Chemistry of pyridoxine in drug design

Shtyrlin, Yu. G.; Petukhov, A. S.; Strel’nik, A. D.; Shtyrlin, Nikita V.; Iksanova, Alfiya G.; Pugachev, Mikhail V.; Pavelyev, Roman S.; Dzyurkevich, M. S.; Garipov, Marsel R.; Balakin, Konstantin V.

doi:10.1007/s11172-019-2504-5

Cited by 43 publications

(21 citation statements)

References 85 publications

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“…The dry residue was dissolved in water and puri ed using preparative reverse phase liquid chromatography (gradient elution with water-methanol). It was obtained as a white amorphous solid; yield 97% (0.35 g); 1 H NMR (DMSO-d 6 , 400 MHz) δ 2.51 (3H, s, CH 3 ), 2.52 (3H, s, CH 3 ), 3.03-3.12 (4H, m, (3,3,8-Trimethyl-1,5-dihydro- [1,3]dioxepino [5,6-c]pyridin-9-yl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (7): phase transfer catalyst tetrabutylammonium bromide (TBAB) (0.92 g, 2.87 mmol), α-D-acetobromoglucose (2.90 g, 7.06 mmol) and a solution of K 2 CO 3 (0.97 g, 7.06 mmol) in 15 mL of water were added sequentially to a solution of compound 6 (1.20 g, 5.74 mmol) in 15 mL of CHCl 3 . The reaction mixture was stirred for 3 hours at 45 o С.…”

Section: Experimental/ Materials and Methodsmentioning

confidence: 99%

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Synthesis, Antitumor Activity and Structure-activity Studies of Novel Pyridoxine-based Structural Analogs of Saccharumoside-B

Pugachev

Agafonova

Гнездилов

et al. 2022

Preprint

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In this work, a series of novel pyridine- and pyridoxine-based saccharumoside-B derivatives were synthesized, and their antitumor activity on nine human tumor cell lines (MCF-7, MDA-MB-231, A-498, SNB-19, M-14, NCI-H322M, HCT-115, HCT-116, PC-3) and cytotoxicity on three conditionally normal cell lines (HEK-293, Chang Liver, MSC) were studied in comparison with camptothecin, doxorubicin and saccharumoside-B. Structure-activity patterns, and in particular the contribution to antitumor activity of the peripheral fragments of the studied pharmacophore were analyzed. Our synthetic explorations also allowed us to propose a new efficient approach to the synthesis of saccharumoside B, which was used as a reference drug.

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Section: Experimental/ Materials and Methodsmentioning

confidence: 99%

“…The chemically multifunctional pyridoxine scaffold (vitamin B6) provides a useful structural platform for the design of modi ed analogs of physiologically active compounds [1]. A good illustration is a series of pyridoxine-based bioisosteric analogs of estradiol described in our papers [2][3][4].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antitumor Activity and Structure-activity Studies of Novel Pyridoxine-based Structural Analogs of Saccharumoside-B

Pugachev

Agafonova

Гнездилов

et al. 2022

Preprint

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“…The starting material for our synthetic route was pyridoxine hydrochloride—also known as vitamin B6—which, despite its polyfunctionalized structure, is a low-cost compound (>US $1 per gram). 12 We envisaged that the presence of hydroxyl groups of different reactivities in vitamin B6 could potentially be explored for the preparation of new tetrahydroindolizinone and tetrahydroindolizine motifs.…”

Section: Methodsmentioning

confidence: 99%

Origin of the Diastereoselectivity of the Heterogeneous Hydrogenation of a Substituted Indolizine

et al. 2020

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In this work, the stereoselective heterogeneous hydrogenation of a tetrasubstituted indolizine was studied. Partial hydrogenation products were obtained in three steps from a substituted pyridine-2-carboxaldehyde prepared from commercial pyridoxine hydrochloride. The hydrogenation of the indolizine ring was shown to be diastereoselective, forming trans- 6b and cis -9 . Theoretical calculations ( ab initio and DFT) were used to rationalize the unusual trans stereoselectivity for 6b , and a keto–enol tautomerism under kinetic control has been proposed as the source of diastereoselectivity.

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“…In our group, we have systematically studied chemistry and biological properties of the pyridoxine (vitamin B6) derivatives [ 12 ]. In previous works, we described a series of QAC based on pyridoxine derivatives [ 13 , 14 , 15 , 16 , 17 ].…”

Section: Introductionmentioning

confidence: 99%

Novel Bis-Ammonium Salts of Pyridoxine: Synthesis and Antimicrobial Properties

et al. 2020

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A series of 108 novel quaternary bis-ammonium pyridoxine derivatives carrying various substituents at the quaternary nitrogen’s and acetal carbon was synthesized. Thirteen compounds exhibited antibacterial and antifungal activity (minimum inhibitory concentration (MIC) 0.25–16 µg/mL) comparable or superior than miramistin, benzalkonium chloride, and chlorhexidine. A strong correlation between the lipophilicity and antibacterial activity was found. The most active compounds had logP values in the range of 1–3, while compounds with logP > 6 and logP < 0 were almost inactive. All active compounds demonstrated cytotoxicity comparable with miramistin and chlorhexidine on HEK-293 cells and were three-fold less toxic when compared to benzalkonium chloride. The antibacterial activity of leading compound 5c12 on biofilm-embedded Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli or Pseudomonas aeruginosa was comparable or even higher than that of the benzalkonium chloride. In vivo 5c12was considerably less toxic (LD50 1705 mg/kg) than benzalkonium chloride, miramistine, and chlorhexidine at oral administration on CD-1 mice. An aqueous solution of 5c12 (0.2%) was shown to be comparable to reference drugs efficiency on the rat’s skin model. The molecular target of 5c12 seems to be a cellular membrane as other quaternary ammonium salts. The obtained results make the described quaternary bis-ammonium pyridoxine derivatives promising and lead molecules in the development of the new antiseptics with a broad spectrum of antimicrobial activity.

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Chemistry of pyridoxine in drug design

Cited by 43 publications

References 85 publications

Synthesis, Antitumor Activity and Structure-activity Studies of Novel Pyridoxine-based Structural Analogs of Saccharumoside-B

Synthesis, Antitumor Activity and Structure-activity Studies of Novel Pyridoxine-based Structural Analogs of Saccharumoside-B

Origin of the Diastereoselectivity of the Heterogeneous Hydrogenation of a Substituted Indolizine

Novel Bis-Ammonium Salts of Pyridoxine: Synthesis and Antimicrobial Properties

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