Editorial

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2 pages, 185 KiB

Open AccessEditorial

Synthesis of Flavonoids or Other Nature-Inspired Small Molecules

by

Giovanni Ribaudo

Molbank 2022, 2022(1), M1313; https://doi.org/10.3390/M1313 - 10 Jan 2022

Cited by 3 | Viewed by 1397

Abstract

Natural compounds are endowed with an intriguing variety of scaffolds, functional groups and stereochemical properties [...] Full article

(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)

Research

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5 pages, 402 KiB

Open AccessCommunication

New Derivatives of Lupeol and Their Biological Activity

by

Hoang-Thuy-Tien Le

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Quoc-Cuong Chau

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Thuc-Huy Duong

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Quyen-Thien-Phuc Tran

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Nguyen-Kim-Tuyen Pham

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Thi-Hoai-Thu Nguyen

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Ngoc-Hong Nguyen

and

Jirapast Sichaem

Molbank 2021, 2021(4), M1306; https://doi.org/10.3390/M1306 - 10 Dec 2021

Cited by 3 | Viewed by 2319

Abstract

The natural product lupeol (1) was isolated from Bombax ceiba leaves, which were used as starting material in the semisynthetic approach. Three new derivatives (2a, 2b, and 3) were synthesized using oxidation and aldolization. Their chemical structures [...] Read more.

The natural product lupeol (1) was isolated from Bombax ceiba leaves, which were used as starting material in the semisynthetic approach. Three new derivatives (2a, 2b, and 3) were synthesized using oxidation and aldolization. Their chemical structures were elucidated by spectroscopic analyses (HRESIMS and NMR). Compounds 3 showed significant α-glucosidase inhibition with an IC₅₀ value of 202 µM, whereas 2a and 2b were inactive. Full article

(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)

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6 pages, 5097 KiB

Open AccessShort Note

2-Oxo-2H-chromen-7-yl 4-chlorobenzoate

by

Diana Becerra

,

Jaime Portilla

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Juan-Carlos Castillo

Molbank 2021, 2021(3), M1279; https://doi.org/10.3390/M1279 - 14 Sep 2021

Cited by 6 | Viewed by 2147

Abstract

We describe the synthesis of 2-oxo-2H-chromen-7-yl 4-chlorobenzoate 3 in 88% yield by the O-acylation reaction of 7-hydroxy-2H-chromen-2-one 1 with 4-chlorobenzoyl chloride 2 in dichloromethane using a slight excess of triethylamine at 20 °C for 1 h. The ester [...] Read more.

We describe the synthesis of 2-oxo-2H-chromen-7-yl 4-chlorobenzoate 3 in 88% yield by the O-acylation reaction of 7-hydroxy-2H-chromen-2-one 1 with 4-chlorobenzoyl chloride 2 in dichloromethane using a slight excess of triethylamine at 20 °C for 1 h. The ester 3 was completely characterized by mass spectrometry, IR, UV–Vis, 1D, and 2D NMR spectroscopy. Full article

(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)

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13 pages, 1583 KiB

Open AccessArticle

2-Chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]styryl}pyrimidine: Synthesis, Spectroscopic and Computational Evaluation

by

Otávio Augusto Chaves

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Vitor Sueth-Santiago

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Douglas Chaves de Alcântara Pinto

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José Carlos Netto-Ferreira

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Debora Decote-Ricardo

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Marco Edilson Freire de Lima

Molbank 2021, 2021(3), M1276; https://doi.org/10.3390/M1276 - 07 Sep 2021

Cited by 1 | Viewed by 1832

Abstract

A novel curcumin analog namely 2-chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]-styryl}pyrimidine (compound 7) was synthesized by three-step reaction. The condensation reaction of protected vanillin with 2-chloro-4,6-dimethylpyrimidine (6) was the most efficient step, resulting in a total yield of 72%. The characterization [...] Read more.

A novel curcumin analog namely 2-chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]-styryl}pyrimidine (compound 7) was synthesized by three-step reaction. The condensation reaction of protected vanillin with 2-chloro-4,6-dimethylpyrimidine (6) was the most efficient step, resulting in a total yield of 72%. The characterization of compound 7 was performed by ¹H and ¹³C nuclear magnetic resonance (NMR), as well as high-resolution mass spectrometry. The experimental spectrometric data were compared with the theoretical spectra obtained by the density functional theory (DFT) method, showing a perfect match between them. UV-visible spectroscopy and steady-state fluorescence emission studies were performed for compound 7 in solvents of different polarities and the results were correlated with DFT calculations. Compound 7 showed a solvatochromism effect presenting higher molar extinction coefficient (log ε = 4.57) and fluorescence quantum yield (ϕ = 0.38) in toluene than in acetonitrile or methanol. The simulation of both frontier molecular orbitals (FMOs) and molecular electrostatic potential (MEP) suggested that the experimental spectra profile in toluene was not interfered by a possible charge transfer. These results are an indication of a low probability of compound 7 in reacting with unsaturated phospholipids in future applications as a fluorescent dye in biological systems. Full article

(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)

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10 pages, 1477 KiB

Open AccessCommunication

Bioactive Antidiabetic Flavonoids from the Stem Bark of Cordia dichotoma Forst.: Identification, Docking and ADMET Studies

by

Nazim Hussain

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Bibhuti Bhushan Kakoti

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Mithun Rudrapal

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Khomendra Kumar Sarwa

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Ismail Celik

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Emmanuel Ifeanyi Attah

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Shubham Jagadish Khairnar

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Soumya Bhattacharya

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Ranjan Kumar Sahoo

and

Sanjay G. Walode

Molbank 2021, 2021(2), M1234; https://doi.org/10.3390/M1234 - 11 Jun 2021

Cited by 20 | Viewed by 3116

Abstract

Cordia dichotoma Forst. (F. Boraginaceae) has been traditionally used for the management of a variety of human ailments. In our earlier work, the antidiabetic activity of methanolic bark extract of C. dichotoma (MECD) has been reported. In this paper, two flavonoid molecules were [...] Read more.

Cordia dichotoma Forst. (F. Boraginaceae) has been traditionally used for the management of a variety of human ailments. In our earlier work, the antidiabetic activity of methanolic bark extract of C. dichotoma (MECD) has been reported. In this paper, two flavonoid molecules were isolated (by column chromatography) and identified (by IR, NMR and mass spectroscopy/spectrometry) from the MECD with an aim to investigate their antidiabetic effectiveness. Molecular docking and ADMET studies were carried out using AutoDock Vina software and Swiss ADME online tool, respectively. The isolated flavonoids were identified as 3,5,7,3′,4′-tetrahydroxy-4-methoxyflavone-3-O-l-rhamnopyranoside and 5,7,3′-trihydroxy-4-methoxyflavone-7-O-l-rhamnopyranoside (quercitrin). Docking and ADMET studies revealed the promising binding affinity of flavonoid molecules for human lysosomal α-glucosidase and human pancreatic α-amylase with acceptable ADMET properties. Based on computational studies, our study reports the antidiabetic potential of the isolated flavonoids with predictive pharmacokinetics profile. Full article

(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)

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5 pages, 700 KiB

Open AccessShort Note

Kokosanolide D: A New Tetranortriterpenoid from Fruit Peels of Lansium domesticum Corr. cv Kokossan

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,

and

Molbank 2021, 2021(2), M1232; https://doi.org/10.3390/M1232 - 10 Jun 2021

Cited by 8 | Viewed by 2379

Abstract

A novel tetranortriterpenoid named kokosanolide D has been isolated from fruit peels of Lansium domesticum. The structure of kokosanolide D was elucidated primarily on the basis of spectroscopic data including infrared, 1D and 2D-NMR, as well as high resolution mass spectroscopy analysis [...] Read more.

A novel tetranortriterpenoid named kokosanolide D has been isolated from fruit peels of Lansium domesticum. The structure of kokosanolide D was elucidated primarily on the basis of spectroscopic data including infrared, 1D and 2D-NMR, as well as high resolution mass spectroscopy analysis and comparison with related compounds previously reported. Full article

(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)

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6 pages, 641 KiB

Open AccessShort Note

N-[7-Chloro-4-[4-(phenoxymethyl)-1H-1,2,3-triazol-1-yl]quinoline]-acetamide

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Molbank 2021, 2021(2), M1213; https://doi.org/10.3390/M1213 - 20 May 2021

Cited by 6 | Viewed by 2440

Abstract

The 1,2,3-triazole is a well-known biologically active pharmacophore constructed by the copper-catalyzed azide–alkyne cycloaddition. We herein reported the synthesis of 4-amino-7-chloro-based [1,2,3]-triazole hybrids via Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition of 4-azido-7-chloroquinoline with an alkyne derivative of acetaminophen. The compound was fully characterized by Fourier-transform [...] Read more.

The 1,2,3-triazole is a well-known biologically active pharmacophore constructed by the copper-catalyzed azide–alkyne cycloaddition. We herein reported the synthesis of 4-amino-7-chloro-based [1,2,3]-triazole hybrids via Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition of 4-azido-7-chloroquinoline with an alkyne derivative of acetaminophen. The compound was fully characterized by Fourier-transform infrared (FTIR), proton nuclear magnetic resonance (¹H-NMR), carbon-13 nuclear magnetic resonance (¹³C-NMR), heteronuclear single quantum coherence (HSQC), ultraviolet (UV) and high-resolution mass spectroscopies (HRMS). This compound was screened in vitro with different normal and cancer cell lines. The drug likeness of the compound was also investigated by predicting its pharmacokinetic properties. Full article

(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)

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5 pages, 866 KiB

Open AccessShort Note

2-Propyl-N′-[1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]pentanehydrazide

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and

Molbank 2020, 2020(4), M1164; https://doi.org/10.3390/M1164 - 26 Oct 2020

Cited by 1 | Viewed by 2027

Abstract

2-Propyl-N′-[1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]pentanehydrazide was obtained in 80% yield via the Einhorn variation of the Schotten–Baumann method by (+)-camphor hydrazide condensation with valproic acid (VPA) chloride. The structure of the titled compound was verified by Raman, FTIR, ¹H-NMR, and ¹³C-NMR spectral analysis [...] Read more.

2-Propyl-N′-[1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]pentanehydrazide was obtained in 80% yield via the Einhorn variation of the Schotten–Baumann method by (+)-camphor hydrazide condensation with valproic acid (VPA) chloride. The structure of the titled compound was verified by Raman, FTIR, ¹H-NMR, and ¹³C-NMR spectral analysis along with FAB-mass spectrometry. Thermal properties of synthesized derivative were elucidated by DSC and its purity by HPLC. The compound was successfully tested as a potential anticonvulsant agent based on models of chemically- and electrically-induced seizures. Full article

(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)

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5 pages, 4534 KiB

Open AccessShort Note

3-Hydroxy-8,14-secogammacera-7,14-dien-21-one: A New Onoceranoid Triterpenes from Lansium domesticum Corr. cv kokossan

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Molbank 2020, 2020(4), M1157; https://doi.org/10.3390/M1157 - 30 Sep 2020

Cited by 11 | Viewed by 2676

Abstract

A new onoceranoid triterpenes, namely 3-hydroxy-8,14-secogammacera-7,14-dien-21-one (1), has been isolated from the fruit peels of Lansium domesticum Corr. cv kokossan. The structure of 1 was determined on the basis of spectroscopic data including infrared, 1D and 2D-NMR, as well as [...] Read more.

A new onoceranoid triterpenes, namely 3-hydroxy-8,14-secogammacera-7,14-dien-21-one (1), has been isolated from the fruit peels of Lansium domesticum Corr. cv kokossan. The structure of 1 was determined on the basis of spectroscopic data including infrared, 1D and 2D-NMR, as well as high resolution mass spectroscopy analysis. Compound 1 showed a weak activity against MCF-7 breast cancer cell lines. Full article

(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)

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5 pages, 493 KiB

Open AccessShort Note

5,5′-Oxybis(1,3,7-trihydroxy-9H-xanthen-9-one): A New Xanthone from the Stem Bark of Garcinia porrecta (Clusiaceae)

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Molbank 2020, 2020(3), M1153; https://doi.org/10.3390/M1153 - 12 Aug 2020

Cited by 1 | Viewed by 2099

Abstract

A new polyoxygenated dimer-type xanthone, namely 5,5′-oxybis(1,3,7-trihydroxy-9H-xanthen-9-one (1), has been isolated from the stem bark of Garcinia porrecta. The structure of 1 was determined based on spectroscopic data, including 1D and 2D-NMR as well as high resolution mass spectroscopy analysis. Full article

(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)

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6 pages, 838 KiB

Open AccessShort Note

2-(3,4-Dihydroxyphenyl)-4-(2-(4-nitrophenyl)hydrazono)-4H-chromene-3,5,7-triol

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Alessandra Gianoncelli

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Molbank 2020, 2020(3), M1144; https://doi.org/10.3390/M1144 - 29 Jun 2020

Cited by 7 | Viewed by 2741

Abstract

On the basis of the knowledge from traditional herbal and folk medicine, flavonoids are among the most studied chemical classes of natural compounds for their potential activity as phosphodiesterase 5 (PDE5) inhibitors. We here describe the preparation of a semi-synthetic hydrazone derivative of [...] Read more.

On the basis of the knowledge from traditional herbal and folk medicine, flavonoids are among the most studied chemical classes of natural compounds for their potential activity as phosphodiesterase 5 (PDE5) inhibitors. We here describe the preparation of a semi-synthetic hydrazone derivative of quercetin, 2-(3,4-dihydroxyphenyl)-4-(2-(4-nitrophenyl)hydrazono)-4H-chromene-3,5,7-triol, that was obtained via a single-step modification of the natural compound. The product was characterized by NMR, mass spectrometry and HPLC. Preliminary molecular modeling studies suggest that this compound could efficiently interact with PDE5. Full article

(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)

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