Synthesis and Identification of Some New Derivatives of ([Benzyl Thio) Benzimidazole -N- (Methylene-5-Yl)] - 4,5- Di Substituted 1,2,4-Triazole and Evaluation of Their Activity as Antimicrobial and Anti-Inflammatory Agents

New 2-Mercaptobenzimidazole derivatives were synthesized. 4,5-disubsitituted 1,2,4-Triazole compounds 1b-2c were synthesized from 2-(benzylthio) benzimidazole compound a, which was then reacted with (NaH) in dioxane at a temperature of (0-5 C°) to produce the salt of compound a. Then the salt was reacted with ethyl chloro acetate to yield Ethyl 2-(benzylthio) benzimidazole acetate compound b. Compound b was converted to triazole derivatives by two pathways. The first pathway was reacting compound b with semicarbazide, thiosemicarbazide and phenylsemicarbazide in DMSO as a solvent to gain compounds 1b-3b, which were then cyclized by refluxed with 2N (NaOH) to yield 1,2,4-triazole derivatives compounds 4b-6b. The second pathway involved the treatment of compound b with hydrazine hydrate to produce N-acetohydrazide-2-(benzyl thio) benzimidazole c. Compound c was refluxed with carbon disulfide (CS2) in KOH alcoholic solution to obtain the salt compound 1c. The salt was treated with hydrazine hydrate to yield 1,2,4-triazole derivative compound 2c. The newly synthesized compounds b-2c were identified by FTIR, 1H-NMR and 13C-NMR and their physical properties were measured. Furthermore, their anti-microbial activities were tested against two Gram-positive and two Gram-negative bacteria and against one strain of fungi. Also, some of these synthesized compounds were tested for their anti-inflammatory activities.

Download Full-text

II. On some derivatives of uramidobenzoic acid

Proceedings of the Royal Society of London ◽

10.1098/rspl.1871.0040 ◽

1872 ◽

Vol 20 (130-138) ◽

pp. 168-178

Keyword(s):

Alcoholic Solution ◽

Short Description ◽

Compound C ◽

Derivatives Of

This acid, of which I gave a short description some time ago, has the composition C 8 H 8 N 2 O 3 . I obtained it in the first instance from the basic compound C 10 H 12 N 2 O 3 , which is one of the products of the action of cyanogen on an alcoholic solution of amidobenzoic acid. Its formation takes place in the manner indicated in the following equation. Since then I have shown that this acid is also formed when urea and amidobenzoic acid are cautiously melted together.

Download Full-text

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

Baghdad Science Journal ◽

10.21123/bsj.6.1.200-208 ◽

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.

Download Full-text

Synthesis of Novel 8-Hydroxy Quinolin Based 1,3,4-oxadiazoles and S-substituted 1,2,4-triazole Derivatives and Evaluation of their Anti-inflammatory, Analgesic, Ulcerogenic and Anti-Microbial Activities

Medicinal Chemistry ◽

10.2174/157340611797928334 ◽

2011 ◽

Vol 7 (6) ◽

pp. 663-673 ◽

Cited By ~ 11

Author(s):

Mohammad Mahboob Alam ◽

Mohammad Shaharyar ◽

Hinna Hamid ◽

Syed Nazreen ◽

Saqlain Haider ◽

...

Keyword(s):

Microbial Activities ◽

Triazole Derivatives ◽

Anti Inflammatory

Download Full-text

The Influence of the Structure of Several New ortho-Hydroxy-Ketone Derived bis-Schiff Bases on Their Antibacterial and Anti-Inflammatory Activity

Revista de Chimie ◽

10.37358/rc.20.1.7840 ◽

2020 ◽

Vol 71 (1) ◽

pp. 244-248

Author(s):

Gladiola Tantaru ◽

Mihai Apostu ◽

Cristina Mihaela Ghiciuc ◽

Antonia Poiata ◽

Alina Stefanache ◽

...

Keyword(s):

Escherichia Coli ◽

Staphylococcus Aureus ◽

Pseudomonas Aeruginosa ◽

Schiff Bases ◽

Antimicrobial Activities ◽

Hydroxy Ketone ◽

Gram Negative Bacteria ◽

Anti Inflammatory ◽

Derivatives Of ◽

Inflammatory Effect

The article presents some bis-Schiff bases - halogenated derivatives of ortho-hydroxy-ketones - with great potential for antimicrobial and antiinflammatory activity. The antimicrobial activities of the Schiff bases were tested in comparison with Chloramphenicol, Nystatin, and Ampicillin upon the following strains: Staphylococcus aureus (ATCC 25923), Sarcina lutea (ATCC 9341), Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27853), Candida albicans (ATCC 1023), Candida glabrata, two Staphylococcus aureus strains, and several clinical isolates (Proteus mirabilis, Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumoniae). Those compounds were found to be active against Gram-positive or Gram-negative bacteria, and had an anti-inflammatory effect comparable to that of Indomethacin.

Download Full-text

Synthesis of 2, 3-Dihydro-1,4-naphthaquinone Derivatives for Targeting the Altered Cancer Cells Metabolism

JOURNAL OF ADVANCES IN CHEMISTRY ◽

10.24297/jac.v12i7.2804 ◽

2013 ◽

Vol 12 (7) ◽

pp. 472-481

Author(s):

Mohammed Hassan Mohammed ◽

Monther Faisal Mahdi ◽

Fadhil Mohsin Hamed

Keyword(s):

Ir Spectroscopy ◽

Antitumor Activity ◽

Cancer Cells ◽

Anticancer Activities ◽

Compound A ◽

Chemical Structures ◽

Compound C ◽

Human Larynx ◽

Derivatives Of

A new four derivatives of 2,3-Dihydro-1,4-naphthaquinonewere synthesizedas possible bioreductiveprodrugs for5-fluorouracil (5-Fu),Mercaptopurine (6-MP), N-acetyl cysteine (NAC)and 3-bromopyrovic acid (3-BPA) to selectively deliver the drugs into the cancer cells and these are:2-((5-fluoro-1,2-dihydropyrimidin-4-yloxy)methyl)-3-hydroxy naphthalene-1,4dione(compound A),2-((9H-purin-6-ylthio)-3-hydroxyl naphthalene-1,4dione(compound B)acetmido-3-((3-methyl-1,4-dihydronaphthalen-2-yl)methylthio)propanoicacid (compound C)and hydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl3-bromo-2-oxopropanoate ( compound D)Their chemical structures were characterized by H1 NMR, IR spectroscopy and elemental microanalysis.The in vitro antitumor activity tests againstHep-2 human larynx cancer cell lineindicated that compound A,B,C and D havesignificant anticancer activities when compared with 5-Fu.

Download Full-text

Synthesis of 2, 3-Dihydro-1,4-naphthaquinone Derivatives for Targeting the Altered Cancer Cells Metabolism

JOURNAL OF ADVANCES IN CHEMISTRY ◽

10.24297/jac.v4i2.2708 ◽

2008 ◽

Vol 4 (2) ◽

pp. 472-481

Author(s):

Mohammed Hassan Mohammed ◽

Monther Faisal Mahdi ◽

Fadhil Mohsin Hamed

Keyword(s):

Ir Spectroscopy ◽

Antitumor Activity ◽

Cancer Cells ◽

Anticancer Activities ◽

Compound A ◽

Chemical Structures ◽

Compound C ◽

Human Larynx ◽

Derivatives Of

Download Full-text

Study of Physico-chemical Characteristics and Pharmacological Effects of 1-Ethyl-Salicyldene-bis-Ethylene-Diamine and Its Complex with Mn(II)

Revista de Chimie ◽

10.37358/rc.19.7.7375 ◽

2019 ◽

Vol 70 (7) ◽

pp. 2534-2537

Author(s):

Gladiola Tantaru ◽

Mihai Apostu ◽

Antonia Poiata ◽

Mihai Nichifor ◽

Nela Bibire ◽

...

Keyword(s):

Schiff Base ◽

Chemical Structure ◽

Antimicrobial Activities ◽

Ethylene Diamine ◽

Chemical Characteristics ◽

Gram Negative Bacteria ◽

Pharmacological Effects ◽

Physico Chemical ◽

Anti Inflammatory ◽

Inflammatory Effect

The paper presents the synthesis of a new complex combination of a Bis-Schiff base with Mn(II) ions with great potential for antimicrobial and anti-inflammatory activity. A new complex of the Salen-type ligand, 1-ethyl-salicylidene-bis-ethylene diamine was synthetized using Mn(II) ions. The chemical structure was confirmed through 1H-NMR and IR spectroscopy. The antimicrobial activities of the Bis-Schiff base and its complex were tested in comparison with Ampicillin, Chloramphenicol, Tetracycline, Ofloxacin and Nystatin. Those compounds were found to be active against Gram-positive or Gram-negative bacteria, and had an anti-inflammatory effect comparable to that of Indomethacin.

Download Full-text

Structure-Activity Relationship and Antimicrobial Evaluation of N-Phenylpyrazole Curcumin Derivatives

Current Bioactive Compounds ◽

10.2174/1573407215666190124115010 ◽

2020 ◽

Vol 16 (4) ◽

pp. 481-488

Author(s):

Heli Sanghvi ◽

Satyendra Mishra

Keyword(s):

Antibacterial Activity ◽

Gram Negative Bacteria ◽

Pyrazole Derivatives ◽

Gram Positive ◽

Gram Negative ◽

E Coli ◽

Curcumin Derivatives ◽

Structure Activity ◽

Electron Donating Groups ◽

Derivatives Of

Background: Curcumin, one of the most important pharmacologically significant natural products, has gained significant consideration among scientists for decades since its multipharmacological activities. 1, 3-Dicarbonyl moiety of curcumin was found to be accountable for the rapid degradation of curcumin molecule. The aim of present work is to replace 1, 3-dicarbonyl moiety of curcumin by pyrazole and phenylpyrazole derivatives with a view to improving its stability and to investigate the role of substitution in N-phenylpyrazole curcumin on its antibacterial activity against both Gram-positive as well as Gram-negative bacteria. Methods: Pyrazole derivatives of curcumin were prepared by heating curcumin with phenyhydrazine/ substituted phenyhydrazine derivatives in AcOH. The residue was purified by silica gel column chromatography. Structures of purified compounds were confirmed by 1H NMR and Mass spectroscopy. The synthesized compounds were evaluated for their antibacterial activity by the microdilution broth susceptibility test method against gram positive (S. aureus) and gram negative (E. coli). Results: Effects of substitution in N-phenylpyrazole curcumin derivatives against S. aureus and E. coli were studied. The most active N-(3-Nitrophenylpyrazole) curcumin (12) exhibits twenty-fold more potency against S. aureus (MIC: 10μg/mL)) and N-(2-Fluoroophenylpyrazole) curcumin (5) fivefold more potency against E. coli (MIC; 50 μg/mL) than N-phenylpyrazole curcumin (4). Whereas, a remarkable decline in anti-bacterial activity against S. aureus and E. coli was observed when electron donating groups were incorporated in N-phenylpyrazole curcumin (4). Comparative studies of synthesized compounds suggest the effects of electron withdrawing and electron donating groups on unsubstituted phenylpyrazole curcumin (4). Conclusion: The structure-activity relationship (SAR) results indicated that the electron withdrawing and electron donating at N-phenylpyrazole curcumin played key roles for their bacterial inhibitory effects. The results of the antibacterial evaluation showed that the synthesized pyrazole derivatives of curcumin displayed moderate to very high activity in S. aureus. In conclusion, the series of novel curcumin derivatives were designed, synthesized and tested for their antibacterial activities against S. aureus and E. coli. Among them, N-(3-Nitrophenylpyrazole curcumin; 12) was most active against S. aureus (Gram-positive) and N-(2-Fluoroophenylpyrazole) curcumin (5) against E. coli (Gram-negative) bacteria.

Download Full-text

Assessment of Cota altissima (L.) J. Gay for phytochemical composition and antioxidant, anti-inflammatory, antidiabetic and antimicrobial activities

Zeitschrift für Naturforschung C ◽

10.1515/znc-2020-0257 ◽

2021 ◽

Vol 0 (0) ◽

Author(s):

Gamze Göger ◽

Muhammed Allak ◽

Ali Şen ◽

Fatih Göger ◽

Mehmet Tekin ◽

...

Keyword(s):

Fatty Acids ◽

Essential Oil ◽

Antioxidant Activities ◽

Antimicrobial Activities ◽

Antidiabetic Activity ◽

Gram Negative Bacteria ◽

Inhibitory Effects ◽

Dicaffeoylquinic Acid ◽

Anti Inflammatory ◽

Phytochemical Profiles

Abstract Phytochemical profiles of essential oil (EO), fatty acids, and n-hexane (CAH), diethyl ether (CAD), ethyl acetate (CAE) and methanol extracts (CAM) of Cota altissima L. J. Gay (syn. Anthemis altissima L.) were investigated as well as their antioxidant, anti-inflammatory, antidiabetic and antimicrobial activites. The essential oil was characterized by the content of acetophenone (35.8%) and β-caryophyllene (10.3%) by GC-MS/FID. Linoleic and oleic acid were found as main fatty acids. The major constituents of the extracts were found to be 5-caffeoylquinic acid, 3,5-dicaffeoylquinic acid, isorhamnetin glucoside, quercetin and quercetin glucoside by LC-MS/MS. Antioxidant activities of the extracts were determined by scavenging of DPPH and ABTS free radicals. Also, the inhibitory effects on lipoxygenase and α-glucosidase enzymes were determined. Antimicrobial activity was evaluated against Gram positive, Gram negative bacteria and yeast pathogens. CAM showed the highest antioxidant activity against DPPH and ABTS radicals with IC50 values of 126.60 and 144.40 μg/mL, respectively. In the anti-inflammatory activity, CAE demonstrated the highest antilipoxygenase activity with an IC50 value of 105.40 μg/mL, whereas, CAD showed the best inhibition of α-glucosidase with an IC50 value of 396.40 μg/mL in the antidiabetic activity. CAH was effective against Staphylococcus aureus at MIC = 312.5 µg/mL. This is the first report on antidiabetic, anti-inflammatory and antimicrobial activities of different extracts of C. altissima.

Download Full-text