Anti-inflammatory activity of isobornylphenol derivatives

Abstract

Nonsteroidal anti-inflammatory drugs and non-narcotic analgesics are widely used to treat various inflammatory diseases of infectious and noninfectious nature [1].The development of new drugs based on terpenophenols, which have a unique set of pharmacological properties [2], is highly promising. The literature teaches that phenols with a bicyclic isobornyl moiety exhibit anti-infection activity [3]. The series of studies performed by us on the synthesis and investigation of terpenophenols showed that some alkylphenols exhibit hemorheological properties and improve brain blood flow [4,5]. Thus, the synthesis of terpenophenols is critical for further studies of their physiological properties.Herein we present results from a study of the anti-inflammatory activity of the synthesized terpenophenols and their aminomethyl derivatives.A series of isobornylphenols (1a-e) with various substituents in the aromatic ring were prepared earlier via alkylation of phenols by the natural monoterpenoid camphene in the presence of the corresponding aluminum phenolates [6][7][8].Continued functionalization of the terpenophenols by introducing aminomethyl moieties using the Mannich reaction synthesized the previously prepared compounds 2a, 2b, and 2d [9] and newly synthesized 2c, the structure of which was confirmed by IR, PMR, and 13 C NMR spectral data.The anti-inflammatory activity of terpenophenols 1-2 was studied using a formalin-induced acute inflammation model in mice [10] (Table 1). Compounds 1a and 2a exhibited reliable anti-inflammatory activity upon parenteral administration. Compound 1a was less active and showed only 10% more inhibition than this control group.

Synthesis and in Vitro Biological Activity Study of Novel Phenol Mannich Base Analogs Containing Spiroheterocycle as Core Compound

“…In addition to that, the lipophilic properties of the drug molecules could be enhanced, if the suitable amine containing reagent is utilized in the Mannich base reaction [2]. The phenolic Mannich bases are classified as the C-Mannich bases which tends to forms C-C bonds and are considered as a very important class of the compounds due to their biological activities such as antibacterial activities [3], [4], antimycobacterial activities [5], [6], anticancer and cytotoxic activities [7]- [9], anti-inflammatory activities [10], [11], antihepatitis-B activities [12,13], antiviral activities [14]- [16], and antifungal activities [17], [18], analgesic activities [19], anticonvulsant activities [20], [21], enzyme inhibition activities [22], antioxidant properties [23], [24], blood pressure regulation [25], [26], and platelet aggregation inhibition activities [27].…”

The First Tetra(meso-аryl)porphyrin with Isobornyl Substituents

“…[9] Therefore, the synthesis of porphyrin macrocycles with such substituents is of interest for the synthesis of hybrid antioxidants. In addition, isobornylphenols exhibit anti-inflammatory and hemorheological activity, [10][11][12][13] what allows to consider isobornylphenolic fragment as a potential pharmacophore group. In this regard, the introduction of these fragments to the periphery of the porphyrin macrocycle is promising in terms of obtaining new biologically active substances.…”

The redox properties and antiradical activity of terpenophenols

“…Антирадикальная и антиоксидантная активность отдельных терпенофенолов показана в химических модельных системах [4], в опытах на животных [5]. Достаточно хорошо изученным соединением является 2,6-диизоборнил-4-метилфенол 1 (Диборнол ® ), обладающий антиоксидантным, антигипоксическим, антитромбогенным, гемореологическим, нейропротекторным действием [6,7]. Биологическая активность фенола 1 сочетается 1 Астраханский государственный технический университет 2 Южный научный центр Российской академии наук, Ростов-на-Дону 3 Институт химии Коми научного центра Уральского отделения Российской академии наук, Сыктывкар *Е-mail: osipova_vp@mail.ru с низкой токсичностью, что обусловливает актуальность его дальнейшего исследования.…”