In vitro Controlled Release of two new Tuberculocidal Adamantane Aminoethers from Solid Pharmaceutical Formulations (II)

Vlachou, Marilena; Siamidi, Angeliki; Spaneas, Dimitrios; Lentzos, Dimitrios; Ladia, Polixeni; Anastasiou, Konstantina; Papanastasiou, Ioannis; Foscolos, Angeliki‐Sofia; Georgiadis, Markos‐Orestis; Karalis, Vangelis; Kellici, Tahsin F.; Mavromoustakos, Thomas

doi:10.1055/s-0043-114012

Cited by 7 publications

(9 citation statements)

References 24 publications

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“…The 1,2-diamine congeners, such as the adamantane derivative SQ-109 18,19 and the camphane aminoalcohols 20 exhibit very low toxicity and improved pharmacokinetic properties. Our lab has also reported antimycobacterial adamantane derivatives [21][22][23] bearing a diarylmethane scaffold. 24 The synthesis of the new adamantane piperazines Ia-c is depicted in Scheme 1.…”

Section: A Rt I C L E I N F O Abstractmentioning

confidence: 94%

Synthesis of diphenoxyadamantane alkylamines with pharmacological interest

Georgiadis

Kourbeli

Ioannidou

et al. 2019

Bioorganic & Medicinal Chemistry Letters

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Section: A Rt I C L E I N F O Abstractmentioning

confidence: 94%

Synthesis of diphenoxyadamantane alkylamines with pharmacological interest

Georgiadis

Kourbeli

Ioannidou

et al. 2019

Bioorganic & Medicinal Chemistry Letters

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“…Based on the fact that 2‐indole carboxamides are targeting MmpL3 transporter functions of M. tuberculosis, we replaced the indole scaffold with the adamantane core in amides 2 c , d , g , h . Our laboratory has previously published various antimycobacterial adamantane adducts with diverse structures …”

Section: Figurementioning

confidence: 99%

Synthesis of New Indole and Adamantane Amido Derivatives with Pharmacological Interest

et al. 2019

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The synthesis and preliminary pharmacological evaluation of new indole and adamantane amido derivatives is described. The design was based on the pharmacophoric properties of 4‐{4‐[4‐(trifluoromethoxy)phenoxy]piperidin‐1‐yl), 6‐[4‐(trifluoro methoxy)phenyl]pyridin‐3‐yl and 4‐(trifluoro)phenyl tails, which are present as side chains in the structures of promising drug candidates, currently in clinical tests. These pharmacophores were incorporated into the indole and adamantane scaffolds, respectively. The new derivatives were evaluated for their antimycobacterial potential. The following amides, N‐[2‐(5‐methoxy‐1H‐indol‐3‐yl)ethyl]‐4‐{4‐[4(trifluoromethoxy)phenoxy]piperidin‐1‐yl}benzamide (1 b) and N‐{4‐[4‐(4‐(trifluoromethoxy)phenoxy)piperidin‐1‐yl]benzyl}‐1H‐indolyl‐2‐carboxamide (2 b), are endowed with antitubercular properties, which merit further investigation.

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“…These observations are in agreement with our findings on molecules of analogous structures, previously reported. [26] Table 2. Results of uniformity tests: crushing strength (hardness), thickness and friability (%)…”

Section: Formulations Of Compound a And Tablet Uniformity Testsmentioning

confidence: 99%

“…For over a decade, we have been interested in adamantane chemistry in an attempt to exploit adamantane's role in a variety of pharmacological activities . Recently, we have been involved with the synthesis of adamantane derivatives with antimycobacterial activity . The adamantane core enhances the lipophilicity of the derivatives, where is present, and acts on the mycobacterial wall .…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and in vitro Controlled Release of New Adamantanodiarylketone Antimycobacterials

et al. 2019

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In the present investigation, the synthesis, the biology and the development of matrix tablet formulations for the in vitro controlled release of new adamantane diarylketone antimycobacterial derivatives, is presented. In the skeleton of the new compounds, a diarylketone, functionalized by a 2‐hydroxypropylenoxy‐3‐butylamine, a 2‐hydroxypropylenoxy‐3‐hexylamine and a 1‐(2‐hydroxyoctyl)piperidin‐4‐yl moiety, is incorporated at the C‐1 adamantane position. The new derivatives were tested against the H37Rv Mycobacterium tuberculosis strain and exhibited satisfactory activity. In view of their lipophilic character, it was intriguing to examine their in vitro dissolution profile in buffer solutions simulating the gastric and intestinal environments. To this end, matrix tablets of the most active compound, {4‐[(adamantan‐1‐yl)phenyl‐4‐(3‐(butylamino)‐2‐hydroxypropoxy)]phenyl}methanone (A), incorporating the appropriate excipients, were prepared using the direct compression method. The preliminary test results show that its dissolution profile is in alignment with the desired pattern for the per os administration of tuberculocidal agents.

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In vitro Controlled Release of two new Tuberculocidal Adamantane Aminoethers from Solid Pharmaceutical Formulations (II)

Cited by 7 publications

References 24 publications

Synthesis of diphenoxyadamantane alkylamines with pharmacological interest

Synthesis of diphenoxyadamantane alkylamines with pharmacological interest

Synthesis of New Indole and Adamantane Amido Derivatives with Pharmacological Interest

Design, Synthesis and in vitro Controlled Release of New Adamantanodiarylketone Antimycobacterials

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