129384-16-3Relevant academic research and scientific papers
Inhibitory effects of benzyl benzoate and its derivatives on angiotensin II-induced hypertension
Ohno, Osamu,Ye, Mao,Koyama, Tomoyuki,Yazawa, Kazunaga,Mura, Emi,Matsumoto, Hiroshi,Ichino, Takao,Yamada, Kaoru,Nakamura, Kazuhiko,Ohno, Tomohiro,Yamaguchi, Kohji,Ishida, Junji,Fukamizu, Akiyoshi,Uemura, Daisuke
supporting information; experimental part, p. 7843 - 7852 (2009/04/11)
Hypertension is a lifestyle-related disease which often leads to serious conditions such as heart disease and cerebral hemorrhage. Angiotensin II (Ang II) plays an important role in regulating cardiovascular homeostasis. Consequently, antagonists that block the interaction of Ang II with its receptors are thought to be effective in the suppression of hypertension. In this study, we searched for plant compounds that had antagonist-like activity toward Ang II receptors. From among 435 plant samples, we found that EtOH extract from the resin of sweet gum Liquidambar styraciflua strongly inhibited Ang II signaling. We isolated benzyl benzoate and benzyl cinnamate from this extract and found that those compounds inhibited the function of Ang II in a dose-dependent manner without cytotoxicity. An in vivo study showed that benzyl benzoate significantly suppressed Ang II-induced hypertension in mice. In addition, we synthesized more than 40 derivatives of benzyl benzoate and found that the meta-methyl and 3-methylbenzyl 2′-nitrobenzoate derivatives showed about 10-fold higher activity than benzyl benzoate itself. Thus, benzyl benzoate, its derivatives, and benzyl cinnamate may be useful for reducing hypertension.
A novel electrochemical method for benzoylation of aminoalcohols with methyl benzoates at room temperature
Arai, Kenji,Tamura, Shohei,Masumizu, Tatsuya,Kawai, Ken-Ichi,Nakajima, Shoichi,Ueda, Akira
, p. 903 - 907 (2007/10/02)
A novel electrochemical method of benzoylating aminoalcohols 2 by use of methyl benzoates 1 at room temperature was developed. 2-Aminoethanols 2 (n=0, R3=H) and 3-aminopropanols 2 (n=1, R3=H) gave the corresponding benzamides 4, as a result of electrochemical transesterification followed by O,N-acyl migration.In contrast, o- and m-aminobenzylalcohols (7a and 7b) and trans-4-(aminomethyl)cyclohexanemethanol (8a) afforded the corresponding benzoic esters, since their acyl migration is hindered.A local anesthetic, procaine, was prepared by using this electrochemical reaction.A mechanism for electrochemical transesterification, which involves a formation of alcoholate anion by a one-electron reduction of alcohol, is presented.
