Search In this Thesis
   Search In this Thesis  
العنوان
Synthesis of some new heterocyclic compounds with expected biological activity from α,β-unsaturated carbonyl compounds
المؤلف
SALAMA KHALAF ABD-ELFATTAH ABOUZEAD,HEMAT
هيئة الاعداد
باحث / HEMAT SALAMA KHALAF ABD-ELFATTAH ABOUZEAD
مشرف / Maher Abd El-Aziz Mahmoud El-Hashash
مشرف / Mowafia Abd EL-Rahman Mohamed Salama
مشرف / Fakhry Abdel-Aziz El-Bassiouny
الموضوع
Uses of α,β–enones in synthesis of new isoxazole derivative-
تاريخ النشر
2009
عدد الصفحات
180.P:
اللغة
الإنجليزية
الدرجة
ماجستير
التخصص
Organic Chemistry
تاريخ الإجازة
1/1/2009
مكان الإجازة
جامعة عين شمس - كلية العلوم - Chemistry
الفهرس
Only 14 pages are availabe for public view

from 180

from 180

Abstract

Chalcones, either natural or synthetic, are known to exhibit various biological activities (Satyanarayana et al., 2004), such as anti-protozoal activities (Dimmock, 1999 and Quintin et al., 2009), anti-bacterial (Ahluwalia et al., 1986, Mulvad et al., 2003 and Yarishkin et al., 2008), cytotoxic (Modzelewska et al., 2006 and Lawrence et al., 2006), anti-HIV (Cheenpracha et al., 2006), as tyrosine kinase inhibitors (Nerya et al., 2004), anti-fungal (Svetaz et al., 2004 and Yarishkin et al., 2008), antioxidant (Mukherjee et al., 2001), anti-inflammatory (Herencia et al., 1998, Hsieh et al., 1998, Hsieh et al., 2000, Lee et al., 2006 and Yang et al., 2007), anti-malarial (Ram et al., 2000, Liu et al., 2001, Dominguez et al., 2005 and Alain et al., 2006), anti-leishmanial (Nielesen et al., 1998, Zhai et al., 1999, Torres-Santos et al., 1999 and Boeck et al., 2006), anticancer (Sinythies 1979, Anto et al., 1995, Bois et al., 1998 and Xia et al., 2000), anti-mitotic (Ducki et al., 1998), anti-tuberculosis (Lin et al., 2002), cardiovascular (Furman et al., 2001), Prostaglandin binding properties (Simmonds et al., 1990), cell differentiation inducing (Park et al., 1998), nitric oxide regulation modulatory (Herencia et al., 2001 and Rojas et al., 2002), anti-hyperglycemic agents (Satyanarayana et al., 2004) and anti-tumor (Gschwendt et al., 1984 and Kumar et al., 2003). 1,3-Diaryl-2-propenones inhibit various enzymes such as CysLT1 (Zawaagstar et al., 1997), COX/5-LOX (Jahng et al., 2004), EGFR tyrosine Kinase (Yang et al., 2001) and tyrosinase (Khatib et al., 2005) that play crucial role in the biochemical pathways of different diseases. Chalcones are key precursors in the synthesis of a large array of biologically important heterocycles (Bennett et al., 1996, Savizky et al., 1998 and Yadav et al., 2005) and 1,4-diketones (Raghavan and Anuradha, 2002).
α,β-Unsaturated ketones are versatile and convenient intermediates for the synthesis of a wide variety of heterocyclic compounds. The α,β-enone moiety of the molecule is a favourable unit for dipolar cycloaddition with numerous reagents providing heterocyclic compounds of different ring sizes with one or several heteroatoms. Their reactions with dinucleophiles usually result in the formation of polycyclic ring systems which may be the skeleton of important heterocyclic compounds. Among the α,β-unsaturated ketones, (chalcones) and their analogues are especially important starting materials or intermediates for the synthesis of naturally occurring flavonoids (Wong et al., 1970, Harborne et al., 1986, Chapman et al., 1994) and various nitrogen-containing heterocyclic compounds. For this reason, their synthesis have been compiled and discussed in various account (Dhar et al., 1981 and Levai et al., 1997). Exocyclic α,β-unsaturated ketones are convenient starting materials for the synthesis of heterocyclic compounds of polycyclic skeletons. Their 1,3-dipolar cycloadditions with different dipoles provide important nitrogen-containing spiroheterocyclic ring systems (Toth et al., 1992, pijewska et al., 1993, Levai et al., 1995, 1999, 2002 and Girgis et al., 2001). Another versatile utilization is the reaction of exocyclic α,β-enones with dinucleophiles to afford polycyclic fused ring systems, e.g. tricyclic pyrazolines (Faidallah et al., 1994, Lorand et al., 1996 and Levai et al., 1998, 2003), tetracyclic benzothiazepines (Levai et al., 2002), tetracyclic benzodiazepines (Hideg et al., 1973 and Toth et al., 1992), thiazines (perjesi et al.,1987 and Levai, 1991), pyrimidines (Deli et al., 1984 and El-Rayyes et al., 1987) and quinazolines (Lorand et al., 1991, Perjesi et al., 1993 and Deli et al., 1985).
In the present review article the most common and useful procedures for the preparation of selected α,β-unsaturated ketones and exocyclic α,β-unsaturated ketones utilized as intermediates for the synthesis of well known heterocyclic ring systems are compiled and discussed