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Journal articles on the topic 'Thiocoumarines'

Author: Grafiati

Published: 4 June 2021

Last updated: 18 February 2022

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1

El-Ahmad, Youssef, and Pierre Reynaud. "Sur le mécanisme de la réaction de meth-cohn-tarnowski de préparation des thiocoumarines." Journal of Heterocyclic Chemistry 25, no. 3 (1988): 711–14. http://dx.doi.org/10.1002/jhet.5570250302.

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2

Mokrov, G. V., S. A. Litvinova, T. A. Voronina, et al. "Design, synthesis, and anticonvulsant evaluation of 4-GABA-3-nitrocoumarines, 1-thiocoumarines, quinolone-2-ones, and their derivatives." Medicinal Chemistry Research 28, no. 11 (2019): 1901–11. http://dx.doi.org/10.1007/s00044-019-02422-5.

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3

Chaudhary, Diksha, Tanay Pramanik, and Soumava Santra. "Thiocoumarins and Dithiocoumarins: Advances in Synthesis and Pharmacological Activity." Current Organic Chemistry 24, no. 16 (2020): 1793–814. http://dx.doi.org/10.2174/1385272824999200812132707.

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Thiocoumarins and dithiocoumarins are two important classes of sulphurcontaining heterocyclic compounds, which are bioisosteres of coumarins. Herein, various synthetic strategies for these two classes of heterocyclic compounds reported in the literature have been discussed. Different solvents, catalysts, reagents and reaction conditions, which were employed successfully for synthesizing thiocoumarins and dithiocoumarins have also been described concisely in this review. Mechanistic overview has been given wherever it was necessary. In addition, a comparative view of various solvents, catalysts

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4

Tiwari, Monika R., and Navin B. Patel. "Synthesis and Pharmacological Activities of Oxadiazole and Pyrimidine Bearing Thiocoumarin Derivatives." Current Microwave Chemistry 8, no. 1 (2021): 33–43. http://dx.doi.org/10.2174/2213335608666210401152153.

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Aims: The study aims to synthesize thiocoumarin scaffolds clubbed with pyrimidine and 1,3,4-oxadiazole ring system under microwave irradiation and describe their pharmacological activities. Background: We report herein an efficient and simple Lewis acid-catalyzed procedure for the synthesis of novel series of thiocoumarin clubbed with pyrimidine and 1,3,4-oxadiazole motifs under microwave irradiation. The microwave-assisted technique has many advantages, such as a higher yield, a clean and selective procedure, shorter reaction time, and simple work-up. Objective: The objective of the present s

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5

Balde, L., N. Rodier, Y. Elahmad, and P. Reynaud. "N-Diméthylaminoéthylcarboxamido-3 imino-2 thiocoumarine." Acta Crystallographica Section C Crystal Structure Communications 43, no. 8 (1987): 1592–94. http://dx.doi.org/10.1107/s0108270187090966.

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6

Karbe, Carolin, and Paul Margaretha. "Photocycloadditions to 1-thiocoumarin." Journal of Photochemistry and Photobiology A: Chemistry 57, no. 1-3 (1991): 231–33. http://dx.doi.org/10.1016/1010-6030(91)85018-c.

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7

Debnath, Mintu, Supriya Sasmal та Debasish Haldar. "Fabrication of egg shell-like nanovesicles from a thiocoumarin-based ε-amino ester: a potential carrier". Journal of Materials Chemistry B 5, № 27 (2017): 5450–57. http://dx.doi.org/10.1039/c7tb00025a.

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8

Arumugam, S., and C. L. Khetrapal. "Nuclear magnetic resonance spectra of oriented bicyclic systems containing heteroatom(s): the spectrum of 2-thiocoumarin." Canadian Journal of Chemistry 64, no. 4 (1986): 714–16. http://dx.doi.org/10.1139/v86-114.

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From the proton nmr studies of 2-thiocoumarin and coumarin, it is concluded that the relative interproton distances in the two oxygen heteroatom bicyclic systems are similar. The values for the phenyl ring protons do not deviate significantly from the regular hexagonal geometry, unlike bicyclic systems with nitrogens as the heteroatoms, such as diazanaphthalenes. Larger values of the indirect spin–spin couplings within the protons of the ring containing the oxygen heteroatom, compared to the values between the ortho protons in the phenyl rings in coumarin and 2-thiocoumarin, correspond to the

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9

Smith, David G., Linda Mitchell, and Elizabeth J. New. "Pattern recognition of toxic metal ions using a single-probe thiocoumarin array." Analyst 144, no. 1 (2019): 230–36. http://dx.doi.org/10.1039/c8an01747f.

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10

Zaitceva, Olesia, Valérie Bénéteau, Dmitry S. Ryabukhin, Benoit Louis, Aleksander V. Vasilyev, and Patrick Pale. "Zeolite‐promoted Synthesis of Coumarins and Thiocoumarins." ChemCatChem 12, no. 1 (2019): 326–33. http://dx.doi.org/10.1002/cctc.201901384.

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11

Choi, Myung Gil, Youn Hwan Kim, Ji Eun Namgoong, and Suk-Kyu Chang. "Hg2+-selective chromogenic and fluorogenic chemodosimeter based on thiocoumarins." Chemical Communications, no. 24 (2009): 3560. http://dx.doi.org/10.1039/b905612b.

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12

Voss, Jürgen, Ronald Edler, and Gunadi Adiwidjaja. "Preparation of New tert-Butyl Substituted Coumarins, Thiocoumarins and Dithiocoumarins." Phosphorus, Sulfur, and Silicon and the Related Elements 182, no. 8 (2007): 1893–905. http://dx.doi.org/10.1080/10426500701340949.

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13

Maresca, Alfonso, Claudia Temperini, Lionel Pochet, Bernard Masereel, Andrea Scozzafava, and Claudiu T. Supuran. "Deciphering the Mechanism of Carbonic Anhydrase Inhibition with Coumarins and Thiocoumarins." Journal of Medicinal Chemistry 53, no. 1 (2010): 335–44. http://dx.doi.org/10.1021/jm901287j.

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14

METH-COHN, Otto, and Brian TARNOWSKI. "A Useful Synthon for Sulphur Heterocycles; I. The Synthesis of Thiocoumarins." Synthesis 1978, no. 01 (2002): 56–58. http://dx.doi.org/10.1055/s-1978-24675.

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15

Ma, Jiahui, Alexander Ripp, Daniel Wassy, et al. "Thiocoumarin Caged Nucleotides: Synthetic Access and Their Photophysical Properties." Molecules 25, no. 22 (2020): 5325. http://dx.doi.org/10.3390/molecules25225325.

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Photocages have been successfully applied in cellular signaling studies for the controlled release of metabolites with high spatio-temporal resolution. Commonly, coumarin photocages are activated by UV light and the quantum yields of uncaging are relatively low, which can limit their applications in vivo. Here, syntheses, the determination of the photophysical properties, and quantum chemical calculations of 7-diethylamino-4-hydroxymethyl-thiocoumarin (thio-DEACM) and caged adenine nucleotides are reported and compared to the widely used 7-diethylamino-4-hydroxymethyl-coumarin (DEACM) caging g

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16

Moon, Jung Ok, Jung Woo Lee, Myung Gil Choi, Sangdoo Ahn, and Suk-Kyu Chang. "Dual signaling of hypochlorous acid by desulfurization of thiocoumarin." Tetrahedron Letters 53, no. 48 (2012): 6594–97. http://dx.doi.org/10.1016/j.tetlet.2012.09.110.

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17

Park, Ji Eun, Myung Gil Choi, and Suk-Kyu Chang. "Colorimetric and Fluorescent Signaling of Au3+by Desulfurization of Thiocoumarin." Inorganic Chemistry 51, no. 5 (2012): 2880–84. http://dx.doi.org/10.1021/ic202080v.

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18

Cha, Sunyoung, Jiyoung Hwang, Myung Gil Choi, and Suk-Kyu Chang. "Dual signaling of m-chloroperbenzoic acid by desulfurization of thiocoumarin." Tetrahedron Letters 51, no. 50 (2010): 6663–65. http://dx.doi.org/10.1016/j.tetlet.2010.10.066.

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19

Szymański, Marian, Andrzej Maciejewski, Jan Kozłowski, and Jacek Koput. "Photophysics of the S2State of Thiocoumarin: A Vibrationally Unequilibrated Luminophore." Journal of Physical Chemistry A 102, no. 4 (1998): 677–83. http://dx.doi.org/10.1021/jp9723978.

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20

Maresca, Alfonso, Claudia Temperini, Lionel Pochet, Bernard Masereel, Andrea Scozzafava, and Claudiu T. Supuran. "Correction to Deciphering the Mechanism of Carbonic Anhydrase Inhibition with Coumarins and Thiocoumarins." Journal of Medicinal Chemistry 58, no. 14 (2015): 5689. http://dx.doi.org/10.1021/acs.jmedchem.5b00969.

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21

Cordaro, Massimiliano, Giovanni Grassi, Antonio Rescifina, Ugo Chiacchio, Francesco Risitano, and Angela Scala. "Stereodefined ring contraction-rearrangement of thiocoumarins to new fused benzo[b]thiophene derivatives." Tetrahedron 67, no. 3 (2011): 608–11. http://dx.doi.org/10.1016/j.tet.2010.11.061.

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22

Munshi, Parthapratim, and T. N. Guru Row. "Electron density study of 2H-chromene-2-thione." Acta Crystallographica Section B Structural Science 58, no. 6 (2002): 1011–17. http://dx.doi.org/10.1107/s0108768102018712.

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The charge-density distribution in 2H-chromene-2-thione (2-thiocoumarin), C9H6OS, has been determined from X-ray diffraction data measured at 90 K using a CCD detector, to a resolution of sinθ/λ < 1.08 Å−1. A multipolar-atom density model was fitted against 6908 reflections with I > 2σ(I) [R(F) = 0.021, wR(F) = 0.022, goodness of fit = 1.81] in order to generate the difference Fourier maps. The topological properties of the molecular electron density in terms of the bond critical points and the evaluation of the dipole moment show that the molecular dipole moment in the crystal is higher

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23

Iwanaga, Hiroki, Katsuyuki Naito, Kazuyuki Sunohara, and Masaki Okajima. "Coumarin and Thiocoumarin Dyes for Guest–Host Type Liquid Crystal Displays." Bulletin of the Chemical Society of Japan 71, no. 7 (1998): 1719–23. http://dx.doi.org/10.1246/bcsj.71.1719.

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24

Klaus, Christian P., Carolin Thiemann, J�rgen Kopf, and Paul Margaretha. "Solid-State Photocyclodimerization of 1-Thiocoumarin (= 2H-1-Benzothiopyran-2-one)." Helvetica Chimica Acta 78, no. 5 (1995): 1079–82. http://dx.doi.org/10.1002/hlca.19950780504.

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25

Cordaro, Massimiliano, Giovanni Grassi, Antonio Rescifina, Ugo Chiacchio, Francesco Risitano, and Angela Scala. "ChemInform Abstract: Stereodefined Ring Contraction-Rearrangement of Thiocoumarins to New Fused Benzo[b]thiophene Derivatives." ChemInform 42, no. 22 (2011): no. http://dx.doi.org/10.1002/chin.201122115.

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26

Inhülsen, Inga, Karin Chin, Maren Göwert, and Paul Margaretha. "Photocycloaddition of 4-(Alk-1-ynyl)-Substituted Coumarins and Thiocoumarins to 2,3-Dimethylbuta-1,3-diene." Helvetica Chimica Acta 94, no. 6 (2011): 1030–34. http://dx.doi.org/10.1002/hlca.201100112.

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27

Nakazumi, Hiroyuki, Yuzoh Kobara, and Teijiro Kitao. "Synthesis and insecticidal activity of 4-(aminomethyl)-2H-1-benzothiopyran-2-ones (thiocoumarins) and related compounds." Journal of Heterocyclic Chemistry 29, no. 1 (1992): 135–39. http://dx.doi.org/10.1002/jhet.5570290124.

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28

KLAUS, C. P., C. THIEMANN, J. KOPF, and P. MARGARETHA. "ChemInform Abstract: Solid-State Photocyclodimerization of 1-Thiocoumarin (= 2H-1- Benzothiopyran-2-one)." ChemInform 26, no. 47 (2010): no. http://dx.doi.org/10.1002/chin.199547168.

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29

Sallam, Mohamed Mohamed Mohamed, Mahmoud Ali Ibraheim, Mohamed Hilmy Elnagdi, and Kamal Usef Sadek. "Reaction with benzo[b]thiophene-2,3-dione A Novel Synthesis of Thiocoumarin Derivatives." Journal f�r Praktische Chemie 327, no. 2 (1985): 333–36. http://dx.doi.org/10.1002/prac.19853270219.

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30

Jung, Jae Chul, Ju Cheun Kim, Oee Sook Park, and Bong Suek Jang. "Synthesis of 4-hydroxy-1-thiocoumarin derivatives-1: An efficient synthesis of thioflocoumafen." Archives of Pharmacal Research 22, no. 3 (1999): 302–5. http://dx.doi.org/10.1007/bf02976367.

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31

Majumdar, Krishna, Pradip Maji, and Amarta Pal. "Sequential Thermal and Catalyzed Claisen Rearrangements Toward the Synthesis of Thiocoumarin-Annulated Furopyrans." Letters in Organic Chemistry 5, no. 3 (2008): 218–23. http://dx.doi.org/10.2174/157017808783955772.

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32

Tanaka, Koichi, and Fumio Toda. "CD Spectral Study on Chiral Arrangement and Enantioselective Reaction of Thiocoumarin in Inclusion Crystal." Molecular Crystals and Liquid Crystals Science and Technology. Section A. Molecular Crystals and Liquid Crystals 313, no. 1 (1998): 179–84. http://dx.doi.org/10.1080/10587259808044272.

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33

NAKAZUMI, H., Y. KOBARA, and T. KITAO. "ChemInform Abstract: Synthesis and Insecticidal Activity of 4-(Aminomethyl)-2H-1- benzothiopyran-2-ones (Thiocoumarins) and Related Compounds." ChemInform 23, no. 30 (2010): no. http://dx.doi.org/10.1002/chin.199230157.

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34

Reddy, P. Vijay Kumar, P. Naveen Kumar, and G. V. P. Chandramouli. "Synthesis and antimicrobial activity of 6,6′-arylidene-bis-[5-hydroxy-9-methyl-2,3-diaryl thieno[3,2-g-]thiocoumarins]." Journal of Heterocyclic Chemistry 42, no. 2 (2005): 283–86. http://dx.doi.org/10.1002/jhet.5570420216.

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35

Mokrov, G. V., T. A. Voronina, S. A. Litvinova, et al. "Synthesis and Anticonvulsant Activity of 4-Amino-3-Nitro-1-Thiocoumarins and 4-Amino-3-Nitroquinolin-2-Ones." Pharmaceutical Chemistry Journal 53, no. 3 (2019): 194–200. http://dx.doi.org/10.1007/s11094-019-01978-1.

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36

Lim, Zelong, David G. Smith, Jacek L. Kolanowski, et al. "A reversible fluorescent probe for monitoring Ag(I) ions." Journal of The Royal Society Interface 15, no. 144 (2018): 20180346. http://dx.doi.org/10.1098/rsif.2018.0346.

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Silver-containing nanomaterials are of interest for their antibiotic properties, for a wide range of applications from medicine to consumer products. However, much remains to be learnt about the degradation of such materials and their effects on human health. While most analyses involve measurement of total silver levels, it is important also to be able to measure concentrations of active free Ag(I) ions. We report here the preparation of a coumarin-based probe, thiocoumarin silver sensor 1 ( TcAg1 ), that responds reversibly to the addition of silver ions through the appearance of a new fluor

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37

Burdzinski, G., G. Buntinx, O. Poizat, and C. Lapouge. "Time-resolved resonance Raman investigation and ab initio calculations of the T1-state structure of thiocoumarin." Journal of Molecular Structure 735-736 (February 2005): 115–22. http://dx.doi.org/10.1016/j.molstruc.2004.10.079.

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38

Levai, Albert, and JÓZsef Jekő. "An efficient procedure for the preparation of 4-methyl-2-thiocoumarins by the reaction of 4-methylcoumarins with lawesson's reagent." Journal of Heterocyclic Chemistry 42, no. 4 (2005): 739–42. http://dx.doi.org/10.1002/jhet.5570420443.

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39

Nguyen, Van-Nghia, Seonye Heo, Sangin Kim, et al. "A thiocoumarin-based turn-on fluorescent probe for hypochlorite detection and its application to live-cell imaging." Sensors and Actuators B: Chemical 317 (August 2020): 128213. http://dx.doi.org/10.1016/j.snb.2020.128213.

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40

Devanathan, S., and V. Ramamurthy. "Photochemistry of .alpha.,.beta.-unsaturated thiones: cycloaddition of thiocoumarin to electron-rich and electron-deficient olefins from T1." Journal of Organic Chemistry 53, no. 4 (1988): 741–44. http://dx.doi.org/10.1021/jo00239a007.

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41

El-Khatib, Rafat Mohamad, and Lobna Abdel-Mohsen Ebaid Nassr. "Reactivity trends of the base hydrolysis of coumarin and thiocoumarin in binary aqueous–methanol mixtures at different temperatures." Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 67, no. 3-4 (2007): 643–48. http://dx.doi.org/10.1016/j.saa.2006.08.023.

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42

Tanaka, Koichi, Fumio Toda, Eiko Mochizuki, et al. "Enantioselective Single-Crystal-to-Single-Crystal Photodimerization of Coumarin and Thiocoumarin in Inclusion Complexes with Chiral Host Compounds." Angewandte Chemie International Edition 38, no. 23 (1999): 3523–25. http://dx.doi.org/10.1002/(sici)1521-3773(19991203)38:23<3523::aid-anie3523>3.0.co;2-g.

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43

Burdzinski, Gotard, Marcin Ziolek, Jerzy Karolczak, and Andrzej Maciejewski. "S2and S1States Deactivation of Thiocoumarin inn-Hexane and Acetonitrile Studied by Femtosecond Fluorescence Upconversion and Transient Absorption Spectroscopies." Journal of Physical Chemistry A 108, no. 51 (2004): 11160–64. http://dx.doi.org/10.1021/jp047373x.

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44

Kumar, Sarvesh, Brajendra K. Singh, Neerja Kalra та ін. "Novel thiocoumarins as inhibitors of TNF-α induced ICAM-1 expression on human umbilical vein endothelial cells (HUVECs) and microsomal lipid peroxidation☆☆☆". Bioorganic & Medicinal Chemistry 13, № 5 (2005): 1605–13. http://dx.doi.org/10.1016/j.bmc.2004.12.013.

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45

Fang, Qian, Huihui Tian, Lei Yang, Song Chen, Xingjiang Liu, and Xiangzhi Song. "A thiocoumarin-based fluorescent probe for detection of hypochlorite with high selectivity over other typical desulfurizing agents (Hg2+/Ag+)." Sensors and Actuators B: Chemical 260 (May 2018): 146–55. http://dx.doi.org/10.1016/j.snb.2017.12.142.

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46

Prasanna, B., and G. V. P. Chandramouli. "SYNTHESIS OF NEW 8-METHOXY-4-METHYL-3-(N-[2′-AMINO-(1′,3′,4′)THIA/OXA-DIAZOL-5′-YL]-SUBSTITUTED METHYL)-AMINO THIOCOUMARINS." Phosphorus, Sulfur, and Silicon and the Related Elements 179, no. 10 (2004): 2059–65. http://dx.doi.org/10.1080/10426500490474914.

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47

Huang, Bing-Nan, Jin-Tao Liu, and Wei-Yuan Huang. "Studies on sulfinatodehalogenation. Part 30. Synthesis of 3-perfluoroalkylated coumarins, thiocoumarins and 2-quinolones by direct perfluoroalkylation with perfluoroalkyl iodides and sodium hydroxymethanesulfinate." Journal of the Chemical Society, Perkin Transactions 1, no. 1 (1994): 101. http://dx.doi.org/10.1039/p19940000101.

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48

Valente, Sergio, та Gilbert Kirsch. "ChemInform Abstract: Facile Synthesis of 4-Acetyl-coumarins, -thiocoumarins and -quinolin-2(1H)-one via Very High α-Regioselective Heck Coupling on Tosylates." ChemInform 42, № 43 (2011): no. http://dx.doi.org/10.1002/chin.201143128.

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49

Klaus, Christian P., and Paul Margaretha. "Wavelength Control in the Photochemical Addition of Tricyclic [g]-Fused 1-Thiocoumarins or Coumarins to Alkenes Yielding Mono- and Bis([2 + 2]-Cycloadducts)." Liebigs Annalen 1996, no. 2 (2006): 291–95. http://dx.doi.org/10.1002/jlac.199619960221.

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50

Shinde, Rupali G., Ayesha A. Khan, and Atanu Barik. "Formation of two centre three electron bond by hydroxyl radical induced reaction of thiocoumarin: evidence from experimental and theoretical studies." Free Radical Research 53, no. 6 (2019): 629–40. http://dx.doi.org/10.1080/10715762.2019.1617417.

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