Organic Communications

A scientific open access journal in the field of synthetic organic chemistry and polymers
Editor-in-Chief: Hasan Seçen
Review Article and Book Review Editor: Turan Ozturk
Synthetic Polymer Section Editor: Mehmet S. Eroglu
Co-Editor-in-Chief: Ahmet C Goren

LATEST ARTICLES

Original Article

Synthesis and evaluation of antiproliferative and mPGES-1 inhibitory activities of novel carvacrol-triazole conjugates

Org. Commun. (2022) 15:4 ; 356 - 377
by İlker Demirbolat , Necla Kulabaş , Merve Gürboğa , Özlem Bingöl Özakpınar , Gamze Çiftçi , Kemal Yelekçi , Jianyang Liu , Per-Johan Jakobsson , Özkan Danış , Ayşe Ogan and İlkay Küçükgüzel

Some novel triazole-bearing acetamide derivatives 9-26 were synthesized starting from carvacrol. All synthesized compounds were characterized by FTIR, 1H-NMR, 13C-NMR, HMBC and MS data. In vitro cytotoxic activities of all synthesized molecules against five cancer lines (human breast cancer MCF-7, human lung cancer A549, human prostate cancer PC-3, human chronic myelogenous leukemia K562, human neuroblastoma SH-SY5Y cell lines) were evaluated by MTT assay. Compounds were also tested on mouse embryonic fibroblast cells (NIH/3T3) to determine selectivity. Eighteen target compounds 9-26 were screened for their mPGES-1 and COX-1/2 inhibitory activities. Of these compounds, 26 (KUC16D425) showed the highest mPGES-1 inhibition at 10 µM. This compound have also been observed to induce apoptosis and inhibit cell migration in MCF-7 cells. In silico molecular docking calculations were performed to understand the binding interactions of compounds with target proteins. ADMET predictions were also done to evaluate drug-like properties of the novel compounds.

DOI
http://doi.org/10.25135/acg.oc.142.2212.2651
Keywords
Carvacrol 1,2,4-triazoles cancer apoptosis mPGES-1 in silico studies
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© 2022 ACG Publications. All rights reserved.
Original Article

Post-synthetic sulfonation of a diphenylanthracene based porous aromatic framework

Org. Commun. (2022) 15:4 ; 346 - 355
by Hakan Bildirir

Post-synthetic modification is an alternative pathway to introduce functionalities into the backbone of porous materials. Sulfonation of porous organic polymers is one of the frequently applied post-functionalization since the sulfonate groups are interesting for various applications such as carbon dioxide storage, proton conduction, ion removal. Moreover, sulfonation drastically improve hydrophilicity of the hydrophobic materials, therefore, makes the final compounds more processable in aqueous media. In this article, a procedure for post-synthetic sulfonation of a diphenylanthracene (DPA) based porous aromatic framework (DPA-PAF) is presented. Oleum (fuming sulfuric acid) was used as the sulfonation agent in acetic acid+water media instead of the conventionally used chlorosulfonic acid in the chlorinated solvents. Aside from macroscopic (visual) observations such as improved dispersibility in water when compared to the parent compound, the introduction of sulfonate groups was confirmed by using infra-red spectroscopy, elemental analysis, and gas sorption (surface area) measurements.

DOI
http://doi.org/10.25135/acg.oc.138.2210.2605
Keywords
Porous organic polymers porous aromatic frameworks PAF-1 post-synthetic modification sulfonation oleum
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© 2022 ACG Publications. All rights reserved.
Communication

Zn(OAc)2•2H2O: An efficient catalyst for the one-pot synthesis of 2-substituted benzothiazoles

Org. Commun. (2022) 15:4 ; 378 - 385
by Kokane Balaji Digambar , Ravi Varala and Sudhakar G. Patil

By condensation from aldehyde and 2-aminothiophenol at 80 0C, environmentally friendly, easily accessible, and inexpensive Zn(OAc)2.2H2O (5 mol%) was used to synthesize electronically and structurally divergent benzothiazoles in moderate to good yields (67-96%). All the 2-substituted benzothiazole analogues were thoroughly characterized by IR, NMR and mass spectral analyses.

DOI
http://doi.org/10.25135/acg.oc.140.2210.2618
Keywords
Catalysis aldehydes 2-aminothiophenol benzothiazoles zinc acetate solvent-free condition
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© 2022 ACG Publications. All rights reserved.
Original Article

Synthesis of some 2-alkyl-5-(4-vinylphenyl)-2H-tetrazole compounds via the Wittig reaction and investigation by X-ray crystallography

Org. Commun. (2022) 15:4 ; 333 - 345
by Doğukan Doyduk and Yılmaz Yildirir

Tetrazoles are frequently used in industry and medicine. However, molecules that have both tetrazole and alkenyl groups are rare. For this purpose, new 2-alkyl-5-(4-vinylphenyl)-2H-tetrazole (BF5a-i, 63-99%) derivative compounds containing both styrene and tetrazole were synthesized with a high yield under mild conditions by the Wittig reaction. Their structures were verified by spectroscopic methods (FT-IR, 1H NMR, 13C-APT NMR, HRMS, and X-Ray crystallography (for BF5a).

DOI
http://doi.org/10.25135/acg.oc.139.2211-2633
Keywords
Tetrazole styrene X-ray crystallography Wittig dehydration
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© 2022 ACG Publications. All rights reserved.