Journals / Bilecik Şeyh Edebali Üniversitesi Fen Bilimleri Dergisi / 2020 / Cilt: 7 - Sayı: 1

Iodine-Catalyzed Addition of Thiophenol to Isoindolsubstitue Chalcones

İsoindolsübstitüe-kalkon Türevlerine İyot Katalizli Tiyofenol Katılması

Pages
161–169
Publication Date
2020-06-28
DOI
—
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

The structures of the obtained new compounds were clarified by 1H-NMR, 13C-NMR, FT-IR and Elemental Analysis spectroscopic methods.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:Chalcone and isoindol derivatives possess significant biological activities.
📊
Key Findings & Data:In this work, new β-mercapto carbonyl compounds (5a-j), (3aR,4S,7R,7aS)-2-(4-(3-(phenylthio)-3-(aryl)pyridyl)aminocarbonyl-propanol)phenyl)-3a,4,7,7a-tetrahydro-1H-7-methanoisoindole-1,3(2H)-dione), were obtained by molecular iodine-catalyzed addition of thiophenol to isoindol substituted chalcone derivatives (3a-j) in high yields.
💡
Conclusion & Impact:The structures of the obtained new compounds were clarified by 1H-NMR, 13C-NMR, FT-IR and Elemental Analysis spectroscopic methods.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Chalcone · Isoindole · Thiophenol

Abstract

Chalcone and isoindol derivatives possess significant biological activities. Also, ıt is known that hybrid molecules carrying these two units in the same structure show biological activity. In addition, -mercaptans are used as the starting material for the synthesis of some bioactive compounds. In this work, new β-mercapto carbonyl compounds (5a-j), (3aR,4S,7R,7aS)-2-(4-(3-(phenylthio)-3-(aryl)pyridyl)aminocarbonyl-propanol)phenyl)-3a,4,7,7a-tetrahydro-1H-7-methanoisoindole-1,3(2H)-dione), were obtained by molecular iodine-catalyzed addition of thiophenol to isoindol substituted chalcone derivatives (3a-j) in high yields. The structures of the obtained new compounds were clarified by 1H-NMR, 13C-NMR, FT-IR and Elemental Analysis spectroscopic methods.

Özet

Kalkon ve isoindol türevleri önemli biyolojik aktivitelere sahip bileşiklerdir. Bu iki birimi aynı yapıda taşıyan hibrit moleküllerinde biyolojik aktivite gösterdikleri bilinmektedir. Ayrıca β-merkaptanlar bazı biyoaktif bileşiklerin sentezi için başlangıç materyali olarak kullanılmaktadırlar. Bu çalışmada, isoindolsübstitüe-kalkon türevlerine (3a-j) moleküler iyot katalizörlüğünde tiyofenol katılarak yeni β-merkapto karbonil bileşikleri, ((3aR,4S,7R,7aS)-2-(4-(3-(feniltiyo)-3-(aril)propanol)fenil)-3a,4,7,7a-tetrahidro-1H-4,7-metanisoindol-1,3(2H)-dion) (5a-j) yüksek verimler ile elde edildi. Elde edilen yeni bileşiklerin yapıları 1H-NMR, 13C-NMR, FT-IR ve Elementel Analiz spektroskopik yöntemleri kullanılarak aydınlatıldı.

🔖

Cite This Article

BUDAK, Y., ÇAKIR, A. D., ÖZBEK, O., GÜRDERE, M. B., CEYLAN, M. (2020). Iodine-Catalyzed Addition of Thiophenol to Isoindolsubstitue Chalcones. Bilecik Şeyh Edebali Üniversitesi Fen Bilimleri Dergisi, Cilt: 7 - Sayı: 1, 161–169. https://ajindex.com/articles/251550

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (11)

  1. Rida, S. M., Labouta, I. M., Salama, H. M., Ghany, Y. S., El-Ghazzaui, E., Kader, O. (1986). Syntheses and in vitro antimicrobial evaluation of some benzimidazol-2-ylmethyl-thioureas, enzimidazol 2-ylacetyl thiosemicarbazides and products of their condensation with monochloroacetic acid. Pharmazie, 41, 475- 478
  2. Bhat, A. R., Singh, D. (1988). Synthesis and biological activities of 4-thiazolidinones and dihydro-3-(2H)- thiophenones. Indian Journal of Pharmaceutical Sciences, 50, 169-171
  3. Pandeya, D., Nair, K. B. (1993). Bridged bis(4-thiazolidinones) and related compounds with antibacterial activity. Pharmazie, 48, 414-417
  4. Franchini, C., Muraglia, M., Corbo, F., Florio, M. A., Di Mola, A., Rosato, A., Matucci, R., Nesi, M., VanBambeke, F., Vitali, C. (2009). Synthesis and biological evaluation of 2-mercapto-1,3-benzothiazole derivatives with potential antimicrobial activity. Archiv der Pharmazie, 342, 605-613
  5. Cesur, N., Cesur, Z., Ergenc, N., Uzun, M., Kiraz, M., Kasimoglu, O., Kaya, D. (1994). Synthesis and antifungal activity of some 2-aryl-3-substituted 4-thiazolidinones. Archiv der Pharmazie, 327, 271-272
  6. Capan, G., Ulusoy, N., Ergenc, N., Kiraz, M. (1999). New 6-phenylimidazo[2,1-b]thiazole derivatives: synthesis and antifungal activity. Monatshefte für Chemie, 130, 1399-1407
  7. Bhatt, J. J., Shah, B. R., Shah, H. P., Trivedi, P. B., Undavia, N. K., Desai, N. C. (1994). Synthesis of antiHIV, anticancer and antitubercular 4-oxo-thiazolidines, 2-imino-4-oxo-thiazolidines and their 5-arylidine derivatives. Indian Journal of Chemistry, 33B, 189-192
  8. Tandon, K.V., Chhor, R. B., Singh, R. V., Rai, S., Yadav, D. B. (2004). Design, synthesis and evaluation of novel 1,4-naphthoquinone derivatives as antifungal and anticancer agents. Bioorganic & Medicinal Chemistry Letters, 14, 1079-1083
  9. Sheela, C. G., Augusti K. T. (1992). Antidiabetic effects of S-allyl cysteine sulphoxide isolated from garlic Allium sativum Linn. Indian Journal of Experimental Biology, 30, 523-526
  10. Mahmoodi, M., Aliabadi, A., Emami, S., Safavi, M., Rajabalian, S., Mohagheghi, M. A., Khoshzaban, A., Kermani, A. S., Lamei, N., Shafiee, A., Foroumadi, A. (2010). Synthesis and in-vitro Cytotoxicity of Polyfunctionalized 4-(2-Arylthiazol-4-yl)-4H-chromenes. Archiv der Pharmazie, 343, 411-416
  11. Katristzky, A. R., Button, M. A. (2001). Efficient syntheses of thiochromans via cationic cycloadditions. Journal of Organic Chemistry, 66, 5595-5600