Synthesis of derivatives of thiophene using methyl 2‐isothiocyanatobenzoate

Deck, Lorraine M.; Turner, S. D.; Deck, Jason A.; Papadopoulos, E. P.

doi:10.1002/jhet.5570380204

Cited by 18 publications

(6 citation statements)

References 20 publications

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“…These values were in accordance with literature data for 4 H -3,1-benzoxazin-4-ones [ 14 , 32 , 37 , 38 , 39 ]. A similar influence of the sulphur-oxygen exchange on the chemical shift of the C-4 carbon was observed for pairs of 2-thien-2-yl and 2-cyano substituted 4 H -3,1-benzothiazin(oxazin)-4-ones [ 32 , 40 ]. The structure of the title compounds was furthermore confirmed by X-ray crystal structure analyses [ 41 ] ( Figure 1 ).…”

Section: Resultssupporting

confidence: 92%

“…On the other hand, the benzothiazinone 5i was the main product of the reaction of 4i with TFAA while the corresponding benzoxazinone 9i was only formed in traces. The formation of 8h is envisaged to occur by a nucleophilic attack of the carboxyl oxygen at the activated thiocarbonyl carbon [ 31 , 32 , 33 , 34 , 35 , 36 ]. Further investigations are needed to clarify the mechanism of this desulphurisation-cyclisation.…”

Section: Resultsmentioning

confidence: 99%

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2-Amino- and 2-Alkylthio-4H-3,1-benzothiazin-4-ones: Synthesis, Interconversion and Enzyme Inhibitory Activities

et al. 2009

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The synthetic access to 2-sec-amino-4H-3,1-benzothiazin-4-ones 2 was explored. Compounds 2 were available from methyl 2-thioureidobenzoates 1, 2-thioureidobenzoic acids 3, and novel 2-thioureidobenzamides 6, respectively, under different conditions. 2-Alkylthio-4H-3,1-benzothiazin-4-ones 5 have been prepared from anthranilic acid following a two step route. Both, benzothiazinones 2 and 5 underwent ring cleavage reactions to produce thioureas 1 and 6, respectively. Twelve benzothiazinones were evaluated as inhibitors against a panel of eight proteases and esterases to identify one selective inhibitor of human cathepsin L, 2b, and one selective inhibitor of human leukocyte elastase, 5i.

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Section: Resultssupporting

confidence: 92%

Section: Resultsmentioning

confidence: 99%

2-Amino- and 2-Alkylthio-4H-3,1-benzothiazin-4-ones: Synthesis, Interconversion and Enzyme Inhibitory Activities

et al. 2009

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“…White crystals, yield: 87 %, mp: 203–205 °C [36] . 1 H NMR (400 MHz, CDCl 3 ) δ 8.56 (d, J =3.5 Hz, 1H, Ar−H), 8.26 (d, J =7.5 Hz, 1H, Ar−H), 7.82–7.75 (m, 2H, Ar−H), 7.63 (d, J =5.1, 1H, Ar−H), 7.47 (t, J =6.8 Hz, 1H, Ar−H), 7.24–7.14 (m, 1H, Ar−H), 5.10 (s, 2H, NH 2 ).…”

Section: Methodsmentioning

confidence: 99%

Novel Benzoic Acid Derivatives Bearing Quinazolin‐4(3H)‐one Ring: Synthesis, Characterization, and Inhibition Effects on α‐Glucosidase and α‐Amylase

Tokalı

2022

ChemistrySelect

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In this study, new benzoic acid derivatives of the quinazolinone ring, which is one of the biologically active members of nitrogen-containing heterocyclic compounds, were synthesized with excellent yields (98-90 %). The structures of the novel compounds (1-12) were characterized with Fourier-transform Infrared (FTIR), Nuclear Magnetic Resonance ( 1 H NMR-13 C NMR), and High-Resolution Mass Spectroscopy (HRMS). α-Glucosidase and α-Amylase inhibition properties were examined to evaluate the anti-diabetic properties of the synthesized compounds. For α-Glucosidase, molecules showed IC 50 in ranging of > 100-3.468 � 0.270 μM and K i s in ranging of > 100-3.310 � 0.326 μM. For α-Amylase, molecules showed IC 50 in ranging of > 100-1.215 � 0.225 μM. 4-[(2-[(4-phenylpiperazin-1-yl)methyl]-4-oxoquinazolin-3(4H)-ylimino)methyl]benzoicacid (10) has the strongest inhibitory effect for both enzymes. It is 5.4 times more potent inhibitor for α-Glucosidase and 34.9 times more potent for α-Amylase than the standard inhibitor Acarbose. Also, the molecular docking study was carried out for the most active compound for the determination of ligand-enzyme interactions. Binding affinities of the most active compound were calculated as À 5.978 kcal/mol and À 5.548 kcal/mol for α-Glucosidase and α-Amylase, respectively. The aromatic ring and the aminomethyl group of the quinazoline and the carboxyl group moieties have played a critical role in the inhibition.

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“…Moreover, various isothiocyanates have been used as starting materials to obtain this heterocycle through other cyclization processes 11–17. Based on the rearrangement of 2‐isothiocyano triarylmethanes in the presence of AlCl 3 Abaev and co‐workers synthesized 2,4‐diaryl‐4 H ‐3,1‐benzothiazines 12.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anticancer Activity of New 2‐Aryl‐4H‐3,1‐benzothiazines

Niewiadomy

Matysiak

Karpińska

2011

Archiv der Pharmazie

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New compounds of 2-aryl-4H-3,1-benzothiazine set were synthesized and tested for their antiproliferative activity as part of our research in the antitumor field. The title compounds were obtained by the reaction of aryl-modified sulfinylbis((2,4-dihydroxyphenyl)methanethione) with 2-aminobenzyl alcohols. The reaction proceeded through thiobenzanilide intermediates, which were converted to the 4H-3,1-benzothiazine fused ring by an endocyclization process. The structures of compounds were identified from elemental, IR, (1) H-NMR, (13) C-NMR, and MS spectra analyses. The cytotoxicity in vitro against four human cancer cell lines was determined. The antiproliferative properties of some compounds were more beneficial than cisplatin studied comparatively.

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Synthesis of derivatives of thiophene using methyl 2‐isothiocyanatobenzoate

Abstract: A variety of 2‐substituted thiophenes is readily obtained from 2‐(2‐thienyl)‐4H‐3,l‐benzothiazin‐4‐one (2), which is formed when thiophene reacts with methyl 2‐isothiocyanatobenzoate (1) in the presence of anhydrous stannic chloride.

Cited by 18 publications

References 20 publications

2-Amino- and 2-Alkylthio-4H-3,1-benzothiazin-4-ones: Synthesis, Interconversion and Enzyme Inhibitory Activities

2-Amino- and 2-Alkylthio-4H-3,1-benzothiazin-4-ones: Synthesis, Interconversion and Enzyme Inhibitory Activities

Novel Benzoic Acid Derivatives Bearing Quinazolin‐4(3H)‐one Ring: Synthesis, Characterization, and Inhibition Effects on α‐Glucosidase and α‐Amylase

Synthesis and Anticancer Activity of New 2‐Aryl‐4H‐3,1‐benzothiazines

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