Synthesis and Antituberculotic Properties of Some Substituted Pyrazinecarbothioamides

1996 ◽  
Vol 61 (7) ◽  
pp. 1102-1108 ◽  
Author(s):  
Martin Doležal ◽  
Jiří Hartl ◽  
Antonín Lyčka ◽  
Vladimír Buchta ◽  
Želmíra Odlerová
Keyword(s):  
Mycobacterium Tuberculosis ◽  
Elemental Analysis ◽  
Nmr Spectra ◽  
Susceptibility Testing ◽  
Pathogenic Fungi ◽  
H Nmr

A series of N-substituted 3-amino-5-thiocarbamoyl-2-pyrazinecarboxamides was prepared. The structure of compounds was confirmed by elemental analysis, IR and 1H NMR spectra. The results of in vitro antifugal and antimycobacterial susceptibility testing shown no activity against pathogenic fungi and some effect on mycobacteria. The highest antituberculotic activity (MIC within 25-50 mg ml-1) against Mycobacterium tuberculosis and other mycobacterial strains in this series was shown by 3-(3-hydroxyphenylamino)-5-thiocarbamoyl-2-pyrazinecarboxamide. The antituberculotic activity of these compounds is mostly influenced by the presence of the thioamide moiety.

Synthesis and Antituberculotic Activity of 5-Alkyl-6-chloro-2-pyrazinecarboxamides and Corresponding Thioamides

1996 ◽  
Vol 61 (7) ◽  
pp. 1109-1114 ◽  
Author(s):  
Jiří Hartl ◽  
Martin Doležal ◽  
Jana Krinková ◽  
Antonín Lyčka ◽  
Želmíra Odlerová
Keyword(s):  
Mycobacterium Tuberculosis ◽  
Elemental Analysis ◽  
Nmr Spectra ◽  
Antimycobacterial Activity ◽  
Partial Hydrolysis ◽  
Alkanoic Acid ◽  
H Nmr ◽  
Homolytic Alkylation ◽  
Lawesson's Reagent

Homolytic alkylation of 6-chloro-2-pyrazinecarbonitrile by alkanoic acid and subsequent partial hydrolysis afforded 5-alkyl-6-chloro-2-pyrazinecarboxamides 1a-1e. Reaction of amides 1a-1e by Lawesson's reagent afforded corresponding thioamides 2a-2e. The structure of compounds was confirmed by elemental analysis, IR and 1H NMR spectra. The assessment of in vitro antimycobacterial activity of the compounds was carried out. The highest antituberculotic activity against Mycobacterium tuberculosis and other mycobacterial strains in this series was shown by 5-(1,1-dimethylethyl)-6-chloro-2-pyrazinecarbothioamide (2e).

Synthesis and Antituberculotic Activity of Some Substituted 3-Arylamino-5-cyano-2-pyrazinecarboxamides

1995 ◽  
Vol 60 (7) ◽  
pp. 1236-1241 ◽  
Author(s):  
Martin Doležal ◽  
Jiří Hartl ◽  
Antonín Lyčka ◽  
Vladimír Buchta ◽  
Želmíra Odlerová
Keyword(s):  
Nucleophilic Substitution ◽  
Elemental Analysis ◽  
Nmr Spectra ◽  
Substituted Anilines ◽  
H Nmr

Nucleophilic substitution of 3-chloro-5-cyano-2-pyrazinecarboxamide by substituted anilines afforded substituted 3-arylamino-5-cyano-2-pyrazinecarboxamides I-X. The structures of compounds were confirmed by elemental analysis, UV, IR and 1H NMR spectra. The assessment of in vitro antimycotic and antimycobacterial activities of the compounds was carried out. The highest antituberculotic activity against M. tuberculosis in this series was shown by 3-anilino- 5-cyano-2-pyrazinecarboxamide (I), whose efficacy was the same as that of pyrazinecarboxamide.

scholarly journals Synthesis and antifungal activity of new salicylic acid derivatives

2017 ◽  
Vol 19 (1) ◽  
pp. 143-148 ◽  
Author(s):  
Alicja Wodnicka ◽  
Elżbieta Huzar ◽  
Maria Krawczyk ◽  
Halina Kwiecień
Keyword(s):  
Salicylic Acid ◽  
Nmr Spectra ◽  
Fungicidal Activity ◽  
Pathogenic Fungi ◽  
Good Activity ◽  
H Nmr ◽  
Step Procedure ◽  
One Step ◽  
Salicylic Acid Derivatives

Abstract A simple one-step procedure for synthesis of 1-methoxy-1-oxoalkan-2-yl salicylates and 1-methoxy-1-oxoalkan-2-yl 2-[(1-methoxy-1-oxoalkan-2-yl)oxy]benzoates by reaction of salicylic acid with several methyl 2-bromoalkanoates was developed. The reactions were carried out in N,N-dimethylformamide (DMF) in the presence of anhydrous potassium carbonate. Conditions for regioselective synthesis of target compounds were established. The developed procedure could be easily applied in the industrial production process. The new salicylic acid derivatives were obtained with satisfactory yields and were characterized by MS and 1H NMR spectra. The fungicidal activity of the prepared compounds was tested in vitro against seven species of plant pathogenic fungi. The best results were observed for 1-methoxy-1-oxoalkan-2-yl salicylates which showed moderate or good activity against Botrytis cinerea and Rhizoctonia solani.

scholarly journals SYNTHESIS AND STRUCTURAL ELUCIDATION OF AMINO ACETYLENIC AND THIOCARBAMATES DERIVATIVES FOR 2-MERCAPTOBENZOTHIAZOLE AS ANTIMICROBIAL AGENTS

2017 ◽  
Vol 9 (2) ◽  
pp. 192
Author(s):  
Aseel Alsarahni ◽  
Zuhair Muhi Eldeen ◽  
Elham Al-kaissi ◽  
Ibrahim Al- Adham ◽  
Najah Al-muhtaseb
Keyword(s):  
Antimicrobial Activity ◽  
Elemental Analysis ◽  
Antimicrobial Agents ◽  
Diffusion Method ◽  
Benzothiazole Derivatives ◽  
H Nmr ◽  
Ft Ir ◽  
Potential Antimicrobial Activity ◽  
C Nmr

<p><strong>Objective: </strong>To design and synthesize amino acetylenic and thiocarbonate of 2-mercapto-1,3-benthiazoles as potential antimicrobial agents.</p><p><strong>Methods: </strong>A new series of 2-{[4-(t-amino-1-yl) but-2-yn-1-yl] sulfanyl}-1,3-benzothiazole derivatives (AZ1-AZ6), and S-1,3-benzothiazol-2-yl-O-alkyl carbonothioate derivatives were synthesised, with the aim that the target compounds show new and potential antimicrobial activity. The elemental analysis was indicated by the EuroEA elemental analyzer, and biological characterization was via IR, <sup>1</sup>H-NMR, [13]C-NMR, DSC were determined with the aid of Bruker FT-IR and Varian 300 MHz spectrometer using DMSO-d<sub>6</sub> as a solvent.<em> </em><em>In vitro </em>antimicrobial activity, evaluation was done for the synthesised compounds, by agar diffusion method and broth dilution test. The minimum inhibitory concentration (MIC) and the minimum bactericidal concentration (MBC) were determined. <em></em></p><p><strong>Results: </strong>The IR, <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, DSC and elemental analysis were consistent with the assigned structures. Compound of 2-{[4-(4-methylpiperazin-1-yl)but-2-yn-1-yl] sulfanyl}-1,3-benzothiazole (AZ1), 2-{[4-(2-methylpiperidin-1-yl)but-2-yn-1-yl]sulfanyl}-1,3-benzothiazole (AZ2), 2-{[4-(piperidin-1-yl) but-2-yn-1-yl]sulfanyl}-1, 3-benzothiazole (AZ6), S-1,3-benzothiazol-2-yl-O-ethyl carbonothioate (AZ7), and S-1,3-benzothiazol-2-yl-O-(2-methylpropyl) carbonothioate (AZ9) showed the highest antimicrobial activity against <em>Pseudomonas aeruginosa </em>(<em>P. aeruginosa</em>), AZ-9 demonstrated the highest antifungal activity against <em>Candida albicans </em>(<em>C. albicans</em>), with MIC of 31.25 µg/ml.</p><p><strong>Conclusion: </strong>These promising results promoted our interest to investigate other structural analogues for their antimicrobial activity further.</p>

Reactions of n-C5H5Co(CO)2 and n-Me3SiC5H4Co(CO)2 with (XCN)2 and X(CN)2 (X = S or Se)

1982 ◽  
Vol 37 (3) ◽  
pp. 292-298 ◽  
Author(s):  
Moisés Morán ◽  
Augusto Ibáñez
Keyword(s):  
Elemental Analysis ◽  
Nmr Spectra ◽  
Polar Solvents ◽  
Mixed Complexes ◽  
H Nmr ◽  
Linkage Isomerism

Abstract The pseudohalogens (XCN)2 (X = S or Se) react with n-C5H5Co(CO)2 and n-Me3SiC5H4Co(CO)2 with formation of the 18 electron complexes, RCo(CO)(XCN)2 (R = n-C5H5 or n-Me3SiC5H4). By reactions with X(CN)2 (X = S or Se), the cyclopentadienyl cobalt dicarbonyls are transformed into the mixed complexes, RCo(CO)(CN)(XVN) (R = n-C5H5 or n-Me3SiC5H4. All the compounds are characterized by elemental analysis, IR, electronic and 1H NMR spectra. The thiocyanogen derivatives undergo linkage isomerism (N→S) in polar solvents.

Infrared, 1H-NMR Spectral Studies of some Methyl 6-O-Myristoyl-α-D-Glucopyranoside Derivatives: Assessment of Antimicrobial Effects

2015 ◽  
Vol 58 ◽  
pp. 122-136 ◽  
Author(s):  
Sarkar M.A. Kawsar ◽  
Khaleda Mymona ◽  
Refat Asma ◽  
Mohammad A. Manchur ◽  
Yasuhiro Koide ◽  
...  
Keyword(s):  
Pathogenic Fungi ◽  
Spectral Studies ◽  
Bacterial Strains ◽  
Substitution Product ◽  
Antifungal Activities ◽  
H Nmr ◽  
Antibacterial And Antifungal Activities ◽  
Fungal Phytopathogens ◽  
Antibacterial And Antifungal

This study was carried out to regioselective myristoylation of methyl α-D-glucopyranoside (1) using the direct acylation method gave the corresponding methyl 6-O-myristoyl-α-D-glucopyranoside (2) in fair yield. A number of 2,3,4-tri-O-acyl derivatives (3-15) of this 6-O-substitution product using a wide variety of acylating agents were also prepared in order to obtain newer derivatives of synthetic and biological importance. The reaction conditions are reasonably simple and yields were very good. The structures of the title compounds (2-15) were established by using analytical, physicochemical techniques and spectroscopic data (IR and 1H-NMR). All the synthesized compounds were employed as test chemicals for in vitro antimicrobial functionality test against Gram-positive Bacillus subtilis, Staphylococcus aureus, Gram-negative Escherichia coli, Pseudomonas aeruginosa bacteria and plant pathogenic fungi Aspergillus niger and Candida albicans. For comparative studies, antimicrobial activity of standard antibiotics, Ampicillin and Nystatin were also carried out against these microorganisms. The study revealed that the tested samples exhibited moderate to good antibacterial and antifungal activities. It was also observed that the test substances were more effective against fungal phytopathogens than those of the human bacterial strains. Encouragingly, a number of tested chemicals showed nearest antibacterial and antifungal activities with the standard antibiotics employed.

A Novel Reductive Cross-coupling Reaction of 2-nitrobenzoic Hydrazides and Aldehydes or Ketones Promoted by the Low-valence Titanium Reagent: An Access to 2,3,4,5-tetrahydro-1H-1,3,4-benzotriazepine-5-one Derivatives

2005 ◽  
Vol 2005 (9) ◽  
pp. 553-555 ◽  
Author(s):  
Daqing Shi ◽  
Chunling Shi ◽  
Liangce Rong ◽  
Juxian Wang ◽  
Qiya Zhuang ◽  
...  
Keyword(s):  
Elemental Analysis ◽  
Nmr Spectra ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Reductive Coupling ◽  
Facile Synthesis ◽  
H Nmr ◽  
Cross Coupling Reaction

A short and facile synthesis of a series of 2,3,4,5-tetrahydro-1H-1,3,4-benzotriazepine-5-one derivatives was accomplished in good yields via the intermolecular reductive coupling reaction of 2-nitrobenzoic hydrazides and aldehydes or ketones promoted by the low-valence titanium reagent (TiCl4/Zn system). Structures were established on the basis of elemental analysis, IR and 1H NMR spectra.

Synthesis of Several Hydroxylated 23-(Benzimidazol-2-yl-, Benzoxazol-2-yl and Benzothiazol-2-yl)norcholanes and Some Related Compounds

1995 ◽  
Vol 60 (2) ◽  
pp. 257-275 ◽  
Author(s):  
Thi Thu Huong Nguyen ◽  
Jiří Urban ◽  
Eva Klinotová ◽  
Jan Sejbal ◽  
Jiří Protiva ◽  
...  
Keyword(s):  
Nmr Spectra ◽  
Succinic Anhydride ◽  
Benzimidazole Derivative ◽  
Acid Chlorides ◽  
H Nmr ◽  
Hydroxy Compounds ◽  
Related Compounds ◽  
Anti Hiv ◽  
C Nmr

The bile acids Ia - Id (lithocholic, chenodeoxycholic, deoxycholic, cholic) and their derivatives (O-acetylated acids and O-acetylated acid chlorides) reacted under various conditions with 1,2-diaminobenzene, 2-aminophenol and 2-aminothiophenol and afforded the title benzimidazoles II and VII, benzoxazoles V and benzothiazoles VI. Alkylation of the benzimidazole derivative IIa with 2-dimethylaminoethyl chloride resulted in 3α-hydroxy-23-[1-(2-dimethylaminoethyl)ben zimidazol-2-yl]- norcholane (IVa). The use of 1,2-diamino-4-methylbenzene enabled the preparation of 3α-acetoxy-23-[5(6)-methylbenzimidazol-2-y l]norcholane (VIII). Reactions of the 3α-hydroxy compounds IVa, Va and VIa with succinic anhydride resulted in the hemisuccinates IVi - VIi. The boric acid mediated condensation of O-acetyllithocholic acid (Ie) with 3,4-diaminopyridine gave compound X which was transformed to 3α-acetoxy-23-[1H-imidazo(4,5- c)pyridin-2-yl]norcholane (IX). The structure of the products was corroborated by the mass, IR, 1H NMR and 13C NMR spectra. Some of the compounds were tested for antileukemic and for the anti-HIV activity in vitro.

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