Synthesis and characterization of n-alkylamino derivatives of vitamin K3: Molecular structure of 2-propylamino-3-methyl-1,4-naphthoquinone and antibacterial activities

Chadar, Dattatray; Camilles, Maria; Patil, Rahul; Khan, Ayesha; Weyhermüller, Thomas; Salunke‐Gawali, Sunita

doi:10.1016/j.molstruc.2015.01.029

Cited by 36 publications

(22 citation statements)

References 27 publications

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“…Recently, Michael additions have been successfully used to synthesize C-N bonds using primary amines to form new analogues for biological testing. Recently, Salunke-Gawali and coworkers have used n -alkylamines and aminophenols to synthesize naphthoquinone derivatives which have been reported to assess their antiproliferative and antibacterial activities [ 98 , 99 ]. Salunke-Gawali and coworkers used single crystal x-ray crystallography to determine the structures of these compounds.…”

Section: Discussionmentioning

confidence: 99%

Synthesis of Naphthoquinone Derivatives: Menaquinones, Lipoquinones and Other Vitamin K Derivatives

Braasch-Turi

Crans

2020

Molecules

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Menaquinones are a class of isoprenoid molecules that have important roles in human biology and bacterial electron transport, and multiple methods have been developed for their synthesis. These compounds consist of a methylnaphthoquinone (MK) unit and an isoprene side chain, such as found in vitamin K1 (phylloquinone), K2, and other lipoquinones. The most common naturally occurring menaquinones contain multiple isoprene units and are very hydrophobic, rendering it difficult to evaluate the biological activity of these compounds in aqueous assays. One way to overcome this challenge has been the application of truncated MK-derivatives for their moderate solubility in water. The synthesis of such derivatives has been dominated by Friedel-Crafts alkylation with BF3∙OEt2. This attractive method occurs over two steps from commercially available starting materials, but it generally produces low yields and a mixture of isomers. In this review, we summarize reported syntheses of both truncated and naturally occurring MK-derivatives that encompass five different synthetic strategies: Nucleophilic ring methods, metal-mediated reactions, electrophilic ring methods, pericyclic reactions, and homologation and side chain extensions. The advantages and disadvantages of each method are discussed, identifying methods with a focus on high yields, regioselectivity, and stereochemistry leading to a detailed overview of the reported chemistry available for preparation of these compounds.

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Section: Discussionmentioning

confidence: 99%

Synthesis of Naphthoquinone Derivatives: Menaquinones, Lipoquinones and Other Vitamin K Derivatives

Braasch-Turi

Crans

2020

Molecules

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“…Methylamine solution (40%), obtained from Loba chemicals; toluene and methanol obtained from Merck Chemicals. Solvents were distilled by standard methods [ 30 , 35 ] and dried wherever necessary.…”

Section: Methodsmentioning

confidence: 99%

“…All compounds were synthesized and characterized using reported procedures as described in references [ 27 , 28 , 29 , 30 , 31 , 32 , 33 ]. 1 g of 2-methyl-naphthalene-1,4-dione (5.80 mmol for M-1 to M-8), 2,3-dibromonaphthalene-1,4-dione (3.2 mmol for Br-1 to Br-8), 2,3-dichloro-naphthalene-1,4-dione (4.4 mmol for Cl-1 to Cl-8), naphthalene-1,4-dione (6.32 mmol for H-1 to H-8) dissolved in 25–30 ml of dichloromethane and magnetically stirred at room temperature (26 °C–28 °C).…”

Section: Methodsmentioning

confidence: 99%

“…As pursuance to the above considerations, we in the present work undertake synthesis and characterization of a series of 2-( n -alkylamino)-3-R-naphthalene-1,4-dione (the n -alkyl group being methyl to octyl) [ 28 , 29 , 30 , 31 , 32 , 33 , 34 ]; as shown in Scheme 1 .

Scheme 1 Synthesis of n -alkylamino derivatives of naphthalene-1,4-dione.…”

Section: Introductionmentioning

confidence: 99%

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1H and 13C NMR chemical shifts of 2-n-alkylamino-naphthalene-1,4-diones

Patil

Jadhav

Salunke‐Gawali

et al. 2021

Heliyon

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1 H as well as 13 C chemical shifts of 32 compounds of C (3) substituted 2-( n -alkylamino)-3R-naphthalene-1,4-dione (where n -alkyl: methyl, to octyl, R = H, Cl, Br, and CH 3 ) are investigated through 1 H, 13 C, DEPT, gDQCOSY, and gHSQCAD NMR experiments and M06-2X/6-311++G (d,p) density functional theory are discussed. Single crystal X-ray structure of Br-3, as well as 18 different derivatives of naphthalene-1,4-diones, are revealed for its inter and intra-molecular hydrogen bonding interactions.

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“…In particular, the simplest protocol (dichloromethane, 28 °C, 24 hours) leads to the adduct of menadione and methylamine in a yield of 40%. 19 Use of ethanol as solvent and a ten-fold excess of amine in the presence of sodium hydroxide for 24 hours gave an increased yield, but complicated the isolation and purification of the product. 20 Further attempts to increase the yield of the amination…”

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confidence: 99%

Convenient Synthesis of 2-Thioimidazolone/Menadione Conjugates via a Two-Step Sequence Starting with Direct Amination of Menadione

Guk

Krasnovskaya²,

Зык³

et al. 2020

SynOpen

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A convenient route to conjugates of 2-thiohydantoins and menadione with linkers of various chemical nature through a two-stage reaction sequence (direct amination of the menadione with a functional amine followed by modification of a functional group) is presented. Optimal conditions for the direct amination of menadione using alkyl amines with substituents such as azide, alkyne, hydroxyl, amine, halogen, and carboxyl have been developed. Further modification of selected functionalities using CuAAC or esterification reactions with 2-thiohydantoines has been performed.

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Synthesis and characterization of n-alkylamino derivatives of vitamin K3: Molecular structure of 2-propylamino-3-methyl-1,4-naphthoquinone and antibacterial activities

Cited by 36 publications

References 27 publications

Synthesis of Naphthoquinone Derivatives: Menaquinones, Lipoquinones and Other Vitamin K Derivatives

Synthesis of Naphthoquinone Derivatives: Menaquinones, Lipoquinones and Other Vitamin K Derivatives

1H and 13C NMR chemical shifts of 2-n-alkylamino-naphthalene-1,4-diones

Convenient Synthesis of 2-Thioimidazolone/Menadione Conjugates via a Two-Step Sequence Starting with Direct Amination of Menadione

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