A novel approach to determining physicochemical and absorption properties of 6-fluoroquinolone derivatives: experimental assessment

Cabrera‐Pérez, Miguel Ángel; González-Dı́az, Humberto; Teruel, C. Fernandez; Plá-Delfina, J.M.; Bermejo, Marival

doi:10.1016/s0939-6411(02)00013-9

Cited by 49 publications

(21 citation statements)

References 20 publications

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“…This has been applied for the description of some physicochemical properties of organic compounds, in quantitative structure toxicity relationship (QSTR), and has also been reported for the modelling of pharmacological activities (Estrada & Molina, 2001). The TOPS-MODE approach has been extended not only to the discovery of novel recoveries but also to the study of the absorption properties of drugs (Cabrera et al, 2002;Estrada & González, 2003).…”

Section: Resultsmentioning

confidence: 99%

“…In this sense, the TOPS-MODE approach has been extended not only to the discovery of novel results but also toward the studying of the physicochemical and absorption properties of drugs (Cabrera et al, 2002;Estrada & González, 2003). On the other hand, most recently published papers in this area make use of reduced or homologous series of compounds to fit the QSAR for antimicrobial drug screening.…”

Section: Applications Of the Tops-mode To The Molecular Design: Modeslabmentioning

confidence: 99%

See 1 more Smart Citation

Antioxidant and Pro-Oxidant Effects of Polyphenolic Compounds and Structure-Activity Relationship Evidence

Yordi¹,

Pérez²,

Matos³

et al. 2012

Nutrition, Well-Being and Health

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Section: Resultsmentioning

confidence: 99%

Section: Applications Of the Tops-mode To The Molecular Design: Modeslabmentioning

confidence: 99%

Antioxidant and Pro-Oxidant Effects of Polyphenolic Compounds and Structure-Activity Relationship Evidence

Yordi¹,

Pérez²,

Matos³

et al. 2012

Nutrition, Well-Being and Health

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“…Only the zones that contribute to the specific side effect were quantified. Estrada and González have explained this procedure in detail for bond spectral moments (Cabrera, 2002). The method, called back-projection analysis (BPA), is general for any molecular descriptor, defined a priori as a sum of local descriptors, at least for linear QSTR/QSARs.…”

Section: Back-projection Analysis and March-insidementioning

confidence: 99%

Simple Stochastic Fingerprints Towards Mathematical Modeling in Biology and Medicine 2. Unifying Markov Model for Drugs Side Effects

2006

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Most of present mathematical models for biological activity consider just the molecular structure. In the present article we pretend extending the use of Markov chain models to define novel molecular descriptors, which consider in addition other parameters like target site or biological effect. Specifically, this mathematical model takes into consideration not only the molecular structure but the specific biological system the drug affects too. Herein, a general Markov model is developed that describes 19 different drugs side effects grouped in eight affected biological systems for 178 drugs, being 270 cases finally. The data was processed by linear discriminant analysis (LDA) classifying drugs according to their specific side effects, forward stepwise was fixed as strategy for variables selection. The average percentage of good classification and number of compounds used in the training/predicting sets were 100/95.8% for endocrine manifestations, (18 out of 18)/(13 out of 14); 90.5/92.3% for gastrointestinal manifestations, (38 out of 42)/(30 out of 32); 88.5/86.5% for systemic phenomena, (23 out of 26)/(17 out of 20); 81.8/77.3% for neurological manifestations, (27 out of 33)/(19 out of 25); 81.6/86.2% for dermal manifestations, (31 out of 38)/(25 out of 29); 78.4/85.1% for cardiovascular manifestation, (29 out of 37)/(24 out of 28); 77.1/75.7% for breathing manifestations, (27 out of 35)/(20 out of 26) and 75.6/75% for psychiatric manifestations, (31 out of 41)/(23 out of 31). Additionally a back-projection analysis (BPA) was carried out for two ulcerogenic drugs to prove in structural terms the physical interpretation of the models obtained. This article develops a mathematical model that encompasses a large number of drugs side effects grouped in specifics biological systems using stochastic absolute probabilities of interaction ((A)pi(k)(j)) by the first time.

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“…With respect to the amines, N-Mannich bases are useful when an increase in their lipophilicity is required. Lipophilicity of the quinolone amines as an important factor in the quinolones intestinal absorption is considered responsible for the poor relationship between in vivo and in vitro activity of quinolones [18]. In these compounds, N-Mannich base formation could suppress the pKa, which means that an important proportion could remain unionized at physiological pH, resulting in improved permeability and thus bioavailability.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, physicochemical characterization and antibacterial activity of novel (benzoylamino)methyl derivatives of quinolones

Breznica-Selmani

Mladenovska

Dräger

et al. 2016

Maced. J. Chem. Chem. Eng.

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Herein we report the synthesis of different derivatives of (fluoro)quinolones norfloxacin, ciprofloxacin and pipemidic acid, by incorporating (benzoylamino)methyl on the free nitrogen of the pyperazinyl moiety. The compounds were structurally characterized by 1D and 2D NMR, FTIR and highresolution mass spectroscopy. In addition, their physicochemical properties were a matter of interest to be correlated with their structure and antimicrobial activity in vitro. Their antimicrobial activities were screened against Gram-positive, Gram-negative bacteria and C. albicans. Higher distribution coefficients and consequently lower water solubility were determined for all synthesized compounds than the ones of the corresponding leading compounds. Inconsequential correlations between the lipophilicity of the compounds and MIC were observed, suggesting that passive diffusion is not the only mechanism for their penetration into bacterial cells. Further studies are needed to determine how substitutions in the (fluoro)quinolone moiety affect the primary target(s), substrate behavior in respect to bacterial transporters and overall bioavailability.Keywords: (benzoylamino)methyl; quinolones; structure; physicochemical properties; antimicrobial activity СИНТЕЗА, ФИЗИЧКОХЕМИСКА КАРАКТЕРИЗАЦИЈА И АНТИБАКТЕРИСКА АКТИВНОСТ НА НОВИ (БЕНЗОИЛАМИНО)МЕТИЛНИ ДЕРИВАТИ НА ХИНОЛОНИВо трудот е прикажана синтеза на различни деривати на (флуоро)хинолони со инкорпорирање на (бензоиламино)метилна група на слободниот азот од пиперазинскиот фрагмент кај норфлоксацинот, ципрофлоксацинот и пипемидинската киселина како водечки соединенија. Синтетизираните соединенија беа структурно карактеризирани со помош на 1D и 2D NMR, FTIR и масена спектрометрија со висока резолуција. Дополнително беа определени физичкохемиските особини на новосинтетизираните соединенија и корелирани со нивната структура и антимикро- 179-197 (2016) 180 бната активност in vitro. Антимикробната активност на новите соединенија беше испитувана на Gram-позитивни и Gram-негативни бактерии и на C. albicans. Сите новосинтетизирани соеди-ненија покажаа повисок коефициент на распределба и соодветно пониска растворливост во вода во однос на водечките соединенија. Корелациите меѓу липофилноста на синтетизираните соединенија и минималната инхибиторна концентрација (MIC) не беа статистички значајни, што укажува на тоа дека пасивната дифузија не е единствениот механизам со кој тие пенетрираат во бактериските клетки. Потребни се понатамошни истражувања за да се испита како супституциите во (флуоро)хинолонското јадро влијаат врз примарната цел(и), супстратното однесување во однос на бактериските транспортери и севкупната биорасположливост.

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A novel approach to determining physicochemical and absorption properties of 6-fluoroquinolone derivatives: experimental assessment

Cited by 49 publications

References 20 publications

Antioxidant and Pro-Oxidant Effects of Polyphenolic Compounds and Structure-Activity Relationship Evidence

Antioxidant and Pro-Oxidant Effects of Polyphenolic Compounds and Structure-Activity Relationship Evidence

Simple Stochastic Fingerprints Towards Mathematical Modeling in Biology and Medicine 2. Unifying Markov Model for Drugs Side Effects

Synthesis, physicochemical characterization and antibacterial activity of novel (benzoylamino)methyl derivatives of quinolones

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