scholarly journals Synthesis of some biologically active 2,4'-bipyridine-5-carbonitriles carrying the 4-hydroxyphenylthio moiety

2009 ◽  
Vol 74 (7) ◽  
pp. 733-743 ◽  
Author(s):  
T. Karabasanagouda ◽  
Vasudeva Adhikari ◽  
G. Parameshwarappa
Keyword(s):  
13C Nmr ◽  
Ammonium Acetate ◽  
Ethyl Cyanoacetate ◽  
Aromatic Aldehydes ◽  
Biologically Active ◽  
The Other ◽  
Mass Spectral Data ◽  
1H And 13C Nmr ◽  
Mass Spectral

A series of new 4-aryl-2'-[(4-hydroxyphenyl)thio]-6oxo-1,6-dihydro- 2,4'-bipyridine-5-carbonitriles (3a-k) and 6-amino-4aryl-2'-[(4-hydroxyphenyl) thio]-2,4'-bipyridine-5-carbonitriles (4a-h) were synthesized from 4-hydroxythiophenol (1). The reaction of 4-hydroxythiophenol with 4-acetyl-2-chloropyridine yielded 1-{2-[(4-hydroxyphenyl)thio]pyridin-4-yl}ethanone (2). Further treatment of 2 with ethyl cyanoacetate in the presence of ammonium acetate with various aromatic aldehydes furnished the compounds 3a-k. On the other hand, condensation of 2 with aromatic aldehydes in the presence of alcoholic malononitrile in ammonium acetate gave compounds 4a-h. The structures of the newly synthesized compounds were established on the basis of their elemental analysis, as well as their IR, 1H- and 13C-NMR and mass spectral data. All the title compounds were subjected to in vitro antibacterial testing against two strains and antifungal screening against two fungi. Some of the compounds showed promising activity.

scholarly journals AN EFFICIENT THREE COMPONENT ONE-POT SYNTHESIS OF -1,2,3,4-TETRAHYDRO-4-OXO- 6-(5-SUBSTITUTED 2-PHENYL-1H-INDOL-3-YL)-2-THIOXOPYRIMIDINE-5-CARBONITRILE AS ANTIMICROBIAL AND ANTITUBERCULAR AGENTS

2021 ◽  
pp. 94-97
Author(s):  
PRABHAKER WALMIK
Keyword(s):  
Spectral Data ◽  
13C Nmr ◽  
Antitubercular Agents ◽  
Mass Spectral Data ◽  
One Pot ◽  
1H And 13C Nmr ◽  
Spectral Techniques ◽  
Mass Spectral ◽  
One Pot Synthesis

Objective: The objective of the study was to synthesis of 1,2,3,4-tetrahydro-4-oxo-6-(5-substituted 2-phenyl-1H-indol-3-yl)-2-thioxopyrimidine-5- carbonitrile derivatives (4a-c). Methods: The structures of all these unknown compounds have been confirmed with the help of physical and spectral techniques such as IR, 1H, and 13C NMR and mass spectral data and these newly synthesized compounds were evaluated for in-vitro antimicrobial and antitubercular activities. Results: Screening studies have demonstrated that the newly synthesized compound 4a exhibited promising antimicrobial and antitubercular properties. Conclusion: The final results revealed that compound 4a exhibited promising antimicrobial and antitubercular properties when compared to the standard drugs.

scholarly journals Green Synthetic Protocol for (E)-1-Aryl-3-(2-morpholinoquinolin- 3-yl)prop-2-en-1-ones and Their Antimicrobial Activity

2019 ◽  
Vol 31 (9) ◽  
pp. 1895-1898
Author(s):  
Relangi Siva Subrahmanyam ◽  
Venkateswara Rao Anna
Keyword(s):  
Antimicrobial Activity ◽  
Spectral Data ◽  
1H Nmr ◽  
13C Nmr ◽  
Mass Spectral Data ◽  
In Vitro Antimicrobial Activity ◽  
Mass Spectral ◽  
Fungal Organisms

We report here an easy, efficient and green synthetic protocol for the (E)-1-aryl-3-(2-morpholinoquinolin-3-yl)prop-2-en-1-ones by the Claisen-Schmidt condensation of 2-morpholinoquinoline-3-carbaldehyde and different substituted acetophenones by using 1-butyl-3-methylimidazolium tetrafluoroborate (Bmim)BF4. The compounds were characterized by using 1H NMR, 13C NMR and mass spectral data and screened there in vitro antimicrobial activity against different bacterial and fungal organisms.

scholarly journals Synthesis and Pharmacological Evaluation of 2-(4-Halosubstituted phenyl)-4,5-diphenyl-1H-imidazoles

2008 ◽  
Vol 5 (3) ◽  
pp. 447-452 ◽  
Author(s):  
G. Nagalakshmi
Keyword(s):  
Anticonvulsant Activity ◽  
Glacial Acetic Acid ◽  
Ammonium Acetate ◽  
Antiinflammatory Activity ◽  
Aromatic Aldehydes ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
H Nmr ◽  
Structural Assignment ◽  
Paw Oedema

In the present study, 2-(4-halosubstituted phenyl)-4,5-diphenyl-1Himidazoles have been synthesized by refluxing benzil and ammonium acetate with different 4-halosubstituted aromatic aldehydes in glacial acetic acid. The structural assignment of this compound has been made on the basis of elemental analysis, UV, IR,1H NMR and Mass spectral data. Toxicity of the compound has been determined. The synthesized compound was evaluated for antiinflammatory activity against carrageenan induced paw oedema and anticonvulsant activity against maximal electro-shock-induced convulsions in rats.

scholarly journals Synthesis of Novel N-Acylhydrazones and Their C-N/N-N Bond Conformational Characterization by NMR Spectroscopy

Molecules ◽  
2021 ◽  
Vol 26 (16) ◽  
pp. 4908
Author(s):  
Rubina Munir ◽  
Noman Javid ◽  
Muhammad Zia-ur-Rehman ◽  
Muhammad Zaheer ◽  
Rahila Huma ◽  
...  
Keyword(s):  
13C Nmr ◽  
Nmr Spectra ◽  
Room Temperature ◽  
Aromatic Aldehydes ◽  
Spectral Studies ◽  
13C Nmr Spectra ◽  
1H And 13C Nmr ◽  
Mass Spectral ◽  
Nmr Techniques ◽  
Ft Ir

In this article, a synthesis of N’-(benzylidene)-2-(6-methyl-1H-pyrazolo[3,4-b]quinolin-1-yl)acetohydrazides and their structural interpretation by NMR experiments is described in an attempt to explain the duplication of some peaks in their 1H- and 13C-NMR spectra. Twenty new 6-methyl-1H-pyrazolo[3,4-b]quinoline substituted N-acylhydrazones 6(a–t) were synthesized from 2-chloro-6-methylquinoline-3-carbaldehyde (1) in four steps. 2-Chloro-6-methylquinoline-3-carbaldehyde (1) afforded 6-methyl-1H-pyrazolo[3,4-b]quinoline (2), which upon N-alkylation yielded 2-(6-methyl-1H-pyrazolo[3,4-b]quinolin-1-yl)acetate (3). The hydrazinolysis of 3 followed by the condensation of resulting 2-(6-methyl-1H-pyrazolo[3,4-b]quinolin-1-yl)acetohydrazide (4) with aromatic aldehydes gave N-acylhydrazones 6(a–t). Structures of the synthesized compounds were established by readily available techniques such as FT-IR, NMR and mass spectral studies. The stereochemical behavior of 6(a–t) was studied in dimethyl sulfoxide-d6 solvent by means of 1H NMR and 13C NMR techniques at room temperature. NMR spectra revealed the presence of N’-(benzylidene)-2-(6-methyl-1H-pyrazolo[3,4-b]quinolin-1-yl)acetohydrazides as a mixture of two conformers, i.e., E(C=N)(N-N) synperiplanar and E(C=N)(N-N)antiperiplanar at room temperature in DMSO-d6. The ratio of both conformers was also calculated and E(C=N) (N-N) syn-periplanar conformer was established to be in higher percentage in equilibrium with the E(C=N) (N-N)anti-periplanar form.

Synthesis and study of some new N-substituted imide derivatives as potential antibacterial agents

2010 ◽  
Vol 64 (5) ◽  
Author(s):  
Abd Khalil ◽  
Moged Berghot ◽  
Moustafa Gouda
Keyword(s):  
Antimicrobial Activity ◽  
Spectral Data ◽  
13C Nmr ◽  
Antibacterial Agents ◽  
Mass Spectral Data ◽  
1H And 13C Nmr ◽  
Mass Spectral ◽  
Starting Compound

AbstractDibenzobarrelene (I) was used as a starting compound for the synthesis of some new 3a,4,9,9a-tetrahydro-4,9-[1,2]benzeno-1H-benzo[f]isoindole-1,3(2H)-diones, N-substituted with: 4-toluenesulfonyloxy, III; butoxy, IV; 3-bromopropoxy, V; 3-(4-phenylpiperazin-1-yl)propoxy, VI; 3-chloro-3-oxopropyl, VIII; 3-(4-phenylpiperazin-1-yl)-3-oxopropyl, IXa; 3-(4-methylpiperazin-1-yl)-3-oxopropyl, IXb; 3-oxo-3-(piperidin-1-yl)propyl, X; 3-morpholino-3-oxopropyl, XI; 3-phenylamino-3-oxopropyl, XII; 2-acetylaminoethyl, XIV; 2-aminoethyl, XV, and 2-acetoxyethyl, XVI. Newly synthesized compounds were characterized by IR, 1H and 13C NMR, and mass spectral data. Selected products were tested for antimicrobial activity.

Hydroxyl-containing bis(sulfonates). Reaction of 1,4-dibromo-2,3-butanedione with water, methanol and sodium sulfite

2021 ◽  
pp. 1-12
Author(s):  
Gerasimos M. Tsivgoulis ◽  
Dimitris G. Vachliotis ◽  
Golfo G. Kordopati ◽  
Panayiotis V. Ioannou
Keyword(s):  
13C Nmr ◽  
Sodium Sulfite ◽  
The Other ◽  
Carbonyl Carbon ◽  
1H And 13C Nmr ◽  
Sodium Sulfonate ◽  
Pure Product ◽  
Methylene Groups ◽  
New Type ◽  
High Yields

Sulfonates are well-known substances with a variety of applications, e.g. as surfactants. On the other hand, bis(sulfonates) bearing hydroxyl or keto group(s) in between the sulfonate groups can be used with or without further modification as starting materials for the preparation of new type of molecules capable to form either complexes or in general supramolecular structures. The synthesis of three hydroxyl-bearing bis(sulfonates), 2-hydroxypropane-1,3-bis(sodium sulfonate) 4, DL-2,3-dihydroxybutane-1,4-bis(sodium sulfonate) 8, and sodium 2,3,4-trihydroxy-1-sulfonate 7 (as by-product) via the Strecker sulfonation are described. Interestingly, under similar conditions, sulfonation of 1,4-dibromo-2,3-butanedione 9 was found to be very complicated and no pure product could be isolated, despite previously reported results on sulfonation of α-halogenated ketones in high yields. There are indications that SO3 2 -  attacks at the carbonyl carbon of 9 followed by rearrangement and expulsion of SO4 2 - . 1,4-dibromo-2,3-butanedione 9, bearing two keto groups next to methylene groups, can potentially exist as enols or in the case of its solution in hydroxylic solvents in the form of hemiketals or geminal diols. This behavior of 9 when is dissolved in CDCl3, CD3OD and D2O was studied by means of UV-Vis, 1H and 13C NMR and the nature of the adducts formed was elucidated.

scholarly journals N-(2-(1H-Indol-3-yl)ethyl)-2-(6-methoxynaphthalen-2-yl)propanamide

Molbank ◽  
10.3390/m1187 ◽  
2021 ◽  
Vol 2021 (1) ◽  
pp. M1187
Author(s):  
Stanimir Manolov ◽  
Iliyan Ivanov ◽  
Dimitar Bojilov
Keyword(s):  
Spectral Data ◽  
13C Nmr ◽  
Title Compound ◽  
High Yield ◽  
Mass Spectral Data ◽  
Mass Spectral

The title compound was obtained in high yield in the reaction between tryptamine and naproxen. The newly synthesized naproxen derivative was fully analyzed and characterized via 1H, 13C-NMR, UV, IR, and mass spectral data.

scholarly journals (1R,4S,5S)-5-((3-Hydroxypropyl)amino)-4-((1-Methyl-1H-tetrazol-5-yl)thio)Cyclopent-2-en-1-ol

Molbank ◽  
10.3390/m1199 ◽  
2021 ◽  
Vol 2021 (2) ◽  
pp. M1199
Author(s):  
Milene A. G. Fortunato ◽  
Filipa Siopa ◽  
Carlos A. M. Afonso
Keyword(s):  
Spectral Data ◽  
13C Nmr ◽  
Ring Opening ◽  
Environmentally Friendly ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
Excellent Yield ◽  
Ring Opening Reaction ◽  
Nucleophilic Ring Opening

Using environmentally friendly conditions, the nucleophilic ring-opening reaction of 6-azabicyclo[3.1.0]hex-3-en-2-ol with 1-methyl-1H-tetrazole-5-thiol provided a novel thiol-incorporated aminocyclopentitol, (1R,4S,5S)-5-((3-hydroxypropyl)amino)-4-((1-methyl-1H-tetrazol-5-yl)thio)cyclopent-2-en-1-ol, in excellent yield (95%). The newly synthesized compound was analyzed and characterized via 1H, 13C-NMR, HSQC, and mass spectral data.

Detailed 1H and 13C NMR structural assignment of three biologically active lignan lactones

2006 ◽  
Vol 63 (1) ◽  
pp. 234-239 ◽  
Author(s):  
Vladimir Constantino Gomes Heleno ◽  
Rosangela da Silva ◽  
Susimaire Pedersoli ◽  
Sérgio de Albuquerque ◽  
Jairo Kenupp Bastos ◽  
...  
Keyword(s):  
13C Nmr ◽  
Biologically Active ◽  
1H And 13C Nmr ◽  
Structural Assignment

SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL EVALUATION OF SOME NEWER BENZIMIDAZOLE DERIVATIVES BY MANNICH REACTION

INDIAN DRUGS ◽  
2019 ◽  
Vol 56 (07) ◽  
pp. 16-22
Author(s):  
N. Kumar ◽  
D Pathak ◽  
Keyword(s):  
Salicylic Acid ◽  
Elemental Analysis ◽  
Mannich Reaction ◽  
Anthelmintic Activity ◽  
Biological Evaluation ◽  
Benzimidazole Derivatives ◽  
Good Activity ◽  
Mass Spectral Data ◽  
Mass Spectral

O-phenylenediamine and salicylic acid were used for the synthesis of 2-(1-(substituted phenylamino) methyl-1H benzo[d] imidazol-2-yl) phenol (2a-2h) derivatives by using various substituted aniline. In the first step, reaction of o-phenylenediamine and salicylic acid yielded 2-(1H-benzo[d]imidazol-2-yl) phenol (1), which on Mannich reaction with substituted aniline gave compounds (2a-2h). The structures of these compounds were characterized by IR, 1H NMR, mass spectral data and elemental analysis. Each analogue was tested in vitro for various types of pharmacological activity of this class of drugs including antibacterial, antifungal and anthelmintic activity. Among the synthesized compounds 2a act as vermifuge and no compound was found to be a vermicide. The compound 2c was found to be most active against E.coli and P. aeurigenosa and 2e be most active against B.subtilis and S.aureus. The derivative 2h shows good activity against C.albicans and A.niger.

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