1- Introduction Benzosuberone based compounds are important classes of biologically active compounds that attracted a great deal of interest in the medicinal chemistry due to their potent biological activities and wide range of pharmaceutical applications [1-6].
Several publications recorded that some of benzosuberone derivatives possess antipyretic, anti-inflammatory, antimicrobial, antiulcer and antitumor activities [1-6]. As an indication for the importance of the benzosuberone based compounds, more than 100 registered patents and hundreds of publications on the chemistry and the pharmaceutical applications of the benzosuberone based compounds. For example, many of the benzosuberone based pyrazoles are known and used as cannabinoid CB1 receptor antagonists drugs, (Figure 1) [7]. Figure 1: A) general Structure of the benzosuberone based pyrazoles cannabinoid CB1 receptor B) cannabinoid CB1 receptor Drug (NESS-0327) Furthermore, The Benzosuberone scaffold have been introduced into bioactive molecules such as benzosuberone based natural products that include; Colchicine, Isocolchicine, Theaflavin, Allocolchicine, Bussealin, Demethylsalvicanol, and Feveline (Figure 2). Several studies were applied on these natural compounds and reported that all of these natural products are antitumor agents [4-6]. Figure 2: Structures of some benzosuberone based natural product From these observations and due to our interest on the benzosuberone based compounds, the current stat of the art, focused on the following aspects: • The main synthetic approaches that used recently for the preparation of benzosuberone scaffold and comparing between these methods by the yield and experimental conditions, since the yield and experimental conditions are the main factors for providing the starting materials with high purity and low price. • The recent chemical reactions applied on the benzosuberone scaffold because these reactions will give a clear picture and good idea for the procedure that recently used and can be used in the near future for the construction of benzosuberone based drugs and benzosuberone based natural products. • Some of the recent synthetic approaches that have been used for the preparation of the benzosuberone based drugs, and biologically active benzosuberone based compounds. • Our recent contributions in the chemistry and the pharmaceutical applications of the biologically active benzosuberone based compounds • At the end, the conclusions and the perspective for the future. 2- Recent Preparations of The benzosuberone scaffold The benzosuberones are …show more content…
The price of 25 g of 1-benzosoberone, as an example, is 10,000 LE, that is very high price for starting martial. Thus, it's important to find facile synthetic approaches for the preparation of benzosuberone with high yield and from different available chemicals. This because the preparation method and the high yield will affect on the production cost and purity of the synthesized compounds through scaling up from the bench scale to the industrial scale production. Thus, herein, I cast light on the recent preparations of the benzosuberone …show more content…
Several catalytic reagents and different conditions were applied for increasing the yield under mild reaction conditions such trifluorormethane-sulfonic acid at room temperature with 93% yield [17]. Friedel-Crafts intramolecular cyclization using Nafion-H in various solvent(s) under reflux temperature yielded 83% [18]. Aluminum trichloride and triethylamine in carbon disulfide were used also and afforded the benzosuberone (2) with 90% yield [19]; additionally, 5-phenylpentanoic acid (6) was cyclized to 2 using H-Beta zeolite in 1,2-dichloro-benzene, under microwave irradiation [20]; or by refluxing with poly phosphoric acid in benzene (Scheme 5) with 82% and 83%, respectively
Several publications recorded that some of benzosuberone derivatives possess antipyretic, anti-inflammatory, antimicrobial, antiulcer and antitumor activities [1-6]. As an indication for the importance of the benzosuberone based compounds, more than 100 registered patents and hundreds of publications on the chemistry and the pharmaceutical applications of the benzosuberone based compounds. For example, many of the benzosuberone based pyrazoles are known and used as cannabinoid CB1 receptor antagonists drugs, (Figure 1) [7]. Figure 1: A) general Structure of the benzosuberone based pyrazoles cannabinoid CB1 receptor B) cannabinoid CB1 receptor Drug (NESS-0327) Furthermore, The Benzosuberone scaffold have been introduced into bioactive molecules such as benzosuberone based natural products that include; Colchicine, Isocolchicine, Theaflavin, Allocolchicine, Bussealin, Demethylsalvicanol, and Feveline (Figure 2). Several studies were applied on these natural compounds and reported that all of these natural products are antitumor agents [4-6]. Figure 2: Structures of some benzosuberone based natural product From these observations and due to our interest on the benzosuberone based compounds, the current stat of the art, focused on the following aspects: • The main synthetic approaches that used recently for the preparation of benzosuberone scaffold and comparing between these methods by the yield and experimental conditions, since the yield and experimental conditions are the main factors for providing the starting materials with high purity and low price. • The recent chemical reactions applied on the benzosuberone scaffold because these reactions will give a clear picture and good idea for the procedure that recently used and can be used in the near future for the construction of benzosuberone based drugs and benzosuberone based natural products. • Some of the recent synthetic approaches that have been used for the preparation of the benzosuberone based drugs, and biologically active benzosuberone based compounds. • Our recent contributions in the chemistry and the pharmaceutical applications of the biologically active benzosuberone based compounds • At the end, the conclusions and the perspective for the future. 2- Recent Preparations of The benzosuberone scaffold The benzosuberones are …show more content…
The price of 25 g of 1-benzosoberone, as an example, is 10,000 LE, that is very high price for starting martial. Thus, it's important to find facile synthetic approaches for the preparation of benzosuberone with high yield and from different available chemicals. This because the preparation method and the high yield will affect on the production cost and purity of the synthesized compounds through scaling up from the bench scale to the industrial scale production. Thus, herein, I cast light on the recent preparations of the benzosuberone …show more content…
Several catalytic reagents and different conditions were applied for increasing the yield under mild reaction conditions such trifluorormethane-sulfonic acid at room temperature with 93% yield [17]. Friedel-Crafts intramolecular cyclization using Nafion-H in various solvent(s) under reflux temperature yielded 83% [18]. Aluminum trichloride and triethylamine in carbon disulfide were used also and afforded the benzosuberone (2) with 90% yield [19]; additionally, 5-phenylpentanoic acid (6) was cyclized to 2 using H-Beta zeolite in 1,2-dichloro-benzene, under microwave irradiation [20]; or by refluxing with poly phosphoric acid in benzene (Scheme 5) with 82% and 83%, respectively