Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(1-adamantyl)-2-substituted thio-1,3,4-oxadiazoles and 5-(1-adamantyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones

Bioorganic & Medicinal Chemistry
Ali A El-EmamJochen Lehmann

Abstract

The reaction of 5-(1-adamantyl)-1,3,4-oxadiazoline-2-thione 2 with iodoethane, 2-dimethylaminoethyl chloride hydrochloride or 2-piperidinoethyl chloride hydrochloride in ethanolic potassium hydroxide yielded the corresponding 5-(1-adamantyl)-2-ethyl or substituted ethylthio-1,3,4-oxadiazoles 3a-c. Interaction of 2 with formaldehyde solution and primary aromatic amines or 1-substituted piperazines, in ethanol at room temperature yielded the corresponding 5-(1-adamantyl)-3-arylaminomethyl-1,3,4-oxadiazoline-2-thiones 4a-m or 5-(1-adamantyl)-3-(4-substituted-1-piperazinylmethyl)-1,3,4-oxadiazoline-2-thiones 5a-h, respectively. All the synthesized compounds were tested for in vitro activities against certain strains of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compounds 2, 5a, and 5e were found as the most active derivatives, particularly against the Gram-positive bacteria. In addition, the antiviral activity of compounds 2, 4a-m, and 5a-h against HIV-1 using the XTT assay was carried out. Compound 2 produced 100%, 43%, and 37% reduction of viral replication at 50, 10, and 2microg/mL concentrations, respectively.

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Citations

Feb 26, 2013·European Journal of Medicinal Chemistry·Navin B PatelGildardo Rivera
Apr 9, 2014·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Lev L GladkovAli A El-Emam
Feb 26, 2013·Chemical Reviews·Lukas WankaPeter R Schreiner
Jan 1, 2008·Acta Crystallographica. Section E, Structure Reports Online·Krzysztof EjsmontJacek Zaleski
Jan 1, 2008·Acta Crystallographica. Section E, Structure Reports Online·Shahzad AhmedAles Ruzicka
Jan 1, 2008·Acta Crystallographica. Section E, Structure Reports Online·Tariq Mahmood BabarZdenka Padelkova
Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·Mahmood-Ul-Hassan KhanIslam Ullah Khan
Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·Uzma AshiqIslam Ullah Khan
Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·Rifat Ara JamalIslam Ullah Khan
Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·Uzma AshiqIslam Ullah Khan
Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online·Abdul-Malek S Al-TamimiAli A El-Emam
Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online·Aamer SaeedMichael Bolte
Jan 6, 2012·Acta Crystallographica. Section E, Structure Reports Online·Hoong-Kun FunPrakash Shetty
Jan 6, 2012·Acta Crystallographica. Section E, Structure Reports Online·Adnan A KadiEdward R T Tiekink
Mar 14, 2012·Acta Crystallographica. Section E, Structure Reports Online·Ali A El-EmamEdward R T Tiekink
Mar 14, 2012·Acta Crystallographica. Section E, Structure Reports Online·Ali A El-EmamEdward R T Tiekink
May 17, 2012·Acta Crystallographica. Section E, Structure Reports Online·Ali A El-EmamHoong-Kun Fun
May 17, 2012·Acta Crystallographica. Section E, Structure Reports Online·Ali A El-EmamTze Shyang Chia
May 17, 2012·Acta Crystallographica. Section E, Structure Reports Online·Ali A El-EmamHoong-Kun Fun
May 17, 2012·Acta Crystallographica. Section E, Structure Reports Online·Siham LahsasniHoong-Kun Fun
May 17, 2012·Acta Crystallographica. Section E, Structure Reports Online·Güneş DemirtaşOrhan Büyükgüngör
Jun 22, 2012·Acta Crystallographica. Section E, Structure Reports Online·Nasser R El-BrollosyEdward R T Tiekink
Jun 1, 2013·Acta Crystallographica. Section E, Structure Reports Online·Abdul-Malek S Al-TamimiEdward R T Tiekink
Jun 1, 2013·Acta Crystallographica. Section E, Structure Reports Online·Abdul-Malek S Al-TamimiEdward R T Tiekink
Jan 1, 2008·Indian Journal of Pharmaceutical Sciences·G Nagalakshmi
Feb 15, 2014·Acta Crystallographica. Section E, Structure Reports Online·Ali A El-EmamHoong-Kun Fun
Jan 24, 2014·Acta Crystallographica. Section E, Structure Reports Online·Ebtehal S Al-AbdullahHoong-Kun Fun
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Mar 9, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Daniel SzulczykMarta Struga
May 5, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Lamya H Al-WahaibiAli A El-Emam
May 9, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ebtehal S Al-AbdullahAli A El-Emam

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