with a copper(I) catalyzed regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles by cycloaddition between azides and terminal alkynes. This azide-alkyne cycloaddition has been labelled as a one of the important key click reaction. Click synthesis describes chemical reactions that are simple to perform, gives high selectivity, wide in scope, fast reaction rate and high yields. Click reactions are not single specific reaction, but serve as a pathway for construction of simple to complex molecules from a variety of starting materials. In the last few decades, 1,2,3-triazoles attracted attention of researchers all over the world because of their broad spectrum of biological activities. Keeping in view the biological importance of 1,2,3-triazole, in this review we focus on the various synthetic routes for the syntheisis of 1,4-disubstituted 1,2,3-triazoles. This review involves various synthetic protocols which involves copper and non-copper catalysts, different solvents as well as substrates. It will boost synthetic chemists to explore new pathway for the development of newer biologically active 1,2,3-triazoles.

The Molecular Diversity Scope of Urazole in the Synthesis of Organic Compounds

2019 ◽  
Vol 16 (7) ◽  
pp. 953-967 ◽  
Author(s):  
Ghodsi M. Ziarani ◽  
Fatemeh Mohajer ◽  
Razieh Moradi ◽  
Parisa Mofatehnia
Keyword(s):  
Biological Activities ◽  
Biological Properties ◽  
Biologically Active ◽  
Microtubule Assembly ◽  
Heterocyclic Molecules ◽  
Biological Perspective ◽  
Highly Active ◽  
Anti Inflammatory ◽  
High Yields ◽  
Short Time

Background: As a matter of fact, nitrogen as a hetero atom among other atoms has had an important role in active biological compounds. Since heterocyclic molecules with nitrogen are highly demanded due to biological properties, 4-phenylurazole as a compound containing nitrogen might be important in the multicomponent reaction used in agrochemicals, and pharmaceuticals. Considering the case of fused derivatives “pyrazolourazoles” which are highly applicable because of their application for analgesic, antibacterial, anti-inflammatory and antidiabetic activities as HSP-72 induction inhibitors (I and III) and novel microtubule assembly inhibitors. It should be mentioned that spiro-pyrazole also has biological activities like cytotoxic, antimicrobial, anticonvulsant, antifungal, anticancer, anti-inflammatory, and cardiotonic activities. Objective: Urazole has been used in many heterocyclic compounds which are valuable in organic syntheses. This review disclosed the advances in the use of urazole as the starting material in the synthesis of various biologically active molecules from 2006 to 2019. Conclusion: Compounds of urazole (1,2,4-triazolidine-3,5-dione) are the most important molecules which are highly active from the biological perspective in the pharmaceuticals as well as polymers. In summary, many protocols for preparations of the urazole derivatives from various substrates in multi-component reactions have been reported from different aromatic and aliphatic groups which have had carbonyl groups in their structures. It is noted that several catalysts have been synthesized to afford applicable molecules with urazole scaffolds. In some papers, being environmentally friendly, short time reactions and high yields are highlighted in the protocols. There is a room to synthesize new catalysts and perform new reactions by manipulating urazole to produce biologically active compounds, even producing chiral urazole component as many groups of chiral urazole compounds are important from biological perspective.

Synthesis of biologically active heterocyclic compounds from allenic and acetylenic nitriles and related compounds

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Marthe Carine Djuidje Fotsing ◽  
Dieudonné Njamen ◽  
Zacharias Tanee Fomum ◽  
Derek Tantoh Ndinteh
Keyword(s):  
Michael Addition ◽  
Heterocyclic Compounds ◽  
Biological Activities ◽  
Biologically Active ◽  
Polycyclic Compounds ◽  
One Step ◽  
Pharmaceutical Properties ◽  
Related Compounds ◽  
Acetylenic Acids ◽  
The Michael Addition

Abstract Cyclic and polycyclic compounds containing moieties such as imidazole, pyrazole, isoxazole, thiazoline, oxazine, indole, benzothiazole and benzoxazole benzimidazole are prized molecules because of the various pharmaceutical properties that they display. This led Prof. Landor and co-workers to engage in the synthesis of several of them such as alkylimidazolenes, oxazolines, thiazolines, pyrimidopyrimidines, pyridylpyrazoles, benzoxazines, quinolines, pyrimidobenzimidazoles and pyrimidobenzothiazolones. This review covers the synthesis of biologically active heterocyclic compounds by the Michael addition and the double Michael addition of various amines and diamines on allenic nitriles, acetylenic nitriles, hydroxyacetylenic nitriles, acetylenic acids and acetylenic aldehydes. The heterocycles were obtained in one step reaction and in most cases, did not give side products. A brief discussion on the biological activities of some heterocycles is also provided.

Activated Carbon/MoO3: Efficient Catalyst for Green Synthesis of Chromeno[d]pyrimidinediones and Xanthenones

2020 ◽  
Vol 23 ◽  
Author(s):  
Niloofar Sabet Mehr ◽  
Shahrzad Abdolmohammadi ◽  
Maryam Afsharpour
Keyword(s):  
Activated Carbon ◽  
Room Temperature ◽  
Bulk Material ◽  
Biological Activities ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Biologically Active ◽  
Efficient Catalyst ◽  
Calcium Blockers ◽  
High Yields

Background: Nanoscale metal oxide catalysts have been extensively employed in organic reactions because they have been found to influence the chemical and physical properties of the bulk material. The chromene (benzopyran) nucleus constitutes the core structure in a major class of many biologically active compounds, and interest in their chemistry consequently continues because of their numerous biological activities. The xanthene (dibenzopyran) derivatives are classified as highly significant compounds which display a number of various bioactive properties. Pyrimidinones have also gained interest due to their remarkable biological utilization such as antiviral, antibacterial, antihypertensive, antitumor and calcium blockers effects. Objective: Our aim in the work presented herein was to prepare activated carbon/MoO3 nanocomposite and explore its role as a green and recyclable catalyst for the synthesis of chromeno[d]pyrimidinediones and xanthenones under ethanol-drop grinding at room temperature. Methods: The activated carbon/MoO3 nanocomposite was prepared successfully via a simple route in which carbonization of gums as new natural precursors was used for the synthesis of activated carbon. This nanocomposite was then effectively used in a reaction of 3,4- methylenedioxyphenol, aromatic aldehydes and active methylene compounds including 1,3-dimethylbarbituric acid and dimedone to synthesize a series of chromeno[d]pyrimidinediones and xanthenones in high yields. The synthesized catalyst was characterized by Fourier transform infrared spectroscopy (FT-IR), Powder x-ray diffractometry (XRD), Scanning electron microscope (SEM), Raman spectroscopy, and also by TGA analysis. Confirmation of the structures of compounds 5(a-g) and 6(a-g) were also established with IR, 1 H NMR and 13C NMR spectroscopic data and also by elemental analyses. Results: A number of 6,8-dimethyl-10-phenyl-6,10-dihydro-7H-[1,3]dioxolo[4΄,5΄:6,7]chromeno[2,3-d]pyrimidine-7,9(8H)-diones and 7,7- dimethyl-10-(4-methylphenyl)-6,7,8,10-tetrahydro-9H-[1,3]dioxolo[4,5-b]xanthen-9-ones were effectively synthesized using activated carbon/MoO3 nanocomposite (0.05 gr) as catalyst under ethanol-drop grinding at room temperature. The desired products were obtained in high yields (93-97%) within short reaction times (15-20 min). Conclusion: This paper investigates the catalytic potential of the synthesized activated carbon/MoO3 nanocomposite for the prepataion of chromeno[d]pyrimidinediones and xanthenones under ethanol-drop grinding procedure. The mildness of the reaction conditions, high yields of products, short reaction times, experimental simplicity, and avoid the use of harmful solvents or reagents makes this procedure preferable for the synthesis of these compounds.

scholarly journals Acetylation-Dependent Binding Analysis of the Yeast Gcn5 Bromodomain Protein

2008 ◽  
Vol 7 (1) ◽  
Author(s):  
Jesús Garzón ◽  
Christopher Kupitz ◽  
Joshua Bailey ◽  
Martin Thompson
Keyword(s):  
Biologically Active ◽  
Histone Acetyltransferases ◽  
Chromatin Binding ◽  
Expression And Purification ◽  
Acetylation State ◽  
One Step ◽  
High Yields ◽  
And Function

The 439 amino acid yeast Gcn5 protein contains a C-terminal bromodomain, which is required for SAGA (Spt-Ada-Gcn5-Acetyltransferase) mediated nucleosomal acetylation and transcriptional coactivation. Bromodomains are acetyl-lysine binding modules found in many chromatin binding proteins and histone acetyltransferases. Recently, both in vivo and in vitro studies indicate that bromodomains are able to discriminate the acetylation state of lysine side-chains within histone proteins. Here, the cloning, expression and bioactivity of a recombinant bromodomain from the yeast Gcn5 protein is described. The bromodomain from Gcn5 was cloned from yeast genomic DNA enabling effective one-step purification by affinity chromatography. Steady-state fluorescence anisotropy was used to quantify the interaction of Gcn5 with acetylated histone H3. The present cloning, expression, and purification procedure enabled the preparation of large quantity and high yields of biologically active recombinant Gcn5 bromodomain for in vitro structure and function studies.

scholarly journals Triterpenoids and Phytosterols Isolated from Pluchea Indica L. Leaves

2019 ◽  
Vol 35 (2) ◽  
Author(s):  
Do Thi Viet Huong ◽  
Phan Minh Giang ◽  
Hoang Thi Sim ◽  
Truong Thi To Chinh
Keyword(s):  
Glucose Transporter ◽  
Biological Activities ◽  
Biologically Active ◽  
Viet Nam ◽  
Onopordum Acanthium ◽  
Nutrition Research ◽  
Glycerol Ester ◽  
Nmr Techniques ◽  
High Yields ◽  
Rats And Mice

Abstract: Taraxasterol acetate, 1-dotriacontanol, taraxasterol, stigmasterol, 2-(prop-1-ynyl)-5-(5,6-dihyroxyhexa-1,3-diynyl)thiophene), stigmasterol 3-O-β-D-glucopyranoside, and β-sitosterol 3-O-β-D-glucopyranoside were isolated from the leaves of Pluchea indica and determined with NMR techniques. Taraxasterol acetate, taraxasterol, and stigmasterol could be isolated in high yields from Pluchea indica growing in Gia Lam, Hanoi, Vietnam.  Keywords: Pluchea indica, phytosterol, triterpenoid, taraxasterol, stigmasterol. References: [1] Đỗ Tất Lợi, Những cây thuốc và vị thuốc Việt Nam, NXB Hồng Đức, Thanh Hóa. (2014) 562 & 604. [2] H. Hussain, A. Al-Harrasi, G. Abba, N.U. Rheman, F. Mabood, I. Ahmed, M. Saleem, T. Van Ree, I.R. Green, S. Anwar, A. Badshah, A. Shah, I. Ali. The genus Pluchea: Phytochemistry, Traditional uses, and Biological activities. Chemistry & Biodiversity. 10(2011), 1944-1969.[3] Đoàn Thanh Tường, Phạm Hoàng Ngọc, Đỗ Đình Rãng. Nghiên cứu về một số cấu tử chính của tinh dầu Cúc tần. Thông báo khoa học Trường Đại học Sư phạm - Đại học Quốc gia Hà Nội. 4 (199) (2015), 45-50.[4] Vũ Việt Nam, Trần Ngọc Ninh, Mc Leod J., Nguyễn Xuân Dũng. Kết quả nghiên cứu một số cây thuộc họ Cúc. Tạp chí Dược liệu. 4 (2) (1999), 44-47. [5] Phan Minh Giang, Đỗ Thị Việt Hương, Nguyễn Ngọc Diệp, Nguyễn Mạnh Quyết. Một số hợp chất terpenoid và acid phenolic từ cây mẫn tưới. Tạp chí Dược liệu. 23 (4) (2018), 195-199.[6] L.M. Khalilov, A. Z. Khalilova A, E. R. Shakurova, I.F. Nuriev, A. S. Kachala, A.S. Shashkov, U.M. Dzhemilev. PMR and 13C NMR spectra of biologically active compunds. XII. Taraxasterol and its acetate from the aerial part of Onopordum acanthium. Chemistry of Natural Compounds. 39 (3) (2003), 285-288.[7] L.J. Goad, T. Akihisha. Analysis of Sterols, Chapman & Hall, London (1997).[8] Phan Minh Giang, Văn Thị Thanh Huyền, Đỗ Thị Việt Hương. Thành phần sterol, glycerol ester và thiophen trong cành cây cúc tần (Pluchea indica L.) của Việt Nam. Tạp chí Khoa học Đại học Quốc gia Hà Nội. 34 (2) (2018), 78-82. [9] B. Sing, S.N. Ram, V.B. Pandey, V. K. Joshi, S. S. Gambhir. Studies on antiinflammatory activity of taraxasterol acetate from Echinops echinatus in rats and mice. Phytotherapy Research, 5 (3) (1991), 103-106.[10] Z. Krajcovicova, A. Vachálková, K. Horváthová. Taraxasterol and -sitosterol: New naturally compounds with chemoprotective/ chemopreventive effects. Neoplasma. 51 (2004), 407-414.[11] J. Wang, M. Huang, J. Yang, X. Ma, S. Zheng, S. Deng, Y. Huang, X. Yang, P. Zhao. Anti-diabetic activity of stigmasterol from soybean oil by targeting the GLUT4 glucose transporter. Food & Nutrition Research, 61(1)(2017), 1364117.

The Immobilized Copper on Nickel Ferrite: A Magnetically Superior Nanocatalyst for Chemoselective and Knoevenagel Synthesis of Bisdimedones and 1,8-Dioxo-octahydroxanthenes under Solvent-Free Conditions

2019 ◽  
Vol 16 (6) ◽  
pp. 939-947 ◽  
Author(s):  
Behzad Zeynizadeh ◽  
Soleiman Rahmani ◽  
Arezu Hallaj
Keyword(s):  
Catalytic Activity ◽  
Aromatic Aldehydes ◽  
Catalyst System ◽  
Solvent Free ◽  
Biologically Active ◽  
Knoevenagel Reaction ◽  
Reaction Conditions ◽  
Step Procedure ◽  
Solvent Free Conditions ◽  
High Yields

Aim and Objective: Nowadays, bisdimedones and 1,8-dioxo-octahydroxanthenes are considered as biologically active materials. Due to this, the synthesis of the mentioned materials is the subject of more interest. Although most of the reported methods have their own merits, however, they generally require the use of expensive reagents, hazardous organic solvents, a tedious workup procedure and reduced recyclability of the applied catalyst system. Overcoming of the above mentioned drawbacks, therefore, encouraged us to investigate the capability of nanostructured NiFe2O4@Cu towards the synthesis of bisdimedones and 1,8- dioxo-octahydroxanthenes under green reaction conditions. Materials and Methods: Nanoparticles of NiFe2O4@Cu were prepared via a two-step procedure including the preparation of NiFe2O4 by solid-state grinding of Ni(OAc)2·4H2O and Fe(NO3)3·9H2O in the presence of NaOH followed by the immobilization of Cu(0) on the surface of NiFe2O4 nucleus via hydrazine hydrate reduction of Cu(NO3)2·3H2O. Results: After the synthesis of NiFe2O4@Cu, the catalytic activity of the Cu-nanocatalyst towards Knoevenagel reaction of aromatic aldehydes with dimedone under different reaction conditions was investigated. The examinations showed that using the molar equivalents of aromatic aldehydes (1 mmol) and dimedone (2 mmol) in the presence of 0.15 g NiFe2O4@Cu under solvent-free conditions chemoselectively afforded structurally different bisdimedone products at 60°C and 1,8-dioxo-octahydroxanthenes at 120°C. Conclusion: In this study, magnetically, nanoparticles of NiFe2O4@Cu were prepared and then characterized using different analyses. The catalytic activity of the prepared Cu-nanocatalyst was also studied towards solvent-free Knoevenagel condensation of aromatic aldehydes with dimedone. All the reactions were carried out within 15-240 min to afford bisdimedone and 1,8-dioxo-octahydroxanthene products in high yields.

scholarly journals Synthesis of Bioactive Fluoropyrrolidines via Copper(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides

2021 ◽  
Author(s):  
Xiao Xu ◽  
Longzhu Bao ◽  
Lu Ran ◽  
Zhenyan Yang ◽  
Dingce Yan ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Biological Activities ◽  
Building Blocks ◽  
Biologically Active ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Inhibition Rate ◽  
Efficient Route ◽  
High Yields ◽  
Structural Blocks

Abstract Chiral pyrrolidinyl units are important building blocks in biologically active natural products and drugs, thereupon, searching approaches for the synthesis of diverse structured pyrrolidine derivatives is of great importance. Meanwhile, owing to the special physicochemical properties of fluorine atoms, the introduction of fluorine containing groups into small molecules often change their activities to a great extent. Herein, we reported an efficient route to chiral 3,3-difluoro- and 3,3,4-trifluoropyrrodinyl derivatives by Cu(I)-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides with less active 1,1-difluoro- and 1,1,2-trifluoroalkenes. A series of new fluorinated pyrrolidines have been prepared in high yields (up to 96%) and excellent stereoselectivities (up to > 20:1 dr and 97% ee), and these unique structural blocks could be readily introduced into some natural compounds and pharmaceuticals. Additionally, antifungal activity investigation against four common plant funguses showed that some products possess general and high biological activities (up to 93% inhibition rate), the comparison with the antifungal activities of corresponding non-fluorinated compounds (low to 13% inhibition rate) revealed that the fluorine atoms at pyrrolidinyl rings play a crucial role in the antifungal activity, which prove the special properties of fluorine atoms in organic molecules.

ISOLEMENT ET QUELQUES CARACTERISTIQUES D'UNE GONADOTROPHINE URINAIRE DE MÉNOPAUSE HOMOGÈNE A L'ELECTROPHORÈSE

1960 ◽  
Vol XXXV (II) ◽  
pp. 225-234 ◽  
Author(s):  
R. Bourrillon ◽  
R. Got ◽  
R. Marcy
Keyword(s):  
Sialic Acid ◽  
Histological Study ◽  
Active Material ◽  
Biologically Active ◽  
New Method ◽  
Female Rats ◽  
Mouse Uterus ◽  
Highly Active ◽  
Zone Electrophoresis ◽  
Human Menopausal Gonadotrophin

ABSTRACT A new method for preparation of Human Menopausal Gonadotrophin involves successively alcoholic precipitation, kaolin adsorption and chromatography on ion exchangers. A highly active material is obtained which corresponds to 1 mg per litre of urine and has an activity of 1 mouse uterus unit at a dose of 0.003 mg. This gonadotrophin possesses both follicle stimulating and luteinizing activities in hypophysectomized female rats, by histological study. It contains 13 % hexose, 10% hexosamine and 8.5 % sialic acid. A further purification, by zone electrophoresis on starch, gives a final product, biologically active at 0.001 mg, which behaves as an homogenous substance in free electrophoresis with mobility −4.76 × 10−5 at pH 8.6.

Biologically Active 2,5-Disubstituted-1,3,4-Oxadiazoles

2009 ◽  
Vol 2 (1) ◽  
pp. 390-406
Author(s):  
Harish Rajak ◽  
Murli Dhar Kharya ◽  
Pradeep Mishra
Keyword(s):  
Heterocyclic Compounds ◽  
Medical Literature ◽  
Biological Activities ◽  
Biologically Active ◽  
Pharmacological Properties ◽  
Clinical Use ◽  
Synthetic Drugs ◽  
Physiologic Activity ◽  
Pharmacologically Active

There are vast numbers of pharmacologically active heterocyclic compounds in regular clinical use. The presence of heterocyclic structures in diverse types of compounds is strongly indicative of the profound effects such structure exerts on physiologic activity, and recognition of this is abundantly reflected in efforts to find useful synthetic drugs. The 1,3,4-oxadiazole nucleus has emerged as one of the potential pharmacophore responsible for diverse pharmacological properties. Medical Literature is flooded with reports of a variety of biological activities of 2,5-Disubstituted-1,3,4-oxadiazoles. The present work is an attempt to summarize and enlist the various reports published on biologically active 2,5-disubstituted-1,3,4-oxadiazoles.

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