Synthesis, Characterization and Biological Studies of Some Bioactive Thiazolotriazole Derivatives

2010 ◽  
Vol 65 (12) ◽  
pp. 1509-1515 ◽  
Author(s):  
Manjunatha Kumsi ◽  
Boja Poojary ◽  
Prajwal Lourdes Lobo ◽  
Nalilu Suchetha Kumari ◽  
Anoop Chullikana
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Good Yield ◽  
Sodium Acetate ◽  
Aromatic Aldehydes ◽  
Antimicrobial Activities ◽  
One Pot ◽  
Biological Studies ◽  
Elemental Analyses

The key precursor rac-2-(4-isobutylphenyl)ethyl-1,2,4-triazole-5-thione (3) was synthesized in good yield from Ibuprofen (1). One-pot three-component reactions of 3 with 5-aryl-furan-2-carboxaldehydes/ substituted aromatic aldehydes and monochloroacetic acid in acetic acid in the presence of acetic anhydride and anhydrous sodium acetate afforded substituted thiazolo[3,2-b][1,2,4]triazole derivatives 4 and 5. The structures of the newly synthesized compounds were elucidated by elemental analyses and spectral data. The compounds were tested for their in-vitro antimicrobial activities.

Cyclisation of 1-Phenyl-4-carboxymethylmercapto-5-arylazo-hydantoins

1981 ◽  
Vol 36 (4) ◽  
pp. 501-504 ◽  
Author(s):  
A. F. A. Shalaby ◽  
M. A. Abdel Aziz ◽  
S. S. M. Boghdadi
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Aromatic Amines ◽  
Sodium Acetate ◽  
Aromatic Aldehydes ◽  
Mannich Bases ◽  
Anhydrous Sodium Acetate ◽  
Primary Aromatic Amines ◽  
Hydantoin Derivatives

Abstract 1-Phenyl-4-carboxymethylmercapto-5-arylazo-hydantoin derivatives (3a-f) were cyclised with acetic anhydride to give the bicyclic products (4a-f). Compounds 4 a, b condensed with aromatic aldehydes in acetic acid and in presence of anhydrous sodium acetate yielding the corresponding arylidene derivatives (5a-c). Compounds 4a, b also couple with aryldiazonium salts to give the expected coloured arylazo compounds (6a-j). 4 a, b reacted with formaldehyde and primary aromatic amines in ethanol to give the corresponding Mannich bases (7a-f).

scholarly journals Thiazolo-Pyrimidine Analogues: Synthesis, Characterization and Docking Studies Guided Antimicrobial Activities

2020 ◽  
Vol 11 (2) ◽  
pp. 9443-9455
Keyword(s):  
Aromatic Aldehydes ◽  
Dna Gyrase ◽  
Docking Study ◽  
Antimicrobial Activities ◽  
Docking Studies ◽  
One Pot ◽  
Standard Drug ◽  
Toluene Sulfonic Acid ◽  
Pyrimidine Analogues

In the current study, bicyclic 1-(7-methyl-3,5-diphenyl-5H-thiazolo(3,2-α)pyrimidine-6-yl)ethanone (4a-l) derivatives have been designed and conveniently synthesized by one-pot three-component method via cyclocondensation of substituted 4-phenylthiazole-2-amine (1a-c), acetylacetone (2) and various aromatic aldehydes (3a-d) in the presence of p-toluene sulfonic acid (PTSA) under acetonitrile solvent medium. The synthesized compounds (4a-l) have been characterized by spectral analysis and subjected to docking study against protein DNA gyrase (PDB Code: 1KZN), and also, the compounds were screened for their in vitro antimicrobial activities. The bioassay of the synthesized compounds envisioned that the compound 4k emerged as a broad-spectrum antibacterial agent, and 4l emerged as a good antifungal agent compared to standard drug.

scholarly journals Regioselective convergent synthesis of 2-arylidene thiazolo[3,2-a]pyrimidines as potential anti-chikungunya agents

RSC Advances ◽  
2020 ◽  
Vol 10 (9) ◽  
pp. 5191-5195 ◽  
Author(s):  
Mohamed Fares ◽  
Patrick M. McCosker ◽  
Muhammad A. Alsherbiny ◽  
Anthony C. Willis ◽  
Timothy Clark ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Sodium Acetate ◽  
Anhydrous Sodium Acetate ◽  
Regioselective Synthesis ◽  
One Pot ◽  
Bromoacetic Acid ◽  
Convergent Synthesis ◽  
The One

Convergent and convenient regioselective synthesis of novel thiazolo[2,3-a]pyrimidines was accomplished using the one-pot reaction of 6-ethylthiouracil, bromoacetic acid, anhydrous sodium acetate, acetic anhydride, acetic acid and suitable aldehyde.

Synthesis and application of some new S-(substituted)thio- and thienoquinoline derivatives as antimicrobial agents

1991 ◽  
Vol 56 (8) ◽  
pp. 1749-1760 ◽  
Author(s):  
Ibrahim M. A. Awad ◽  
Abdu E. Abdel-Rahman ◽  
Etify A. Bakhite
Keyword(s):  
Antimicrobial Agents ◽  
Thioglycolic Acid ◽  
Aromatic Aldehydes ◽  
Antimicrobial Activities ◽  
Phenyl Isocyanate ◽  
Gram Negative Bacteria ◽  
Elemental Analyses ◽  
Thiosemicarbazide Derivatives ◽  
Methyl Phenyl

Ethyl (4-aryl-3-cyano-5,6,7,8-tetrahydro-2-quinolinylthio) acetate (IIa, IIb) were prepared and reacted with hydrazine hydrate to give hydrazines IIIa, IIIb which underwent cyclization into thienoquinoline derivatives IVa, IVb. Reaction of IIIa, IIIb with phenyl isocyanate yielded semicarbazides Va, Vb. Similarly, IIIa, IIIb and IVb were interacted with methyl/phenyl isothiocyanates affording the corresponding thiosemicarbazide derivatives VIa - VId and XIVa, XIVb respectively. On the other hand, condensation of IIIb with acetylacetone gave the pyrazole VII treatment with ethoxide furnished VIII. Also, IIIa, IIIb and IVa, IVb reacted with aromatic aldehydes to afford hydrazones IXa - IXf and XIa - XIf respectively. Cyclodehydration of IXd - IXf with thioglycolic acid furnished 4-thiazolidinone derivatives Xa - Xc. Moreover, IVb was reacted with formic acid/acetic anhydride to give XII and XIII. Diazotization of IVb gave azide XV which underwent Curtius rearrangement into XVI. The structures of all newly synthesized compounds were confirmed by elemental analyses and spectral data. Also, the most of these compounds were tested in vitro for their antimicrobial activities against some Gram-positive and Gram-negative bacteria.

scholarly journals Synthesis, In Silico Prediction and In Vitro Evaluation of Antitumor Activities of Novel Pyrido[2,3-d]pyrimidine, Xanthine and Lumazine Derivatives

Molecules ◽  
2020 ◽  
Vol 25 (21) ◽  
pp. 5205
Author(s):  
Samar El-Kalyoubi ◽  
Fatimah Agili
Keyword(s):  
Lung Cancer ◽  
Cancer Progression ◽  
Aromatic Aldehydes ◽  
Docking Study ◽  
Molecular Docking Study ◽  
One Pot ◽  
Three Component Reaction ◽  
Elemental Analyses ◽  
Heterocyclic Derivatives

Ethyl 5-arylpyridopyrimidine-6-carboxylates 3a–d were prepared as a one pot three component reaction via the condensation of different aromatic aldehydes and ethyl acetoacetate with 6-amino-1-benzyluracil 1a under reflux condition in ethanol. Additionally, condensation of ethyl 2-(2-hydroxybenzylidene) acetoacetate with 6-amino-1-benzyluracil in DMF afforded 6-acetylpyridopyrimidine-7-one 3e; a facile, operationally, simple and efficient one-pot synthesis of 8-arylxanthines 6a–f is reported by refluxing 5,6-diaminouracil 4 with aromatic aldehydes in DMF. Moreover, 6-aryllumazines 7a–d was obtained via the reaction of 5,6-diaminouracil with the appropriate aromatic aldehydes in triethyl orthoformate under reflux condition. The synthesized compounds were characterized by spectral (1H-NMR, 13C-NMR, IR and mass spectra) and elemental analyses. The newly synthesized compounds were screened for their anticancer activity against lung cancer A549 cell line. Furthermore, a molecular-docking study was employed to determine the possible mode of action of the synthesized compounds against a group of proteins highly implicated in cancer progression, especially lung cancer. Docking results showed that compounds 3b, 6c, 6d, 6e, 7c and 7d were the best potential docked compounds against most of the tested proteins, especially CDK2, Jak2, and DHFR proteins. These results are in agreement with cytotoxicity results, which shed a light on the promising activity of these novel six heterocyclic derivatives for further investigation as potential chemotherapeutics.

scholarly journals One-Pot Multicomponent Synthesis of Methoxybenzo[h]quinoline-3-carbonitrile Derivatives; Anti-Chagas, X-ray, and In Silico ADME/Tox Profiling Studies

Molecules ◽  
2021 ◽  
Vol 26 (22) ◽  
pp. 6977
Author(s):  
Hegira Ramírez ◽  
Katiuska Charris ◽  
Esteban Fernandez-Moreira ◽  
Benjamín Nogueda-Torres ◽  
Mario V. Capparelli ◽  
...  
Keyword(s):  
In Silico ◽  
Ammonium Acetate ◽  
Aromatic Aldehydes ◽  
Multicomponent Synthesis ◽  
Activity Profile ◽  
One Pot ◽  
X Ray ◽  
Elemental Analyses ◽  
The One

Several methoxybenzo[h]quinoline-3-carbonitrile analogs were designed and synthesized in a repositioning approach to developing compounds with anti-prostate cancer and anti-Chagas disease properties. The compounds were synthesized through a sequential multicomponent reaction of aromatic aldehydes, malononitrile, and 1-tetralone in the presence of ammonium acetate and acetic acid (catalytic). The effect of the one-pot method on the generation of the target product has been studied. The compounds were in vitro screened against bloodstream trypomastigotes of T. cruzi (NINOA and INC-5 strains) and were most effective at showing a better activity profile than nifurtimox and benznidazole (reference drugs). A study in silico on absorption, distribution, metabolism, excretion, and toxicity (ADME/Tox) profiling to help describe the molecular properties related to the pharmacokinetic aspects in the human body of these compounds was reported. In addition, X-ray data for the compound 2-Amino-5,6-dihydro-4-(3-hydroxy-4-methoxy-phenyl)-8-methoxybenzo[h]quinoline-3-carbonitrile 6 was being reported. Spectral (IR, NMR, and elemental analyses) data on all final compounds were consistent with the proposed structures.

Syntheses and Cytotoxicity Screening of some Novel 1,2,4-Triazine Derivatives against Liver Carcinoma Cell Lines

2020 ◽  
Vol 17 ◽  
Author(s):  
W. Abd El-Fattah
Keyword(s):  
Acetic Anhydride ◽  
Cell Lines ◽  
Carcinoma Cell ◽  
Aromatic Aldehydes ◽  
Liver Carcinoma ◽  
Anticancer Activities ◽  
Carcinoma Cell Lines ◽  
Elemental Analyses ◽  
Triazine Derivatives ◽  
C Nmr

: In this work, 1,2,4-triazine derivatives were synthesized and evaluated for anticancer activities. Series of 1,2,4-triazine derivatives (4a, b) were prepared via the reaction of N-benzoyl glycine (1) with aromatic aldehydes in presence of fused sodium acetate and acetic anhydride to give 1,3-oxazolinone derivatives (2a, b), followed by condensation with 1-(ethoxycarbonyl) hydrazine (3) in glacial acetic acid. Compounds (4a, b) then reacted with acetic anhydride, ethyl chloroacetate and 2,4-dinitrophenyl hydrazine yielded the corresponding to N-acetyl derivatives (5a, b), N-(ethoxycarbonyl) methyl derivative (6) and 1,2-disubstituted hydrazine (7), respectively. The structures of the 1,2,4-triazine derivatives were confirmed by IR, 1H, 13C NMR, MS and elemental analyses. Anticancer activity of some 1,2,4-triazine derivatives (4-7) have been investigated. The results revealed that compounds 4a (IC50= 2.7μM), 5a (IC50= 1.5μM), and 5b (IC50= 3.9μM) show promising inhibitory growth efficacy compared to a standard antitumor drug (IC50= 4.6μM). These three compounds can be considered as potential agents against human hepatocellular carcinoma cell lines (HepG-2).

scholarly journals Synthesis and Biological Evaluation of Aminonaphthols Incorporated Indole Derivatives

2014 ◽  
Vol 2014 ◽  
pp. 1-12 ◽  
Author(s):  
Saundane Anand Raghunath ◽  
Kirankumar Nandibeoor Mathada
Keyword(s):  
Radical Scavenging ◽  
Antitubercular Activity ◽  
Antimicrobial Activities ◽  
Biological Evaluation ◽  
Secondary Amines ◽  
Anticancer Activities ◽  
One Pot ◽  
Antioxidant Power ◽  
Mic Value

An efficient one pot condensation of naphthols (1), 2,5-disubstituted indole-3-carboxaldehydes (2), and secondary amines (3) has been achieved using dichloromethane as a solvent, stirring at room temperature. Some of the new [(disubstituted amino)(5-substituted 2-phenyl-1H-indol-3-yl)methyl]naphthalene-ols (4) derivatives were prepared in good yields. The significant features of this method are simple work-up procedure, inexpensive nontoxic solvent, shorter reaction times, and excellent product yields. The structures of newly synthesized compounds (4a–r) are confirmed by their elemental analysis, FTIR, 1H and 13C NMR, and mass spectral data. These compounds were screened for their in vitro antioxidant, antimicrobial, antitubercular, and anticancer activities. Among the synthesized compounds (4a–r), the compound 4e exhibited highest activity for radical scavenging and ferric ions reducing antioxidant power activities; compounds 4b, 4h, and 4k showed good metal chelating activity. Compounds 4n and 4q showed excellent antimicrobial activities with MIC value 08 µg/mL against tested strains. Compounds 4h, 4k, 4n, and 4q exhibited promising antitubercular activity with MIC value 12.5 µg/mL. Compounds 4k and 4q exhibited 100% cell lysis at concentration 10 µg/mL against MDA-MB-231 (human adenocarcinoma mammary gland) cell lines.

scholarly journals Synthesis of Some Novel Fused Imidazo [2, 1-b] [1, 3] Thiazole and Imidazo [2, 1-b] Thiazolo [5, 4-d] Isoxazole Derivatives

2012 ◽  
Vol 9 (3) ◽  
pp. 1518-1525 ◽  
Author(s):  
Hamid Reza Jaberi ◽  
Hadi Noorizadeh
Keyword(s):  
Acetic Acid ◽  
Sodium Acetate ◽  
Carbon Disulphide ◽  
Thiazole Derivatives ◽  
H Nmr ◽  
Nmr Data ◽  
Elemental Analyses ◽  
New Compounds ◽  
Isoxazole Derivatives ◽  
C Nmr

In this work we describe the synthesis of some novel fused imidazo [2, 1-b] [1, 3] thiazole derivatives. The reaction of 1, 2-diaminoethane 1 with carbon disulphide in H2O/ETOH as solvent furnishes 4, 5-dihydro-1H-imidazol-2-thiol 2 under reflux condition. the reaction of 4,5-dihydro-1H-imidazol-2-thiol on treatment with ethylchloro acetate and aromatic aldehyde in presence of anhydrous sodium acetate and acetic acid as solvent to give (Z)-2-(arylidene)-5,6-dihydroimidazo [2,1-b] [1,3] thiazol-3(2H)-one 3a-j. Compounds 3a-j was condensed with hydroxylamine to give 3-(aryl)-2, 3, 6, 7-tetrahydroimidazo [2, 1-b] [1,3] thiazolo [5, 4-d] isoxazole 4a-j. The structures of the new compounds were established by elemental analyses, IR,1H NMR and13C NMR data.

scholarly journals Synthesis and Antimicrobial Activities of Some New Synthesized Imide and Schiff's Base Derivatives

2013 ◽  
Vol 2013 ◽  
pp. 1-6 ◽  
Author(s):  
Nermien M. Sabry ◽  
Eman M. Flefel ◽  
Mohamed A. Al-Omar ◽  
Abd El-Galil E. Amr
Keyword(s):  
Acetic Acid ◽  
Fusidic Acid ◽  
Spectroscopic Data ◽  
Glacial Acetic Acid ◽  
Aromatic Aldehydes ◽  
Antimicrobial Activities ◽  
Schiff’S Bases ◽  
Schiff’S Base ◽  
Antimicrobial Screening ◽  
Positive Controls

A series of 2,6-bis(substituted thiazolopyrimi-dinyl) pyridine(2a,b)and corresponding Schiff's bases(3a–j)were synthesized from 2,6-bis-(3-amino-2-methyl-4-oxo-9-substituted-3,4-dihydropyrido-[30,20 : 4,5]-thieno[3,2-d]pyrimidin-7-yl)pyridines(1a,b)as starting materials. The compounds1a,bwere reacted with 2,3,4,5-tetrachlorophthalic anhydride in glacial acetic acid to give the corresponding bis-imides(2a,b). But they are treated with aromatic aldehydes in refluxing ethanol to afford the Schiff’s base derivatives(3a–j). The antimicrobial screening showed that many of these newly synthesized compounds had good antimicrobial activities comparable to streptomycin and fusidic acid as positive controls. The detailed synthesis, spectroscopic data, and antimicrobial activities of the synthesized compounds were reported.

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