KaydedilenlerDerginizi ekleyin

Dergiler / Ata-Kimya Dergisi / 2024 / Cilt: 4 Sayı: 2

Siklohekzen ve Siklohekzadienlerden Bromosiklitollerin Sentezi

Syntheses of Bromocyclitos via Cyclohexene and Cyclohexadienes

Hülya Çelik(Ağrı İbrahim Çeçen Üniversitesi)0000-0003-0805-0523
Süleyman Göksu(ATATURK UNIVERSITY)0000-0003-1280-3954
Hasan Seçen(ATATURK UNIVERSITY)0000-0002-5388-6111
Sayfa
51–58
Yayın Tarihi
2024-11-23
🏛️Bu makalenin bibliyografik verileri ve tam metin bağlantısı DergiPark üzerinden sağlanmıştır.
DergiPark Kaydı ↗
✨

Yapay Zeka Hızlı Bakış & Çıkarımlar

AI Insight
⚡ TL;DR(1 Cümlede Hızlı Çıkarım)

Elde edilen ürünlerin yapıları aydınlatıldı ve oluşum mekanizmaları detaylı bir şekilde tartışıldı.

📌 3 Maddede Bu Makale

🎯
Amaç & Hipotez:Siklitoller, önemli biyolojik aktiviteleri nedeniyle yoğun şekilde araştırılan bileşiklerdir.
📊
Temel Bulgular & Veri:Bu çalışmada, siklohekzen, 1,3-siklohekzadien ve 1,4-siklohekzadien temel alınarak yeni bromosiklitol analoglarının sentezi gerçekleştirildi. cis-Hidroksilleme, asetilleme ve alilik bromlama reaksiyonları ile siklitol analoğu ürünler elde edildi.
💡
Sonuç & Katkı:Elde edilen ürünlerin yapıları aydınlatıldı ve oluşum mekanizmaları detaylı bir şekilde tartışıldı.
🔬Tür:Araştırma Makalesi
📍Kapsam:Genişletilmiş Akademik Örneklem
⚙️Değişkenler:Bromosiklitol · sentez · 1-3-siklohekzadien

Özet

Siklitoller, önemli biyolojik aktiviteleri nedeniyle yoğun şekilde araştırılan bileşiklerdir. Bu çalışmada, siklohekzen, 1,3-siklohekzadien ve 1,4-siklohekzadien temel alınarak yeni bromosiklitol analoglarının sentezi gerçekleştirildi. cis-Hidroksilleme, asetilleme ve alilik bromlama reaksiyonları ile siklitol analoğu ürünler elde edildi. Elde edilen ürünlerin yapıları aydınlatıldı ve oluşum mekanizmaları detaylı bir şekilde tartışıldı.

Abstract

Cyclitols are compounds that have been intensively researched due to their important biological activities. In this study, new bromocyclitol analogues were synthesized based on cyclohexene, 1,3-cyclohexadiene and 1,4-cyclohexadiene. Cyclitol analogues were obtained by cis-hydroxylation, acetylation and allylic bromination reactions. The structures of the obtained products were elucidated and their formation mechanisms were discussed in detail.

🔖

Bu Makaleye Atıf Yap

Çelik, H., Göksu, S., Seçen, H. (2024). Siklohekzen ve Siklohekzadienlerden Bromosiklitollerin Sentezi. Ata-Kimya Dergisi, Cilt: 4 Sayı: 2, 51–58. https://doi.org/10.62425/atakim.1563688

📄 Tam Metin PDF Okuyucu

📄

PDF görüntüleyici hazırlanıyor...

Kaynakça (28)

  1. Kübler K, Chemistry of condurango bark. Arch Pharm. 1909; 246, 620-660.
  2. Dangschat G, Fischer HOL. Über die konstitution des condurits und über einige Cyclohexan-tetrole. Naturwissenschaften. 1939; 27: 756-757.
  3. Kindl H, Hoffmann-Ostenhof O, Cyclites: biosynthesis, metabolism, and occurrence. Fortschrit Chem Organ Naturst. 1966; 24:149.
  4. Plouvier V. A new cyclitol, leucanthemitol, isolated from Chrysanthemum leucanthemum. Studies on some other anthemia. Compt Rend hebd Se’Acad Sci Paris. 1962; 255:360-362.
  5. Balcı M, Sütbeyaz Y, Seçen H, Conduritols and related compounds. Tetrahedron. 1990; 46:3715-3742.
  6. Ramanathan, JD, Craigie JS, McLachlan J, et al. The occurrence of D-(+)-1425-cyclohexanetetrol in Monochrysis lutheri droop. Tetrahedron Lett. 1966; 7: 1527-1531.
  7. Craigie JS, McLachlan, J, Tocher RD. Some neutral constituents of the Rhodophyceae with special reference to the occurrence of the floridosides. Can J Bot. 1968; 46:605-611.
  8. Zhang Z, Zhang M. Crystal and molecular structure of natural product toxocarol. Jiegou Huaxue (J. Struc. Chem.) 1987; 6:128-131. Chem Abstr. 1988, 108:167846.
  9. Legler G. Glucosidases. In: Methods in Enzymology. Academic Press, 1977; 368-381.
  10. Kensho L, Yamashita F, Nagai T, et al. Use of conduritol to inhibit increase of blood sugar level. Eur.Pat. Appl. EP, 474, 358, 1990, Chem. Abstr. 116:248434.
  11. Pulverer G, Beuth J, Ko, HL, et al. Glycoprotein modifications of sarcoma L-1 tumor cells by tunicamycin, swainsonine, bromoconduritol or 1-desoxynojirimycin treatment inhibits their metastatic lung colonization in Balb/c-mice. J Cancer Res Clin Oncol. 1988, 114:217-220.
  12. Datema R, Romero PA, Legler, G, et al. Inhibition of formation of complex oligosaccharides by the glucosidase ınhibitor bromoconduritol. Proc Natl Acad Sci USA. 1982; 79:6787-6791
  13. Datema R, Romero A, Rott R, et al. On the role of oligosaccharide trimming in the maturation of Sindbis and influenza virus. Arch Virol. 1984; 81:25-39.
  14. Trudel, GC, Herscovics AH, Paul C. Inhibition of myoblast fusion by bromoconduritol. Biochem Cell Biol. 1988; 66:1119-1125.
  15. Montefiori DC; Robinson Jr WE, Mitchell WM. Antibody-independent, complement-mediated enhancement of HIV-1 infection by mannosidase I and II inhibitors. Antiviral Res. 1989; 11:137-146.
  16. Silber AM, Candurra NA, Damonte EB. The effects of oligosaccharide trimming inhibitors on glycoprotein expression and infectivity of Junin vırus. FEMS Microbial Lett. 1993, 109:39-43.
  17. Guo ZX, Haines AH, Taylor, RJK. The reaction of dilithium tetrachlorocuprate and dilithium tetrabromonickelate with unsaturated epoxides - the preparation of novel analogs of the antıviral agent, bromoconduritol. Synlett. 1993; 607-608.
  18. Baran A, Kazaz C, Seçen H, Sütbeyaz Y. Synthesis of haloconduritols from an endo cycloadduct of furan and vinylene carbonate. Tetrahedron. 2003; 59: 3643–3648.
  19. Langlois JB, Alexakis, A. Copper‐catalyzed asymmetric allylic alkylation of racemic cyclic substrates: application of dynamic kinetic asymmetric transformation (DYKAT). Adv Synth Catal. 2010; 352(2‐3): 447-457.
  20. Alvarez E; Nunez MT; Martin, VS. Mild and stereocontrolled synthesis of iodo-and bromohydrins by halogen-tetrakis (isopropoxy) titanium opening of epoxy alcohols. J Org Chem. 1990; 55:3429-3431.
  21. Tschamber T, Backenstrass F, Fritz, H et al. (1992). Catalytic one-pot osmylation of cyclohexadienes: Stereochemical and conformational studies of the resulting polyols. Helv Chim Acta. 1992, 75:1052-1060.
  22. Selander, N, Szabo, KJ. Synthesis of stereodefined substituted cycloalkenes by a one-pot catalytic boronation–allylation–metathesis sequence. Adv Synth Catal. 2008; 350:2045-2051.
  23. Donohoe, T J, Mitchell, L, & Waring, M J, et al. Scope of the directed dihydroxylation: Application to cyclic homoallylic alcohols and trihaloacetamides. Org Biomol Chem. 2003, 1:2173-2186.
  24. Laserna V, Fiorani, G, Whiteoak, CJ, et al. Carbon dioxide as a protecting group: Highly efficient and selective catalytic access to cyclic cis-diol scaffolds. Angew Chem Int Ed. 2014; 53: 10416-10419.
  25. Uemura S, Ohe K, Fukuzawa S, et al. Dominant cis-diacetoxylation of alkenes with tellurium(IV) oxide and lithium bromide in acetic acid. J Organomet Chem. 1986; 316:67-78.
  26. Wohl–Ziegler bromination. (n.d.). In Wikipedia. Erişim September 30, 2024, from https://en.wikipedia.org/wiki/WohlZiegler_bromination
  27. Van Rheen V, Cha, DY, Hartley, WM. Catalytic osmium tetroxide oxidation of olefins: cis-1,2-cyclohexanediol. Org Synt Coll Vol. 1988; 6:342.
  28. Datema R, Romero A, Rott R, et al. On the role of oligosaccharide trimming in the maturation of Sindbis and influenza virus. Arch Virol. 1984; 81:25-39.