1-(5-乙酰氧基甲基-2-呋喃基)-1,2,3,4-四氢-9H-吡啶并[3,4-b]吲哚 | 115107-77-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 中文名称: 1-(5-乙酰氧基甲基-2-呋喃基)-1,2,3,4-四氢-9H-吡啶并[3,4-b]吲哚
• 英文名称: 1-(5-Acetoxymethyl-2-furyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole
• 英文别名: 2-acetoxymethyl-5-(2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-furan；1-(5-Acetoxymethyl-2-furyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indol；1,2,3,4-Tetrahydro-acetylflazin, 2-dehydroxycarbonyl-；[5-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)furan-2-yl]methyl acetate
• CAS: 115107-77-2
• 化学式: C₁₈H₁₈N₂O₃
• 分子量: 310.353
• InChiKey: GGDJZDNQSLPWHW-UHFFFAOYSA-N

物化性质

• 沸点：
  488.4±40.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  67.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(5-乙酰氧基甲基-2-呋喃基)-1,2,3,4-四氢-9H-吡啶并[3,4-b]吲哚 在 盐酸 、 potassium dichromate 、 硫酸 、 溶剂黄146 作用下， 反应 1.5h， 生成 [5-(4,9-dihydro-3H-β-carbolin-1-yl)-furan-2-yl]-methanol
  参考文献：
  名称：

  多年生黑麦草（黑麦草perenne L.）的生物碱。第四部分 分离出新的碱，Perlolyrine；氢溴酸盐二水合物的晶体结构及其碱的合成

  摘要：

  一种新的生物碱全氟林，1-（5-羟甲基-2-呋喃基）-9 H-吡啶并[3,4- b ]吲哚（6b），已从黑麦草（Gralium perenne L。）（禾本科）中分离出来。碱的结构揭示由X其氢溴酸盐二水合物的C射线分析16 ħ 12 Ñ 2 ö 2，溴化氢，2H 2 O（空间群P，一个= 7·81，b = 10·55，C ^ = 10·55Å，α= 79·2β= 72·9，γ = 78·8°），通过重原子法，在光谱数据的辅助下进行的。R的最终值2360次反射为0·129；试图完善空间组P 1中的结构的尝试失败。生物碱是由色氨酸和5-乙酰氧基甲基-2-甲酰基呋喃合成的。3，4-二氢和1,2,3,4-四氢衍生物也已经从色胺开始合成。讨论了Perlolyrine及其还原衍生物在电子冲击下分解的方式。已显示全草碱存在于干草中，而不是后处理过程中的假象。

  DOI：

  10.1039/j39700001091
• 作为产物：
  描述：

  5-乙酰氧基甲基-2-呋喃醛 在 盐酸 、 对甲苯磺酸 作用下， 以 乙二醇二甲醚 、 乙醚 、 苯 为溶剂， 反应 5.0h， 生成 1-(5-乙酰氧基甲基-2-呋喃基)-1,2,3,4-四氢-9H-吡啶并[3,4-b]吲哚
  参考文献：
  名称：

  日本清酒和酱油中的 β-咔啉：Flazin 和黄色物质 YS（Perlolyrine）的合成和生物活性

  摘要：

  日本清酒和酱油中的β-咔啉flazin (1) 和perlolyrine (2, 物质YS) 分别从L-色氨酸或色胺的甲酯开始合成。测定1和2对单胺氧化酶A和B的抑制作用，并与harmine和harmaline的抑制作用进行比较。

  DOI：

  10.1002/ardp.19883210212

文献信息

• Design and synthesis of furyl/thineyl pyrroloquinolones based on natural alkaloid perlolyrine, lead to the discovery of potent and selective PDE5 inhibitors
  作者：Hongbo Zheng、Lin Li、Bin Sun、Yun Gao、Wei Song、Xiaoyu Zhao、Yanhui Gao、Zhiyu Xie、Nianzhao Zhang、Jianbo Ji、Huiqing Yuan、Hongxiang Lou

  DOI：10.1016/j.ejmech.2018.02.039

  日期：2018.4

  Based on perlolyrine (1), a natural alkaloid with weak PDE5 potency from the traditional Chinese aphrodisiac plant Tribulus terrestris L., a series alpha-substituted tetrahydro-beta-carboline (TH beta C) derivatives were synthesized via T(+)BF4(-)-mediated oxidative C-H functionalization of N-aryl TH beta Cs 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. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Flazin as a Promising Nrf2 Pathway Activator
  作者：Hirotoshi Fuda、Satoshi Miyanaga、Takayuki Furukawa、Satomi Umetsu、Sae Joko、Yuning Roan、Hirotaka Suzuki、Shu-Ping Hui、Mitsugu Watanabe、Hitoshi Chiba

  DOI：10.1021/acs.jafc.9b04600

  日期：2019.11.20

  Flazin is a beta-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 < 500 mu M) and the highest capacity to activate the Keap1-Nrf2 system. It provided the largest (>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.
• β-Carbolines from Japanese Sake and Soy Sauce: Synthesis and Biological Activity of Flazin and Yellow Substance YS (Perlolyrine)
  作者：Wieslaw P. Gessner、Arnold Brossi、Michael E. Bembenek、Creed W. Abell

  DOI：10.1002/ardp.19883210212

  日期：——

  The β‐carbolines flazin (1) and perlolyrine (2, substance YS) occuring in Japanese sake and soy sauce were synthesized starting with the methyl ester of L‐tryptophan or tryptamine, respectively. The inhibition of the monoamine oxidases A and B by 1 and 2 were determined and compared with the inhibitory effects of harmine and harmaline.

  日本清酒和酱油中的β-咔啉flazin (1) 和perlolyrine (2, 物质YS) 分别从L-色氨酸或色胺的甲酯开始合成。测定1和2对单胺氧化酶A和B的抑制作用，并与harmine和harmaline的抑制作用进行比较。
• The alkaloids of perennial rye-grass (Lolium perenne L.). Part IV. Isolation of a new base, perlolyrine; the crystal structure of its hydrobromide dihydrate, and the synthesis of the base
  作者：J. A. D. Jeffreys

  DOI：10.1039/j39700001091

  日期：——

  A new alkaloid, perlolyrine, 1-(5-hydroxymethyl-2-furyl)-9H-pyrido[3,4-b]indole (6b), has been isolated from Lolium perenne L. (Graminae). The structure of the base was revealed by an X-ray analysis of its hydrobromide dihydrate C16H12N2O2,HBr,2H2O (space group P, a= 7·81, b= 10·55, c= 10·55 Å, α= 79·2 β= 72·9, γ= 78·8°), by use of the heavy-atom method, assisted by spectroscopic data. The final value

  一种新的生物碱全氟林，1-（5-羟甲基-2-呋喃基）-9 H-吡啶并[3,4- b ]吲哚（6b），已从黑麦草（Gralium perenne L。）（禾本科）中分离出来。碱的结构揭示由X其氢溴酸盐二水合物的C射线分析16 ħ 12 Ñ 2 ö 2，溴化氢，2H 2 O（空间群P，一个= 7·81，b = 10·55，C ^ = 10·55Å，α= 79·2β= 72·9，γ = 78·8°），通过重原子法，在光谱数据的辅助下进行的。R的最终值2360次反射为0·129；试图完善空间组P 1中的结构的尝试失败。生物碱是由色氨酸和5-乙酰氧基甲基-2-甲酰基呋喃合成的。3，4-二氢和1,2,3,4-四氢衍生物也已经从色胺开始合成。讨论了Perlolyrine及其还原衍生物在电子冲击下分解的方式。已显示全草碱存在于干草中，而不是后处理过程中的假象。