scholarly journals The Addition of Hydrogen Bromide to Cinnamic Acid and the Oxygen Effect

1949 ◽  
Vol 22 (2) ◽  
pp. 60-65 ◽  
Author(s):  
Osamu Simamura ◽  
Makoto Takahasi
Keyword(s):  
Cinnamic Acid ◽  
Hydrogen Bromide ◽  
Oxygen Effect

scholarly journals The Addition of Hydrogen Bromide to Cholesteryl Bromide and the Oxygen Effect

1940 ◽  
Vol 15 (10) ◽  
pp. 442-448 ◽  
Author(s):  
Yoshiyuki Urushibara ◽  
Keiiti Nambu ◽  
Toshio Ando
Keyword(s):  
Hydrogen Bromide ◽  
Oxygen Effect

PREPARATION OF CAFFEIC AND DIHYDROCAFFEIC ACIDS BY METHODS SUITABLE FOR INTRODUCTION OF C14 INTO THE β-POSITION

1959 ◽  
Vol 37 (12) ◽  
pp. 1431-1438 ◽  
Author(s):  
A. C. Neish
Keyword(s):  
Acetic Acid ◽  
Benzoic Acid ◽  
Caffeic Acid ◽  
Malonic Acid ◽  
Cinnamic Acid ◽  
Catalytic Hydrogenation ◽  
Benzoyl Chloride ◽  
Protocatechuic Acid ◽  
Barium Carbonate ◽  
Hydrogen Bromide

3,4-(Dibenzyloxy)-benzoyl chloride (m.p. 95°) was prepared from the corresponding acid, and reduced to 3,4-(dibenzyloxy)-benzaldehyde (m.p. 86°) by Rosenmund's method. The over-all yield of this aldehyde was 52%, based on the barium carbonate used for preparation of the acid. The aldehyde was debenzylated by hydrogen bromide in acetic acid, and the protocatechualdehyde thus obtained was condensed with malonic acid, to give caffeic acid. Condensation of 3,4-(dibenzyloxy)-benzaldehyde with malonic acid gave 3,4–(dibenzyloxy)-cinnamic acid (m.p. 206–208°) which was converted to dihydrocaffeic acid by catalytic hydrogenation. The over-all yields of caffeic and dihydrocaffeic acids were 36% and 39%, respectively, based on barium carbonate. Protocatechuic acid was readily obtained by hydrogenolysis of 3,4-(dibenzyloxy)-benzoic acid; the yield was 70% based on carbonate.

The Oxygen Effect in the Reaction of Cyclopropane with Bromine and with Hydrogen Bromide

1939 ◽  
Vol 61 (8) ◽  
pp. 2139-2142 ◽  
Author(s):  
M. S. Kharasch ◽  
M. Z. Fineman ◽  
F. R. Mayo
Keyword(s):  
Hydrogen Bromide ◽  
Oxygen Effect

PREPARATION OF CAFFEIC AND DIHYDROCAFFEIC ACIDS BY METHODS SUITABLE FOR INTRODUCTION OF C14 INTO THE β-POSITION

1959 ◽  
Vol 37 (1) ◽  
pp. 1431-1438 ◽  
Author(s):  
A. C. Neish
Keyword(s):  
Acetic Acid ◽  
Benzoic Acid ◽  
Caffeic Acid ◽  
Malonic Acid ◽  
Cinnamic Acid ◽  
Catalytic Hydrogenation ◽  
Benzoyl Chloride ◽  
Protocatechuic Acid ◽  
Barium Carbonate ◽  
Hydrogen Bromide

3,4-(Dibenzyloxy)-benzoyl chloride (m.p. 95°) was prepared from the corresponding acid, and reduced to 3,4-(dibenzyloxy)-benzaldehyde (m.p. 86°) by Rosenmund's method. The over-all yield of this aldehyde was 52%, based on the barium carbonate used for preparation of the acid. The aldehyde was debenzylated by hydrogen bromide in acetic acid, and the protocatechualdehyde thus obtained was condensed with malonic acid, to give caffeic acid. Condensation of 3,4-(dibenzyloxy)-benzaldehyde with malonic acid gave 3,4–(dibenzyloxy)-cinnamic acid (m.p. 206–208°) which was converted to dihydrocaffeic acid by catalytic hydrogenation. The over-all yields of caffeic and dihydrocaffeic acids were 36% and 39%, respectively, based on barium carbonate. Protocatechuic acid was readily obtained by hydrogenolysis of 3,4-(dibenzyloxy)-benzoic acid; the yield was 70% based on carbonate.

Novel Piperazine Amides of Cinnamic Acid Derivatives as Tyrosinase Inhibitors

2018 ◽  
Vol 16 (1) ◽  
pp. 36-44 ◽  
Author(s):  
Zehra Tuğçe Gür ◽  
Fatma Sezer Şenol ◽  
Suhaib Shekfeh ◽  
İlkay Erdoğan Orhan ◽  
Erden Banoğlu ◽  
...  
Keyword(s):  
Cinnamic Acid ◽  
Active Site ◽  
Agaricus Bisporus ◽  
Biological Activities ◽  
Docking Simulation ◽  
Cinnamic Acid Derivatives ◽  
In Silico Docking ◽  
Amide Derivatives ◽  
Tyrosinase Inhibitors ◽  
Further Development

Background: A series of novel cinnamic acid piperazine amide derivatives has been designed and synthesized, and their biological activities were also evaluated as potential tyrosinase inhibitors. Methods: Compounds 9, 11 and 17 showed the most potent biological activity (IC50 = 66.5, 61.1 and 66 µM, respectively). In silico docking simulation was performed to position compound 11 into the Agaricus bisporus mushroom tyrosinase’s active site to determine the putative binding interactions. Results and Conclusion: The results indicated that compound 11 could serve as a promising lead compound for further development of potent tyrosinase inhibitors.

Sign in / Sign up

Export Citation Format

Share Document