Towards the Sustainable Synthesis of Biologically Active Molecules in Green Solvents

Topic Information

Dear Colleagues,

Over the past decades, sustainability has become an imperative issue. In the field of organic synthesis, both academic and industrial scientists are making efforts to develop more environmentally friendly chemical processes. In the manufacturing, chemical, and pharmaceutical industries, the solvents employed in synthetic methodologies represent 75–80% of the total waste generated. Indeed, the demand for sustainable alternatives that can replace hazardous solvents has become a subject of intense research today. It could be possible to reduce the environmental impact of chemical transformation through the choice of a suitable solvent, such as through the employment of green solvents derived from renewable sources. This Special Issue plans to give an overview of the most recent advances in the field of the sustainable synthesis of biologically active molecules. The issue aims to provide selected contributions on advances in the preparation of bioactive compounds in green solvents, such as deep eutectic solvents (DES), alcohols and polyols, supercritical CO₂, etc. Potential topics include, but are not limited to: Synthetic methodologies with a low environmental impact; The green synthesis of heterocycles; The more eco-friendly synthesis of compounds with possible applications in the biological pharmacological field; The synthesis of organic compounds in deep eutectic solvents; The synthesis of organic compounds in green alcohols; Synthetic strategies in supercritical CO₂.

Dr. Antonio Salomone
Dr. Serena Perrone
Topic Editors

Keywords

Participating Journals

Journal Name	Impact Factor	CiteScore	Launched Year	First Decision (median)	APC
Catalysts catalysts	3.8	6.8	2011	12.9 Days	CHF 2200	Submit
Chemistry chemistry	2.4	3.2	2019	13.4 Days	CHF 1800	Submit
Molbank molbank	0.6	0.7	1997	13.9 Days	CHF 500	Submit
Molecules molecules	4.2	7.4	1996	15.1 Days	CHF 2700	Submit
Sustainable Chemistry suschem	-	-	2020	31.2 Days	CHF 1000	Submit

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Published Papers (5 papers)

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All Catalysts Chemistry Molbank Molecules Sustainable Chemistry

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Supplementary material:
Supplementary File 1 (ZIP, 1292 KiB)
Supplementary File 2 (MOL, 6 KiB)
Supplementary File 3 (INCHI, 2 KiB)
Supplementary File 4 (MOL, 6 KiB)
Supplementary File 5 (CIF, 1633 KiB)

7 pages, 1280 KiB  

Open AccessCommunication

New Allyl Derivative of Curcumin: Synthesis and Crystal Structure of (1E,6E)-4-allyl-1,7-bis(4′-allyloxy-3′-methoxyphenyl)hepta-1,6-diene-3,5-dione

by Anna A. Druzina, Olga B. Zhidkova, Sergey A. Anufriev, Ekaterina V. Dubasova, Ivan V. Ananyev, Samya Banerjee, Igor B. Sivaev and Vladimir I. Bregadze

Molbank 2024, 2024(4), M1905; https://doi.org/10.3390/M1905 - 24 Oct 2024

Viewed by 506

Abstract

A new allyl derivative of curcumin containing three allyl groups (1E,6E)-4-allyl-1,7-bis(4′-allyloxy-3′-methoxyphenyl)hepta-1,6-diene-3,5-dione was synthesized by the reaction of curcumin with the excess of allyl bromide in the presence of K₂CO₃ in acetone under reflux. The triple-allylated curcumin [...] Read more.

A new allyl derivative of curcumin containing three allyl groups (1E,6E)-4-allyl-1,7-bis(4′-allyloxy-3′-methoxyphenyl)hepta-1,6-diene-3,5-dione was synthesized by the reaction of curcumin with the excess of allyl bromide in the presence of K₂CO₃ in acetone under reflux. The triple-allylated curcumin was characterized by ¹H and ¹³C-NMR spectroscopy and single-crystal X-ray diffraction analysis. Full article

(This article belongs to the Topic Towards the Sustainable Synthesis of Biologically Active Molecules in Green Solvents)

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Figure 1

Figure 1
<p>The independent unit in the crystal of <b>2</b> is the representation of non-hydrogen atoms, shown as probability ellipsoids of atomic displacements (<span class="html-italic">p</span> = 0.5). The dotted line shows the H-bond.</p> Full article ">Figure 2
<p>The energy frameworks in the crystal packing of (1<span class="html-italic">E</span>,6<span class="html-italic">E</span>)-4-allyl-1,7-bis(4′-allyloxy-3′-methoxyphenyl)hepta-1,6-diene-3,5-dione (<b>2</b>).</p> Full article ">Scheme 1
<p>Synthesis of curcumin derivative with two allyl substituents at the central methylene carbon.</p> Full article ">

attachment

Supplementary material:
Supplementary File 1 (PDF, 2217 KiB)
Supplementary File 2 (MOL, 3 KiB)
Supplementary File 3 (INCHI, 901 B)
Supplementary File 4 (MOL, 3 KiB)

8 pages, 973 KiB  

Open AccessCommunication

Synthesis and In Vitro Antibacterial Evaluation of Mannich Base Nitrothiazole Derivatives

by Phelelisiwe S. Dube, Dylan Hart, Lesetja J. Legoabe, Audrey Jordaan, Digby F. Warner and Richard M. Beteck

Molbank 2024, 2024(1), M1793; https://doi.org/10.3390/M1793 - 18 Mar 2024

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Abstract

Nitrothiazole derivatives have been reported to exhibit activity against aerobic, anaerobic, and microaerophilic bacteria. This activity profile makes the nitrothiazole compound class an ideal lead source against Mycobacterium tuberculosis, which flourishes in varied environments with different oxygen concentrations. In this work, we [...] Read more.

Nitrothiazole derivatives have been reported to exhibit activity against aerobic, anaerobic, and microaerophilic bacteria. This activity profile makes the nitrothiazole compound class an ideal lead source against Mycobacterium tuberculosis, which flourishes in varied environments with different oxygen concentrations. In this work, we investigated six nitrothiazole derivatives for antitubercular activity. The compounds exhibited potent activity, with compounds 9 and 10 possessing an equipotent MIC₉₀ value of 0.24 µM. The compounds were investigated for cytotoxicity against HEK293 cells and hemolysis against red blood cells, and they demonstrated no cytotoxicity nor hemolytic effects, suggesting they possess inherent antitubercular activity. Full article

(This article belongs to the Topic Towards the Sustainable Synthesis of Biologically Active Molecules in Green Solvents)

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Figure 1

Figure 1
<p>Nitrothiazole derivatives with antitubercular activity.</p> Full article ">Figure 2
<p>Bar graph presentation of antitubercular activity.</p> Full article ">Scheme 1
<p>Synthesis of Nitrothiazole-Mannich base derivatives. <b>Reagents and conditions</b>: (i) DCM, TEA, 0 °C, 24–36 h; (ii) NH4SCN, EtOH, reflux, 4–8 h; (iii) piperidine (5 eq), aldehyde (5 eq), EtOH, reflux, 24–36 h.</p> Full article ">Scheme 2
<p>Structures of fragments formed during ionization.</p> Full article ">

attachment

Supplementary material:
Supplementary File 1 (ZIP, 1728 KiB)
Supplementary File 2 (MOL, 2 KiB)
Supplementary File 3 (INCHI, 723 B)
Supplementary File 4 (MOL, 2 KiB)
Supplementary File 5 (CIF, 2173 KiB)

7 pages, 1222 KiB  

Open AccessShort Note

(3-(4-Chlorophenyl)-4,5-dihydroisoxazol-5-yl)methyl Benzenesulfonate

by Loubna Mokhi, Karim Chkirate, Xiaodong Zhang, Mohsine Driowya and Khalid Bougrin

Molbank 2023, 2023(4), M1732; https://doi.org/10.3390/M1732 - 22 Sep 2023

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Abstract

A novel single crystal of (3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl)methyl benzenesulfonate has been synthetized via a one-pot sequential strategy under sonication. The single crystal has been investigated using X-ray diffraction analysis. Hydrogen bonding between C–H···O and C–H···N produces a layer structure in the crystal. According to a [...] Read more.

A novel single crystal of (3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl)methyl benzenesulfonate has been synthetized via a one-pot sequential strategy under sonication. The single crystal has been investigated using X-ray diffraction analysis. Hydrogen bonding between C–H···O and C–H···N produces a layer structure in the crystal. According to a Hirshfeld surface analysis, interactions H···H (28.9%), H···O/O···H (26.7%) and H···C/C···H (15.8%) make the largest contributions to crystal packing. The optimized structure and the solid-state structure that was obtained through experiments are compared using density functional theory at the B3LYP/6-311 G + (d,p) level. The computed energy difference between the lowest unoccupied molecular orbital (LUMO) and highest occupied molecular orbital (HOMO) is 4.6548 eV. Full article

(This article belongs to the Topic Towards the Sustainable Synthesis of Biologically Active Molecules in Green Solvents)

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Figure 1

Figure 1
<p>Characteristic ¹H, ¹³C NMR of compound (<b>5</b>).</p> Full article ">Figure 2
<p>The title molecule with labeling scheme and 50% probability ellipsoids.</p> Full article ">Figure 3
<p>View of the Hirshfeld surface of [3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl]methyl benzenesulfonate mapped (<b>a</b>) over dnorm in the range -0.2185 to 1.3206 a.u., (<b>b</b>) over shape-index map. (<b>c</b>) Electrostatic potential energy in the range −0.05 to 0.05 a.u. measured using the STO-3 G basis set at the theoretical level of Hartree–Fock.</p> Full article ">Scheme 1
<p>One-pot synthesis of compound <b>5</b>.</p> Full article ">

attachment

Supplementary material:
Supplementary File 1 (ZIP, 1130 KiB)
Supplementary File 2 (MOL, 2 KiB)
Supplementary File 3 (INCHI, 588 B)
Supplementary File 4 (MOL, 2 KiB)
Supplementary File 5 (CIF, 1344 KiB)

11 pages, 3616 KiB  

Open AccessShort Note

2-(N-allylsulfamoyl)-N-propylbenzamide

by Ayoub El mahmoudi, Karim Chkirate, Loubna Mokhi, Joel T. Mague and Khalid Bougrin

Molbank 2023, 2023(3), M1678; https://doi.org/10.3390/M1678 - 30 Jun 2023

Cited by 1 | Viewed by 1110

Abstract

In this work, a new compound, 2-(N-allylsulfamoyl)-N-propylbenzamide, has been synthesized via a tandem one-pot reaction under sonication. The rotational orientations of the allylsulfamoyl and the amide groups in the title molecule, C₁₃H₁₈N₂O₃ [...] Read more.

In this work, a new compound, 2-(N-allylsulfamoyl)-N-propylbenzamide, has been synthesized via a tandem one-pot reaction under sonication. The rotational orientations of the allylsulfamoyl and the amide groups in the title molecule, C₁₃H₁₈N₂O₃S, are partly determined by an intramolecular N—H···O hydrogen bond. In the crystal, a layer structure is generated by N—H···O and C—H···O hydrogen bonds plus C—H···π (ring) interactions. A Hirshfeld surface analysis indicates that the most important contributions to crystal packing are from H···H (59.2%), H···O/O···H (23.5%), and H···C/C···H (14.6%) interactions. The optimized structure calculated using density functional theory at the B3LYP/6–311 G (d,p) level is compared with the experimentally determined structure in the solid state. The calculated highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy gap is 5.3828 eV. Full article

(This article belongs to the Topic Towards the Sustainable Synthesis of Biologically Active Molecules in Green Solvents)

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Figure 1

Figure 1
<p>The title molecule with labeling scheme and 50% probability ellipsoids. An intramolecular hydrogen bond is depicted by a dashed line. Only the major component of the disorder is shown.</p> Full article ">Figure 2
<p>A portion of one layer viewed along the c-axis with N—H···O and C—H···O hydrogen bonds depicted, respectively, by violet and black dashed lines. The C—H···π(ring) interactions are depicted by green dashed lines and non-interacting hydrogen atoms are omitted for clarity.</p> Full article ">Figure 3
<p>Packing viewed along the c-axis with intermolecular interactions depicted as in <a href="#molbank-2023-M1678-f002" class="html-fig">Figure 2</a> and non-interacting hydrogen atoms omitted for clarity.</p> Full article ">Figure 4
<p>View of the Hirshfeld surface of 2-(<span class="html-italic">N</span>-allylsulfamoyl)-<span class="html-italic">N</span>-propylbenzamide. (<b>a</b>) Mapped over d_norm in the range of −0.4420 to 1.2928 a.u., (<b>b</b>) mapped over shape index. (<b>c</b>) Electrostatic potential energy in the range of −0.05 to 0.05 a.u., calculated using the STO-3 G basis set at the Hartree–Fock level of theory.</p> Full article ">Figure 5
<p>The Hirshfeld surface plotted over d_norm and the main non-covalent interactions in the crystal packing of 2-(<span class="html-italic">N</span>-allylsulfamoyl)-<span class="html-italic">N</span>-propylbenzamide.</p> Full article ">Figure 6
<p>Two-dimensional fingerprint plots for the title compound showing (<b>a</b>) all interactions, and delineated into (<b>b</b>) H···H, (<b>c</b>) H···O/O···H, (<b>d</b>) C···H/H···C, (<b>e</b>) N···H/H···N, (<b>f</b>) O···C/C···O, (<b>g</b>) N···O/O···N, (<b>h</b>) O···O, and (<b>i</b>) S···H/H···S interactions. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.</p> Full article ">Figure 7
<p>The energy band gap of 2-(<span class="html-italic">N</span>-allylsulfamoyl)-<span class="html-italic">N</span>-propylbenzamide.</p> Full article ">Scheme 1
<p>Synthesis of compound <b>4</b>.</p> Full article ">

attachment

Supplementary material:
Supplementary File 1 (PDF, 238 KiB)
Supplementary File 2 (MOL, 2 KiB)
Supplementary File 3 (INCHI, 535 B)
Supplementary File 4 (MOL, 2 KiB)

3 pages, 364 KiB  

Open AccessShort Note

4,7-Dimethoxy-6-propyl-2H-1,3-benzodioxole-5-carbaldehyde

by Dmitry V. Tsyganov and Victor V. Semenov

Molbank 2023, 2023(3), M1676; https://doi.org/10.3390/M1676 - 27 Jun 2023

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Abstract

A simple intermediate for the synthesis of methoxy-analogues of coenzymes Q with substituents having various chain lengths based on natural polyalkoxyallylbenzene apiol has been developed. Full article

(This article belongs to the Topic Towards the Sustainable Synthesis of Biologically Active Molecules in Green Solvents)

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Scheme 1

Scheme 1
<p>Aldehyde <b>6</b> was obtained by the formylation of dihydroapiol <b>5</b>.</p> Full article ">

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