Synthesis and Antimicrobial Activity Evaluation of Novel Oxadiazino/Thiadiazino‐Indole and Oxadiazole/Thiadiazole Derivatives of 2‐Oxo‐2<i>H</i>‐benzopyran

Deokar, Hrushikesh; Chaskar, J.; Chaskar, Atul

doi:10.1002/jhet.1761

Cited by 11 publications

(7 citation statements)

References 26 publications

(22 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[16] It was reported that, novel heterocycles containing indole ring have antimicrobial activities against the bacteria Staphylococcus aureus, Salmonella typhi, Escherichia coli and two fungal species Candida albicans, Aspergillus niger. [17] On the other hand indole containing heterocycles were used as antiinflammatory, anticonvulsant agents, antitumor agents in the human cell line and cardioselective antiischemic ATP-sensitive potassium channel (KATP) opener activity. [18,19] Anticancer activity of various tricyclic and tetracyclic indoles, against human Egyptian Journal of Chemistry http://ejchem.journals.ekb.eg/ nasopharyngeal carcinoma (HONE-1) and gastric adenocarcinoma (NUGC-3) cell lines were studied by Hong et al [3,20] Khaledi et al [21], synthesized some indole derivatives which have antioxidant activities on DPPH radical scavenging and inhibition of lipid peroxidation.…”

Section: Introductionmentioning

confidence: 99%

Dihydropyrimidines as Precursors for Synthesizing of Oxoketene gem-Dithiol and 1,2-Dithiol-3-Thione, a Facile Synthesis and Convenient Reaction Transformations

2020

View full text Add to dashboard Cite

In the present work the authors could synthesize the substrates oxoketene gem-dithols 5, ketene dithioacetal 6 and 1,2dithiol-3-thione 39 from compounds bearing both nucleus indole and dihydropyrimidines together due to their biological and pharmacological activities. In this paper, and as a result of biological and pharmacological activities of oxoketene gemdithiols, ketene dithioacetal and/or 1,2-dithiol-3-thione; we synthesized various derivatives of them via indole and dihydropyrimidine in the form of either condensed or fused derivatives. We used ecofriendly methods such as pure orange juice as a green solvent and as an acid catalyst in the same time to prepare, 1-[2-imino-4-(1H-indol-3-yl)-6-methyl-1,2,3,4tetrahydropyrimidin-5-yl]-ethan-1-one 4a and/or 1-[4-(1H-Indol-3-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl]ethan-1-one 4b. Subsequently, the substrate 4b was treated with different reagents to afford, 1-(4-(1H-indol-3-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3,3-dimercaptoprop-2-en-1-one 5 and/or 1-(4-(1H-indol-3-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3,3-bis(methylthio)prop-2-en-1-one 6. Compounds 5 and/or 6 were used as synthons to get various heterocyclic compounds such as 3-(4-(1H-indol-3-yl)-6-methyl-2-(piperidin-1-yl)-1,4-dihydropyrimidine-5-carbonyl)-2-thioxochroman-4-one 16 and/or 4'-(1H-indol-3-yl)-2-mercapto-6'-methyl-6-(methylthio)-2'-thioxo-1',2',3',4'-tetrahydro-[4,5'-bipyrimidine]-5-carbaldehyde 18. The newly synthesized compounds have been in vitro examined as antimicrobial agents, and some of them showed a promising activity. All newly synthesized compounds have been characterized by means of elemental analyses, IR, 1 H-NMR and MS.

show abstract

Section: Introductionmentioning

confidence: 99%

Dihydropyrimidines as Precursors for Synthesizing of Oxoketene gem-Dithiol and 1,2-Dithiol-3-Thione, a Facile Synthesis and Convenient Reaction Transformations

2020

View full text Add to dashboard Cite

show abstract

“…Various 3‐substituted indoles had been used as starting materials for the synthesis of a number of alkaloids, agrochemicals, pharmaceuticals, and perfumes. Also, 3‐substituted indole derivatives possess various types of broad spectrum's biological activities such as antimicrobial, antitumor, hypoglycemic, anti‐inflammatory, analgesic, and antipyretic activities . Moreover, the substitution at the 3‐position of the indole ring can take place by introducing an additional heterocyclic ring, such as imidazole (topsentins, nortopsentins) , dihydroimidazole (discodermindole) , oxazole , thiazole , quinazoline , pyrimidine as shown in Figure , and pyrazoline .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Screening for Anti‐inflammatory and Antimicrobial Activity of Novel Indolyl Chalcone Derivatives

Sayed

El‐Dean

Ahmed

et al. 2018

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Because of the great biological importance of substituted indole derivatives, in the present study, a series of pyrazolylindole, thiazolylindole, and pyrimidinylindole derivatives have been synthesized with good yield. The precursor indolyl chalcone 2a–d was prepared by reaction of 3‐chloro‐1H‐indole‐2‐carbaldehyde 1 with different ketones. Then, compounds 3b–d, 4, and 5a–d have been synthesized by the reaction of chalcones 2a–d with hydrazine, phenylhydrazine, and thiosemicarbazide. When the chalcone derivative 2b subjected to react with hydroxylamine hydrochloride gave isoxazolylindole derivative 6b. N‐thiazolidine pyrazolyl indole 7 was obtained by reacting compound 5a with ethyl chloroacetate. On the other hand, when chalcone derivative 2b allowed to react with urea and thiourea gave the corresponding pyrimidinylindole derivatives 8 and 9. Finally, when chalcone derivative 2b reacted with ethyl cyanoacetate or malononitrile gave pyridinylindole derivatives 10 and 11. The structures of the all synthesized compounds were elucidated on the basis of spectral analysis infrared, NMR, and mass spectroscopy. Some of the synthesized compounds were screened for their antimicrobial and anti‐inflammatory activity. Compound 4b was the highest antibacterial activity against all strains of bacteria with values higher than those of the corresponding reference antibiotics (ciprofloxacin and levofoxacin, respectively) and almost the same as (gemifloxacin, moxifloxacin, clindamycin, gentamycin, and streptomycin). Compounds 4, 5, 6, and 7 showed high anti‐inflammatory activity compared with the standard drug indomethacin.

show abstract

“…The most commonly reported methodology for the synthesis of this group of compounds uses N,N′ ‐diacylhydrazines which treated with diphosphorus pentasulfide or Lawesson's reagent undergo cyclization forming the desired heterocyclic arrangement. Other sources describe also exchange of oxygen atom in 1,3,4‐oxadiazoles to sulfur using thiourea , the cyclization of bithioureas , or thiosemicarbazides with another compounds containing a carbonyl group .…”

Section: Introductionmentioning

confidence: 99%

Convenient Synthesis and Biological Activity of Mono and Diacyl 2,5‐Dimercapto‐1,3,4‐thiadiazole Derivatives

Jasiak

Kudelko

Wróblowska

et al. 2017

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Synthesis and Antimicrobial Activity Evaluation of Novel Oxadiazino/Thiadiazino‐Indole and Oxadiazole/Thiadiazole Derivatives of 2‐Oxo‐2H‐benzopyran

Cited by 11 publications

References 26 publications

Dihydropyrimidines as Precursors for Synthesizing of Oxoketene gem-Dithiol and 1,2-Dithiol-3-Thione, a Facile Synthesis and Convenient Reaction Transformations

Dihydropyrimidines as Precursors for Synthesizing of Oxoketene gem-Dithiol and 1,2-Dithiol-3-Thione, a Facile Synthesis and Convenient Reaction Transformations

Synthesis, Characterization, and Screening for Anti‐inflammatory and Antimicrobial Activity of Novel Indolyl Chalcone Derivatives

Convenient Synthesis and Biological Activity of Mono and Diacyl 2,5‐Dimercapto‐1,3,4‐thiadiazole Derivatives

Contact Info

Product

Resources

About