24126-93-0Relevant academic research and scientific papers
Synthesis of analogues of natural antimitotic glaziovianin A based on dill and parsley seed essential oils
Tsyganov, Dmitry V.,Konyushkin, Leonid D.,Semenova, Marina N.,Semenov, Victor V.
, p. 285 - 287 (2016/08/09)
Glaziovianin A and its analogues were synthesized in six steps starting from allylpolyalkoxybenzenes separated from essential oils of dill (Anetum graviolens) and parsley (Petro-selinum sativum) seeds.
Efficient Synthesis of Glaziovianin A Isoflavone Series from Dill and Parsley Extracts and Their in Vitro/in Vivo Antimitotic Activity
Semenov, Victor V.,Tsyganov, Dmitry V.,Semenova, Marina N.,Chuprov-Netochin, Roman N.,Raihstat, Mikhail M.,Konyushkin, Leonid D.,Volynchuk, Polina B.,Marusich, Elena I.,Nazarenko, Vera V.,Leonov, Sergey V.,Kiselyov, Alex S.
, p. 1429 - 1438 (2016/06/09)
A concise six-step protocol for the synthesis of isoflavone glaziovianin A (GVA) and its alkoxyphenyl derivatives 9 starting with readily available plant metabolites from dill and parsley seeds was developed. The reaction sequence involved an efficient conversion of the key intermediate epoxides 7 into the respective β-ketoaldehydes 8 followed by their Cu(I)-mediated cyclization into the target series 9. The biological activity of GVA and its derivatives was evaluated using a panel of seven human cancer cell lines and an in vivo sea urchin embryo assay. Both screening platforms confirmed the antimitotic effect of the parent GVA (9cg) and its alkoxy derivatives. Structure-activity relationship studies suggested that compounds 9cd and 9cf substituted with trimethoxy- and dillapiol-derived B-rings, respectively, were less active than the parent 9cg. Of the evaluated human cancer cell lines, the A375 melanoma cell line was the most sensitive to the tested molecules. Notably, the target compounds were not cytotoxic against human peripheral blood mononuclear cells up to 10 μM concentration. Phenotypic readouts from the sea urchin assay unequivocally suggest a direct microtubule-destabilizing effect of isoflavones 9cg, 9cd, and 9cf.
Facile method for the large-scale synthesis of 6,7,4′-trihydroxyisoflavanone
Liu, Jing,Yang, Zhangyou,Luo, Shenglin,Hao, Yuhui,Ren, Jiong,Su, Yongping,Wang, Weidong,Li, Rong
, p. 3296 - 3303 (2015/10/12)
6,7,4′-Trihydroxyisoflavanone, the main source of which is extracted from soybeans, has been found to have diverse significant bioactivities. A large-scale, cost-effective, and facile chemical synthesis of 6,7,4′-trihydroxyisoflavanone is presented herein. Its synthesis is characterized by three steps with an overall yield of 71% and a purity or more than 99.0%. This reaction can be scaled up to multikilogram quantities, providing a solid basis for its further bioactivity studies and drug development. With this same method, 6,7,3′,4′-tetrahydroxyisoflavanone, an analog of 6,7,4′-trihydroxyisoflavanone, also can be largely prepared, indicating this modified synthetic method is potentially available for large-scale synthesis of a broad range of multihydroxyl isoflavanones.
Synthesis of various kinds of isoflavones, isoflavanes, and biphenyl- ketones and their 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activities
Goto, Hideyuki,Terao, Yoshiyasu,Akai, Shuji
experimental part, p. 346 - 360 (2009/12/27)
Forty-eight kinds of isoflavones (8), thirty-one isoflavanes (9), and forty-seven biphenyl-ketones (10, 10') were synthesized from eleven kinds of substituted phenols (11) and six phenylacetic acids (12). Among them, seventy-five compounds are new. The radical scavenging activities of these compounds were evaluated using 1,1- diphenyl-2-picrylhydrazyl (DPPH) at pH 6.0. We found that thirty-nine out of forty-three compounds having a catechol moiety on either the A- or the B-ring exhibited a high activity (ED50=12-54 μM) similar to that of catechin. In these cases, the remaining part of their structure seemed to have little effect on their activity. Many 6- or 8-hydroxyisoflavanes (9E-I) and their biphenyl-ketone derivatives (10E-H) also showed a high activity (ED50=50=26-32 μM). This study suggests that natural isoflavones have the possibilities of exhibiting antioxidant activities through the hydroxylation at the C6-, C8-, or C3'-position or the formation of the isoflavanes (9) and/or the biphenyl-ketone derivatives (10') by metabolism or biotransformation.
Isocladrastin and kashmigenin - two isoflavones from Iris kashmiriana
Razdan,Kachroo,Qadri,Kalla,Taneja,Koul,Dhar
, p. 947 - 949 (2007/10/03)
From the rhizomes of the Iris kashmiriana, two new isoflavones, isocladrastin and kashmigenin, were characterized as 3′-hydroxy-6,7-4′-trimethoxy-isoflavone and 4′-hydroxy-3′,5′-dimethoxy-6,7-methylenedioxy-isoflavone, respectively. Also, junipegenin-B has been found present in this plant species. Copyright
ONE-STEP CONVERSION OF FLAVANONES INTO ISOFLAVANONES: A NEW FACILE BIOMIMETIC SYNTHESIS OF ISOFLAVONES
Kinoshita, Takeshi,Ichinose, Koji,Sankawa, Ushio
, p. 7355 - 7356 (2007/10/02)
One-step chemical conversion of flavanones into isoflavones by use of thallium trinitrate (TTN) is reported, and the mechanism of a 2,3-aryl migration in this reaction is discussed in relation to in vivo rearrangement process of flavanone precursors in the isoflavone biosynthesis.
ON THE LEUKART REACTION OFDEOXYBENZOINS: ISOLATION AND CHARAKTERIZATION OF 2,3,4,5-TETRAARYLPYRIDINE DERIVATIVES
Villa, Maria Jesus,Dominguez, Esther,Lete, Esther
, p. 1943 - 1954 (2007/10/02)
The Leukart reaction of deoxybenzoins has been examined.The deoxybenzoins (1b-c) possessing a phenolic substituent in the ortho position to the carbonyl group react with formamide to afford, besides the known stilbene, pyrimidine and isoflavone derivative
