Nitroimidazoles, Part 3. Synthesis and anti-HIV Activity of New N-Alkyl-4-nitroimidazoles Bearing Benzothiazole and Benzoxazole Backbones

Al‐Soud, Yaseen A.; Al-Sa’doni, Haitham H.; Amajaour, Houssain A. S.; Al-Masoudib, Najim A.

doi:10.1515/znb-2007-0406

Cited by 21 publications

(10 citation statements)

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“…The following chemicals, used in this study, were purchased from Acros and were used as received: piperidine, morpholine, thiomorpholine, piperazine, N -alkylpiperazines, N -arylpiperazines, ethyl N -piperazinecarboxylate. 1-(1-Benzyl-2-ethyl-4-nitro-1 H -imidazol-5-yl)piperazine was prepared according to a literature procedure [ 39 ]. Silica-gel for column chromatography was purchased from Macherey-Nagel GmbH & Co (Germany).…”

Section: Methodsmentioning

confidence: 99%

Synthesis, and Antitumor Activity of Some N1-(Coumarin-7-yl) Amidrazones and Related Congeners

et al. 2011

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A series of new N1-(coumarin-7-yl)amidrazones incorporating N-piperazines and related congeners were synthesized by reacting the hydrazonoyl chloride derived from 7-amino-4-methylcoumarin with the appropriate piperazines. The chemical structures of the newly prepared compounds were supported by elemental analyses, 1H-NMR, 13C-NMR, and ESI-HRMS spectral data. The antitumor activity of the newly synthesized compounds was evaluated. Among all the compounds tested, 7-{2-[1-(4-(1-benzyl-2-ethyl-4-nitro-1H-imidazol-5-yl)piperazin-1-yl)-2-oxopropylidene]hydrazinyl}-4-methyl-2H-chromen-2-one (3n) was the most potent against MCF-7 and K562 cells, with IC50 values of 20.2 and 9.3 μM, respectively.

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Section: Methodsmentioning

confidence: 99%

Synthesis, and Antitumor Activity of Some N1-(Coumarin-7-yl) Amidrazones and Related Congeners

et al. 2011

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“…This could lead to the discovery of more potent and selective analogues that will allow the elucidation of their molecular mode of action. (11)(12)(13)(14)(15)(16)(17)(18)(19)(20) te indol analog 22, s ciljem da se razviju novi nenukleozidni inhibitori reverzne transkriptaze (NNRTI). Novosintetiziranim spojevima ispitano je djelovanje na HIV-1 i HIV-2 u MT-4 stanicama.…”

Section: Discussionmentioning

confidence: 99%

“…Based on these pharmacological activities, and in continuation of our work on 4-nitroimidazoles (17)(18)(19)(20), we report here the synthesis of new 5-substituted piperazinyl-4--nitroimidazole derivatives and the evaluation of their anti-HIV activity. EXPERIMENTAL Melting points are uncorrected and were measured on a Büchi melting point apparatus B-545 (Büchi Labortechnik AG, Switzerland).…”

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confidence: 98%

Nitroimidazoles. V. Synthesis and anti-HIV evaluation of new 5-substituted piperazinyl-4-nitroimidazole derivatives

Al‐Soud

Al‐Masoudi²,

Hassan³

et al. 2007

Acta Pharmaceutica

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A series of 2-alkylthio-1-[4-(1-benzyl-2-ethyl-4-nitro-1H- -imidazol-5-yl)-piperazin-1-yl]ethanones (3-9) and alkyl-[4-(1-benzyl-2-ethyl-4-nitro-1H-imidazol-5-yl)-piperazin-1-yl)ketones (11-20) as well as the indole analogue 22 were synthesized from 4-nitro-5-piperazinyl imidazole derivative 1, with the aim to develop newly non-nucleoside reverse transcriptase inhibitors (NNRTIs). The newly synthesized compounds were assayed against HIV-1 and HIV-2 in MT-4 cells. Compound 4 showed inhibition of HIV-1 (EC50 0.45 microg mL-1) and HIV-2 (0.50 microg mL-1), while 11 showed inhibition of HIV-1 (EC50 2.48 microg mL-1, SI = 4).

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“…Based on the imidazole pharmacological importance of imidazole derivatives and in contituation of our previous work on imidazole analogues with their antiviral and anticancer activity, [22][23][24][25][26][27][28][29] we report here new derivatives of nitroimidazole-containing piperazine derivatives and evaluation of their anticancer activity as well as the molecular docking study.…”

Section: Introductionmentioning

confidence: 95%

Synthesis, anticancer activity and molecular docking studies of new 4-nitroimidazole derivatives

Al‐Soud¹,

Alhelal²,

Saeed³

et al. 2021

Arkivoc

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Imidazoles have occupied a unique position in heterocyclic chemistry, and its derivatives have attracted considerable interests in recent years for their versatile properties in chemistry and pharmacology. Herein, we report the synthesis of 3-(1-benzyl-2-ethyl-4-nitro-1H-imidazol-5-ylsulfanyl)-1-(4-substituted phenyl-piperazin-1-yl)-propan-1-one 5a-p by reaction of 3-(1-benzyl-2-methyl-4-nitro-1H-imidazol-5-ylsulfanyl)-propanoyl chloride (3) with piperazine nucleophiles. Eighteen compounds were assessed for their antiproliferative inhibition potency against four human cancer cell lines (MCF-7, PC3, MDA MB231 and Du145). Compounds 5f and 5k were the most potent anticancer agents on MCF-7 cell lines cell line with IC50 value of 1.0 µg/mL, while 5d and 5m exhibited cytotoxic effect on PC3 and DU145 cell lines with IC50 values of 4.0 and 5.0 µg/mL, respectively. The molecular docking of compounds 5f, 5d and 5m has been studied.

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Nitroimidazoles, Part 3. Synthesis and anti-HIV Activity of New N-Alkyl-4-nitroimidazoles Bearing Benzothiazole and Benzoxazole Backbones

Cited by 21 publications

References 0 publications

Synthesis, and Antitumor Activity of Some N1-(Coumarin-7-yl) Amidrazones and Related Congeners

Synthesis, and Antitumor Activity of Some N1-(Coumarin-7-yl) Amidrazones and Related Congeners

Nitroimidazoles. V. Synthesis and anti-HIV evaluation of new 5-substituted piperazinyl-4-nitroimidazole derivatives

Synthesis, anticancer activity and molecular docking studies of new 4-nitroimidazole derivatives

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