• Title/Summary/Keyword: Claisen-Schmidt condensation

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Synthesis of Biologically Active Chalcones and their Anti-inflammatory Effects

  • Jeon, Jae-Ho;Kim, Si-Jun;Kim, Cheol-Gi;Kim, Jin-Kyung;Jun, Jong-Gab
    • Bulletin of the Korean Chemical Society
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    • v.33 no.3
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    • pp.953-957
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    • 2012
  • Chalcones have been reported to have various biological activities including antitumor, antiparasitic, antileishmanial, antioxidative, superoxide scavenging, antibacterial, and PTP1B activity. Due to the limited natural resources, we had to prepare sizable quantities of biologically active chalcones for bio-tests. Therefore, Claisen-Schmidt condensation between substituted acetophenones and corresponding aldehydes enabled us to prepare chalcones for inflammatory studies. Chalcones thus prepared showed significant suppression of nitric oxide (NO) production at $10{\mu}M$.

Synthesis and Antimicrobial Activity of Novel Tetrahydrobenzothienopyrimidines

  • Amal Abdel Haleem Mohamed Eissa;Ashraf Ahmed Moneer
    • Archives of Pharmacal Research
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    • v.27 no.9
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    • pp.885-892
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    • 2004
  • Due to the rapidly growing number of resistant strains of bacteria, the search for antibacterial agents with new modes of action will always remain an important and challenging task. Thus, the reaction of 2-substituted or. unsubstituted-4-(4-acetylanilino)-5,6,7,8-terahydrobenzo[b] thieno[2,3-d]pyrimidine derivatives 1-3 with the hydrazine derivatives, semi and / or thiosemi-carbazides, provided the corresponding hydrazones 4-6 and semi and/or thiosemicarbazones 7-9. Claisen-Schmidt condensation of compounds 1 or 2 with the appropriate aldehyde yielded the chalcones 10, 11 which, when treated with hydroxylamine hydrochloride gave rise to the isoxazoline-containing compounds 12, 13. Furthermore, reacting the respective chalcones 10, 11 with different hydrazines, urea and/or thiourea, furnished compounds 14, 15, 16, and 17 respectively. Representative compounds were tested for their antimicrobial activity against Candida Albicans and certain gram-positive and gram-negative bacteria. Their MICs were then determined. Compound 15e, showed a broad spectrum of activity while most of the other com-pounds showed varying antimicrobial activity.

Design, Synthesis and Biological Evaluation of Some Novel Chalcones-sulphonamide Hybrids

  • Khanusiya, Mahammadali;Gadhawala, Zakirhusen
    • Journal of the Korean Chemical Society
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    • v.62 no.5
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    • pp.377-385
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    • 2018
  • A new class of Chalcone-Sulphonamide hybrids has been designed by condensing appropriate sulphonamide scaffold with substituted chalcones tethered by chloroacetyl chloride as a multi-target drug for therapeutic treatment. Chalcones were prepared by Claisen-Schmidt condensation of a substituted aldehyde with para aminoacetophenone. These Chalcone-Sulphonamide hybrids were screened by means of their antibacterial activity by NCCLS method. Among all these compounds, 5e and 5c displayed more potent growth inhibitory activity against Staphylococcus epidermidis and Pseudomonas aeruginosa bacteria respectively. Further, these hybrids were evaluated for their antifungal activity, among all hybrid 5a exhibited potent antifungal activity. The synthesized compounds were characterized by FT-IR, $^1HNMR$, $^{13}CNMR$ and HR-LCMS and spectral study supports the structures of synthesized Chalcone-Sulphonamide hybrids.

Chalcones-Sulphonamide Hybrids: Synthesis, Characterization and Anticancer Evaluation

  • Khanusiya, Mahammadali;Gadhawala, Zakirhusen
    • Journal of the Korean Chemical Society
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    • v.63 no.2
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    • pp.85-93
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    • 2019
  • A panel of chalcone-sulphonamide hybrids has been designed by tethering appropriate sulphonamide scaffold with substituted chalcones as a multi-target drug for anticancer screening. Chalcones were prepared by Claisen-Schmidt condensation reaction of a substituted aldehyde with para aminoacetophenone. All the synthesized compounds were evaluated against selected five cancer cell lines, MCF-7 (Breast cancer), DU-145 (Human prostate Carcinoma), HCT-15 (Colon cancer), NCIH-522 (stage 2, adenocarcinoma; non-small cell lung cancer) and HT-3 (Human cervical cancer). Most of the synthesized chalcone-sulphonamide hybrids showed amended cytotoxic activity against various cancer cell lines which may be attributed to the linkage of sulphonamide with chalcone skeleton. The synthesized compounds were characterized by FT-IR, $^1H$ NMR, $^{13}C$ NMR and HR-LCMS and spectral study assert the structures of synthesized sulphonamide-chalcone hybrids.

The Kinetics and Mechanism of the Nucleophilic Addition of Thiourea for Benzoyl Styrene Derivatives (Benzoyl styrene유도체에 대한 Thiourea의 친핵성 첨가반응 메카니즘과 그 반응속도론적 연구)

  • Lee, Ki-Chang;Yoon, Chul-Hun;Hwang, Sung-Kwy;Ryu, Jung-Uk
    • Journal of the Korean Applied Science and Technology
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    • v.12 no.2
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    • pp.107-113
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    • 1995
  • Benzoyl styrene derivatives were synthesized by Claisen-Schmidt condensation. It was measured that nucleophilic addition of thiourea for benzoyl styrene made use of ultraviolet spectrophotometery at a wide pH $1.0{\sim}13.0$ range in 5% $dioxane-H_2O$ at $40^{\circ}C$. On the basis of general base catalysis, substitutent effect, and confirmation of addtion reaction product, the nucleophilic addtion kinetics of thiourea for benzoylstyrene derivatives were measured by pH change. It maybe concluded that a part was unrelated to pH and another part was in proportion to concentration of hydroxide ion : Above pH 10.0. It was in propotion to concentration of hydroxide ion, a part having no concern with pH was added to the neutral thiourea molecule. From the results of measurement the reaction rate and there findings, nucleophilic addition of thiourea to benzoylstyrene derivative was proposed a fitting mechanism.