Synthesis of 2-(4-Propyloxyphenyl)benzothiazole

Ha, Sie‐Tiong; Koh, Teck-Ming; Ong, Siew-Teng; Lee, Teck-Leong; Sivasothy, Yasodha

doi:10.3390/m609

Cited by 6 publications

(5 citation statements)

References 10 publications

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“…Analytical TLC on silica gel, 1:9 ethyl acetate/hexane R f = 0.65; white solid; 99.66 mg, yield 74%; mp 113–114 °C (lit . mp 113.3 °C); 1 H NMR (CDCl 3 , 400 MHz): δ 8.03–8.00 (m, 3H), 7.89 (d, J = 8.0 Hz, 1H), 7.49–7.45 (m, 1H), 7.37–7.33 (m, 1H), 7.00–6.98 (m, 2H), 4.02 (t, J = 6.4 Hz, 2H), 1.89–1.81 (m, 2H), 1.08 (t, J = 7.2 Hz, 3H); 13 C{ 1 H} NMR (CDCl 3 , 100 MHz): δ 168.1, 161.7, 154.4, 135.0, 129.3, 126.4, 126.35, 124.9, 123.0, 121.7, 115.0, 69.9, 22.7, 10.7; FT-IR (KBr) 3060, 2962, 1636, 1603, 1485, 1436, 1256, 1222, 1168, 1117, 1063, 1017, 960 cm –1 .…”

Section: Methodsmentioning

confidence: 99%

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Iron(III)-Catalyzed Regioselective Synthesis of Electron-Rich Benzothiazoles from Aryl Isothiocyanates via C–H Functionalization

et al. 2023

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We report herein a direct synthetic route for the preparation of 2-arylbenzothiazoles using aryl isothiocyanates and electron-rich arenes. The synthetic route involves triflic acid promoted addition of the arenes to aryl isothiocyanates followed by FeCl3-catalyzed C–S bond formation via C–H functionalization. The approach provides the advantage of synthesis of benzothiazoles without the conventional use of aryl aldehyde/carboxylic acid precursors employing the less expensive iron(III) catalyst.

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Section: Methodsmentioning

confidence: 99%

“…Analytical TLC on silica gel, 1:9 ethyl acetate/hexane R f = 0.65; white solid; 99.66 mg, yield 74%; mp 113−114 °C (lit. 32…”

Section: Radical Scavenger Experiments For Cross-coupling Reaction (W...mentioning

confidence: 99%

Iron(III)-Catalyzed Regioselective Synthesis of Electron-Rich Benzothiazoles from Aryl Isothiocyanates via C–H Functionalization

et al. 2023

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“…Benzothiazole is an important heterocyclic compound having both nitrogen and sulphur. Hence, it is used in the field of molecular design, optical, liquid and electronic properties [12]. Benzothiazole and its derivatives have been of great interest in the last three decades, because of its highly pronounced biological applications, such as, antitumour [13], anti-inflammatory [14], analgesic [15], anti-microbial [16], anti-leishmanial [17], anti-convulsant [18], anti-malarial [19], potential anti-HIV agents [20] and selective inhibition of HIV Type 1 reverse transcriptase [21].…”

Section: Introductionmentioning

confidence: 99%

Pharmacological investigation of 2-aminobenzothiazolium-4-methylbenzenesulphonate: Synthesis, spectral characterization and structural elucidation

Murugesan

Chandramohan

Raja

et al. 2015

Journal of Photochemistry and Photobiology B: Biology

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“…Biologists became interested in this sequence when it was discovered that glutamate neurotransmission inhibitors also occur in Riluzole (6-tri uoromethoxy -2-benzothiazolamines). According to its diversi ed molecular nature and extraordinary optical, liquid, and electronic properties, benzothiazole has received an overwhelming response (Khokra et al 2011; Bhat and Belagali 2014; Ha et al 2009). In the manufacturing of such dispersed azo coloring 2-aminobenzothiazole is used.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, spectral characterization and biological activities of Ag(I), Pt(IV) and Au(III) complexes with novel azo dye ligand (N, N, O) derived from 2-amino-6-methoxy benzothiazole

Kyhoiesh¹,

Al-Adilee

2022

Chem. Pap.

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The novel ligand 2-[2 ' -(6-methoxybenzothiazolyl)azo]-3,5-dimethyl benzoic acid (6-MBTAMB), derived from 2-amino-6-methoxy benzothiazole, has been used to synthesize a series of new metal complexes of Ag(I), Pt(IV) and Au(III). The metal complexes were characterized by elemental analyses (CHNS), molar conductivity, crystal structure (XRD), spectroscopic techniques: FT-IR, 1 H NMR, 13 C NMR, UV-Vis, mass spectra, thermal analysis (TG-DTA), FE-SEM and magnetic properties. Results con rmed that the azo dye ligand behaves a tridentate and coordinates to the metal ion via nitrogen atom of azomethine group of heterocyclic benzothiazole ring, nitrogen atom of the azo group which is the farthest of the benzothiazole molecule and carboxylic oxygen. Antimicrobial properties of all newly synthesized azo compounds are also demonstrated against bacterial pathogenic organisms and fungi. These complexes are more effective against bacteria and less effective against fungi compared to standard antibacterial drugs (Novobiocin) and antifungal drugs (Cycloheximide). By using the DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging test, it was discovered that the complexes had good antioxidant properties. In addition, the (6-MBTAMB) and metal complexes were docked with the crystal structure of FGF Receptor 2 (FGFR2) kinase domain harboring the pathogenic gain of function K659E mutation identi ed in endometrial cancer using the Molecular Operating Environment module (MOE). In vitro studies on human endometrial cancer cell lines (MFE-296) as well as healthy human umbilical vein endothelial cells (HUVEC) show uptake of the intact compounds by the cancer cells and increased activity against the cancer cells. HighlightDiazo-coupling was used to synthesize the heterocyclic azo dye ligand (6-MBTAMB).Newly synthesized azo compounds have been con rmed by various spectroscopic techniques.Antimicrobial, antioxidant, anticancer, and molecular docking were used to evaluate 6-MBTAMB with metal complexes. MFE-296 cells were more responsive to 6-MBTAMB and Au(III)-Complex Cytotoxicity with IC 50 of 6-MBTAMB is 100.4 µg/ml and Au(III) metal complex is 43.44 µg/ml in MFE-296 cell line.

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Synthesis of 2-(4-Propyloxyphenyl)benzothiazole

Abstract: A new 2-(4-propyloxyphenyl)benzothiazole was synthesized and its IR, 1H and 13C NMR and MS spectroscopic data are presented

Cited by 6 publications

References 10 publications

Iron(III)-Catalyzed Regioselective Synthesis of Electron-Rich Benzothiazoles from Aryl Isothiocyanates via C–H Functionalization

Iron(III)-Catalyzed Regioselective Synthesis of Electron-Rich Benzothiazoles from Aryl Isothiocyanates via C–H Functionalization

Pharmacological investigation of 2-aminobenzothiazolium-4-methylbenzenesulphonate: Synthesis, spectral characterization and structural elucidation

Synthesis, spectral characterization and biological activities of Ag(I), Pt(IV) and Au(III) complexes with novel azo dye ligand (N, N, O) derived from 2-amino-6-methoxy benzothiazole

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