Synthesis of some heterocyclic compounds derived from indole as antimicrobial agents

Sayed, Mostafa; El‐Dean, Adel M. Kamal; Ahmed, Mostafa; Hassanien, Reda

doi:10.1080/00397911.2017.1403627

Cited by 48 publications

(25 citation statements)

References 35 publications

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“…As reviewed from earlier literature reports, such compounds containing indole and pyrimidine were found to be potent as antitumor, antimicrobial, and antioxidant agents . Based on these previous facts and in continuation of our work in the field of synthesis of organic compounds with high biological activity, here, we described a method for introducing pyrimidine moiety in two positions of indole, hopefully improving the potency of the synthesized compounds. We aimed to synthesize molecules comprising these two pharmacophores in a single molecular framework.…”

Section: Introductionmentioning

confidence: 84%

Design, synthesis, and characterization of novel pyrimidines bearing indole as antimicrobial agents

Sayed

El‐Dean

Ahmed

et al. 2018

J Chinese Chemical Soc

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Pyrimidines and pyrimidine bearing indole derivatives are very important species in organic chemistry due to their wide use as bioactive compounds with a broad range of good biological activities. Due to the wide spread of different species of bacteria and fungi nowadays, in the present work, a novel series of indolyl‐pyrimidines (2–13) were synthesized starting from 3‐chloro‐1H‐indole‐2‐carbaldehyde (1). Elemental analysis, IR, 1H‐NMR, 13C‐NMR, and mass spectral data elucidated the structure of newly synthesized compounds. All compounds were screened for their in vitro antibacterial and antifungal activity, and they demonstrated promising results; all the new compounds synthesized from compound (1), which allowed reactions with thiourea and ethyl cyanoacetate, gave the target compound (2), which was used as a precursor for the synthesis of indolylthiazolopyrimidine derivatives (3–8) by reactions with halocarbonyl compounds such as chloroacetone, phancyl bromide, and chloroacetic acid through alkylation of the mercapto group followed by cyclization through a nucleophilic attack. When compound (2) subjected to react with hydrazine hydrate gave 4‐indolyl‐2‐hydrazinopyrimidine (5), the latter compound, when allowed to react with ethyl chloroacetate or diethyloxalate, gave indolylpyrimidotriazine derivatives (10,11); in contrast, when the compound reacted with acetic anhydride or formic acid, it gave triazolopyrimidine derivatives (12, 13).

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Section: Introductionmentioning

confidence: 84%

Design, synthesis, and characterization of novel pyrimidines bearing indole as antimicrobial agents

Sayed

El‐Dean

Ahmed

et al. 2018

J Chinese Chemical Soc

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“…Indoles and their derivatives constitute an important class of heterocyclic compounds. In addition the chemistry and pharmacology of indole have been of great interest to medicinal chemists because indole derivatives possessed various biological activities, such as anti-inflammatory [1][2][3], antibacterial [4,5], antimicrobial [6,7],antifungal [8], antihypertensive [9] , anticonvulsant [10][11][12][13][14][15][16] activities. It is interesting to note from chemical literature that various new pharmacophores like oxadiazoles [17][18][19], thiazolidinones [20][21][22][23][24][25] and azetidinones [26][27][28][29] were also found to possess wide spectrum of anticonvulsant activity in various experimental models.…”

Section: Introductionmentioning

confidence: 99%

“…It was observed that compound having phenyl group (compound 5) as substituent showed the least activity (40 %) while compound 4 substituted with 4-methoxyphenyl ring exhibited the maximum percent protection (60 %) against seizures. Compounds (6,7 and 8) substituted with 3-methoxy-4-hydroxy phenyl ring(6), N,N-dimethylphenyl ring (7) and 4-hydroxyphenyl ring (8) exhibited 50 % inhibition of seizures.…”

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confidence: 99%

Synthesis and Anticonvulsant Studies of Thiazolidinone and Azetidinone Derivatives from Indole Moiety

Saini

Archana

2018

Drug Res (Stuttg)

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Abstract2-Amino-5-(3’-indolomethylene)-1, 3 , 4 - oxadiazole (3) undergoes facile condensation with various aromatic aldehydes to gave 2-substitiuted arylidenylamino-5-(3’- indolomethylene) – 1, 3 , 4 – oxadiazole (4–8). Cyclocondensation of (4–8) with thioglycolic acid and triethylamine yielded 3-[5’-(3”- indolomethylene)- 1’, 3’, 4’- oxadiazol-2’-yl]- 2- (substituted aryl)-4- thiazolidinones (9–13) and 1-[5’-(3”- indolomethylene) -1’, 3’, 4’- oxadiazol - 2’- yl ] -4-(substituted aryl) -2- azetidinones (14–18). The structures of these compounds were established on the basis of analytical and spectral data. The newly synthesised compounds were evaluated for their anticonvulsant activity and acute toxicity.

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Section: Introductionmentioning

confidence: 99%

“…The great number of heterocyclic compounds is used in medicine as drugs for miscellaneous diseases. The drugs that have the heterocyclic core in their frame have some specific activity such as antifungal activity, 46 anti-inflammation, 47 antibacterial, 48 antioxidants, 49 anticonvulsant, 50 antiallergic, 51 herbicidal activity, 52 and and anticancer. 49 Although a number of studies have been reported on bioactivity of ferrocene and xanthone individually, 1-6,44,53-55 based on our knowledge, there is still no report on anticancer polymers bearing ferrocene and xanthone in the main chain.…”

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confidence: 99%

Novel anticancer and antibacterial organometallic polymer based on ferrocene as a building block and xanthone bioactive scaffolds: Synthesis, characterization, and biological study

Lakouraj

Hasantabar

Tashakkorian

et al. 2018

Polymers for Advanced Techs

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Poly(azine ferrocene‐triazole‐xanthone amide) (PAFTXA) was successfully synthesized from azine ferrocene bisacetylene (AFcB) and 2,7‐(N‐2‐azidoacetamide) xanthone (NAzX) by using click chemistry protocol. In this paper, innovative AFcB moiety incorporated in this procedure as a monomer. This monomer was prepared in three steps from ferrocene scaffold, and the synthetic processes were discussed in details. Characterization of the synthesized novel intermediate materials, monomer, and the resulting polymer was performed by nuclear magnetic resonance, Fourier transform infrared, thermal gravimetric analysis, differential scanning calorimetry, and ultraviolet‐visible spectrophotometer. In addition, the in vitro antibacterial activity of the polymer was appraised against Gram‐positive and Gram‐negative bacteria by using minimum inhibitory concentration method. Moreover; antitumoral effects of synthesized polymer were evaluated on Hela, MCF‐7, and Saos cancer cell lines and compared with normal fibroblast cell line by means of 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide assay. Promising antiproliferative effects were detected on both epitheloid and mesenchymal cancer cell lines depending on PAFTXA concentration and time. Survey on its characteristic features revealed the proficiencies of our prepared biomaterial such as its high thermal stability as well as valuable antitumoral and antibacterial capabilities that make it an appreciable candidate for further bioapplications.

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Synthesis of some heterocyclic compounds derived from indole as antimicrobial agents

Cited by 48 publications

References 35 publications

Design, synthesis, and characterization of novel pyrimidines bearing indole as antimicrobial agents

Design, synthesis, and characterization of novel pyrimidines bearing indole as antimicrobial agents

Synthesis and Anticonvulsant Studies of Thiazolidinone and Azetidinone Derivatives from Indole Moiety

Novel anticancer and antibacterial organometallic polymer based on ferrocene as a building block and xanthone bioactive scaffolds: Synthesis, characterization, and biological study

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