Synthesis of Schiff’s Bases of 1,2,4-Triazole Derivatives under Microwave Irradiation Technique and Evaluation of Their Anti-diabetic Activity

2021 ◽  
Vol 08 ◽  
Author(s):  
Krishna Chandra Panda ◽  
B.V.V Ravi Kumar ◽  
Biswa Mohan Sahoo
Keyword(s):  
Hydrazine Hydrate ◽  
Carbon Disulphide ◽  
Potassium Hydroxide Solution ◽  
Ring Closure ◽  
Biologically Active ◽  
Schiff’S Bases ◽  
Standard Drug ◽  
Triazole Derivatives ◽  
Schiff's Bases

Background: Schiff bases play key role for the generation of a large number of biologically active compounds via cycloaddition, replacement and ring closure reactions. Objective: The objective of this study is to optimize the purity and yield of product, reaction time, eco-friendly reaction by the help of microwave assisted organic synthesis. Methods: New series of Schiff’s bases of triazole derivatives were achieved via multicomponent reactions. The starting material benzohydrazide 1 was obtained by esterification of bezoyl chloride with methanol in presence of concentrated sulphuric acid followed by the reaction with hydrazine hydrate. Benzohydrazide was allowed to react with carbon disulphide in ethanolic potassium hydroxide solution to yield potassium dithiocarbazinate 2 which undergoes cyclization by reacting with hydrazine hydrate to afford 4-[amino]-5-phenyl-4H-1,2,4-triazole-3-thiol (3). Further, various Schiff’s bases 4a-f were obtained by reacting 1,2,4-triazole-3-thiol with different substituted benzaldehydes under microwave irradiations as a green and eco-friendly energy source. Results: The structures of the newly synthesized compounds were elucidated in accordance with their spectral data and elemental analysis. Conclusion : The obtained compounds exhibited significant in-vivo anti-diabetic activity as compared to the standard drug Metformin. The anti-diabetic effect was investigated by using Alloxan-induced diabetic model.

scholarly journals Synthesis of Some New 1,2,4-Triazoles Derived from 2-Mercaptobenzimidazole

2009 ◽  
Vol 6 (1) ◽  
pp. 200-208
Author(s):  
Baghdad Science Journal
Keyword(s):  
Physical Properties ◽  
Hydrazine Hydrate ◽  
Schiff Bases ◽  
Alkaline Medium ◽  
Spectral Methods ◽  
Ring Closure ◽  
Triazole Derivatives ◽  
Specific Reactions ◽  
Derivatives Of

New 1,2,4-triazole derivatives of 2-mercaptobenzimidazole (MB) are reported. Ethyl (benzimidazole-2-yl thio) acetate (1) has been prepared by condensing 2-mercaptobenzimidazole with ethylchloroacetate. The ester (1) on reacting with hydrazine hydrate gave the corresponding acetohydrazide(2)which was reacted separately with phenylisocyanate and phenylisothiocyanate, followed by ring closure in an alkaline medium giving 3-[(benzimidazole-2-yl thio) methyl]-4-phenyl-1,2,4-triazole-5-ol and 3-[(benzimidazole-2-yl thio) methyl]-4-phenyl-1,2,4-triazole-5-thiol respectively (6,7). Reaction of acetohydrazide (2) with CS2 and ethanol/KOH, gave dithiocarbazate salt (8). Cyclization of (8) with hydrazine hydrate gave 3-[(benzimidazole-2-yl thio) methyl]-4-amino-1,2,4-triazole-5-thiol (9). Furthermore, new Schiff bases (3a-e) were prepared through the reaction of the acetohydrazide (2) with aromatic aldehydres. The prepared compounds were identified by spectral methods FTIR, UV. Measurements of some physical properties and some specific reactions, were carried out.

scholarly journals Synthesis and Screening of Biologically Active Schiff bases of Benzothiazoles and its Zinc and Lanthanum Metal Complexes

2021 ◽  
Vol 37 (1) ◽  
pp. 187-193
Author(s):  
D. G. Anuse ◽  
V. J. Desale ◽  
B. R. Thorat ◽  
D. D. Anuse ◽  
S. G. Jagadhani ◽  
...  
Keyword(s):  
Metal Complex ◽  
Metal Complexes ◽  
Schiff Bases ◽  
Zinc Chloride ◽  
Biological Activities ◽  
Biologically Active ◽  
Lanthanum Chloride ◽  
Schiff’S Bases ◽  
Schiff's Bases ◽  
Derivatives Of

The substituted 2-Aminobenzothiazole and ethyl 2-(4-formyl-3-hydroxyphenyl)-4-methylthiazole-5-carboxylate in methanol mix together and heat the reaction mixture for overnight, It gives Schiff’s bases (derivatives of substituted aminobenzothiazole) 3. This compound 3 when treated with Zinc Chloride it gives Zinc metal complex of Schiff’s bases 4 and if compound 3 was treated with Lanthanum chloride gives Lanthanum metal complex of Schiff’s bases 5, which shows marked biological activities.

scholarly journals Revealing Anti-viral Potential of Bio-active Therapeutics Targeting SARS-CoV2- polymerase (RdRp) in Combating COVID-19: Molecular Investigation on Indian Traditional Medicines

2020 ◽  
Author(s):  
Dhanasekaran Sivaraman ◽  
Puspharaj selvadoss Pradeep
Keyword(s):  
Rna Polymerase ◽  
Clinical Importance ◽  
Biologically Active ◽  
In Vivo Studies ◽  
Rna Dependent Rna Polymerase ◽  
Standard Drug ◽  
Traditional Medicines ◽  
Clinical Recommendation

Spread of severe acute respiratory syndrome coronavirus (SARS-CoV-2) made a historic transition between December 2019 to March 2020. In the present scenario SARS-CoV-2 as becomes a major burden on public health and economic stability of societies around the globe. From the substantial evidences gained from the pandemic of SARS-CoV-2 and MERS-CoV (Middle East respiratory syndrome coronavirus), scientists and clinicians strongly believes that these pathogenic viruses share common homology of some biologically active enzymes which includes RNA-dependent RNA polymerase (RdRP), 3-chymotrypsin-like protease (3CLpro), papain-like protease (PLpro) etc. RdRP relatively grabs higher level of clinical importance in comparison with other enzyme target. Indian system of traditional medicine pioneering the therapy towards infectious disease since several centuries. In view of this potential therapeutic leads from some of the Indian medicines along with standard drug favipiravir subjected to docking investigation targeting SARS-CoV-2- RNA dependent RNA polymerase (RdRp). Residual proximity analysis reveals 18 out of 28 compounds reveals potential binding affinity of about 100% with the target amino acid residue (618 ASP, 760 ASP,761 ASP), 7 out of 28 reveals 75% binding efficacy and 3 out of 28 reveals 25% binding efficacy with that of the target residue. Hence further clinical validation may be warranted with proper in-vitro and in-vivo studies prior to the clinical recommendation in treating COVID-19 patient’s.

scholarly journals Synthesis and Antimicrobial Activity of Some 1-arylideneamino-4-(4-chlorobenzylidene)-2-methyl- 1H-imidazolin-5(4H)-one Compounds

2019 ◽  
Vol 35 (2) ◽  
pp. 822-828
Author(s):  
Cong Tien Nguyen ◽  
Dao Thi Hong Dinh ◽  
Thin Van Nguyen ◽  
Giang Duc Le ◽  
Hien Cao Nguyen
Keyword(s):  
Antimicrobial Activity ◽  
Hydrazine Hydrate ◽  
Spectral Data ◽  
1H Nmr ◽  
Aromatic Aldehydes ◽  
Antimicrobial Activities ◽  
Gram Negative Bacteria ◽  
Schiff’S Bases ◽  
Gram Negative ◽  
Schiff's Bases

4-Chlorobenzylidene-2-methyl-(4H)-oxazol-5-one, which were prepared from 4-chlorobenzaldehyde and acetylglycine in reaction with hydrazine hydrate in ethanol gave 1-amino-4-(4-chlorobenzylidene)-2-methyl-1H-imidazolin-5(4H)-one. However, treatment of 4-chlorobenzylidene-2-methyl-(4H)-oxazol-5-one with hydrazine hydrate in pyridine yielded 3-(4-chlorophenyl)propanohydrazide. Reaction of 1-amino-4-(4-chlorobenzylidene)-2-methyl-1H-imidazolin-5(4H)-one with aromatic aldehydes gave eight corresponding Schiff’s bases namely 1-arylideneamino-4-(4-chlorobenzylidene)-2-methyl-1H-imidazolin-5(4H)-ones. The structure of the 3-(4-chlorophenyl)propanohydrazide and the imidazoline-5-one compounds was confirmed by IR, 1H-NMR and MS spectral data. The Schiff’s bases were tested for antimicrobial activities against several strains of Gram-positive, Gram-negative bacteria, molds and yeasts.

New heterocycles from thienopyridocinnolines

1998 ◽  
Vol 76 (4) ◽  
pp. 469-476 ◽  
Author(s):  
M ZA Badr ◽  
A A Geies ◽  
M S Abbady ◽  
A A Dahy
Keyword(s):  
Acetic Anhydride ◽  
Hydrazine Hydrate ◽  
Nitrous Acid ◽  
Ammonium Acetate ◽  
Carbon Disulphide ◽  
Sodium Ethoxide ◽  
Ring Closure ◽  
Ethyl Chloroformate ◽  
Intramolecular Ring

3-Cyano-4-(p-tolyl)pyrido[3,2-c]cinnolin-2(1H) thione 3 was reacted with α -halo ketones, esters, or amides to give the intermediates, S-alkylated products 5b-h, respectively, which underwent intramolecular ring closure reactions with ethanolic sodium ethoxide to give thienopyridocinnolines 6a-h. Pyrimidothienopyridocinnolines 9 and 11 were obtained by treatment of oxazino compound 8 with hydrazine hydrate and ammonium acetate. Treatment of hydrazino derivative 13 with acetylacetone, triethylorthoformate, carbon disulphide, ethyl chloroformate, and acetic anhydride afforded triazolopyrimidothienopyridocinnolines 14-16, 18, and 21, while with nitrous acid the corresponding tetrazolo compound 19 was produced.Key words: thienopyridocinnolines; their pyrimido, triazolopyrimido, and heteroannelated systems.

scholarly journals An in vivo evaluation of anti-inflammatory, analgesic and anti-pyretic activities of newly synthesized 1, 2, 4 Triazole derivatives

2021 ◽  
Vol 21 (1) ◽  
Author(s):  
Tabinda Azim ◽  
Muhammad Wasim ◽  
Muhammad Shoaib Akhtar ◽  
Irfan Akram
Keyword(s):  
Acetic Acid ◽  
Immersion Test ◽  
Potential Candidate ◽  
In Vivo Evaluation ◽  
Standard Drug ◽  
Reference Drug ◽  
Male And Female ◽  
Triazole Derivatives ◽  
Anti Inflammatory

Abstract Background In recent years, 1, 2, 4-triazole and its derivatives have been reported to be pharmacologically significant scaffolds. They possess analgesic, anti-tubercular, anti-inflammatory, anti-convulsant, anti-oxidant, anti-fungal, anti-cancer, anxiolytic and anti-depressant activity. This study was designed and conducted to evaluate the potential anti-inflammatory, analgesic and antipyretic activities of Triazole derivatives. Methods Swiss albino (male and female) mice weighing 20-30 g (10-24 weeks female), (5-14 weeks male) and Wister Kyoto rats (male and female) weighing 200-300 g (8-10 weeks old) were used for the present study. Anti-inflammatory activity was checked using Lambda carrageenan (λ) and egg albumin-induced paw edema models. Analgesic via Writhing Reflex induced by acetic acid and formalin, furthermore anti-pyretic activity was assessed by yeast induced pyrexia. Results Both of the test compounds exhibited encouraging anti-inflammatory analgesic and antipyretic results when compared with standard drug ibuprofen. The maximum inhibition of edema for the compound (S)-1-(4-Amino-5-mercapto-4H-1,2,4-triazole-3-yl) ethanol [3] was found to be (91)% as compared to reference drug ibuprofen (82)%, while (S)-1-(6-Phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)ethanol [5e] showed equipotent results to ibuprofen (81)%. The derivatives were also screened for their anti-nociceptive activity by Acetic acid writhing and tail immersion test. Compound 3 showed a significant reduction in wriths (83)% as compared to standard drug ibuprofen 71.5% and [5] showed comparable results to ibuprofen by exhibiting 70% reduction in writh at the same dose as that of standard drug, moreover, there were no signs of toxicity being observed after administration of high doses of test compounds to mice. Conclusions It is evident from the results that compounds 3(compound A) and 5(compound B) are a potential candidate for anti-inflammatory, analgesic and anti-pyretic and the scaffold could be used for further structural modifications. Further studies would help to evaluate their molecular mechanism of action regarding these beneficial activities.

scholarly journals Synthesis of New Heterocyclic Derivatives from 4-(3, 5-Dimethyl-1-phenyl-1H-pyrazol-4-ylazo)- benzoic acid

2010 ◽  
Vol 7 (1) ◽  
pp. 727-736 ◽  
Author(s):  
Baghdad Science Journal
Keyword(s):  
Hydrazine Hydrate ◽  
Acid Hydrazide ◽  
Azo Compounds ◽  
Basic Medium ◽  
Chloride Salt ◽  
Aminobenzoic Acid ◽  
Schiff’S Bases ◽  
Schiff's Bases ◽  
Thiosemicarbazide Derivative ◽  
Hydrazide Derivative

In this work pyrazolin derivatives were prepared from the diazonium chloride salt of 4-aminobenzoic acid. Azo compounds were prepared from the reaction of an ethanolic solution of sodium acetate and calculated amount of active methylene compound namely, acetyl acetone to obtain the corresponding hydrazono derivative (1). Cyclocondensation reaction of compounds (1) with hydrazine hydrate and phenyl hydrazine in boiling ethanol affording the corresponding pyrazoline-5-one derivatives of 4-aminobenzoic acid (2,3). Then compound (3) was reacted with thionyl chloride to give the corresponding acid chloride derivative(4), followed by conversion into the corresponding acid hydrazide derivative (5) carboxylic acid thiosemicarbazide (11), esters (14,15), thioesters (16,17) and amides (18,19), when treated hydrazine hydrate, thiosemicarbazide, alcohols, alkylthiol and secondary amines in dry refluxing benzene; respectively. Schiff's bases (6-8) were prepared by refluxing of compound (5) with different aldehydes and ketons, then two compounds from the Schiff's bases were cyclized with ?-mercapto acetic acid to give (9 and 10). Furthermore, 1,2,4-triazole derivative (12) have been also prepared by refluxing thiosemicarbazide derivative with sodium hydroxide solution (4%) followed acidification of the result using (10%)hydrolic acid. Moreover, a thiadiazole derivative (13) has been prepared by treatment of thiosemicarbazide derivative with concentrated sulfuric acid as cyclyzing agent. Finally, oxadiazole derivative (20) has prepared by condensation of its acid hydrazide derivative with carbon disulfide in basic medium.

Fractions of Boswellia serrata suppress LTA4, LTC4, Cyclooxygenase-2 activities and mRNA in HL-60 Cells and reduce lung inflammation in BALB/c mice.

2020 ◽  
Vol 17 ◽  
Author(s):  
Kapil K. Soni ◽  
Deepak Meshram ◽  
Temitope O. Lawal ◽  
Udeshi Patel ◽  
Gail B. Mahady
Keyword(s):  
Body Weight ◽  
Lung Inflammation ◽  
Biologically Active ◽  
Intragastric Administration ◽  
Boswellia Serrata ◽  
Standard Drug ◽  
Cox 2 ◽  
Anti Inflammatory

Background: Purified fractions from a Boswellia serrata Roxb. Ex. Colebr. (Burseraceae) extract (ETOH and DCM) contain biologically active compounds that are well known for having inflammation inhibitory properties. In this work, the purified fractions were tested in-vitro for LTC4, LTA4 and COX-2 activities using ELISA and qPCR was performed to determine gene regulation in human leukemia (HL-60) Cells. Two D-imaging tomography was performed to determine the anti-inflammatory activities of the fractions in BALB/c mouse model of lung inflammation. Objective: To evaluate anti-inflammatory activities of bioactive compounds of Boswellia serrata purified fractions. Methods: In-vitro MTT assay was performed in HL-60 cell lines for measuring the toxicity/viability of the cells. ELISA tests were performed for evaluating LTA4, LTC4 and COX-2 activities. qPCR was performed to evaluate the expression of mRNA in HL-60 cells. In-vivo experiments were performed in OVA sensitized and challenged BALB/c mice at two doses of Boswellia serrata purified fraction containing 6% Boswellic acid of 50 and 100mg/kg body weight were given orally and the standard drug dexamethasone (DXA, 4 mg/kg body weight) and reduction in lung inflammation was assessed by using an IVIS Xenogen in-vivo fluorescence imaging system. Results: A purified fraction of Boswellia serrata ETOH extracts reduced leukotriene-C4-synthase activity by 52%, leuktotriene-A4-hydrolase activity by 22% and COX-2 activity by 99% with an IC50 of 12.5µg/ml. Intragastric administration of the purified fraction of Boswellia serrata at two doses of 50mg/kg b.w. and 100mg/kg b.w., respectively along with 2-3% HPMC resulted in a ~51% (P value <0.01) reduction in OVA induced lung inflammation in BALB/c mice as observed by imaging tomography. Treatment of the OVA challenged mice with a standard drug dexamethasone (DXA) reduced inflammation by ~66% with significant value (P<0.0001). Conclusion: The present study describes that Boswellia serrata ethanolic extracts purified fraction (ETOH-BS) possess significant anti-inflammatory activities in HL-60 and in BALB/c and further supports for its use as Ayurvedic medicines traditionally in the treatment of lung disorders including allergy and asthma.

Microwave-assisted synthesis of novel Mannich base and conazole derivatives containing biological avtive pharmacological groups

2020 ◽  
Vol 17 ◽  
Author(s):  
Yıldız Uygun Cebeci ◽  
Sule Ceylan ◽  
Neslihan Demirbas ◽  
Şengül Alpay Karaoğlu
Keyword(s):  
Antimicrobial Activity ◽  
Active Sites ◽  
Sodium Ethoxide ◽  
Mannich Bases ◽  
Biologically Active ◽  
Secondary Amines ◽  
Microwave Assisted Synthesis ◽  
Standard Drug ◽  
Triazole Derivatives ◽  
Microwave Assisted

Background: The aim of this study is to synthesize new Mannich bases and conazol derivatives with biological activity by the microwave-assisted method. Introduction: 1,2,4-Triazole-3-one (3) acquired from tryptamine was transformed to the corresponding carbox(thio)amides (6a-c) via several steps. Compounds, 6a-c, were refluxed with sodium hydroxide to yield 1,2,4-triazole derivatives (7a-c). Compounds 3 and 7a-c on treatment with different heterocyclic secondary amines in an ambiance with formaldehyde afforded the Mannich bases 8-15 having diverse pharmacophore units with biologically active sites. The reaction of compound 3 and 2-bromo-1-(4-chlorophenyl) ethanone in the presence of sodium ethoxide gave the corresponding product yielded the corresponding 2-substituted-1,2,4-triazole-3-one, 16, which was reduced to 1,2,4-triazoles (17). Synthesis of compounds 18, 19, and 20 were carried out starting from compounds 17 with 4-chlorobenzyl chloride (for 18), 2,4- dichlorobenzyl chloride (for 19), and 2,6-dichlorobenzyl chloride (for 20). Method: The conventional technique was utilized for the synthesis of compounds, 3-7, and microwave-assisted technique for the compounds, 8-20. That is, green chemistry techniques were applied during these reactions. The structures molecules were elucidated on the foundation of 1H NMR, 13C NMR, FT-IR, EI-MS methods, and elemental analysis. Novel synthesized molecules were investigated for their antimicrobial activity using MIC (minimum inhibitory concentration) method. Results and Discussion: Aminoalkylation of triazole derivatives 3 and 7a–c with fluoroquinolones such as ciprofloxacin and norfloxacin provided an enhancement to the bioactivity of Mannich bases 8-11 against the tested microorganisms. The MIC values ranged between <0.24 and 3.9 μg/mL”. Moreover, molecules 10 and 11 have more effective on M. smegmatis than the other compounds by the MIC values of <1 μg/mL. They have shown very good antituberculosis activity. Conclusion: Most of the synthesized structures were observed to have excellent antimicrobial activity against most microorganisms taken into account. These molecules have activity better than the standard drug ampicillin and streptomycin.

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