Durable fluorescent cotton textile by immobilization of unique tetrahydrothienoisoquinoline derivatives

Marae, Islam S.; Sharmoukh, Walid; Bakhite, Etify A.; Moustafa, O. S.; Abbady, M. S.; Emam, Hossam E.

doi:10.1007/s10570-021-03871-1

Cited by 40 publications

(14 citation statements)

References 59 publications

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“…Treatment of 1,3-dicarbonyl compounds 1a , b with cyanothioacetamide in refluxing ethanol in the presence of piperidine as a basic catalyst resulted in a regioselective cyclocondensation reaction affording the corresponding 7-acetyl-8-(3- and -4-nitrophenyl)-4-cyano-1,6-dimethyl-6-hydroxy-5,6,7,8-tetrahydroisoquinoline-3(2 H )-thiones 2a , b in 93–96% yield (Scheme ). The pathway of this reaction is similar to that reported before. − …”

Section: Resultssupporting

confidence: 86%

“…Additionally the α-carbonyl stereogenic center is base-labile. From the single-crystal X-ray data of compound 5d in the current paper and those of other reported related compounds, − ,− it is apparent that the cis , trans–cis isomer crystallized: aryl, acetyl, and hydroxy are cis / trans / cis with a hydrogen bonding between acetyl and hydroxy. Only one diastereoisomer is isolated as a reaction product during the course of the current investigation and previously reported ones. − ,− All reactions of starting compounds 2a , b which take place far away form their three consecutive stereogenic centers resulted in no epimerization processes. − ,− …”

Section: Resultsmentioning

confidence: 50%

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Nitrophenyl-Group-Containing Heterocycles. I. Synthesis, Characterization, Crystal Structure, Anticancer Activity, and Antioxidant Properties of Some New 5,6,7,8-Tetrahydroisoquinolines Bearing 3(4)-Nitrophenyl Group

et al. 2022

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Regioselective cyclocondensation of 2,4-diacetyl-5hydroxy-5-methyl-3-(3-nitrophenyl/4-nitrophenyl)cyclohexanones 1a,b with cyanothioacetamide afforded the corresponding 7-acetyl-4-cyano-1,6-dimethyl-6-hydroxy-8-(3-and -4-nitrophenyl)-5,6,7,8tetrahydrosoquinoline-3(2H)-thiones 2a,b. Reaction of compounds 2a,b with ethyl iodide, 2-chloroacetamide ( 4a), or its Naryl derivatives 4b−e in the presence of sodium acetate trihydrate gave 3-ethylthio-5,6,7,8-tetrahydroisoquinoline 3 and (5,6,7,8tetrahydroisoquinolin-3-ylthio)acetamides 5a−i, respectively. Cyclization of compounds 5b−d,f,g into their isomeric 1-amino-6,7,8,9-tetrahydrothieno[2,3-c]isoquinoline-2-carboxamides 6b−d,f,g was achieved by heating in ethanol containing a catalytic amount of sodium carbonate. Structures of all synthesized compounds were characterized on the basis of their elemental analyses and spectroscopic data. The crystal structure of 5,6,7,8-tetrahydroisoquinoline 5d was determined by X-ray diffraction analysis. In addition, the biological evaluation of some synthesized compounds as anticancer agents was performed, and only six compounds showed moderate to strong activity against PACA2 (pancreatic cancer cell line) and A549 (lung carcinoma cell line). Moreover, the antioxidant properties of most synthesized compounds were examined. The results revealed high antioxidant activity for the most tested compounds.

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Section: Resultssupporting

confidence: 86%

Section: Resultsmentioning

confidence: 50%

Nitrophenyl-Group-Containing Heterocycles. I. Synthesis, Characterization, Crystal Structure, Anticancer Activity, and Antioxidant Properties of Some New 5,6,7,8-Tetrahydroisoquinolines Bearing 3(4)-Nitrophenyl Group

et al. 2022

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“…The starting compounds, 7-acetyl-8-aryl-4-cyano-1,6-dimethyl-6-hydroxy-5,6,7,8-tetrahydroisoquinoline-3(2 H )-thiones 1a – c , and 8-aryl-4-cyano-1,6-dimethyl-7,8-dihydroisoquinoline-3(2 H )-thiones ( 2a – c ), were prepared following the reported methods as shown in Scheme . Heating compounds 1a – c or 2a – c with equimolar amount of chloroacetone in ethanol in the presence of exactly equimolar quantity of sodium acetate trihydrate on a water bath for 40 min gave the target compounds, 3-acetonylsulfanyl-7-acetyl-8-aryl-1,6-dimethyl-6-hydroxy-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles 3a – c and 3-acetonylsulfanyl-8-aryl-1,6-dimethyl-7,8-dihydroisoquinoline-4-carbonitriles 4a – c , respectively (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Pyridine Derivatives as Insecticides. Part 3. Synthesis, Crystal Structure, and Toxicological Evaluation of Some New Partially Hydrogenated Isoquinolines against Aphis gossypii (Glover, 1887)

Bakhite

Marae

Gad

et al. 2022

J. Agric. Food Chem.

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Three new series of isoquinolines, that is, 7-acetyl-3-acetonylsulfanyl-8-aryl-1,6-dimethyl-6-hydroxy-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles (3a–c); 3-acetonylsulfanyl-8-aryl-1,6-dimethyl-7,8-dihydroisoquinoline-4-carbonitriles (4a–c); and 7-acetyl-8-aryl-1,6-dimethyl-3-ethylsulfanyl-7,8-dihydroisoquinoline-4-carbo-nitriles (6a,b) were carefully synthesized. Also, pyrazoloisoquinoline 7 was used as a precursor for synthesis of 7-ethylsulfanyl-4-phenyl-1-thiocarbamoyl-3,5,9a-trimethyl-3a,4,9,9a-tetrahydro-1H-pyrazolo[3,4-g]isoquinoline-8-carbonitrile (8); 7-benzyl-sulfanyl-4-phenyl-1-thiocarbamoyl-3,5,9a-trimethyl-3a,4,9,9a-tetrahydro-1H-pyrazolo[3,4-g]isoquinoline-8-carbonitrile (9); and 7-ethylsulfanyl-1-(4-oxo-4,5-dihydrothiazol-2-yl)-4-phenyl-3,5,9a-trimethyl-3a,4,9,9a-tetrahydro-1H-pyrazolo[3,4-g]isoquinoline-8-carbonitrile (10). Moreover, the crystal structures of two representative compounds were determined. Eleven new compounds 3a, 4a, 3b, 4b, 3c, 4c, 6a, 6b, 8, 9, and 10 were screneed for their toxicological activity against nymphs and adults of Aphis gossypii by using acetamprid, as a reference. After 24 h of treatment, the bioefficacy results indicate that all tested isoquinolines exhibit toxicological activity that varied from very high to low against nymphs and adults of Aphis gossypii, some compounds showing activity near to that of acetampirid and only one compound which possesses higher activity against nymphs and adults of Aphis gossypii than that of acetampirid itself.

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“…The modification was done using 3-glycidoxypropyl) trimethoxy-silane and 3-(trimethoxysilyl) propyl-N,N,N-dimethyloctadecyl ammonium chloride. Marae et al [165] fabricated fluorescent cotton fabrics incorporated with tetrahydrothienoisoquinoline derivatives, which have quite high durability, as the tetrahydrothienoisoquinoline derivatives are water insoluble. Tetrahydrothienoisoquinoline is well known for its medicinal and biological properties.…”

Section: Durability and Comfort Of Lignin Incorporated Textilesmentioning

confidence: 99%

Insights into the Sustainable Development of Lignin‐Based Textiles for Functional Applications

Raman

Sankar

Abhirami

et al. 2022

Macro Materials & Eng

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The modification of textiles by the incorporation of nanofillers to incorporate multifunctional properties is emerging as an active area of research. The use of lignin, a biowaste material in textiles to create properties like UV blocking, flame retardancy, antimicrobial properties, etc. paves the way toward creating sustainable textiles with an additional advantage of utilizing a biowaste into a value-added product. The futuristic tailoring of lignin chemistry through functionalization is an entrancing field of research. It incorporates the inherent properties of lignin with the extraneous characteristics of attached matrix polymers. Such modifications aid to enhance the miscibility of lignin with various polymeric matrices, which help to magnify the capabilities of lignin/polymer composites. The review throws light on how lignin can be explored to tailor the properties of textiles in an effective manner. The UV blocking efficiency, flame retardancy as well as antimicrobial properties imparted to textiles by the presence of lignin are discussed in detail. An outlook on the durability and comfort of lignin incorporated textiles is also discussed. An effort is also taken to compare lignin with other commonly used fillers in textile materials. All the available data on lignin-based textiles are consolidated in a comprehensive manner in this review.

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Durable fluorescent cotton textile by immobilization of unique tetrahydrothienoisoquinoline derivatives

Cited by 40 publications

References 59 publications

Nitrophenyl-Group-Containing Heterocycles. I. Synthesis, Characterization, Crystal Structure, Anticancer Activity, and Antioxidant Properties of Some New 5,6,7,8-Tetrahydroisoquinolines Bearing 3(4)-Nitrophenyl Group

Nitrophenyl-Group-Containing Heterocycles. I. Synthesis, Characterization, Crystal Structure, Anticancer Activity, and Antioxidant Properties of Some New 5,6,7,8-Tetrahydroisoquinolines Bearing 3(4)-Nitrophenyl Group

Pyridine Derivatives as Insecticides. Part 3. Synthesis, Crystal Structure, and Toxicological Evaluation of Some New Partially Hydrogenated Isoquinolines against Aphis gossypii (Glover, 1887)

Insights into the Sustainable Development of Lignin‐Based Textiles for Functional Applications

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