scholarly journals Synthesis, Characterization of Novel Schiff’s Bases of 2-(1H-tetrazol-5-yl) Pyridine and Evaluation of their Antitubercular Activity

2021 ◽  
Vol 1 (2) ◽  
Author(s):  
Popat Mohite ◽  
Vinayak Deshmukh ◽  
Ramdas Pandhare ◽  
Bankar MS
Keyword(s):  
Mycobacterium Tuberculosis ◽  
Hydrazine Hydrate ◽  
Spectral Data ◽  
Schiff Bases ◽  
Aromatic Aldehyde ◽  
Antitubercular Activity ◽  
Moderate Activity ◽  
Pyridine Derivatives ◽  
Ethyl Chloroacetate

This study aimed to prepare some new 2-(1H-tetrazol-5-yl) pyridine derivatives from Pyridine Nitrile as a starting materials and to evaluate the antitubercular activity against Mycobacterium Tuberculosis. The first step involves the reaction of 2-(1H-tetrazol-5-yl) pyridine with ethyl chloroacetate to form ethyl [5-(pyridin-2-yl)-1H-tetrazol-1-yl] acetate (A). In step II it was further treated with hydrazine hydrate to form 2-[5-(pyridin-2-yl)-1H-tetrazol-1-yl] acetohydrazide (B). The compound B was treated with different aromatic aldehyde to form N'-[(E)-substituted phenylmethylidene]-2-[5-(pyridin-2-yl)-1H-tetrazol-1-yl] acetohydrazide (Schiff Bases) (C1–C10). The compounds obtained were identified by spectral data. The antitubercular activity of synthesized compounds were evaluated against Mycobacterium Tuberculosis. The compound C4 and C10 was found to possess potent activity while compounds C2 and C3 shows moderate activity.

scholarly journals Structure-Based Drug Design and Characterization of Sulfonyl-Piperazine Benzothiazinone Inhibitors of DprE1 from Mycobacterium tuberculosis

2018 ◽  
Vol 62 (10) ◽  
Author(s):  
Jérémie Piton ◽  
Anthony Vocat ◽  
Andréanne Lupien ◽  
Caroline S. Foo ◽  
Olga Riabova ◽  
...  
Keyword(s):  
Mycobacterium Tuberculosis ◽  
Drug Design ◽  
Antitubercular Activity ◽  
Cysteine Residue ◽  
Drug Candidate ◽  
Structure Based Drug Design ◽  
Content Type ◽  
Active Site Cysteine ◽  
Covalent Adducts

ABSTRACT Macozinone (MCZ) is a tuberculosis (TB) drug candidate that specifically targets the essential flavoenzyme DprE1, thereby blocking synthesis of the cell wall precursor decaprenyl phosphoarabinose (DPA) and provoking lysis of Mycobacterium tuberculosis. As part of the MCZ backup program, we exploited structure-guided drug design to produce a new series of sulfone-containing derivatives, 2-sulfonylpiperazin 8-nitro 6-trifluoromethyl 1,3-benzothiazin-4-one, or sPBTZ. These compounds are less active than MCZ but have a better solubility profile, and some derivatives display enhanced stability in microsomal assays. DprE1 was efficiently inhibited by sPBTZ, and covalent adducts with the active-site cysteine residue (C387) were formed. However, despite the H-bonding potential of the sulfone group, no additional bonds were seen in the crystal structure of the sPBTZ-DprE1 complex with compound 11326127 compared to MCZ. Compound 11626091, the most advanced sPBTZ, displayed good antitubercular activity in the murine model of chronic TB but was less effective than MCZ. Nonetheless, further testing of this MCZ backup compound is warranted as part of combination treatment with other TB drugs.

scholarly journals Synthesis and Preliminary Evaluation of Benzofuran-Oxadiazole Conjugates as Potential Antitubercular Agents

2019 ◽  
Vol 31 (4) ◽  
pp. 965-970 ◽  
Author(s):  
Veerabhadrayya S. Negalurmath ◽  
Obelannavar Kotresh ◽  
Mahantesha Basanagouda
Keyword(s):  
Mycobacterium Tuberculosis ◽  
Spectral Data ◽  
13C Nmr ◽  
Antitubercular Activity ◽  
Preliminary Evaluation ◽  
Antitubercular Agents ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
Mycobacterium Tuberculosis H37rv ◽  
Mycobacterium Phlei

In the present study, a series of benzofuran-oxadiazole conjugates 7(a-o) was designed, synthesized and characterized through IR, 1H NMR, 13C NMR and mass spectral data. All the compounds were screened for preliminary antitubercular activity against Mycobacterium phlei and Mycobacterium tuberculosis H37RV. Among all the target compounds, the compound possessing chlorine (7k, MIC 1.56 μg/mL) and bromine (7m, MIC 1.56 μg/mL) on 6th position of benzofuran showed highest activity against Mycobacterium phlei. Whereas, bromine on either 5th position (7l, MIC 3.125 μg/mL) or 6th position (7m MIC 3.125 μg/mL) on benzofuran exhibited highest activity for Mycobacterium tuberculosis (H37 RV).

scholarly journals Microwave Assisted Synthesis and Characterization of Schiff Base of 2-Amino Benzimidazole

2018 ◽  
Vol 10 (4) ◽  
Author(s):  
Garima Shrivastava ◽  
Manjul Shrivastava
Keyword(s):  
Schiff Base ◽  
Spectral Data ◽  
Aromatic Aldehyde ◽  
Synthesis And Characterization ◽  
Microwave Assisted Synthesis ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
Microwave Assisted

New Schiff base (2-[(1H-benzimidazol-2-ylimino) methyl]-4,6- diiodophenol) was synthesized by the condensation of aryl/hetero aromatic aldehyde (3,5diiodosalicylaldehyde) with 2- amino benzimidazole under conventional and microwave conditions and characterized through IR, HNMR and Mass spectral data and CHN analysis

scholarly journals Synthesis and Characterization of Thiazolo Pyridin-2-Amine and Their Schiff Bases

2019 ◽  
pp. 1-5
Author(s):  
Mangesh Vijay Sonawane ◽  
Sandip Balu Chaudhari ◽  
Jaywant Prakash Sonawane ◽  
Suryakant Sudhakar Patil ◽  
Mahesh Rajendra Sonawane ◽  
...  
Keyword(s):  
Ammonium Nitrate ◽  
Schiff Bases ◽  
Aromatic Aldehyde ◽  
Room Temperature ◽  
Ammonium Thiocyanate ◽  
Catalytic Amount ◽  
Ceric Ammonium Nitrate ◽  
Synthesis And Characterization ◽  
Efficient Synthesis

The efficient synthesis of thiazolo pyridine 2-amine(3) by reaction of 2-amino pyridine with ammonium thiocyanate(2). The reaction carried out in presence of ceric ammonium nitrate and Dimethyl Sulphoxide as a solvent. The aromatic aldehyde reacts with synthesized compound thiazolo pyridin-2-amine (3) by using catalytic amount of Ni (NO3)2 .6H2O at room temperature. Advantages of this protocol are its very good yields.

scholarly journals Synthesis and characterization of novel porphyrin Schiff bases

2008 ◽  
Vol 73 (1) ◽  
pp. 1-6 ◽  
Author(s):  
Lei Wang ◽  
Yaqing Feng ◽  
Jinqiang Xue ◽  
Li Yukun
Keyword(s):  
Schiff Base ◽  
Energy Transfer ◽  
Spectral Data ◽  
Schiff Bases ◽  
Chemical Properties ◽  
Synthesis And Characterization ◽  
Intramolecular Energy Transfer ◽  
Porphyrin Moiety

Novel porphyrin Schiff bases were synthesized by a simple Schiff base condensation in refluxing toluene between 5-(4-aminophenyl)-10,15,20-triphe?nylporphyrin (ATTP) 3 and styryl aldehydes 4-6 or p-halobenzaldehydes 7-9. The newly synthesized porphyrin Schiff bases were characterized on the basis of their chemical properties and spectral data. A good intramolecular energy transfer from the styryl unit to the porphyrin moiety was found.

scholarly journals Structure and function of the transketolase from Mycobacterium tuberculosis and comparison with the human enzyme

Open Biology ◽  
2012 ◽  
Vol 2 (1) ◽  
pp. 110026 ◽  
Author(s):  
Elizabeth Fullam ◽  
Florence Pojer ◽  
Terese Bergfors ◽  
T. Alwyn Jones ◽  
Stewart T. Cole
Keyword(s):  
Mycobacterium Tuberculosis ◽  
Structural Model ◽  
Consensus Sequence ◽  
Antitubercular Activity ◽  
Cofactor Binding ◽  
Human Enzyme ◽  
And Function ◽  
Novel Drug ◽  
Invariant Residue

The transketolase (TKT) enzyme in Mycobacterium tuberculosis represents a novel drug target for tuberculosis treatment and has low homology with the orthologous human enzyme. Here, we report on the structural and kinetic characterization of the transketolase from M. tuberculosis (TBTKT), a homodimer whose monomers each comprise 700 amino acids. We show that TBTKT catalyses the oxidation of donor sugars xylulose-5-phosphate and fructose-6-phosphate as well as the reduction of the acceptor sugar ribose-5-phosphate. An invariant residue of the TKT consensus sequence required for thiamine cofactor binding is mutated in TBTKT; yet its catalytic activities are unaffected, and the 2.5 Å resolution structure of full-length TBTKT provides an explanation for this. Key structural differences between the human and mycobacterial TKT enzymes that impact both substrate and cofactor recognition and binding were uncovered. These changes explain the kinetic differences between TBTKT and its human counterpart, and their differential inhibition by small molecules. The availability of a detailed structural model of TBTKT will enable differences between human and M. tuberculosis TKT structures to be exploited to design selective inhibitors with potential antitubercular activity.

scholarly journals Structure-based drug design and characterization of sulfonyl-piperazine benzothiazinone inhibitors of DprE1 from Mycobacterium tuberculosis

2018 ◽  
Author(s):  
Jérémie Piton ◽  
Anthony Vocat ◽  
Andréanne Lupien ◽  
Caroline Foo ◽  
Olga Riabova ◽  
...  
Keyword(s):  
Mycobacterium Tuberculosis ◽  
Drug Design ◽  
Antitubercular Activity ◽  
Cysteine Residue ◽  
Drug Candidate ◽  
Structure Based Drug Design ◽  
Active Site Cysteine ◽  
Covalent Adducts ◽  
Active Site Cysteine Residue

ABSTRACTMacozinone (MCZ) is a tuberculosis (TB) drug candidate that specifically targets the essential flavoenzyme DprE1 thereby blocking synthesis of the cell wall precursor decaprenyl phosphoarabinose (DPA) and provoking lysis of Mycobacterium tuberculosis. As part of the MCZ back-up program we exploited structure-guided drug design to produce a new series of sulfone-containing derivatives, 2-sulphonylpiperazin 8-nitro 6-trifluoromethyl 1,3-benzothiazin-4-one, or sPBTZ. These compounds are less active than MCZ but have a better solubility profile and some derivatives display enhanced stability in microsomal assays. DprE1 was efficiently inhibited by sPBTZ and covalent adducts with the active site cysteine residue (C387) were formed. However, despite the H-bonding potential of the sulfone group no additional bonds were seen in the crystal structure of the sPBTZ-DprE1 complex with compound 11326127 as compared to MCZ. Compound 11626091, the most advanced sPBTZ, displayed good antitubercular activity in the murine model of chronic TB but was less effective than MCZ. Nonetheless, further testing of this MCZ backup compound is warranted as part of combination treatment with other TB drugs.

scholarly journals Synthesis of New Some Imidazole Derivatives Containing ?-Lactam Ring

2016 ◽  
Vol 13 (2) ◽  
pp. 307-316
Author(s):  
Baghdad Science Journal
Keyword(s):  
Nmr Spectroscopy ◽  
Acetic Anhydride ◽  
Hydrazine Hydrate ◽  
Schiff Bases ◽  
Aromatic Aldehyde ◽  
13C Nmr ◽  
13C Nmr Spectroscopy ◽  
Chloroacetyl Chloride ◽  
Lactam Ring ◽  
Ft Ir

In this work 5-methylene-yl - (2-methy –oxazole-4-one) (1H) imidazole (1) were synthesized from the reaction of L-Histidine with acetic anhydride and which converted to the of 5-methylene-yl-(2-methyl 3-amino imidazole-4-one)-1H-imidazole (2) by reaction with hydrazine hydrate. Schiff bases (3-6) were synthesized from the reaction of compound (2) with different aromatic aldehyde. Reaction of compounds (3-6) with chloroacetyl chloride gives azetidinone one derivatives (7-10). These compounds were characterized by FT-IR and some of them with 1H-NMR and 13C-NMR spectroscopy.

scholarly journals Synthesis and characterization of some novel 1,2,4-triazoles, 1,3,4-thiadiazoles and Schiff bases incorporating imidazole moiety as potential antimicrobial agents

2015 ◽  
Vol 65 (2) ◽  
pp. 117-132 ◽  
Author(s):  
Mohamed Reda Aouad ◽  
Mouslim Messali ◽  
Nadjet Rezki ◽  
Adeeb Al-Sheikh Ali ◽  
Alain Lesimple
Keyword(s):  
Hydrazine Hydrate ◽  
Schiff Bases ◽  
Antimicrobial Agents ◽  
Potassium Hydroxide Solution ◽  
Acid Hydrazide ◽  
Aromatic Aldehydes ◽  
Mass Spectral ◽  
H Nmr ◽  
Acidic Conditions

Abstract (1,4,5-Triphenylimidazol-2-yl-thio)butyric acid hydrazide (3) was obtained via alkylation of 1,4,5-triphenylimidazol-2- thiol (1) with ethylbromobutyrate, followed by addition of hydrazine hydrate. Treatment of acid hydrazide 3 with carbon disulfide in an ethanolic potassium hydroxide solution gave the intermediate potassium dithiocarbazinate salt, which was cyclized to 4-amino-5-[(1,4,5-triphenylimidazol- -2-yl)thiopropyl]-2H-1,2,4-triazole-3-thione (4) in the presence of hydrazine hydrate. Condensation of compound 3 with alkyl/arylisothiocyanate afforded the corresponding 1-[4-(1,4,5-triphenylimidazol-2-ylthio)butanoyl]-4-alkyl/arylthiosemicarbazides (5-7), which upon refluxing with sodium hydroxide, yielded the corresponding 1,2,4-triazole - -3-thiols 8-10. Under acidic conditions, compounds 4-6 were converted to aminothiadiazoles 11-13. Moreover, the series of Schiff bases 14-18 were synthesized from the condensation of compound 3 with different aromatic aldehydes. The newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR and mass spectral analyses. They were also preliminarily screened for their antimicrobial activity.

scholarly journals Synthesis, Characterization and Evaluation of Anti-tubercular Activity of Ofloxacin Chalcone Conjugates

2021 ◽  
pp. 22-30
Author(s):  
Ramakrishna Chintakunta ◽  
Venkata Subbareddy Gopireddy
Keyword(s):  
Mycobacterium Tuberculosis ◽  
Melting Point ◽  
Antitubercular Activity ◽  
Deionized Water ◽  
Synthesis And Characterization ◽  
Spectroscopic Methods ◽  
Compound A ◽  
Chalcone Derivatives ◽  
Ft Ir

Synthesis and characterization of Ofloxacin Chalcone derivatives were carried out and evaluated for their antitubercular activity. Synthesized Ofloxacin Chalcone derivatives (Compound A to F). These molecules are characterized by analytical methods (TLC), melting point, and Spectroscopic methods (FT-IR, Mass, NMR). The evaluated antitubercular activity of molecules of synthesized compounds and Ciprofloxacin Pyrazinamide, and Streptomycin as standard drugs. concentrations of synthesized derivatives were prepared (0.8, 1.6, 3.12, 6.25, 12.5, 25, 50, 100 µg/ml) by using sterile deionized water as a solvent. Antitubercular Assay was Performed by Mycobacterium tuberculosis using the MABA method. Analyzed MIC values. Compound E showed the best results among 6 Compounds at a very low concentration at 3.12 µg/ml.

Sign in / Sign up

Export Citation Format

Share Document