29700-20-7Relevant academic research and scientific papers
Application of metal free aromatization to total synthesis of perlolyrin, flazin, eudistomin U and harmane
Santhanam, Srinath,Ramu, Abinaya,Baburaj, Baskar,Kalpatu Kuppusamy, Balasubramanian
, p. 2121 - 2127 (2020/03/04)
Application of our recently reported metal free reaction conditions to the total synthesis of the four different and selective biologically interesting β-carboline natural products is reported. Using this simple methodology, flazin, perlolyrine, eudistomin U and harmane containing heteroaryl and alkyl substituents at C1 position were synthesized in good yields. (Figure presented.).
Flazin as a Promising Nrf2 Pathway Activator
Fuda, Hirotoshi,Miyanaga, Satoshi,Furukawa, Takayuki,Umetsu, Satomi,Joko, Sae,Roan, Yuning,Suzuki, Hirotaka,Hui, Shu-Ping,Watanabe, Mitsugu,Chiba, Hitoshi
, p. 12844 - 12853 (2019/11/21)
Flazin is a β-carboline-derived alkaloid found in Japanese fermented foods. Here, the potential of flazin as an antioxidant food was studied with particular reference to its effect on the Kelch-like ECH-associated protein 1 (Keap1)-nuclear factor erythroid 2-related factor 2 (Nrf2) system in human hepatocytes (C3A). Flazin and flazin analogues including the decarboxylated derivative perlolyrine were chemically synthesized and compared with each other and with chlorogenic acid and curcumin. Among these compounds, flazin showed the lowest cytotoxicity (IC50 3-fold of the control) cytoprotection ability against a pro-oxidant, although its radical absorbance capacity was relatively low. Flazin increased the expressions of Nrf2-dependent phase II enzyme genes and their products (NQO1, GSTP, and GSH proteins). The strong cytoprotection ability of flazin associated with low log ?P (0-3) is shared by sulforaphane and 3,5-dihydroxy-4-methoxybenzyl alcohol, suggesting the potential value of flazin and flazin-rich foods for the prevention of oxidation-related health disorders.
Design and synthesis of furyl/thineyl pyrroloquinolones based on natural alkaloid perlolyrine, lead to the discovery of potent and selective PDE5 inhibitors
Zheng, Hongbo,Li, Lin,Sun, Bin,Gao, Yun,Song, Wei,Zhao, Xiaoyu,Gao, Yanhui,Xie, Zhiyu,Zhang, Nianzhao,Ji, Jianbo,Yuan, Huiqing,Lou, Hongxiang
supporting information, p. 30 - 38 (2018/03/08)
Based on perlolyrine (1), a natural alkaloid with weak PDE5 potency from the traditional Chinese aphrodisiac plant Tribulus terrestris L., a series α-substituted tetrahydro-β-carboline (THβC) derivatives were synthesized via T+BF4--mediated oxidative C–H functionalization of N-aryl THβCs with diverse potassium trifluoroborates. Following Winterfeldt oxidation afforded the corresponding furyl/thienyl pyrroloquinolones, of which 5-ethylthiophene/ethylfuran derivatives 20a–b were identified as the most potent and selective PDE5 inhibitors. Among the enantiomers, (S)-20a and (S)-20b (IC50 = 0.52 and 0.39 nM) were found to be more effective than their (R)-antipode, display favorable pharmacokinetic profiles, exert in vitro vasorelaxant effects on the isolated thoracic aorta, and exhibit in vivo efficacy in the anesthetized rabbit erectile model.
Cu-catalyzed mild and efficient oxidation of THβCs using air: Application in practical total syntheses of perlolyrine and flazin
Zheng, Bo,Trieu, Tien Ha,Meng, Tian-Zhuo,Lu, Xia,Dong, Jing,Zhang, Qiang,Shi, Xiao-Xin
, p. 6834 - 6839 (2018/02/23)
A mild, efficient and environmentally benign method for synthesis of aromatic β-carbolines via Cu(ii)-catalyzed oxidation of 1,2,3,4-tetrahydro-β-carbolines (THβCs) was developed, in which air (O2) was used as the clean oxidant. This method has advantages such as environmentally friendliness, mildness, very good tolerance of functional groups, high yielding and easy experiment operation. In addition, this new methodology was successfully applied in the efficient and practical total syntheses of β-carboline alkaloids perlolyrine and flazin.
Isolation and Identification of an Antiproliferative Compound from Fructose-Tryptophan Maillard Reaction Products
Lee, Sang Hoon,Jeong, Su Jeong,Jang, Gwi Yeong,Kim, Min Young,Hwang, In Guk,Kim, Hyun Young,Woo, Koan Sik,Hwang, Bang Yeon,Song, Jin,Lee, Junsoo,Jeong, Heon Sang
, p. 3041 - 3047 (2016/05/19)
This study was performed to isolate and identify a compound with antiproliferative activity against human stomach cancer cell lines, from fructose-tryptophan Maillard reaction products (MRPs). The MRPs, prepared from a fructose-tryptophan solution heated at 130 °C for 2 h, were fractionated into five solvent fractions: n-hexane, chloroform, ethyl acetate, butanol, and water. The highest antiproliferative activity was found in the chloroform fraction (85.93% at 200 μg/mL), and the active compound from this chloroform fraction was purified by silica gel column chromatography, TLC, and preparative HPLC. The antiproliferative activity (IC50) of the active compound was 42.24 μg/mL, and the active compound was identified as perlolyrine (C16H10N2O2) by 1H/13C NMR, DEPT, HMBC, and LC-ESI-MS. Therefore, this research may be useful in developing perlolyrine as a functional therapeutic agent.
Transition-metal-catalyzed C-H bond functionalizations: Feasible access to a diversity-oriented β-carboline library
Wu, Ningjie,Song, Feijie,Yan, Lipeng,Li, Juan,You, Jingsong
, p. 3408 - 3414 (2014/04/03)
Diversification of the β-carboline skeleton has been demonstrated to assemble a β-carboline library starting from the tetrahydro-β- carboline framework. This strategy affords feasible access to heteroaryl-, aryl-, alkenyl-, or alkynyl-substituted β-carbolines at the C1, C3, or C8 position through three categorically different types of transition-metal- catalyzed C-C bond-forming reactions, in the presence of multiple potentially reactive positions. These site-selective functionalizations include; 1) the Cu-catalyzed C1/C3-selective decarboxylative C sp 3-C sp 2 and C sp 3-C sp coupling of hexahydro-β-carboline-3-carboxylic acid with a C-H bond of a heteroarene or terminal alkyne; 2) the chelation-assisted Pd-catalyzed C1/C8-selective C-H arylation of hexahydro-β-carboline with aryl boron reagents; and 3) the chelation-assisted Pd-catalyzed C1/C3-selective oxidative C-H/C-H cross-coupling of β-carboline-N-oxide with arenes, heteroarenes, or alkenes. The saturated structural feature of the hexahydro-β-carboline framework can increase reactivity and control site selectivity. The robustness of these approaches has been demonstrated through the synthesis of hyrtioerectine analogues and perlolyrine. We believe that these strategies could provide inspiration for late-stage diversifications of bioactive core scaffolds.
[2+2+2] Cycloadditions of alkynylynamides - A total synthesis of perlolyrine and the first total synthesis of "isoperlolyrine"
Dassonneville, Benjamin,Witulski, Bernhard,Detert, Heiner
, p. 2836 - 2844 (2011/06/23)
The total syntheses of the carboline alkaloids perlolyrine and "isoperlolyrine" are reported. Key-steps of the syntheses are Negishi coupling reactions on alkynylynamides and their metal-catalyzed [2+2+2] cycloadditions with nitriles to form the β- and γ-
β-Carboline Alkaloids, I. - Syntheses of 1-Aryl and 1-Alkenyl-β-carbolines by Palladium-Catalyzed Coupling Reactions
Bracher, Franz,Hildebrand, Dirk
, p. 1315 - 1320 (2007/10/02)
1-Chloro-β-carboline (6) is prepared in three steps starting from tryptamine (3).Palladium-catalyzed coupling reactions of 6 with aryl boronic acids offer an easy access to the alkaloids komaroine (11) and perlolyrine (15).Pavettine (16) is prepared by co
